General Episode Description:In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore how AI is rapidly reshaping buyer behavior and forcing a complete rethink of how companies sell, market, and build trust.Sabrina shares how search behavior has fundamentally shifted toward AI-generated answers, reducing click-throughs and changing how buyers consume information. She explains why this creates new challenges in clarity, especially around the “build vs buy” decision, and why sales teams must now work harder to guide buyers through uncertainty.The conversation also dives into the growing importance of trust, the evolving relationship between sales and marketing, and how organizations can use AI effectively without losing the human connection that ultimately drives decisions. What You’ll Learn:The New Buyer Behavior: How AI-driven search and LLMs are reducing clicks and changing how buyers gather information.The “Muddy Middle” Problem: Why AI has blurred clarity around what buyers actually need and whether they should build or buy.Selling in an AI World: How sales teams must adapt when buyers are more informed but also more uncertain.Sales and Marketing Alignment: Why tighter collaboration is critical to address buyer confusion and build trust earlier.Using AI Without Losing Trust: Where AI enhances the sales process and where it can damage credibility.Key Topics:Shift from keyword search to question-based search behaviorAI-generated answers reducing traditional website trafficAEO vs SEO: optimizing for AI engines, not just search enginesBuyers arriving more educated but with incomplete or misleading contextThe disruption of the “why change” conversation in salesBuild vs buy vs AI: a more complex decision landscape for buyersMarketing’s role in answering buyer questions upfront and building trustThe risk of poor AI experiences damaging brand perceptionUsing AI for preparation versus customer-facing interactionsTurning AI efficiency into better personalization and human engagementGuest Spotlight: Sabrina ParsonsSabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, a leading business planning and financial forecasting platform. With experience leading both sales and marketing, she brings a unique perspective on how companies build sustainable revenue engines. Sabrina is also a strong advocate for women in leadership and technology, and has guided her company through multiple waves of technological change. Resources & Mentions:Palo Alto SoftwareLivePlanConcept: AEO (AI Engine Optimization) vs traditional SEOConcept: Build vs Buy vs AI decision-makingConcept: Trust equation in modern salesExample: Customer experience with AI chatbots (Oura Ring case)🎧 Listen now and follow Selling Intelligence for more insights on AI, modern buyer behavior, and building high-performing revenue teams.Mark Petruzzi (00:31)Welcome to Selling Intelligence. Our guest today is Sabrina Parsons, CEO of Palo Alto Software, makers of LivePlan, one of the world's leading business planning and financial forecasting platforms. Sabrina has been the helm at the company, this company that has over four decades of history leading through multiple waves of technology disruption.Before stepping into the CEO role, she ran both sales and marketing, giving her a uniquely integrated view of how companies grow, how buyers decide, and what it really takes to build a revenue engine that lasts. She is a passionate advocate for women in leadership and technology, a thread we'll weave in throughout today's conversation as well. So three topics we'd like to cover with you and with Sabrina today.how AI is reshaping buyer behavior and what that means for how you sell. We've covered that many times on our podcasts already, but we really are excited about Sabrina's perspective and her experiences in that area as well. The second one is why the human element, why trust, story building and storytelling.And relationships are the only sustainable differentiators that we really can build in today's business climate. And third and finally, what sales and marketing leaders must do differently today and how that integrates into the CEO role and also the board of directors. What can the boards be doing to help their sales and marketing leaders evolve in the way that they need to?Sabrina, welcome to Selling Intelligence.Sabrina Parsons (02:13)Great, thanks Mark, I'm really happy to be here.Mark Petruzzi (02:15)All right, let's dive right into topic one. ⁓ Topic one, AI and the changing buyer. So Sabrina, you've described the buyer behavior online as having shifted more dramatically in the last 18 months than in the prior decade. What are you actually seeing? Why does it matter so much for how we sell and how we need to sell in the future?Sabrina Parsons (02:35)that's a great question. And I'm pretty sure as soon as I start talking, all the listeners are going to say, because we've all experienced, I think, a very similar change in how we interact online. In the last 18 months and even more so in the last 12 months, we have all seen the way our interaction on search has changed.particularly with these new AI synopsis that you see at the top of the page.And while there will be articles and sites that are cited in this AI, what's happened is that fewer people are clicking through because they go, they have a question, they type it into Google, and they're typing questions now into Google. used to be that we would type keywords, right? And then you'd see what happened. And now people are typing questions into Google and then the or whatever search engine, but, Googlestill probably the most used. And then what they're getting back, it scratches the itch for the most part. And so they're getting this information and then maybe they're moving on, right? So that's one huge change in behavior and we're all seeing it, right? You have interacted and chosen not to go forward because your question is answered or you found what you need. ⁓ So that new way that we're getting...all of this information displayed, it means fewer click-throughs, and so companies that are selling have to deal with that. The other thing is that search engines are really leaning on and preferringwhen you can put content out there that actually gives answers, because that's what people are looking for, right? It's how do I, those types of questions, how do I do this? How do I sell? How do I market? How do I, all of these how do I's, that's what people are doing. ⁓ And then the other thing that I think we all know is that people are for the most part, very familiar with LLMs, right? With all these AI chat box. And many peopleare using them instead of search engines, which I will say if you are, think about it because it's a very expensive search engine. It uses a lot of energy to do an AI query. And every time we're usingAI when you could just use a search engine, we're wasting energy. So it's something that, you know, not everybody always knows, but there's an appropriate use for AI, but it doesn't matter, right? Behavior has changed, and we're all trained now in this new behavior. And it feels like it's just been like instant, like in the last 12 months, because changing behavior used to be a huge thing, right?From a sales perspective, people like you would teach salespeople how to help change behavior. And like we have seen behavior change just so quickly this time around.KK Anderson (05:23)overnight. so how does that change how we sell?Sabrina Parsons (05:27)So that's a great question. I mean, it has to, right? Because when you're selling, used to be that your marketing team could just make sure like, are search results going to come up on first page versus second page? And if not, let's just buy pay-per-click ads and make sure that they come up.in those results. And it's like that doesn't work anymore. So a lot of what you have to do in terms of how to change how you're selling is address this new way that content is consumed. So you really have to think through, am I providing answers? And it's not just content that fits keywords, right? It's content that's actually giving answers. And then in the way you format your content, if you wantto be AEO forward, right? It used to be just SEO, search engine optimized. Now we're AI chat bot optimized. If you want to be AEO forward, you really have to rethink how you're putting your content together, what kind of sort of synopsis you have that's easy for AEO to grab.Do you have the right FAQ schema? It's just a, you know, it's a different way that the LLMs are crawling through information. And so you just have to make those changes.KK Anderson (06:46)Right. And I'll just add to that. It's all about that trust equation. Right. And so that's what our prospects for all of us, you who are running businesses and running sales organizations, they're all looking to, they're looking for value and that value is what's driving trust. And that trust equation ⁓ is going to what finally converts. And so when your buyers do get on the phone with you finally,They're going to be so much more educated. going to know so much more. They will probably have an LLM, create a table stack ranking, the three top options to solve their problem. And so they're going to be so much more educated when they get on the phone with your team as well, which is another, when you get sort of that sales process behavior that it just, all the changes at top of funnel are filtering down.into that as well. Everything changes.Sabrina Parsons (07:37)and I think that's important, right? And salespeople know this because they're getting confronted. It's like they used to have their process, the information, they've done their homework on the prospect. And now you have to be prepared to understand what are they seeing in chatbots, what is coming through, what kind of, because the other part is that it doesn't necessarily, itThere are opportunities to help someone understand that the landscape may be more nuanced than the AI LLM has put out there, right? But you have to do your homework ahead of time. You have to understand what they're seeing, how much more research, so to speak, they think they have, and then how do you address that, particularly, KK, like you said, just from that trust side of the equation.KK Anderson (08:25)And Mark, I'll give the next one to you here in a second, but just to kind of cap that off, it makes the concept of selling to your customers' outcomes even more important because it's not necessarily about educating them on your product or your service or what you're doing. It's how do you take that, how do you take what they think they know or they don't know or the absence or the void and convert that into something that's important to them, which is the outcome that they're trying to achieve.Sabrina Parsons (08:50)Exactly.Mark Petruzzi (08:50)Excellent. So Sabrina, at AGS, we talk about a two-sale mentality. The first sale is just why change. The second sale is why you and why now. If you're not accomplishing both of these processes within a selling model, then you're not winning the deal.You know, there are companies that are really good in understanding clients, understanding why they want to change, but they're not as good on the, you know, differentiating themselves in the market. There are even more companies that are the other way around that really just don't spend enough time understanding, you know, what are the risks here? Why change it all? And their pipelines get bloated and then get very, very lean quickly.because they have a lot of clients that just say, or prospects that just say, I don't need to change and I'd rather not write out another $3 million check. So where does AI driven buyer behavior disrupt that first sale the most in your opinion?Sabrina Parsons (09:56)You know, I think number one, it's disrupting in terms of what that client thinks they need help with, right? It was very clear. think there's now, it used to be very clear, this is what my tool might do. And I very much understand how I can help the client. And the client...for the most part understands what they need and how you can help them. And I think AI has blurred all the edges, right? As we're all learning how to use it, it's blurred all of that where it's like, well, do I need that tool? What can AI do for me instead? Should I change my process and adopt this new tool or do I just need to get better at prompts for AI or should somebody in my organization vibe code something and dosomething that's more internal and specific to us. And so it's almost like the buy birth versus build is a much murkier, muddier question, right? Because, and it doesn't always mean that the tool isn't actually the best thing for them. It's just that your buyer is now.confused and wondering like, maybe I don't need the tool, maybe AI can just do it for me. And so I think we've just that clarity that used to be a little bit easier with those two things like, you know, what do I need and how does your tool help me? Like that's just muddy now. It's now like, I don't know what I need. Do I need your tool or do I just need, you know?some internal AI expert or maybe I need both. And so I think thatit's just made things muddier. And so the salesperson has to help that prospect understand that and see and clarify and then show them those benefits of like, you don't want the pain of learning all of this. We've got you. We have done it and we've integrated this into our tools. So you get the best of all the worlds without having to figure it out.KK Anderson (12:00)really insightful. You are spot on with that. so you and you've kind of seen this from both the market. I know the world is changing every day, every month. It's different than it was yesterday with every recording and every time we publish a podcast, something else has changed, right? But you've seen this from both the marketing head of marketing seat and the head of sales seat, know, at LivePerson. So in this new world,that we're in, like how did these two function, sales and marketing? how, I mean alignment between the two has always been a problem, right? And so what are some ways that you're seeing like that overlap, that handshake to happen more effectively in this new era? Like talk to me about that.Sabrina Parsons (12:38)that's a really good question because I think you you're right. There's always a little bit of headbutting, and sales is sometimes out selling things. I mean even headbutting with product as well, right? Where sales will sometimes sell things the product doesn't have yet and sales will say well marketing you're not keeping up. We need these materials you don't have. So I think that's always been a little bit more, you know, that's always been something thatdepartments have butted heads against. think right now marketing and sales have an opportunity ⁓ to really understand when you have this much gray area and fuzziness around, what is it that the client actually thinks they need? You can very much...be in a space where you believe you have the best tool and they actually need you, but now the client's not sure they need you. So marketing has to help make that case, right? Marketing has to be playing this new AEO game. Marketing has to also understandWhat are the things that these clients think they might be able to do without us and address those, right? It's all about answering those questions, answer forward, give that information and address. And then I think even more so that trust of really truly we are the right organization with the right expertise that you can trust because we all know and the clients constantly worried aboutIf I just use AI, is it real? Is it true? Is it hallucinating? And so marketing teams, think, really have to help lead the path to clear away the maybe misgivings people have between, do I use AI without the tool? If I use the tool, do I use it with AI?Or does the tool have everything I need? If marketing does a good job of helping someone understand that, why you shouldn't be an AI by yourself, why we've brought AI into our tool and it's going to be even better, then the salesperson can take it from there and do some personalization for that client when they're selling to say, let's actually have specific examples of why our tool is going to be better off for you than if youare off on your own trying to be an AI prompt writer all of a sudden.KK Anderson (15:00)and moving into sort of this next topic around trust and story and the human advantage, you know, we all, it seems like what was super cool, ChatGVT, Claude, prompts, generative AI, six months ago is now just table stakes, right? And so we're all getting, it's almost like we're using, now we're using these tools that are very quickly table stakes.the same outreach sequences, the same content generators, you see the same, you know, M dashes and hope your hope to see male funds you doing well. Like you, can just spot it immediately. You know, you know, immediately when you're looking at something that's AI generated, right? So, so talk to me a little bit about how you can lever for sales specifically, right? How you can leverage AI, but still actually create differentiation. Like what are, what are some of the things you guys do with your team?Sabrina Parsons (15:48)that's agreat question. I I think that there's an appropriate use of AI even when people recognize it, right? And I think that's important. I think that AI should be used to make some jobs easier. I think there are some writing that AI can do that is appropriate and AI does it faster and it streamlines it and that's okay. But I think it's really important to recognizesort of where a client does not want to see that, where a client does not want to feel that. If a salesperson is trying to sell and part of what they're saying is, we're going to bring personalized account management to you and that.client is like, really? Because I just had a horrible chat bot interaction with your website and there was no person and it was a robot and I don't believe you. And so that's where like we have to define.where it's okay to use AI, where you're hurting yourself when people know it's AI, and you need to be very careful. And then using AI appropriately internally to be very prepared for your sales calls. AI can prepare you.at a speed at which we haven't seen. And so you have no excuse not to be prepared, understand the exact situation your client is in, have researched their company, have researched them. I mean, it's easy to do now. And so it's almost like we can't get away with not doing that because that's how you prove that we're real people and we're taking the time to be real people. But it does have to flow all the way through. You don't want...that person to have had some interaction with a pre-sales chat bot that was terrible. And you're to have to fight that because there's a lot of people out there who are like, don't, there's going to be some negative connotations because people have had bad interactions. And so how do you address them? And interestingly, if you can get marketing to play ball with you and you do some of these,some of these interactions better than everybody else, that's right now at least, know, God knows in six months, but right now that's gonna make you stand out. ⁓ I was talking to someone who had an aura ring and had an issue with the aura ring, went to the website and was super annoyed that they could not get a real person. Just so annoyed.And it was a chat bot and said, I spent 10 minutes fighting the stupid chat just to try to get a person. And then finally said, forget it. Fine. I'll interact with the chat bot. And they said, in three minutes, the chat bot had looked up my data, knew that my battery wasn't working, and told me that they were sending me a new aura ring the next day. Right? And so all of a sudden, he's like, I felt like such an idiot.Mark Petruzzi (18:36)Ha ha ha.KK Anderson (18:39)This is awesome!Sabrina Parsons (18:40)Yeah, he's like, I push back on it so much because I've had such terrible experiences and I really didn't want to use it. And then it turns out if I had just embraced it, I would have been better off. But that's the opportunity, particularly for marketing and sales to work really well together, because there are people who are doing it terribly. So don't be those people.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson continue their conversation with Sunil Rao, founder and CEO of Tribble, diving deeper into SaaS fatigue, agentic execution, and the challenge of scaling institutional knowledge in enterprise sales.Sunil breaks down how AI agents are reshaping the way work gets done by becoming the interface across systems, eliminating the need for constant tool-switching, and enabling teams to operate from a single layer of intelligence. He also shares how modern GTM teams can capture and scale expertise across conversations, documents, and internal knowledge to improve performance over time.The discussion closes with a look at the human side of selling, where trust, collaboration, and real customer engagement remain irreplaceable even as AI automates more of the workflow. What You’ll Learn:SaaS Fatigue and the Shift to Agents: Why the future interface is not more tools, but a single AI layer that connects everything.Agentic Execution in Practice: How AI can capture context across calls, RFIs, and RFPs to generate smarter, more personalized responses.Scaling Institutional Knowledge: How to turn tribal knowledge, conversations, and documents into a usable system of intelligence.The Failure of Static Content Systems: Why traditional enablement platforms fall behind the speed of modern business.Human + AI Collaboration: Where automation should take over and where human judgment, trust, and relationships still win.Key Topics:“Kiss your apps goodbye” and the rise of agents as the new interfaceEliminating tool-switching and browser tab overload for GTM teamsCapturing context across the full sales lifecycle, not just at the RFP stageUsing AI to coach reps in real time during customer interactionsBuilding knowledge graphs from calls, documents, and internal conversationsDenoising and validating data from sources like Slack, Gong, and CRM systemsWhy knowledge bottlenecks exist due to limited subject matter expertsThe limits of traditional enablement programs and static content librariesDesigning AI systems with humans in the loop for approval and quality controlReallocating 30% of seller time from admin work to customer engagementGuest Spotlight: Sunil RaoSunil Rao is the founder and CEO of Tribble, an AI-native platform that helps enterprise sales teams automate and optimize go-to-market workflows. With a background as an engineer at SAP and a leader at Salesforce, Sunil brings a unique perspective on both the technical and human sides of enterprise selling. At Tribble, he focuses on building systems that scale knowledge, improve response quality, and enable teams to operate more efficiently with AI. Resources & Mentions:TribbleConcept: Agentic workflows in go-to-marketKnowledge graphs for sales and GTM intelligenceSaaS consolidation and interface shift to AIThe Hard Thing About Hard Things by Ben HorowitzSuperintelligence by Nick BostromConcepts: “SaaS fatigue” and “tribal knowledge” in enterprise organizations🎧 Listen now and follow Selling the Cloud for more insights on AI-driven GTM strategy, enterprise sales transformation, and the future of work.Mark Petruzzi (00:31)So Sunil, let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and unused platforms. If you built a company in the enterprise software space going right at all of that overflow, how did you design Tribble to be part of the solution rather than be another product out there that's part of the problem and the challenges?Sunil Rao (00:54)I think from the very early days, one of the things we thought about deeply was, hey, where is this all going? If I think for two, three, five years, what do we think happens? And it was very clear to us that there's a consolidation that's going to take place across where people want to go to get their information.when we see what was happening with ChatGPT and you think about how this kind of AI can be pervasive across systems, this is one of the things I was telling someone recently. If you go back on the internet, you go to the Wayback Machine, which is a website that allows you to go back in time, you can go see the 2023 December page for Tripple. It says, kiss your apps goodbye at the very top. Say hello to agents. And that, I think, was very indicative of, this is what's going to happen. We probably did that message too early because no one knew what an agent was in 2023.But I think that's where we are right now, right? It's like, hey, there's this new interface, right? I can talk to an agent or I can talk to software and I can give it access to all the other systems I work with. So I kind of don't need to go to all those systems again, right? I can do the work through this proxy.And the way that we always describe it is like in the future, you know, when you onboard a new employee, what do you do? You say, here's your license to system one, system two, system three, system four. And they're sitting on their chair and their browser tabs and they're swiveling from one to another, to another, to another.That kind of all goes away. So I think when I think about SaaS fatigue, think agents actually are going to change and become the interface. And Trivel, for us, when we think about go-to-market technology, we want that to be the interface when we think about the respond process and the engage process. That's our bet. And underneath the hood, we have many systems we integrate with. But I had a prospect ask me this the other day. They're like, hey, if we're using your tool, do I need to go to these other systems? And the short answer is no, you don't.Get everything you need right over here.KK Anderson (02:35)So walk us through like what an agentic execution actually looks like in practice. So like when a sales team sends triple an RFP, what's happening behind the scenes? Like how much is automated versus augmented, if you will.Sunil Rao (02:49)Yeah, so I'll give you two examples, KK. I think one, let's think about a company that responds heavily to RFPs and that's a big portion of their business. The RFP coming to you isn't the first point of contact with the customer, right? And depending on the size of the organization and how big this engagement is, it might be something more like, hey, we've had an initial call with the team and they shared with us that they're going to issue an RFP. So there's some discovery being done. We learned some requirements. We learned some players at the table, the different business units that are relevant here.Fast forward a week, another call takes place. Different team members at both organizations are on a call. Information is shared. Then you get to another call and then they issue an RFI, which is the precursor to the RFP.So it's one document that gets sent over and then you got to answer a bunch of questions. Then you finally get to the RFP, which then ends up becoming a bigger proposal. But we think about the journey across all these touch points as opportunities to collect context. So one of the things we do is we show up on the call for each of these touch points. We collect context. We coach the folks live on the call on what data to collect.and how to think about this so that when it comes time to build the response, it's contextual on all the data we've collected for this specific prospect, but every other conversation we've had and where we've won bids and where we've lost them. And that way we can see, historically, when you've answered no to this question for this type of company, you've lost the deal. So one of two things, either explain you can do it because it's on your roadmap or actually put it on your roadmap. Right. And these are the kinds of insights we can glean because we're integrated to thethe systems behind the scene, as we come across these insights, we can go write the data back directly. The agent will go and update a ticket in JIRA, or it'll go make an update in Salesforce directly. And it's done throughout the journey, throughout the process. So that's kind how we think about it across the lifecycle.Mark Petruzzi (04:30)that's excellent. Excellent. So let's go to topic three here, scaling institutional knowledge. We use this, the term kind of tribal knowledge and a lot of the work we do in engendric space ourselves. So yeah, let's dive into that. One of the most interesting things about Tribble, that it's not just about speed, it's about scaling the...the expertise, scaling the process, making those processes better over time as well. You've described the problem of a limited number of experts having the necessary knowledge. In your experience at Salesforce and now at Tribble, why is knowledge scaling such a massive bottleneck in most enterprise organizations, particularly within their sales function?Sunil Rao (05:15)Depending on how big the organization is and what products you sell, historically for me, one of the things that I've experienced firsthand, when you're selling a complex product or you're selling into a vertical where the business processes are very specific and non-standard and it's not something everyone knows, you usually will have a gap in terms of the understanding of the field team and what it is that the customer wants. So how do you speak the language of the customer is always a term that we used a lot in my career.And whether you're in financial services, health, whether you're in CPG, retail, manufacturing.There are processes that are very specific to that industry. So how do you enable the field teams to know what it is the customer's pains are and what they need? And how do you build the right software to meet those needs? So I think that ends up in, thinking back five, 10 years ago, how do you scale that within a company? Well, you create these enablement organizations. You create enablement programs. You take everyone to Vegas for kickoff, and you show them 800 bajillion PowerPoint presentations and hope they remember it for the year. And of course they do, because that works every single time.Right? And when you show up, you've now enabled everyone and they're talking about the product. I think that that kernel, it.The one consistent theme that we've seen and I've experienced it firsthand is you still need to leverage these SMEs during the sales process and you tap them on the shoulder and bring them in. And whether they're sales engineers, they're industry experts, technical architects, program architects, whatever you call them, they all have some level of knowledge and there's too few of them in the organization. So that's what I think about when I think about the scarcity of that type of resource and how do you scale it? So for us, we've always thought of, you've got data in docs.Those documents will inform a certain amount of the business process. You've got knowledge now in these large language models that we can tap into.And there's tribal knowledge, right? We know that Mark actually is really, really good at this one feature in that product that no one else in the company knows, but it's not written down anywhere. It's in Mark's brain, right? So like, has Mark mentioned that on a call? Is that something that's come out in calls with customers? How do you tap into that kernel, right? So we take that data from the calls. We take the data from the documents and everything we're observing across all the calls in the company. And we create a graph of the experts in the company and who has what tribal knowledge and what documents.have what knowledge. So we're trying to solve it in that way Mark of how do you scale the expert? Will you create a backup of them and you try to understand in the organization where you can go to for what.KK Anderson (07:36)And so that's, does that one explain why you're, you're ingesting all kinds of secondary information like Slack conversations or conversations between engineering or product or sales teams? That is that part of how you do that?Sunil Rao (07:49)that you before something becomes a document people are usually talking about it on slack or on callsKK Anderson (07:54)So how do you, like a couple of things come to mind. Number one, like how do you ingest that much information without just having a lot of junk? know, like 80 % of gong conversations are junk and there's a maybe a golden nugget in there. you, mean, it seems like a lot of memory, a lot of space.Sunil Rao (08:11)You haveto compress it. You have to de-noise it, and then you have to compress it. So we actually have, it's funny, when I was geeking out with the engineers on this, we were thinking, look, and I've done sales as well. Sometimes people say things on calls that are not necessarily factual, right? So we have to attribute for the fact that it happens, and especially with gone calls, you have a lot of salespeople saying a lot of stuff on calls.But then you have this idea of ground truth, which pertains to your product information that we're connected to systems of record that we pull data. So we'll look at the data that's coming in and the really noisy stuff, which is gone calls call transcripts, and we'll cross check it. We'll almost fact check it with what we know is in the main store. And if there's anything new gleaned, we will pull that out and denoise and get rid of all the back and forth that's not necessary to store. But we try to pull out the key facts. We try to understand, hey, who was on this call? What were they discussing?which people were saying which things, what regions, locations, product lines, segments were discussed. So anything that pertains to go to market is what we try to pull out of this and then we store it in what we call our knowledge graph. And that allows us to like pull out the signal from the noise if you will, KK. And then we will fact check some of that.And we'll also use the folks using the product to actually validate if information is correct or not. So that way we move from this vast ocean of noise to a usable data set that's otherwise really hard to get to.KK Anderson (09:28)it's really, reallyMark Petruzzi (09:29)most companies, as we all know here, have invested heavily in content libraries, knowledge bases, sales enablement platforms. Yet somehow the right answer is not there when the rep needs it. Why do traditional knowledge management systems fail in high-velocity sales environments? And again, how does Tribble andthe things that you do overcome some of those challenges.Sunil Rao (09:55)It's almost like a short circuit cheat code, right? Because I remember the Russian December.to get high spot loaded with all of our content. When I was at Salesforce working with marketing and it was like the stretch going into Christmas and we're all building the 40 different variations of first call decks and second call decks and these subvertical plays and you'd create and it's this one moment in time where all the content gets created gets uploaded to these systems and it's not any one system. It's just the way it was done, right? You have to have a central place where people can download this content.But the problem with that is you do it at some frequency that's not fast enough for the speed of the business. Information is changing at the rate at which product is being released at the company. And there are just new pieces of information that are coming out. So tapping into the higher velocity data sources, like conversational data, whether it's coming from Slack, whether it's come from Teams, or it's coming from call transcripts, and corroborating that with data that's being created by organizations like product marketing, I think you can move a lot faster.then you can also provide information that's based on new information as opposed to information from six months ago. And you can also use the human in the loop to validate the new stuff.And AI obviously gives you a lot of leverage to do that. So I think that's why it's just a different way of thinking. Think about the lifetime of the asset and how long it's relevant and how quickly we can distribute the load of people validating that it's still correct instead of it being one poor person that's responsible for updating this repository every six months, which tends to be the bottleneck in a lot of orgs.KK Anderson (11:25)Wow. So moving on to our last topic here around the human element, right? And where AI should take over and we're at must step back. So you started your career as an engineer who would look at the sales leader and be like, no, heck no, absolutely not. Can't do it. Not going to do it. Right. And now you're a CEO who's deeply embedded in the go-to-market strategy. So,What did you learn about the human side of selling that you could not have understood when you were on the engineering side of the business?Sunil Rao (11:56)I appreciate the sales side of it so much more now. even think back.⁓ to like my initial days as an engineer, I just never understood this side of the house because it was just, it was, it was illogical to me. It would be like, why are you positioning something that, know, how, how are you positioning what's real versus not? And not to say salespeople don't do that, but I think you tend to think more now as a consultant that's helping your customer solve a problem and you see the paths and the opportunities. And it's a very different way of thinking than the very rigid way of like.the logical way of like, this is true now or not true now and therefore we can't do it. So I think the change for me really was more, hey, how do you build trust with people? How do you kind of show up and actually bring value and meet them where they are, but then also work with them to build the future together? And I think that opens up.a much more collaborative kind of trust-based relationship. And ultimately, that's what this whole thing is. It's, hey, do you trust me to help you solve the problem? I might not be there 100 % at this moment, but I will get there with you. And I think that that mentality allows you to both portray a vision that you can go on together, but also attack problems with the reality of what you have now. So it was just a mindset shift, would say, KK.Mark Petruzzi (13:08)So Sunil, there seems like there's a bit of attention in the ⁓ product philosophy from the perspective of, know, one of the things you guys do and do so well is automating the RP process, something very specific, very process oriented and some of the info sec ⁓ questionnaires, which are all pretty.technical and repetitive. But I love and get very impressed by the way that you talk about the human side of all this and as you just described, like the things you've learned along the way about the human side of selling. So where's the line? right now, it's gonna change like in about 12 hours, but it's right now, like where's the line? You know, what should AI own?And in your mind, like what should really remain human, at least for now?Sunil Rao (14:00)You know, if you asked me this question like 10 years ago, I think a lot of people will say the same thing. I wouldn't have guessed that sales, enterprise sales, heavily relationship based sales would be one of the last things to go. I would not have guessed that. And I think that that intuition comes from the fact that this is very much a very trust-based human-based business where you're going in and helping these companies transform and helping build relationships to do that.So I think from that perspective, it's where it's disrupting and changing things.There are a couple of implications of that, right? Like how do you bring folks along for the ride? And you mentioned product tension. Like we think deeply about, you automate the thing end to end or do you make the surface area where the AI does the work that's really rote and repetitive, but you still have the human in the loop to go in and have the knobs and dials to finalize what needs to go out. So I think our product philosophy has been that, right? Because we've been selling to these teams that are operating where they have to do a lot of the manual repetitive work, but also be theapprovers and now it's can we give you the tooling to remove some of the manual repetitive work? You still maintain the approver status, but now you can handle a lot more throughput as an organization, right? So that impacts UX decisions and product philosophy. Humans aren't going anywhere for a little while. I mean, this stuff will move and you're right, in 12, 24 hours, 48 hours, it's probably gonna jump even further. But I think the rate with which it goes into the company is still gonna be slower than we think.KK Anderson (15:21)And it goes back to this idea of AI is becoming table stakes. So you're giving sales teams the gift of time with your technology. And so it becomes a question of what are sellers going to do with that time? And that's where they get their edge. That's where they can increase the strength of their relationships and their networks and how they can bring value and help individuals, help others, help their customers.Tell me your kind of philosophy around that. What do you want your sales team doing with their time that you're giving them back?Sunil Rao (15:53)go meet more customers, go out in the field, go take them out to dinner, like understand.KK Anderson (15:57)Do theSunil Rao (15:57)Show up, go do a ride along, understand how they sell to their customers and what are they trying to achieve. If you're stuck trying to update fields in a document at your desk and you're not out there, then you're not really doing the job that you can have the highest leverage doing. So I think, I feel KK, I could have said the same thing selling cloud CRM software 10 years ago and probably 20 years before that selling it. Ultimately, there's always a percentage of the job that is stuff that's getting in the way. And I think I look at this notas replacing the role, it's if you look at the role and you see the jobs to be done of the role, there's probably about 30 % of the jobs that they're doing that you can just take out. And when you take that out across an org of like 500 people, you're not replacing those people, but you're kind of changing the role and making it better suited for the best outcome for that individual. And that's the way I look at the re kind of composition of the work.KK Anderson (16:47)And for a salesperson who's working on a commission, being able to take 30 % of redundant admin BS that they don't want to do and giving them that time back to be able to grow and expand accounts, that puts more money in their wallet.Sunil Rao (17:02)It's like reducing your tax rate.KK Anderson (17:04)Reducing your tax rate. love it.Mark Petruzzi (17:06)I like that a lot. Okay, let's move to one of our most fun parts of this and finish up with some rapid fire questions. This is an interesting one for you because you've been, you you've come from the engineering side. You're a CEO now. You've done some really great years of sales and sales leadership along the way. But what was the first thing you ever sold?either professionally or as a kid.Sunil Rao (17:33)This takes me way back. I'm pretty sure the first thing I ever sold was a trading card.And I used to collect a lot of trading cards like baseball, like Marvel Comics cards. And I remember having to sell some of these like in trades in order to buy more, right? It was always just to get more cards. So it's like, how do you find the right optimal thing? So I think the first selling aspect of it was like, hey, get someone to like really like this, right? Like, and then they buy from you.KK Anderson (18:03)Relationship Selling 101, right? With your buddy down the street. come for a sleepover and I'll give you this card or you give me your card or whatever. Okay, favorite business book that influenced how you think about go to market or AI or kind of where you are now.Sunil Rao (18:18)favorite business book. I've been reading, you know, there's been one of all time, I would say, The Hard Thing About Hard Things by Ben Horowitz. That was just like a classic, right? And I think it was like a very good eye-opening thing, walking into a storm. So that would be my rapid-fire answer, but there's a lot more.KK Anderson (18:37)Is there, I'm curious if there's one that's related to AI though, that specifically has helped shape the way you're thinking about things. I know it's probably not written yet.Sunil Rao (18:44)specifically, would say ⁓ there is a book called, so there are a there's a short paper ⁓ that was, I think it's called, gosh, I'm forgetting the name now.I'll talk about the book instead. Superintelligence by Nick Bostrom. That was a really good read. That was probably 10 plus years ago. And I think that was the first time I heard this idea of like this, you know, when you, when you're building these superintelligence systems, you know, there's this thing called the paperclip problem, right? And if you like tell the thing to go build paperclips forever, you might find yourself in a world that has been completely converted into paperclip factories. And it's basically taken out all the humans in the world, but it's not doing it because it's malicious. It's like your instruction was notprecise enough, right? So anyway, that I would say is AI related, a little more of like critical thinking on where this could go.KK Anderson (19:30)wow.Mark Petruzzi (19:31)that was a great book and it was at the perfect time. It was late enough in the history of our world for him to have a really strong point of view and have some data behind it, but still so speculative versus what we're seeing just 10 years ago or 10 years later from there. So what's the best piece of advice you've received?when you were transitioning from a corporate executive to a startup founder.Sunil Rao (20:00)best piece of advice is...Mark Petruzzi (20:02)And that could evenbe from yourself, like something you just came up with and said, you know what, I gotta do this now.Sunil Rao (20:08)I would say it's actually the realization that a lot of people have advice and opinions. I think, especially when you're out and you're doing this for the first time, know, I, my personality is to seek advice and like really learn from the experience of so many others that have done tremendous things. but also keeping in mind that you need to carve in path, like your own path in your own way. so that's been, it's been, it's been good to keep in mind becauseYou realize very quickly that no one has all the answers and no one's really figured it out. There are people that have done amazing things, but you have to kind of take all of that and make your own path out of it. So that was a good realization for me.KK Anderson (20:43)so interesting. And even as an entrepreneur myself, sometimes the people that love you the most or they're closest to you are the ones giving you the worst advice. Like, are you crazy? Why are you doing this? You're quitting your job? You're doing what? ⁓ Okay, on the advice line here, what's some advice that you would give your 21 year old self?Sunil Rao (21:02)there's many things that I won't say here, but I think from ⁓ what was interesting to me is, the...I've always wanted to build something and I've pursued endeavors in the past as well. So this is not the first time that I kind of thought about startups and building something. think taking the jump earlier and believing in yourself a lot sooner is something that, you know, it's just like, you can go make a dent in the world. doesn't like, you don't need permission. Go do it now.Mark Petruzzi (21:29)beautiful. All right, well, Sunil, thank you so much for taking the time with us. And this has been a great discussion. And I always like to thank our audience who we are so appreciative of, and we so enjoy connecting with you all every week.So thanks again and then I always have to do a special thank you to KK, my partner and all this and yeah, it's ⁓ just too much fun for us to even have to say that we're doing work here. ⁓ And people like you make it really fun. So thanks so much, Sunil.Sunil Rao (22:06)Thank you for having me.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling Intelligence Podcast, Mark Petruzzi and KK Anderson sit down with Sunil Rao, founder and CEO of Tribble, to explore how AI is reshaping enterprise sales, go-to-market execution, and the future of software itself. Sunil shares why AI-driven productivity alone is no longer enough to create advantage, how the rise of agents is changing what software should do, and why trust, personalization, and institutional knowledge are becoming even more important in a world flooded with AI-generated noise.The conversation dives into the productivity paradox, the coming consolidation of fragmented SaaS tools, and the shift from software that assists humans to systems that can actually take action on their behalf. What You’ll Learn:The Productivity Paradox: Why AI makes everyone faster at the same time, raising the bar instead of creating instant advantage.AI and New Work Creation: How efficiency gains in one part of the workflow can create new review, oversight, and decision-making work elsewhere.Differentiation in an AI World: Why personalization, timing, and relevance matter more now that everyone has access to the same tools.From SaaS to Agents: What separates AI-assisted software from agentic systems that can actually do the work.Trust in Autonomous Systems: Why transparency, confidence, and clear decision logs are critical when AI operates inside core business systems.Key Topics:The treadmill problem in modern sales productivityWhy AI has upgraded everyone at the same timeThe flood of low-quality outbound and the need for precision engagementUsing digital exhaust and customer signals to guide better sales conversationsWhy traditional scaling models relied on people because software could not solve the problem yetHow fast-moving foundation models are changing product designThe coming consolidation of SaaS point solutionsWhy the future interface may be lighter, with more approvals and fewer manual workflowsBuilding AI-native products that can evolve with each new model releaseReducing SaaS fatigue by designing for orchestration, not more app sprawlGuest Spotlight: Sunil RaoSunil Rao is the founder and CEO of Tribble, an AI-native platform built to help enterprise sales teams scale knowledge and automate critical go-to-market workflows. Before founding Tribble, Sunil began his career as a software engineer at SAP and later held leadership roles at Salesforce, including GM of Consumer Goods. Tribble was founded in 2023 and has quickly gained traction for helping companies automate RFP responses and improve GTM efficiency with AI-native workflows. Resources & Mentions:TribbleSalesforce Ventures generative AI fundRFP automation and response workflowsAI agents versus traditional SaaS applicationsSaaS consolidation and platform orchestrationThe role of trust and transparency in AI adoption🎧 Listen now and follow Selling Intelligence Podcast for more conversations on AI, modern go-to-market strategy, and the future of enterprise sales.Mark Petruzzi (00:31)Welcome to today's episode of Selling Intelligence Podcast. I'm thrilled to welcome Sunil Rao, founder and CEO of Tribble, an AI native platform that's fundamentally changing how enterprise sales teams scale knowledge and automate critical go-to-market workflows. Sunil's journey has been fascinating. He started as a software engineer at SAP.moved into leadership roles at Salesforce, including and general manager of consumer goods, and then founded Tribble in 2023. Tribble was quickly added to Salesforce's ventures, $500 million generative AI fund, and has since revolutionized RFP automation, helping companies like Clary, Sword Health, and others slash response times by up to 80%.Today we're exploring a critical challenge facing every sales leader. AI is making us more productive, but the bar keeps rising. It's like running on a treadmill at full speed and just when you your stride, the incline keeps going up. How do you stay ahead when everyone else has access to the same productivity gains? We're gonna focus on four critical themes. The productivity paradox, why AI-driven efficientisn't enough to win anymore. From software to agents, building AI that actually does the work, not just assists, scaling institutional knowledge, the hidden competitive mode in enterprise go-to-market, and the human element, where AI should take over and where it must step back. Sunil.First off, we're really happy to have you here. Thank you for taking the time with us and welcome.Sunil Rao (02:10)Thanks for having me. It's nice to be with you all.Mark Petruzzi (02:12)Excellent. So topic one, the productivity paradox. Let's start with what you have called the treadmill problem. Every sales team now has access to AI tools, chat GPT, co-pilot, all these niche engagement and enablement platforms. And all sales teams are getting more productive, or at least the ones that are investing in this. But here's the thing, if everyone's running faster, you're not actually getting ahead. You're keeping up with the pack.And worse, buyers' expectations are rising because they know that you have these tools. So how do you think about this productivity paradox?Sunil Rao (02:47)Productivity paradox, it's interesting because I think there's a couple of ways that I like to think about it. You obviously have this tremendous technology. It's almost magical. It's been distributed to everyone almost simultaneously. And they're all able to see how much productivity it brings into all aspects of their job. But I back to beginning of when we started Tribble, and this is when Chat GPT has just come out, November of 2022.And everyone had that aha moment of, whoa, this thing can write coherently for such a long time. It can actually write code. It can write snippets of code. And it just started to become a way for you to use in your workflow versus going to Google, searching for information. This thing can synthesize knowledge. So when you look at that and that impact,It already was a tremendous time saver for a lot of smaller jobs. But I think what's been going on and what's been happening over the last few years with these foundation models getting better and better, it gets to the point now where these systems can run for hours on end and complete much more complex tasks. And that's where it's more interesting where, you know, what was not possible to solve with software three years ago.is possible today. And that's where agents come in and everything comes in. it's interesting because like you have that happening in one side and it's really magical technology. But then at the same time, you kind of create new work.when you have access to this technology, because now everyone's a creator. And I see this a lot in the engineering side. Everyone's writing more code, and then it's the question of who's reviewing it. If everyone's writing more content to go in documents, who is doing the human check? So you have this trade-off of, yes, there is efficiency in one part of the process, but you end up creating some work elsewhere. So I think it's the paradox, because it actually changes the distribution of where work is being done.KK Anderson (04:30)Really, really interesting. So when we think about it from, you know, a sales or revenue perspective, right? It's, you know, for, for so many years, it was, do you have this Salesforce CRM? Do you have this outreach, you know, program set up? Do you have this automation set up? And it was, you were always running to keep ahead and to keep up to pace with all of the different technologies that were available. And that was just sort of table stakes.Right? And now with AI, as you just said, like everybody has it. And so now it's how you use AI is, is, and how you become a, differentiator using AI is the new game. Because otherwise it's this, we, you know, ⁓ as Doug Landis, one of our good friends and colleagues says is we're in a culture of sameness right now.Sunil Rao (05:15)Mm-hmm.KK Anderson (05:16)an era of sameness, I think is what he says. So talk to us a little bit about that. So now here we are, we all overnight got Chappie, GBT and these amazing programs. How do we differentiate ourselves in this world of AI?Sunil Rao (05:30)it's an interesting way to think about it, right? It's almost like everyone got upgraded, but exactly to the same level. So then how do you differentiate is the It's how do you stand out from the pack? And, you know, and I take the example of outbound and emails. Like I think what's happened, it's both a gift and curse.KK Anderson (05:37)Yes.Sunil Rao (05:45)I mean, I'd it's more of a curse because now there's so much garbage when it comes to outbound, right? In terms of mass generation of emails that are not personalized, that are not targeted. And I still think that the age old, you know, what makes you really good about that style of top of the funnel engagement is when you are very personalized and targeted. think that just actually gets even more amplified as an important way to stand out, right? Don't, don't try to sell something to the masses. Really think about what signals.indicate that this may be a buyer that's interested and engage with them on the journey at the right time becomes way more important. Because otherwise, you're just feeding into the sea of noise that's being generated because we have these tools that can mass create this content. So I think there's that aspect of it. How can we be much more tailored on the engagement side? And I think about it at different parts of the funnel. For us at Tribble, we think deeply about this problem.when we talk about our customers using our products and how they engage with their customers. So we look at it from two sides of that coin. Mark, you'd shared our respond product, which is all about responding to RFPs, responding to customers. You have to be very particular about what it is you do as a business, how you differentiate.And that's informed by your conversations, your knowledge basis and all this stuff internally allows you to differentiate against your competition. But then on the engaged side, where we have software that helps BDRs, SDRs and others engage with their customers. Like we think really about what is the information that we have captured in all the digital exhaust with all the touch points we've had with this customer that indicate that this is in fact something that they're interested in. And how can we in real time kind of guide that conversation and coach it? So we get to the.And I think customers really want that level of detail and personalization because otherwise you're kind of feeding the sea of noise like you've said.KK Anderson (07:29)All of a sudden to be human is to be cool.Mark Petruzzi (07:30)Yeah.Sunil Rao (07:32)I mean, I think people arepurposefully putting spelling mistakes in LinkedIn posts because it's like now become a sea of, and you see it, right? When you look at the posts and you see the dashes, the end dashes or the dead giveaway of ChatGP, everyone's using them now.KK Anderson (07:43)yeah. The dashes,Mark Petruzzi (07:44)100KK Anderson (07:45)I can't, emojis make my blood curl now. I'm like, ⁓ you know?Sunil Rao (07:50)KK,like, here's a funny question. I actually thought about this the other day. I actually don't know how to type the dash on the keyboard. So it's like, where is it coming from?KK Anderson (07:55)I don't know.Mark Petruzzi (07:56)That is great. You know what, Sunil, when you mentioned the top of funnel and what's happening there, that's an area that KK and I spend a lot of time with our clients to make sure that they don't fall into this AI paradox where five years ago, before we were in the,KK Anderson (07:57)really don't? That's awesome!Mark Petruzzi (08:18)Gen. AI era before it even had a name. You saw that there was so much outbound going to prospects and customers. And what we found is there's been more damage in that than benefit in a lot of companies, meaning they are pushing more potential clients away than in some cases they're ever bringing through the door.So taking you back to your time at Salesforce and when you were running your go-to-market operations initiatives there and seeing all the inefficiencies that were happening with customers of Salesforce but also right in with Salesforce as well, what was the breaking point for you that made you realize traditional approaches to sales productivity were just fundamentally broken?Sunil Rao (09:07)You know, I think it's.Once again, this comes back to the point earlier of what is now solvable by software simply wasn't solvable five years ago, right? So what did you do? The problem was solved by hiring humans and kind of building processes, building checks, building scaling functions, building these expert groups within the company that house knowledge that would scale the rest of the organization. You invest heavily in resources like that and all the supporting functions and resources to keep them going. And I think, you know, thatthat goes far and frankly if you don't have the technology you have today, that's the only way to do it at the time.For me, the inflection point clearly was the rate of change of the technology outside that was indicative that, hey, if I had to build a company from scratch today, I would probably not staff it the same way, given where tech is at this moment in time. That was 2022, right? And then you go forward in time one year, the number of people factors down even further because the technology is now improving at an exponential rate. And you fast forward another two years and it's crazy how fast things are moving. So I think, like I would saythe tools and capabilities and what it is that you are building from a scaling standpoint, as more is becoming available outside, really how quickly can you factor that into the organization and how quickly can you grow? Like this has to be top of mind for every executive at every company right now, right? And I think that that is changing at such a fast pace that folks are just open to having those conversations now and like really thinking, how do we build this differently?KK Anderson (10:32)And it, does it become less fragmented? Right. Or more fragmented. You're adding in, there's a big one million AI products and solutions out there. And there's one, you know, go to market inside this, this, this company. Right. Like, how do you even begin to look at and think about.you know, how you're gonna weave in and out all of these products and how they're gonna talk to each other and I don't know, talk to me a little bit about that.Sunil Rao (10:55)Our thesis on this is there's a mass consolidation coming. And I don't think that that is a very unique point of view. I think most people realize it. The general purpose nature of the underlying technology serves itself very well to addressing many use cases. And what I mean by that is when we started the company, thought about a category and we were, the vision was always to do something much broader and go to market, but then you kind of say, hey, what's the thing I'm going to do tomorrow really, really well?And we picked RFP. And the reason for that was it's a known problem. People knew how to buy software in that domain. And there's a lot of pain there. But that being carved out as a product category, and this is true for any other category of software, these are artificial boundaries created as, this is a category of software. There's a level of functional kind of capability locked in it, technical difficulty to enter it and build it.But there's no reason sometimes these adjacent categories shouldn't be talking to each other. So think, KK, to your question, I think people will expect tools to do a lot more. Hey, I want you to be a tool that does x, y, and z, not I need a tool for each of these. I think the last decade with all this fragmentation of SaaS and so many point solutions, there's just fatigue in buying. And AI is now going to be a consolidation on top of that. Because the beauty of this technology is it can connect to the downstream systems and become the new interface ontop of several so it can orchestrate across them right and I think a lot of the companies that are building like us have that as an advantage.KK Anderson (12:18)Makes a lot of sense. let's take us into the second topic here from software to agents, just as you're talking about, and building AI that actually does the work and not just assists in the work. And you've made a very deliberate choice with Tribble, and you didn't build another SaaS app, right? You built an agent. ⁓ So talk to us about the fundamental difference betweenAI assisted software and truly agentic AI. I think a lot of our audience and sales leaders would like to really understand that. And why does that distinction matter for go-to-market teams?Sunil Rao (12:54)I think there are a couple of implications of thinking about it. just to orient how I think about this and what we think about it at Tribble. Software up until the point where this new stack of technology, specifically LLMs, vector databases, and everything that goes into the new kind of architecture has historically been, you know,You have a database and then you have a UX on top of that database and you have a whole bunch of workflow capability automation and even AI as it was, I it has been around forever, right? It just changes what it actually is. And that's been the way things have been built, but it really is predicated on this transactional data store on which a user interface exists for teams of humans to go operate. AndYou know, lot of companies have done really well. And even my previous employer working at Salesforce, one of the things they did really well is they did the cloud first really fast. And I still remember when we were talking to customers 10 years ago, comforting them that the cloud was a safe place to put their data, right? Now that's, that's not a problem anymore because folks have like taken that modality as a good, it's a good way to scale subscription model makes sense. Software makes sense when you deploy it in the cloud. ⁓and all of that stuff. So now what happens in the last three years is we've got technology that allows you to kind of short circuit some of those layers. So when we think about what is an agent-first product, well, what is the layer between where the data is stored and how it's served up to the user? And in which cases do you even need to serve it up to the user anymore? The entire idea of user interface for us, for us to go in there, see the knobs and dials, and change things.Mark Petruzzi (14:20)Thanks.Sunil Rao (14:25)I think that doesn't go away because obviously humans are in every company and they will continue to be for the foreseeable future. Then the question is, okay, what parts of that process maybe can we automate away where they don't need to see it, right? It doesn't get served up to the UX. So I think it changes the way you think about how you build these products becausewhen you have this broker in between you and where the data is stored, and you can rely on that broker to do some of the work for you, it's kind of like having a really, really capable employee that's going to do stuff and you trust them to do it. So like, if you had that as part of it, do you need to see a screen that's as busy? Maybe not. Do you maybe need to see as many screens? Maybe not. Maybe you just have approval buttons instead of actually seeing the detail every time. So there's these architectural implications in how you build the products. And I think, youBut the thing that also changes when you build it this way is when these foundation models, like these companies like Anthropic and OpenAI, they're moving at blistering speed. If your two model releases behind...you're not harnessing like 60 IQ points of new capability. So how do you build a product that can seat itself on top of that innovation and harness it as it comes out? That's the way you have to build software in the future. Now, if you built it the old way and you sprinkle the new stuff on top, you still have to bring along the old stuff for the ride, right? And, you know, lot of big companies have very, very smart people. I've worked with many of them. And when you have a large customer base using the old stuff, it's really hard to just go to the new stuff.Mark Petruzzi (15:25)Hmm.Sunil Rao (15:48)have to think about how you bring the old stuff along for the ride, right? So I think that's the way I like to think about it. When you're AI native, you've been given the privilege to make some choices that allow you to move a lot faster. And this could also just be true of startups, right? think it's like we're seeing it at an accelerated rate.KK Anderson (16:02)It's a master class.Mark Petruzzi (16:03)and Sunil, of the things KK will tell you about working with me is that, and I know it myself, I'm always focused on productivity. I use that word too many times in a day. And I've learned, having worked with many CEOs, having been a CEO myself, that you learn how these CEOs, some of themget caught up into the process and the control access or the control aspect rather is the right word of being a CEO versus an enablement aspect and just a value add role. And it's going to happen, it is happening the same way with agents just as you described. So I love how you describe this, the agents,have to be autonomous. This is not another form of automation. We're moving through much more productivity and ability to learn, get better, get smarter, do a particular job better. Now what I'm seeing now is a lot of customers and clients are looking at it and saying, okay, well, they're monitoring the agents. They want to see it just like a CEO that wants to be copied onevery email from every VP and up within a company. tell us a little bit about how you, like how do you feel that, how do you make that change? How do you get a client to look at this and say, I'm gonna be bringing these agents into your business with I know you're gonna have to do your due diligence and you're gonna have to really get confident in it.But when you get confident in it, let them roll. Look at them just like human employees, just unfortunately for us humans, they're a lot more productive. They don't take a vacation. They work 24-7, we don't.Sunil Rao (17:54)You know, I think Mark, it's a very timely question and KK, I think you said something along these lines at the very beginning. Trust.Right? Like it's never been more important and it's relevant to the fact that we have the sea of sameness, right? How do you trust that this is a real message meant for me? How do I trust that, you know, how do I trust this relationship from the very beginning? Are you just treating me as one of the many masses? I think that theme comes into even product strategy and how we think about where we show up with our customers.So if you are going to use a product, especially if you're going to use a product that you give a level of autonomy to, and it's going to go in right against your master and your systems of records, you better trust it. So then it's like, okay, how do you build that trust? What kind of transparency do you put into the product? do you make it very clear? The log of decisions that were made, right?Sunil Rao (18:40)Makes sense.Mark Petruzzi (18:41)let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and many unused platforms. Yeah, you built the company in the enterprise software space to go right at that. How did you design Tribble to avoid becoming part of the problem and rather being part of the solution?Sunil Rao (19:01)I think one of the things we deliberately did in the early days was really think about like, where are things going, right? Just in the next three to five years, what do we think happens? If you go back to ⁓ the way back machine, which allows you to see kind of websites from.can take look at Tribble's website in like December, 2023. had the headline, Kiss Your Apps Goodbye, Say Hello to Agents. And that was, founded the company in 2023, but it was very clear to us that, hey, this idea of having all these applications.KK Anderson (19:23)I love it.Mark Petruzzi (19:30)Cool, okay, so we'll jump in so let me go read that one again and we'll go and we'll do that question one more time.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode, Mark Petruzzi and KK Anderson sit down with Doug Landis to explore why storytelling has become one of the most powerful skills in modern sales. From lessons learned in the film industry to practical strategies for enterprise selling, the conversation highlights how narratives help sellers build trust, create alignment, and close deals faster.Doug explains that buyers don’t actually buy products; they buy the story attached to the outcome those products create. When sellers focus on telling clear, meaningful stories rather than listing features, they make it easier for buyers to understand the value and communicate it internally. The discussion also dives into the shift from traditional inside-out selling (focused on CRM data and internal information) to an outside-in approach, where sellers study the buyer’s business, strategy, and external signals to craft a more relevant narrative.What You’ll LearnWhy storytelling is more powerful than product features in salesHow great stories help buyers remember your solution and sell it internallyThe difference between rambling and effective storytelling in conversationsWhy sellers should shift from inside-out CRM preparation to an outside-in perspectiveHow understanding your buyer’s business leads to stronger trust and bigger dealsWhy trust-driven selling can accelerate deal cycles and increase deal sizePractical ways sales leaders can build storytelling into their team cultureKey topics covered include:How great stories help buyers sell your solution internallyThe difference between rambling and structured storytellingWhy sellers should spend more time on outside-in researchHow AI tools can help sellers synthesize external insights fasterWhat leaders can measure to prove trust-driven selling worksRapid-fire insights on sales habits, books, and early lessonsDoug also shares a powerful reminder: people don’t buy features; they buy the outcome the story promises, whether that’s solving a problem, improving their business, or simply getting their Sundays back. Mark Petruzzi (00:31)Now that is some, that's really, really great stuff, Doug. And I'm gonna share a little bit about how I use, how I've learned to use stories into my selling process. And not only my selling process, running companies, working with private equity firms, communicating with people in all kinds of ways. And it really came down to about 15 years ago,Doug Landis (00:45)Mmm, yes.Mark Petruzzi (00:56)I was involved with a couple of ⁓ and brought in by friends of mine in a couple of films and TV series. I invested in a couple of them for a little bit of a while. was like, forget about enterprise software and selling. And I'm going to be running around with Steven Spielberg soon. That didn't happen. But we did pretty well with these movies.And I'll give you an example. Somebody I've done work with is a filmmaker by the name of Michael Corente. And he's just one example of about a half a dozen that I got to work with. But he's a producer. That's what he focuses on. And in the entertainment industry, I learned there are no, well, there are, I found in my career, there are no better storytellers, not even than the writers. Of course they know how to tell stories.Doug Landis (01:20)So cool.Mark Petruzzi (01:44)but the producers that are out there getting investments and everything else. And man man, Michael was one of them. He's done some amazing things. He's created some really just incredible films that he made happen and he does a lot of stuff with Netflix now and Hulu and incredible stuff. So my point in this is for everyone in business,Doug Landis (01:48)Yep.Mark Petruzzi (02:09)Find your way of getting exposed to individuals like that. Now we all can't typically just call up and get to know a producer. I just happen to have some friends in the industry that I grew up with and got in that track. But maybe it's about writers. It's about different people who run businesses that you just look at. And just learn that side of the equation becauseIt's as specific as you define it, in my opinion, and it's also as generic as just like if you learn how to be a good storyteller, you're going to be successful in business and life. Like I use these same skills with my two children. they love to hear stories. It's just incredible. good.Doug Landis (02:48)Amen.KK Anderson (02:49)People will like you, Yeah.Doug Landis (02:53)Well, I got a caveat to that.I have a caveat to that. Everybody loves somebody who is a good storyteller. Everybody despises somebody who not despise that's pretty aggressive, but it's not a big fan of the people who ramble. They think they're telling a story and they're just it's just one ginormous run on sentence that you never know where going to end. Because reality is it right like it's like no one wants to be the person stuck at the party with I ⁓ I got to sit next to them. ⁓ they never shut up. They always sayKK Anderson (03:09)Yes.1,000.Mark Petruzzi (03:17)Excel.youKK Anderson (03:23)Is there any time?Doug Landis (03:26)All they do is talk your ear off or they just talk about themselves, right? They don't ask, they don't treat it as a conversation, right? So like, this is what happens. I mean, this is why I always think selling is just a series of conversations. We're having a conversation to see if it makes sense for us to have another conversation. And if so, who else should be involved? What's interesting is in conversations in everyday life, we tell stories, right? So like, just get better at being really clear and succinct about the story that you're trying to tell. And I think it's hard.Mark Petruzzi (03:28)Yeah. ⁓KK Anderson (03:45)ThankMark Petruzzi (03:45)Yep. Yep.Doug Landis (03:52)Like I think it's hard to be able to do on the fly because you have to be really thoughtful. It's a muscle, like practicing your discovery muscle, just like practicing your negotiation muscle. These are muscles that you have to practice. ⁓ I love it.KK Anderson (04:06)And you gottaget good at telling stories on theDoug Landis (04:08)And so you need to know what stories you need to know what stories are the best stories to go tell for this particular audience in this particular moment. Right. And so that's why I say like, if it's a first conversation with a with a prospect or a buyer, I need to be really thoughtful about what stories do I want to tell? What stories do I want to bring in the conversation? I'm thoughtful enough about what questions I'm going to ask. I'm thoughtful about what about what products I might talk about or, or, or maybe infuse into the conversation.KK Anderson (04:26)Right.Doug Landis (04:34)Why don't I just spend the extra minutes to be thoughtful about the story or stories I might want to tell in the conversation.KK Anderson (04:39)and practice it.So I wanna also talk about what happens when we're not in the room as sellers with our buyers. We know that they have to turn around and very often, I mean, the last number I saw was like on average, anything over $25,000 would go to a CFO of all things. Like even people who've had buying authority and budget for...Doug Landis (05:01)Yeah.KK Anderson (05:04)most of their careers no longer do because of what's happening right now. And so who you're talking to, they have to turn around and sell it internally, they have to be your champion. And I will tell you, the stories are what they remember. So if they're gonna turn around and go talk to their coworker about it or get buy-in, they're probably going to be telling that story. Like, you told me the story, they'll be able to recite it.Whereas like you said, the multiple choice question, like they're gonna be like, can't remember. I don't really remember what it does, but it sounded cool.Doug Landis (05:32)I can't remember which vendor actually says they can integrate with Salesforce or with, with all of that. I can't remember. Like honestly, even if I'm looking at two solutions, I'm like, shoot, I don't remember which one actually is like, yeah. ASC 2019 integrated like, well, I don't remember. Right. Cause they're all saying the same thing. By the way, here's the, here's a little, here's a little tagline. You can share with everybody. Well, if everybody listening, people don't.KK Anderson (05:35)Yeah.Mark Petruzzi (05:44)Jesus.KK Anderson (05:47)Yeah.Doug Landis (05:58)buy products. They buy the story attached to it. Right. It's connected to an outcome. It's like, Oh, this, if I, this is one of my favorites. we, we do a lot of work with Salesforce and MuleSoft and it's like, do know how many people are in the API integration world are working on Sundays because all of a sudden integration went down on Friday. And if it's not up and working on a Monday, then guess what? They're not actually doing transactions. Oh no. SoImagine if you buy a solution like MuleSoft, you never have to work a Sunday again, now you can hang out with your kids. That's the story I'm telling you in my head as I'm trying to solve for this integration problem that I have. It's like, I want my Sundays back. Not like I want a faster integration solution. I mean, that's nice, but like, no, I want my Sundays back.KK Anderson (06:33)Right.Mark Petruzzi (06:41)And Doug, the way you just said that is great because some people would answer your question is, well, people want solutions. But no, I mean, that's a solution. You're giving them a solution, but it's the net effect of that solution on you and to your life and your response. Excellent. Let's, and your organization.Doug Landis (06:58)Yep. your organization and like your team and like thethings that yeah, the things that you care about. Like this is how, this is how they're making decisions. It's the story that they're crafting in their head. And it's, what, by the way, like we've all done this, right? We've had to buy solutions. I was a box and I'm like spending a million dollars on the solution. And I'm like, I gotta go sell this internally. I tell you what, I'm to go create a story and I'm going to, I'm going to paint this picture and I'm going to create that story.Mark Petruzzi (07:04)Yeah. Yeah.Doug Landis (07:24)that can connect everybody so that we can all be aligned. Because it's way easier than be like, here's everything it does. People will be like, okay, great, why does that matter to me? It doesn't matter to me. The one thing on list matters to me. But guess what? I build a story to tell, and it's a lot easier for me to tell. I can get way more alignment and buy-in.Mark Petruzzi (07:43)Yeah, you just defined it there. Okay, let us move to topic three, outside-in strategy and one-shot selling, the world we live in today. So most AI sales tools organize internal CRM data, right? You've worked in the Salesforce space for many years, I have as well. We look at some of the challenges there. We look at even bigger challenges in dynamics and other products.And we all know that these CRM systems are just, they don't have a great deal of just accurate data and things to be able to lever as we go forward. So you built something outside in here and what's, if you built in that process, what's broken about an inside out preparation versus an outside in?Doug Landis (08:30)I don't think there's anything broken. think it's just short-sighted. here, I'll give a little context to this. So, you know, my co-founder, ⁓ he was brought in to go do these ginormous product stories, build these product stories for Mark at Salesforce. Giant, like, you know, we're going to change the way Marriott interacts with their customers in the next 20 years. okay. How are we going to do that? How Salesforce going to power that? We've to build a narrative from a product perspective.Well, you what he did and what great sellers do is like, well, okay, what do I need to know and understand about Marriott's customers? What do I need to know and understand about how Marriott does business, how they think about themselves, how they brand themselves, how their competitors think about them. That's all external information that we need to synthesize to get a deep, deep understanding. What does the CEO think about strategically over the next five years, 10 years about the business? The reality isis most people are using AI technology to build internal sales AI solutions based on Salesforce data, gone calls or zoom info, chorus information, calendars and emails, right? And notes. Cool. To me, that's all kind of lagging indicator data. It's important. I'm not saying it's not important. It is important, but it's only half the picture because that's all usually a lot of stuff about information that's already happened. Right? We've had these meetings, we've had these conversations. They said, no,They said, yes, like these are the people that we know. That's cool. But then when I'm getting ready to go have a conversation with somebody, I need all that outside in perspective. I need to understand the nuances of an article or a webinar, a podcast that my buyer was on and they said something specifically about what they're really thinking about. You know, it's like, if I just heard that the CIO of an organization said, we are literally on a spending freeze for the next six months,until we re until we integrate. Let's just take Salesforce as an example. They just bought Informatica, right? We they are a customer of ours. We're working with them. And you know what? Do know how often I get the hold on? We can't actually talk to you right now because we're so deeply ingrained in this Informatica integration from a people from a process from a product perspective that like we're a little distracted. Like, okay, cool. Guess what? I'm not going to bother any of the MuleSoft folks. I'm actually going to go work with Salesforce core.If I didn't know that I keep bugging them and they're gonna be like, dude, leave me alone. So the outside in perspective gives you information and insights that most of us miss. And partially because it took us, used to take a tremendous amount of time to aggregate all that information, to contextualize it and synthesize it around the opportunity that you have. But now you can do it in four minutes.KK Anderson (11:03)you know, it's something, it's interesting because you're getting on the phone with your buyers and everything in the CRM is basically about the company, about yourself, your company as a seller, who you're representing. It's all very self-centered, obviously. And as you said, lagging, lagging. And you want to be able to see and use a tool like a StoryPath, which is incredible at doing this, at kind of getting in that outside-in approach.so that it actually helps you when you're in that customer conversation to approach it from their perspective. I mean, if I had a dollar for every time I've said this, I would be a billionaire. It's like, when you're in a customer conversation, you wanna be sitting on the same side of the table as them. You wanna pretend like your email is kk at you'llsoft.com or whoever it is that you're trying to sell to. Like you're not even, you're not there to educate. You're there toDoug Landis (11:42)Amen.Yeah.KK Anderson (11:54)you know, solve a problem, right? And so, you know, thinking, kind of thinking about this, this kind of different paradigm. If I'm a seller and I'm spending so much time reading through the Salesforce history and all of a sudden getting really scared because I know there was a closed last deal in 2024 with a different rep and I had no notes and they didn't log anything and I don't know anything and I'm about to call this person and I'm like, you interested yet? Right.That's just like what a salesperson's like, you know, all of a sudden all of their self-limiting beliefs are creeping up and their confidence is shattered because they're seeing what's in CRM, right? What is your world like? How is that different when you use a tool that is outside looking in versus inside looking out?Doug Landis (12:19)HahahaI think there's a couple of different ways to think about it. Like when I'm thinking about an opportunity, I need, what is my strategy to win? Like org chart, who's who, like we know we got a multi-thread, we know there's all these things, what's my strategy to win? What are the thread lines, what are the through lines that I can pull on that are connected to us that actually can help us orient around our differentiation? So.I need to think strategically. So I need a strategist. I need an analyst to help me analyze all this information and show me the things that matter the most. Show me the things that matter the most. And I need it quickly. Because if I'm jumping from meeting to meeting, I got to get booted rather quickly, right? Oftentimes, it's like, you know, it's six or seven o'clock at night, I look at my calendar tomorrow, my ⁓ I have a call at 8am. I am so not ready for that. Right? And so like, cool, what how do Iwhat's most important for me to get out of this conversation? I want them to say, great, this sounds interesting. I want to learn more. I want them to say, I want to have another conversation. Great. Well, then how do I prepare for that? Think strategically about the plan for the account. I think analytically about where are the opportunities, where are the threads that I want to connect. And then I start to of craft my narrative for the conversation. All that information is external insights, external signaling.that I want to, that I want to tap into so that I can pull into the conversation and sound credible. Sound like I understand what they're trying to put myself on the other side of the table sitting next to them is ultimately what I'm trying to do. Right. And that's what outside in information really does. My perspective.KK Anderson (14:01)And so instead of spending 80 % of your time researching what's in CRM, what would you say? Do your 20 % to know what's there, what the history is, and then 80 % to swap it? Yep.Doug Landis (14:10)Yeah, totally.Great. Yeah. mean, the 20, the, the stuff in CRM, you know, it's, know, it's, just even think about this because we ingest all this information and we look at a gong call. It's like 90 % of it's trash. There's 10 % of that conversation. It's really valuable. It's like, they said these things. Cool. That's what I want. Right. I learned these little thing nuggets. That's what I want. Everything else, the commerce, all those otherorientation of the conversation, this question. It's like, all right, that's interesting. That's why CRM data is helpful. It's like, what have we already tried? Who have we already talked to? But to be honest, a real true enterprise seller is gonna go, cool, I'm not even gonna look at what's already happened. I'm gonna put myself in their shoes and try and think about what are they trying to accomplish? What's getting in their way? What is that gonna do for them if they accomplish this?who else is involved in this, I'm gonna put myself in their business first. And then I'll go back into CRM and be like, hey, have we done some of this? Or do we have a way in, right?KK Anderson (15:06)Doug, I have met my soulmate in selling.Doug Landis (15:08)YouMark Petruzzi (15:08)HahahaKK Anderson (15:09)I like I have metmy soulmate in selling. just so thrilled to know you. Okay. I'm going to take us to the last topic, because this is the fastest hour that has gone by. know our listeners will do it in two parts, but before we get to the rapid fire, which is everybody's favorite, I do want to at least cover a little bit of this leadership in the AI era, sales leadership in the AI era, because know, boards...Doug Landis (15:13)Mmm.HaKK Anderson (15:32)are gonna fund what they can measure. so we know that story sell, that trust sells, that we have to go through this process of why change, why you, why now. What are two or three ways or indicators, I guess, leaders can do to go to their boards and say, trust-driven selling is working.We need to try this. Like how, what's the proof? What's the proof story?Doug Landis (15:58)Yeah.I mean, so this investor that I was talking to this morning, we were talking about this, you know, like if sellers really truly develop that level of trust with their buyers, that they truly understand how to become a trusted advisor, which is ultimately what kind of what we're talking about here. And the simple fact that buyers are already 80 % through the buying process or 90 % through the buying process. Guess what that means? We can close deals faster. We can close deals.KK Anderson (16:19)Hmm, there's a good leading indicator.Doug Landis (16:22)We can close deals faster. And he literally said, he's like, I have our portfolio companies are there, especially smaller deals, man. They're getting done in 24 hours. Like, boom, not two weeks, 24 hours. I closed a deal a week ago in 24 hours. It's like, that was easy. Great. Let's do more of those. ⁓ big deals. I think we can accelerate the conversion rates, the conversion rates across whatever stages you have, because again,If the buyer's already done this invisible evaluation and it didn't take them nine weeks to do it, they did it in two days. So like, cool. We now can move a lot faster. So I think speed of closing, speed of conversions important. I also think to be honest, if you are truly showing up and speaking your buyer's language and understand their ontology, guess what? Deals are going to be bigger.KK Anderson (16:56)Mm-hmm.Doug Landis (17:05)It doesn't come down to feature function. We're not like, I'm not just comparing two features and it just becomes a price war. It's like, no, we have a real strategic relationship here because I get you and I know what you're trying to do over the next five to 10 years. And we're in this together. I mean, I was talking to a president to a week ago and he's like, Hey, talk to me about your pricing. This is a true conversation. Talk to me about your pricing. I don't, I'm not negotiating, but I'm just going to get a sense. Cause I'm going to meet with the CEO next week. And I was like, cool. Here's the deal. I don't negotiate.price is the price. mean, unless you want to do a three year deal cash upfront, then we can talk about it. But guess what? I set the price to where it's a non issue. And he's like, we'll explain that. And I did and he's like, Okay, that makes sense. So this isKK Anderson (17:43)I remember the reaction I heard when youfirst told me your price. I was like, what? That's it?Doug Landis (17:47)And it's just like, here's the deal. don't want this to be, I want a long-term relationship. want, like, I understand the value that we're delivering and are we leaving money on the table? Probably. there potential upgrades in the future? Absolutely. But I don't, it's not about price. It's about delivering value.KK Anderson (17:53)Mm-hmm.Love it.You're so good, Doug.Mark Petruzzi (18:03)let's to our last here that both KK and I love, and that's our rapid fire segment. First question for you, first thing you ever sold.Doug Landis (18:04)What?Younewspapers. I think I was like 10 years old, selling door to door. I'm like, Hey, I'm selling the Palo Alto Times and they and you already get the San Francisco Chronicle, but you want the Palo Alto Times because it's local.KK Anderson (18:22)⁓so good.Mark Petruzzi (18:23)And see now that's beautiful. You had differentiation even then in your product.Doug Landis (18:24)HahahaYeah.KK Anderson (18:29)Okay, a storyteller that you admire.Doug Landis (18:31)⁓ Simon Sinek starts, starts with why, like I just, stories live in the why, right?KK Anderson (18:33)Yes.Mark Petruzzi (18:37)For sure.Okay, one practice every sales leader should adopt this quarter.Doug Landis (18:43)start asking your sellers for the story of the deal. What's the story of the deal? Start practicing storytelling more frequently, like have create story time in your team meetings where somebody steps up and they tell a story. And then you go through the exercise of, that really a story? Was that just a sequence of events? Because the more you, you infuse story into your culture, the more it becomes easier to actually communicate and share stories with your customers.KK Anderson (19:08)Boom. Okay, my favorite advice that you would give to your 21 year old self.Doug Landis (19:13)This is a doozy, because on the one hand, I'm kind of like, just keep doing what you're doing. Life is great. On the other hand, it's like, you can work on the people pleasing a little earlier in life, because that doesn't necessarily get you what you think it's going to get you.Mark Petruzzi (19:29)Interesting. Okay, last one, your favorite non-business book.Doug Landis (19:32)Michael Singer's The Surrender Experiment. It's incredible story. Have you read it?Mark Petruzzi (19:35)read that one. Wow.I have not, no, but I will.Doug Landis (19:38)It's so good.It's actually so it's really cool. It's what anybody that's in business should read it because it's really all about like, look, there's only so much we can control in our life. Right. So you have like a hippie living in his van in Florida, ⁓ who's a total yogi becomes the CEO of a multi-billion dollar publicly traded software company. And he talks about his entire journey and how he continued to surrender to kind of the flow of life, even in some of the most challenging times. It's a great book.KK Anderson (20:05)Okay, well, we'll definitely put thelink to that in the show notes. I'm gonna get that one for sure. Okay, Doug, this has been so much fun. So much fun. Thank you. I can just say thank you on behalf of our audience. You just did a great job. I appreciate it. Mark, you're awesome as always.Doug Landis (20:15)Thank you. It's been great.Thank you.Mark Petruzzi (20:23)Thank you. Thank you. What a great show. So thank you all. Appreciate it again, Doug, and all the best.Doug Landis (20:25)Cool.KK Anderson (20:30)All right.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Doug Landis, Co-Founder of StoryPath.ai and host of Sales Stories, to unpack how AI is reshaping the buyer seller relationship and why most sales teams are still playing by outdated rules.Doug shares why AI has enhanced the buyer’s world more than the seller’s, what he calls the invisible evaluation, and how today’s buyers are 80 to 90 percent through their decision process before ever speaking to a rep.The conversation dives deep into the crisis of sameness in modern sales, why traditional discovery no longer works, and how trust and story have become the last true differentiators in a crowded market.If you are leading a sales team, building a pipeline, or navigating complex enterprise deals, this episode will challenge how you think about first meetings, process, and positioning in an AI driven world.What You’ll Learn:AI and the Buyer Shift: Why 89 percent of B2B buyers are using generative AI and how 83 percent of the journey now happens without a seller.The Invisible Evaluation: How buyers are researching, comparing, and shortlisting vendors without leaving digital breadcrumbs.The Crisis of Sameness: Why AI tools are causing sellers to sound identical and how that kills differentiation.First Meeting Reimagined: How to show up with a hypothesis, point of view, and buyer language instead of running outdated discovery scripts.Trust and Story as Strategy: Why storytelling is not case studies and how narrative builds alignment across large buying committees.CEO of the Territory: Why modern reps must think like business leaders, not process followers.Key Topics:AI’s impact on B2B buying behaviorRethinking the traditional sales processDiscovery versus hypothesis led sellingBuilding trust through empathy and buyer ontologyStory as a tool for alignment and influenceCoaching sales teams in a new paradigmDifferentiation in enterprise SaaS and AI marketsGuest Spotlight: Doug LandisDoug Landis is Co-Founder of StoryPath.ai, an AI native guided selling and storytelling platform designed to help sellers show up with differentiated perspectives, not just better automation. He previously led global sales productivity at Salesforce, served as Chief Storyteller at Box, and was a growth partner at Emergence Capital.Doug is also the host of Sales Stories and a long time advocate for trust based, story driven enterprise selling.🎧 Listen now and follow Selling the Cloud for more insights on modern go to market strategy, enterprise sales, and how to win in a one shot world.Mark Petruzzi (00:34)Welcome to Selling the Cloud. Our guest today is Doug Landis. We're very fortunate to have Doug, who is the co-founder of StoryPath.ai, host of the Sales Stories podcast. He's a storyteller and he's just successfully built early stage companies time and time again. Doug has led global sales productivity at Salesforce.He served as the chief storyteller at Box and spent seven years as a growth partner at Emergence Capital, helping SaaS companies scale smarter. He has sold everything from newspapers and ice cream to enterprise databases and cloud software. Today, he's really focused on and really enjoying building up StoryPath.ai.StoryPath is an AI native guided selling and storytelling platform that helps sellers show up with differentiated perspective, not just better automation. Three topics we'll cover today. How AI has changed buying behavior more than selling behavior. Why trust and story are the only real differentiators left. And how sellers can compare differently and win in a one shot world.Doug, we're so fortunate, as I said, to have you here, and welcome to Selling the Cloud.Doug Landis (01:50)Thank you. So great to be back. That was all I think I was on a long time ago. I don't even remember what we were talking about back then. And you know, it's interesting as you were doing the, you're going through the intro, I was thinking, I was like, well, given the fact that it feels like everything's shifting to be AI native AI first, everything's all AI. Just does the podcast shift to like selling AI instead of selling the cloud?Mark Petruzzi (01:53)Be back.Doug Landis (02:14)By the way, not yet. Just for a little side note, was on a webinar with about 250 operational leaders, sales and rev ops leaders. And I asked the question, Mike, what percentage on average of your entire go-to-market tech stack is still pure SaaS versus AI? And the answer was at least 85 % of their stack was still pure SaaS. So while we say everything is moving AI and it's moving fast, really fast.There's still so much that's already like fully baked in. so now everyone's been trying to figure out like, how do we actually, make it additive instead of completely rip and replace. But anyway, so the pod selling the cloud is still relevant for awhile.Mark Petruzzi (02:52)Yes and no, we're actually working on exactly that now, Doug. So you're hitting us right at the...KK Anderson (02:56)Your ears must have been burning, Dad, because we've been talking about aDoug Landis (02:57)really?sit in a space all the time like, hmm.Mark Petruzzi (03:01)No, no,you do, you actually put out these ideas without even saying it. Because I actually came up with this idea last night and shared it with KK. So I was waiting. you know, we'll talk more about that, Doug. And so maybe you influenced me without even knowing it. But there are things that are changing. There are things that we want to make sure our audience is changing with it.Doug Landis (03:10)No way, that's amazing.Mark Petruzzi (03:25)And it's just really, it's incredible to have you here and you keep getting smarter than even the last time we had you here. So we love it. a couple times you've said something that really stuck with us through your writing, through your podcast. It's all blurred to me because I've listened to all of it over time now.but that AI has enhanced the buyer's world more than the seller's. What do most sales teams misunderstand about what's happening right now? And how can they change their approaches and their processes to be able to really make sure that we are clicking and fitting with the new buyer's world that is out there?Doug Landis (04:06)Hmm.Such a great conversation to have. I love this. You know, when AI first hit the scene, I think everybody asked like, okay, what does this mean to me? What is this? How can I use this? And I think what the reality is for buyers and sellers, AI has dramatically changed how they engage with each other. The relationship between buyers and sellers is changing pretty dramatically. If you think about it for buyers, know, AI has actually become a real superpower for them.You know, they can aggregate data, they can run analysis, they can do things so much faster than ever before. They're just leveling up overnight. And so I'll share some statistics with you. think that are really, really important to understand how what's changing and shifting in this relationship. If you think about this, LLM traffic is projected to overtake traditional search by the end of 2026. So what that means is more than 50 % of your buyers are going straight to a chat bot to begin their buying journey.So think about that and why is that? And the reality is this as agents have gotten better, you know, it's really interesting is what they can do in minutes or hours is what it used to take buyers weeks and months. So the buying process used to be months long and now they can actually go through it in hours because what an agent is doing is an agent will actually look at their, they will form preferences.And they're going to do it in a way that like humans do. But what's crazy is the amount of information they can, they can analyze is stuff that buyers would normally think about over time. Things like, I don't know, think about the data points of like user reviews, right? Or community sentiment or tech, technical documentation or support quality or integration pricing, all of that. And agent can analyze all that in seconds. And a buyer would normally take, you know, weeks or months to go through that. So if you think about it,Statistically speaking, what is it? 89 % of B2B buyers are using gen AI in their purchasing process. The crazy thing is 83 % of the buyer's journey happens without a seller. So that means if a seller is only involved in 17 % of the buyer's activities, then sellers need to show up a little differently. They need to understand and almost anticipate the fact that the buyers are going through a buying process without them.We call this the invisible evaluation. They're evaluating solutions and they're evaluating ways to think about solving problems without any of us knowing. So if you think about like, we've all bought software, right? And so we normally would think about buying software, like maybe we'll go to a webinar, we'll go to a website, we'll talk to some people, we'll reach out to an SDR, we'll download a white paper. That is leaving signal. That's leaving breadcrumbs all over the internet. And solutions out there could pick up on that and be like, ⁓ hey,Doug is out exploring something to solve for forecasting. Awesome. I can reach out to him. can do some, you I can do some outbound now all that's happening in a chat bot and there are no more breadcrumbs. And so like how do sellers know how to marketers know how to brands know that their buyers are actually out there in market. It's really, really difficult. The problem is sellers show up.And I fundamentally think this is going to change the entire sales process. When you think about sales process, what do we think about the traditional sales process? We're going to take a buyer through like, you know, all these stages, discovery demo, you know, negotiation, more discovery, multi-threading, all of that buyer. like, no, I have two questions. I've whittled this down to three vendors. And when sellers try and go backwards, it's like, as a buyer, I'm, losing my mind.Mark Petruzzi (07:20)Doug, you, wow, would. And I'll tell you, I'd love to share a couple thoughts on that, that maybe can even, you know, maybe escalate us even a little more in some of this analysis. So I have been personally on a journey for about seven years where I have been telling all my clients, anyone who reads anything I put out that, you know,It's a different process. was a different process seven years ago even. At least that's when I figured out. Probably was five years before that. But with all the tools that were out there, buyers wanted to buy differently. And I was amazed that some of the best sales reps that I've ever worked with were not responding to that. Some of them were, and I've been able to turn teams of sales reps intointo really understanding the buyer journey and understanding that the seller journey means nothing in all And I'm so proud of what I've done with some clients, but I've seen some clients just not wanna go there. They just won't. That was seven years ago. Now you compound all this with AI and what you just described so articulately, there is like, it's all.whole new game. Like we almost have to get these sales leaders like bats that they can run around sort of hitting sales reps a little bit on the head and saying like, you have to believe now. It's so different. It's not even there's no resemblance. So it's incredible. But I love how you set that up. And I'd love to go deeper into what do we do with with that? And how do we getDoug Landis (08:44)Hahaha.KK Anderson (08:50)So.Mark Petruzzi (08:58)the most stubborn sales reps to understand that we're in a new paradigm.KK Anderson (09:03)Well, and Doug, before you answer that, let me just add on. let me add onto that. So the buyer motion has changed, but we still have to go, we still have to take them through the process of what I call running the bases, like in baseball, right? And you still have to go through this whole idea of what we call the two-cell.Doug Landis (09:05)Great question.Mark Petruzzi (09:05)It'sokay.KK Anderson (09:23)process, is like our sale is getting that buyer to articulate why they need to change. What is the problem they need to fix? And the second sale is why you and why now? And so if they're, when they're coming to you, and this I know is where something like Story Path is so incredibly powerful. We've seen it firsthand with our clients, but if you're getting to that first conversation and that buyer is like, dude, I already know this. I don't want to hear this, right?Like what are, what's your advice to the sales leaders out there who are working on this with their sales team? They still have to close that first sale. They still have to like make that psychological invisible sale happen. Talk me through like, what does all this mean?Doug Landis (10:00)Well, look, I mean, why change? Why now? Why us or why change? Why us? Why now? The whatever flow you use is still relevant, 100 % relevant. The difference is sellers need to show up anticipating the fact that buyers have already been thinking about this. And so instead of going through the traditional discovery questions, which is, you know, kind of a Spanish inquisition of stupid questions, it's like, I need to like, let's just call a timeout. My hunch is you've already analyzedYou've already deeply understand the problem you're trying to solve. You've already analyzed all the different options out there. You've done all the analysis if you're a modern buyer like most of the buyers that I'm speaking to. So the first question is, since you've already done that, you probably have a pretty good idea why changing right now, why changing from what you're currently doing might make sense. I have a hypothesis about it. I'd love to share that with you, but I'm curious as to as if you've actually gotten to that point already.KK Anderson (10:51)So the upfront contract, the way you set it up.Doug Landis (10:52)Interesting, right? It's likeRight. It's all, it's all how you set it up. It's like, if I anticipate the fact that they've already done this and they've got a pretty good understanding as to why change might make sense. Awesome. Let's have that discussion. I've got a perspective about it because I talked to other people just like you all the time. And I'd be happy to share that. ⁓ but I also want to know if you're, if you've already done the analysis and you're already there because most of the buyers I talked to you already have. Right. SoIt's almost like, it's almost like kind of making an assumption. I'm not going to tell them that they've already done this, but I'm going to kind of, it's a little bit of assumption that's like, you know, if this is a big enough problem here and a hair on hair on problem that we continue to see, then my hunch is you've already done some around it.KK Anderson (11:32)Talk us through,I've heard you say this multiple times now, what you call the crisis of sameness.Doug Landis (11:37)Well, so unfortunately, the crisis is so on the seller side, we all thought like, AI is going to make us so much more productive, we're going to become superhuman sellers, right. And the reality is, sellers are all using the same, you know, custom GPT that they built, they're all using chat, GPT or gems, they're all using kind of their own internal data. And they're showing up with the same messaging, the same pitch, the same everything because they don't underbecause they haven't stopped and said, wait a minute, if my buyer's 80 % of the way through the buying process, if they already have a pretty good idea of why change, why changing might make sense and why it might make sense now versus waiting and what are kind of my best options. And if I take them through a standard pitch or use the same email kind of framing that everybody else is using, then I sound like just like everybody else. There's no differentiation. And I think that's one of the challenges. I literally was talking to an investor right before this call.And I was sharing this with him because this is kind of a part of our core thesis is as an organization is we've to get people away sellers away from sounding just like everybody else. And he was like, I literally have gotten 11 of the same emails in the last 24 hours. It's they look in, they look and feel the same. And so it's like, okay, if we're, if we're all kind of following the same playbook and we're using the same tooling,then how do we really start to differentiate? And I think the first thing is you got to first understand where your buyers are now. That's the very first step. The second for a seller to get out of this crisis of sameness is you got to start thinking about being different, you know, and we have a whole thesis on that. That's through trust and story.Mark Petruzzi (13:04)and you know what Doug and KK, I'm gonna ⁓ kind of bust this out, I think, to a whole level here with some of these thoughts. So, and this is why KK and I are so good together and why we're so impactful for our clients because we have these debates all the time. So I'm gonna bring one of our debates to this podcast. KK just described the four bases, like you've gotta go around the four bases and she's incredible.from a process standpoint, sales competency perspective, and I totally get the perspective. I kind of think it's gone to a different point here. And when I show up to a sales process, I kind of think of like I'm showing up to play baseball with the Savannah Bananas, that group that does all that goofy, crazy stuff, right?Doug Landis (13:51)Love that.Mark Petruzzi (13:51)So what I have to do is I first have to understand what are the rules today, like real quickly, not deep, but what are the rules that we're gonna go to to play this game? Let me do my research, let me learn how they played every other game they've ever had. Let me come in with that. And then I wanna see, are we even using bases? Or are we just hitting home runs and catching balls behind their back, whatever they do.Doug Landis (14:15)HaMark Petruzzi (14:16)So I think that's where we are here as well. And that's why I also feel like the concept of the sales rep being a CEO of their territory is real again. And we all watched over 10 years, 12 years, the last 10 years, 12 years, all the technology that sales leaders were putting in place.Doug Landis (14:30)Yeah.Mark Petruzzi (14:39)They then started to say, well, we don't really need people that could be the CEO of their territory. We're going to give them great process and great technology. And hey, it works. Worked. They were growing, especially in SaaS companies, super fast during this time. So I don't argue with the success. But before that, and I think now again, you need at least a subset of your sales team to have that level of intellect and curiosity.and really figure those things out. So I'll weave that together if you don't mind with a question, a more specific question. So if we think buyers are now 80, 90 % through their decision process before they even talk to a seller, how should it change how the rep shows up in a first meeting? And my hypothesis here is that a good one, right? Like you almost have to go in and figure out what gamenot to call this a game, but what are the rules of this process before you even jump in? And you gotta be smart enough to be able to figure that out, which also comes down to the talent management, making sure you have the right people and the right roles.Doug Landis (15:35)Yeah.Yep. it's interesting, you know, it's, would, I would argue what a seller needs to do in the first meeting and first conversation today is arguably the same that I've been touting for years, which is show up with a point of view, show up with a hypothesis, anticipate, try and anticipate where you think they might be might by the way, is a very important word because I'm a linguist at heart because you can't tell somebody where they are. If you come in and tell the buyer where they are, to be like,GFY, you don't know me. ⁓ think, wait, here's, I wanna actually address that, by the way, I love the of the metaphor of the Savannah banana baseball team versus traditional baseball in terms of the shift that's happening. I believe there's two parts actually going on. There's the operational piece of selling which still exists. We still need to understand where does procurement fit in this process.KK Anderson (16:19)Yeah.Doug Landis (16:31)What about security? What about legal review? We'd like, those are operational things that we need to do to get the deal done. Correct, right? We still need to do that. Also, people likely still need to see some sort of demo. They need to understand how this might look and feel and fit in their environment, right? They may conceptually understand the problem they're trying to solve and the options, but you know, they can do all that through these chatbots, but they also then need to look and feel and think more deeply about the integration and how the data flow and then...What kind of risks is this gonna create? So like there's, me, that's kind of the operational stuff of the process. And that's where I agree with KK and that like, there are still bases that we still have to, you know, touch, right, to get a deal done. However, I'm gonna put on my Savannah banana outfit and go like, the way I get to those bases might be a little different,I might, by the way, run to second and then go to third and then to first and then to home. I might go like high five the pitcher, right? Right? So, but here's the key. The key is in order for me to leave home, the home base in order to go to any base that makes the most sense. I have to show up with a perspective and a point of view and an understanding of where my buyer is. And I have to speak their language. I have to understand their ontology. I have to understandMark Petruzzi (17:20)There you go. Yep.Doug Landis (17:42)you know, who they sell to and what they're trying to accomplish with their customers. And that's the language that I need to speak. And if I just show up and I'm speaking my language and I'm asking my discovery questions and I'm putting all the pressure on the buyer to go answer my questions as a buyer, I don't want that interaction anymore. And guess what? I shouldn't have to have it. I shouldn't have to have it. Right. So, and so like,KK Anderson (18:03)Totally appreciate thatDoug Landis (18:06)I'm going to go into the conversation and say, like, let's just say, Mark, I'm trying to sell to you. I'd say, like, Mark, I have a hunch. My hunch is you're so sophisticated that you've already done an insane amount of analysis about the problems that you're currently trying to solve. Just a hunch. And that you've already kind of whittled this down, your selection down to maybe one, two, three different potential partners to work with. My hunch is you also have very specific questions that you haven't really wrapped your arms around yet.And the reality is those questions, that's kind of where I want to spend our time.Mark Petruzzi (18:35)And right after I gave you a big giant hug and said, wow, you get me, Doug, would then be like, yes, and Doug, here's what I need. I need to get X, Y, and Z done. And if we get those things done in a positive way, you got my business. And we're gonna do it really fast because you get me already, Doug. that.Doug Landis (18:35)How does that sound?Yeah. That's, mean, and, and, and, so this is, this is the new reality, right? And I think the challenge is both at a leadership level is we got to quit forcing reps to follow this process. And we also at the leadership level, we need to coach our reps to be able to show up with a really, really strong point of view and an understanding of how to speak our, our buyer's language and understand their ontology. The challenge is if I'm a rep and I have a territory and like, I'm the CEO of my territory, but my territory has like,50 different verticals, different kind of companies and different industries, I got a context switch and that's really hard. Instantly, I've got a series of meetings, I've got calls back to back because my BDR is crushing it and setting up meetings, which we know is really hard. But now I'm going from talking to somebody on oil and gas to manufacturing to retail. I'm like, ⁓ how do I do that? And so what's easier for me is to let me just go through my playbook, follow, ask my questions.KK Anderson (19:28)Mm-hmm.Doug Landis (19:47)do some validation, talk a little bit about us. ⁓ Unfortunately, it happens way too early. And then the buyer's like, all right, well, you sound just like everybody else. Cool.KK Anderson (19:58)Yep. So true. You, I you are articulating this so well. Really. It's incredible. the value hypothesis is critical and you know, well, I don't want, we, don't want to go too far into Story Path, but the very first time I logged into Story Path, the first question it asked me was, what is your value hypothesis? Who are you? What percent are you selling to? What challenge are they trying to solve? And why are they trying to solve it?Doug Landis (20:00)It's hardThank you.KK Anderson (20:20)right, so that you can know exactly kind of what your POV is. So let's move on to the second topic here about trust and story and how they help us win the deal. And so in this kind of world of sameness where we're flipping between industries and on back-to-back calls and we all sound the same, right, a lot of times we're reciting the same case studies, the same stories, and sometimesLike sometimes a salesperson will literally feel like a broken record because they say the same thing 100 times, right? And so, you you and I both know that that story is not just case studies. ⁓ Most case studies aren't even real stories. Like, let's be, let's be real, right? They've taken on a life of their own over time. And so, you know, talk to me about, about what it is.Tell me about why story is so important and how that helps build trust.in the firstDoug Landis (21:10)Well, I mean, look, here's the thing. think, well, there's two parts to this, right? So again, our core thesis is to really truly differentiate as a seller today. It's all about trust and story. Trust is understanding your buyer in a really, really deep way. I was about to use intimate, but that's weird. But like truly understanding your buyer,Mark Petruzzi (21:27)YouDoug Landis (21:29)having, putting yourself in their shoes, having the assumption that like, you know, Mark's already 80 % through the process. He's done the analysis. I understand your language and ontology. That's all going to build trust, right? And I can take that from the company level all the way down to the individual level. And we'll talk a little bit more about that. When I'm sharing back, when I'm communicating back with Mark as my buyer, I want to communicate back in a way that is easy for him to understand, a way that demonstrates some level of empathy, connection, right? Andeasy for him to internalize and turn around and go share with others. Because Mark is one of 17 people. If the deal is over $250,000, thanks to my friend Jen Allen, she just posted a whole bunch of stats. If a deal is over $250,000, there's like 17 buyers now involved in the process, or on the buying team. That's crazy. So guess what? Mark has to go talk to 16 other people and try and build alignment. Like is this a problem that is worth solving? Can we get everybody on the same page?If I just go, here's all the facts and stats about our product, here's what we do, here's how we do it, here's our case studies, Mark has to internalize all that and be like, all right, I'm gonna do the best I can to try and share this. However, what if you were to flip this? What if you were to reframe the way in which you orient the conversation and share a level of, here's what I think I understand and then.and weave that into a narrative, into a story that is a very short, very crisp, easy to digest for Mark, then guess what? I'm earning the next conversation. I'm earning a deeper relationship. I'm building that connection with empathy because story is how we naturally communicate. We can use facts and stats and data to back up the story.But when we just lead with all these statements, it's really difficult for us as listeners, as human beings to remember that. I mean, just think about school, multiple choice questions. At the end of a test, if you were to ask me like, do you remember that question? I'd be like, nope, blacked out. All right, the essays I remember.KK Anderson (23:23)So,love what you're saying, Doug, and I couldn't agree more. And where my head is going is are things like you're telling a day in the life story or a future state story or here's where you are now. Tell me a little bit more about when you'reDoug Landis (23:35)Totally.Bunch of different types. There's a bunch of different story types that you can actually tell. Yeah. Current state to future state. Look, at the end of the day, a story is really about from two. You're taking, you're trying to help somebody imagine going on a journey from somewhere to somewhere else. Right. It's either I'm taking from first base to second base or from first to third. I don't know. Right. So like, and so you can tell that from, from the experience of another customer that was similar and the journey that they went on.KK Anderson (23:50)first face to say and juggling balls behind your back.Doug Landis (24:03)You can tell that from the standpoint of like, hey, by the way, it could just also be like a, hey, Mark, we're just starting to get to know each other and starting to unpack like the connective tissue of this problem that we think might actually be bigger. So let's, let's, let's talk about the next conversation and talk about the story, about the flow of our, of our ongoing conversations. Cause I know there are 16 other people involved in this and how that might look and feel. There are a number of different stories that we can tell. Oftentimes telling a customer story is a really great way to demonstrate some level of credibility.The problem is, sorry marketers, I love you. Stop following the old school frameworks. Problem, solution, ROI. No characters, companies aren't characters. I don't know how to go tell that story, so what do I do? I say, well, yeah, know, Mark, this reminds me of conversation I was having with Cisco. They're like, okay, how is that even relevant? They're not even like, it's like apples and tree bark.Mark Petruzzi (24:36)Mm-hmm.Doug Landis (24:56)doesn't even connect. You know, it's like, oh, okay. And then I'm trying to draw some connected tissue, because that's the only story I remember. And again, take that territory where I've got 100 different industries. How do I remember stories, customer stories for every single industry? And so it's like, so there's a bunch of different stories you can tell, right? So how about tell your own personal story? Right? Your own personal aha story, because you understand if I understand Mark's world really well, I'd like, you know what, here was my experience.KK Anderson (25:00)Right.for the opportunity to ask questions.Doug Landis (25:21)You know, I've, I understand your problem that you're experiencing because I've actually had something similar. So maybe it's a personal story. Maybe it's a, you know, maybe there's a, you know, a why so, many stories live in the why not the what or the how. Right. So like, why did we decide to go? So, so for example, why did we, why as an organization, did we decide to tackle this particular problem? Why have we made it our mission to help people solve for this particular problem?KK Anderson (25:35)What do you mean by?Doug Landis (25:46)Why, why did I decide to come work for this company? I decided to come work for this company. started, decided to start Story Path because I fundamentally want to change the world of enterprise sales, period. Right? So like, guess what? I know Mark loves enterprise sales. He and I are aligned because this is what we both want to do. So like, I just told my own personal why story or I could tell my personal why story. And it's like, all of a sudden now we're building connection.Right? So there's, it's just a lot of different stories that we can tell in every conversation. I think there's a couple of things. One, we're not thoughtful enough to just take a minute and be like, what stories do I actually want to tell in this upcoming conversation? Just take a minute. Just think about that. How do I want to incorporate those stories in the conversation? Which one should I be ready, ready for? The problem is, is a lot of people just don't understand actually how to tell stories. and we haven't really helped them. Well, we are now as a company.I mean, at the end of the day, Story Path is the story company.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this conversation on Selling the Cloud, Glenn Poulos dives deep into what it really takes to scale a distribution business from startup to successful exit. From growing Gap Wireless from 1 million dollars in revenue to 84 million over 15 years, Glenn shares the strategic decisions, mindset shifts, and leadership disciplines that enabled sustainable growth in the telecom technology sector.Glenn unpacks the importance of franchise vendor relationships, why brand positioning determines sales velocity, and how to structure an organization with the right people in the right seats. He also tackles one of the most critical dynamics in distribution: building trust with manufacturers while managing the real risk of going direct.The episode closes with a practical and grounded perspective on AI in sales. Glenn explains how to use AI as a powerful assistant across departments without sacrificing the human connection that ultimately closes enterprise deals. Plus, stay for the rapid fire segment where he shares hard lessons from selling his first company, advice for his 21 year old self, and the sales habits he still practices today.What You’ll Learn:Scaling from Startup to Exit: The key inflection points that helped grow Gap Wireless from 1 million to 84 million in revenue.Brand Strategy in Distribution: Why representing top tier brands is essential for competitive sales positioning.Right People, Right Seats: How organizational structure and disciplined hiring drive long term growth.Manufacturer Trust Dynamics: Navigating co-selling, exclusivity, and the risk of vendors going direct.AI as an Assistant, Not a Replacement: How to use AI for research, prep, legal review, and financial insights without losing the human edge.Sales Discipline That Compounds: Daily habits that create visibility, opportunity, and long term career growth.Key Topics:Franchise distribution models in telecom and technologyRelationship first selling in enterprise B2BOrganizational design and leadership evolutionManaging vendor partnerships and channel conflictAI in sales operations, finance, marketing, and legalCareer defining mistakes and lessons learnedGuest Spotlight: Glenn PoulosGlenn Poulos is a sales expert, author, and serial entrepreneur with over 40 years of experience in complex B2B selling. He co-founded Gap Wireless and scaled it into a multi million dollar distribution company before its acquisition. Today, Glenn leads ProgUSA and is widely recognized for his thought leadership on sales growth, leadership, and the practical application of AI in business.🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping the future of enterprise sales.Mark (00:31)So let's move to topic three, scaling a distribution business from startup to exit in the telecom technology sectors, as a whole. So let's talk a little bit about your journey building Gap Wireless. You co-founded it in 2007, hit a million dollars in revenue that first year.Glenn Poulos (00:33)Okay.Sure.Mark (00:51)and I believe it was 15 years later, sold to 10 WS. What were the major inflection points or really what were the decisions that enabled you to scale in the way that you scaled?Glenn Poulos (01:02)So numerous things. at the end, we were 1 million in the first year when we sold it to NWS and we did 84 million in revenue. So over the 15 year period, we grew from 1 to 84 million. And again, we were a small company, right? So I mean, was, you know, and at the, when we exited, there were 44 people.Right. So it was pretty good, pretty good growth. Right. So, in a distribution company or in many, I've been into the distribution my whole life. So really can't comment much on any other kind of company because I've never really experienced them. Right. But, it's the first thing is always focusing on the relationships before the transactions. Right. So that no need to really beat that to death.the people piece is very important. The relationships with the, the customers, the employees and the suppliers is critical, right? when you're a distributor, the key is having the key, the killer brands under your moniker, right? Like you need access, franchise to access.to the key brands, right? And the kind of world that we were in ⁓ and I've been in is one where it's kind of a, we'll call it monogamy based franchise relationship. Meaning I wasn't, I'm not the Rexel or Ingram Micro that has every brand and I'm a trillion dollar corporation, right? That's not what we are, right? We're a multimillion dollar company. And so, the screws, we would only represent this screw company.Right. There were other competitors, but our goal and our job was to get a franchise relationship with ABC screw and sell their screws and their screws only no competitive. Right. And so we would build the market for them. We were approached that company. They were maybe in Italy. They make the best screws in Italy. And we'd say we want an exclusive franchise relationship.with you guys in Canada, the US, North America, Central America, wherever it was we were selling, wherever the territory was available. And so you get that, you wanna build that relationship with the vendor early and that's the most important thing really because you wanna be having the best brands to present to the customers. Then it shifts and the customer becomes the most important, right? But if you, let's say you have the customers but you have the D, E and F brand.it's game over, right? Like I won't even, I challenge people, sales guys and gals that when they get a job, spend a few months and figure out where you are in the pecking order of the world of your market, right? Are you guys the number three, the number four, the number five, the number two, the number one? If you're below number two, I say quit and get a better job at a better company because you can't, you can't replace today, right? Once today's gone, it's gone. And so if you're trying to promote brands that are well down the stack ofwhat people want to buy and what have you, you waste too much time selling the company and not enough time selling the solution and the product, right? So you want to have those vendor relationships. and so ⁓ some of the other things about about building the business, you know, is learning how to step back and put the right people in the right seats, right? So ⁓ structure first, people second.And everything has a process, right? So what do I need in order to be successful? And then do I have the right people in my organization to occupy those seats? And if not, I find the right person and put them in the right seat. I don't say, hey, our finance things are growing. We got more challenges in finance and we've got,Jack and Sally and you know Sally's been here longer and she's doing a good job and whatever let's give it to Sally. No it's like I need a director of finance now or I need a CFO what are the rules for the CFO? Does Sally or Jack have possessed that? Anyone else in the company? No I have to recruit out of the company.And I'm sorry, don't, it's nothing personal, right? You got to the right person in the right seat. And so, and that allows the founder to step back a bit and focus on the higher level visionary type functions of the running the company, right? And guiding the direction, knowing that the different, the different roles are well covered, right?so I'll just take a quick breath and see if there are any specific questions about that orKK Anderson (04:48)It's so,it's fascinating and so interesting. we do a lot of, and I do a lot of work with distribution companies and with manufacturers alike. And so one of the things that comes up a lot is trust, right? Distributors worry about manufacturers going direct. Manufacturers worry about losing control of the customer experience and conversation and getting to talk about their product. So from your perspective as the distributor.what actually builds that trust with the manufacturers? And is that, from your perspective as well, difficult to be able to trust the manufacturers with your pipeline, with your customer base, going, know, co-selling, if you will?Glenn Poulos (05:28)so yeah, that is like the key of it all. Like, I mean, that's really like, that's like a like a masterclass what you're just asking there, right? Like, you can go in so many different directions. But but ⁓ and I hear you so well what you're what you're asking me the theyou have to be a little bit paranoid. You have to be pragmatic, and, sometimes you just have to, you you just have to let it be what it's going to be and accept it and, sometimes move on. Right. In the sense that, the company I'm in now, it's not a huge company. we have 11 franchise relationships. And so I have to balance the needs, wants and concerns of those companies, but some are bigger than others. Yeah. My main brand and what have you. And yeah, II if I get them to a certain point, they might go direct, right? So it's a bit of a balanced mediocrity, right? If you grow them to a certain value, it's cheaper for them to open an office in that country and put in direct salespeople. But the thing is, it'll happen, right? And so you always want to be using that brand to leverage new brands coming on board.in the possibility that you might lose it. Because you can't defend against an inevitability, right? And so I sort of like trust.KK Anderson (06:36)to you beforewhere lost like a manufacturer's gun directGlenn Poulos (06:40)Yeah, so essentially we sort of, unless they're a company that's pure distribution focused, ⁓ where they only sell through distribution, it's just about doing a good job and stuff. But if when it's a difference between going direct and distribution, if they might go direct, then if they hit 5 million, you can, you can basically count your days until they go direct.because mathematically it's cheaper to go to rec at 5 million. So if you can get them from one to 5 million, you're kind of in the sweet spot making lots of money. They got a lot of ifs and buts about whether they will or won't go to rec, but above that, it starts to get risky, right? In terms of...like sharing the information and what have you, I believe in, like I call it humble bragging early and, and always. Right. And so I like, for instance, with my guys, they'll, they'll call me and they'll say, Hey, I'm just on the way home from, you know, XYZ. And they're looking at a new, discombobulator 50 grand, like blah, blah, blah. I go, that's amazing. Did you tell the vendor?Right. And they're like, no, I said, you should have called the vendor and told them. And I said, you got a humble brag, right? and, what I mean by humble bragging is like, you don't want to do it in a, in a way that's like negative in, in any kind of capacity. You want to say, you know, Jack, my God, I just had an amazing call. I just had to share it with you. We're in an XYZ. They're looking at a discombobulator. They might need two of them. It's 50, a hundred K. my God. I might need your help with the demo, And so what's the vendor doing? He's thinking, ⁓Mark (07:37)ThankGlenn Poulos (08:03)Bob's in at XYZ, Bob's got two discombobulators on the go. That's a hundred grand. I could really use that towards my quota. What can I do to help Bob get the deal? And also what's happens is, that Sally from the competitor who maybe there's two distributors, right, calls and says, I got wind that there's like a week later calls. got wind that XYZ might be looking for some discombobulators. Nope. That's covered by, by Glenn's company or whatever, right? Stay away.And they, because that's what just manufacturers often do. They divide up the landscape, right? It's like, nope, we've already, we're already working with someone there back off, right? And, and so I believe in being very liberal in my new company here, small as we are, my ERP system, I had custom programming done so all my vendors can log in and look at the funnel and see only theirfunnel items, obviously they can't see my other vendors, but, and, they can see most of it, but not all of the records, right? Like the internal chatter box notes they can't see, but there's a more generic note section. can, they can see probabilities, dates, products, who's involved in center, et cetera. Right. and so I'm not sure I directly answered your question, but I mean, Oh, okay.KK Anderson (09:08)For good, you absolutely did.You did, thank you.Mark (09:11)Beautiful.All right, well, let's move to our final topic. you know, this is a popular one or maybe popular is not the right word. It's it's just out there everywhere we look. AI and technology and sales. how do you use tools without losing that human connection that you've shared within your book and within a lot of the work you do online? What's what's great about what you've achieved in thesocial media world and the media world. you're a LinkedIn top voice. your focus and a lot of what you do today, you describe yourself as an AI and sales growth expert. But after spending 40 years building relationships, mostly face to face and mostly over the phone, how are you thinking about AI's role in sales with all this new capability we all have?Glenn Poulos (09:58)Okay, so my, and of course this is my opinion, right? Obviously. And, and so some people might argue or they touted it for different, there's so many things on social media now about using AI and I'm like, yeah, no, no, I don't think so. But, so I, I think of AI and I want to use AI to remove friction and, not replace the connection. Right. And so I treat it like a strong assistant in every department.Right? Finance, marketing, operations, sales, legal. And so it can help you with research, with prep, with summaries, with drafts, with ideas. Right. And but not to replace it. Like, for instance, I know I didn't try this, but I mean, we have.you know, we, in my organization, have like BDRs and they're actually in the Philippines and they phone customers and they try to get new names onto our list. And do you use the stuff that prod sells? Right? Yes or no, blah, blah, whatever. Then they pass our insight guys who try to massage it any opportunities that it goes to the outside people. Right? There's literally no way that could be done by AI because maybe in a few years it might be able to, but,But not right now because I mean the stuff we're selling is to like super geeky guys that drive pickup trucks and climb towers with 500 kilovolts on it and it's just too There's no way you can have a meaningful conversation. It's very very specific, right? So It can assist you but it can't replace right? We like we don't get appointment setting or anything like that. SoIt's like building a deck, right? You can screw the screws into the deck with your, with a hand by a screwdriver, you can get a power drill, right? I mean, you're still building the deck. It's still your design and whatever the other area, for instance, you want to do some social media posts, right? And it's like, okay, well, you know, this, this week's topic is on this or this month's topic is on that. I mean, if I say to myself, Glenn, give me 30 ideas that I can talk about this month on sales growth, right? Or on funnel management.I mean, I could come up with two. If I need to come up with 30, I would take a month, right? But AI can give me the 30 in a few seconds, right? And you could even say, write all 30 posts for me. And I mean, people would all unfollow me if I just posted those. You have to then humanize it, right? And you have to socialize it. And so the research and prep part is amazing.But also the other areas like any new contracts we drop into a legal element and it looks at all the points, insurance and terms and termination and liability and it says, look at this point, look at this point, this point's one way, it's not a two way clause, et cetera. And I mean, I don't really wanna read 80 page documents ⁓ and so it helps with that.And so, and also I'm not a strong financial accounting guy, right? Like, mean, I'm generic knowledge, but I'm not a CFO. And so you can put your financials for this year and last year and your cashflow state and everything. And you can say, can you give me some advice on, and it comes up with amazing insights into that, that you'd have to hire a $250,000 CFO.To give you right and nor do you need them full-time? But you can still get the value right and so so it's an amazing assistant and And that's the way we're using it and that's and we've gotten incredible ⁓ Incredible value out of it, right and so YeahKK Anderson (13:12)love that analogy. it's Mark and I talk often about how it's almost like sales is in a giant pendulum swing, right? It's, you know, we've always heard people buy from people they trust, right? Over the last, 10, 15 years, the AI sales tech world has exploded. have every kind of engagement platform, CRM, MarCom.Glenn Poulos (13:24)Yeah.KK Anderson (13:34)every kind of tech you could possibly want to support sales and marketing. And it almost got to a point where everything was so automated and so robotic that, you know, we lost the humanness, right? And now here we are on the other, we've swung all the way back thanks to AI. And, you know, it's like AI can speed things up, but trust still closes deals. And so, you know,Glenn Poulos (13:46)Yeah.Yeah.KK Anderson (13:56)I love this analogy, this idea that AI should be your assistant because what must always stay human is the connection. I've quoted him before, but Rory Baden who runs Brand Builders Group, he always says that your humanness is now your greatest uniqueness. That's awesome. Yeah.Glenn Poulos (14:00)Yeah.That's awesome. awesome.Yeah. The, saw an interesting spec this morning where.And it really resonated with me is that YouTube now is spending the most of its time filtering out all the AI clips because, and, and I'm like, really? And then it went on to say like, you're probably still seeing a ton of them, but you have no idea how many they're filtering out of the babies in danger. You know what I mean? And all the baby dancing and, and the, there is obviously the AI stuff, right? Or like people lying with tigers and bears and things, and it's all AI generated and it's just polluting YouTube.to the point where they're seeing some of their core user base like log off because there's no longer, there's no longer a value. It's just like, this is all AI. I'm not getting anything from it. It's not even real. Like I don't want to be a part of it. Right. So YouTube's like, uh, addressing that as much as they can, but you, individual can use AI to create an amazing content that isn't babies dancing on gorillas or whatever,you know, and get a lot of value out of it, right? But it has to be human. Yeah. Yeah.KK Anderson (15:12)and you make it human, you make it human and it's super powerful.I couldn't agree more.Glenn Poulos (15:18)Yeah.Mark (15:20)All right,well, we're coming towards the end here and we're moving to the area that KK and I love the most. And that's some of the rapid fire questions that we do with every guest. They're all almost always the same or very close to the others. So first one, what was the first product or service you have ever sold?Glenn Poulos (15:23)Okay.So the first product that I sold was probably when I was nine, I got a job at my parents' motel. We lived in a motel. Our house was attached to the motel. And I sold rooms to strangers coming in off the street that needed a place to sleep. my second job as a teenager was I worked in a jewelry store selling jewelry and stuff like that.KK Anderson (15:59)Natural born salesman,Glenn Poulos (16:00)so.Mark (16:00)and what Glenn, that brings me and makes me think of the show Schitt's Creek. So if you haven't seen that.Glenn Poulos (16:06)So yeah, exactly the motel was exactly like Schitt's Creek, except ourmotel, our house was at the end, not in the middle. ⁓ but that's, that's where we, that was my life growing up, was living at Schitt's Creek. Absolutely. Yeah. Yeah.Mark (16:17)That's fun. That's fun.KK Anderson (16:19)That is awesome. Okay,what is the biggest mistake you've made in your career and what did you learn from it?Glenn Poulos (16:25)So, well, the biggest mistake I made in my career was I sold my first company on an all stock deal. And before the stock, before I had a chance to sell the stock as an insider, the company went bankrupt and I lost millions of dollars and gave them my company for free. So I realized that when you sell your business, you need a mostly cash deal. So.KK Anderson (16:46)it's hard to hear that.Glenn Poulos (16:46)Yeah. So thatwas why I started Gap Wireless because I sold my first company for quite a bit of money and we had three partners, but we only took stock and the company ended up having a lot of problems that we didn't realize or investigate, I guess. And they went bankrupt before we had a chance to sell our shares and we ended up broke basically. yeah, horrible story. ⁓Mark (17:05)Yeah, but I'mKK Anderson (17:06)like you redeemedMark (17:06)sure it was the baseline of all your success afterwards. So cool. Best piece of advice you have ever received from a mentor or a business partner?KK Anderson (17:06)yourself.Glenn Poulos (17:17)I guess, you got to learn the skills you want to learn how to follow up, ⁓ you know, you want to do research and rapport and whatever ⁓ the tools evolve over time. ⁓ But the base skills stay the same. You need to be good at the basics, right? it'sMark (17:32)Yeah, you know thatthat really resonates with me. I kind of remind people of that and remind myself of that. Maybe too much, but it's I mean the basics really drive everything else from there.Okay, I can't take this one from KK because it's our favorite one. Yeah.KK Anderson (17:45)I know, it's my favorite question. You've tried to take it from me, Mark. I'm getting in there. Glenn,Glenn Poulos (17:50)Okay.KK Anderson (17:54)advice you would give your 21-year-old self.Glenn Poulos (17:56)so the advice I would give my 21 year old self is that my favorite saying is you only get forever to make another impression, right? And my 21 year old self would say, no, mom said, you got to make a good first impression. And I'm like, yeah, that's right. Me. But every impression in your career needs to be treated as a first impression because imagine you're sitting beside your adversary at work.Mark (18:15)Mm-hmm.Glenn Poulos (18:19)sales territory and a growing expanding company, that's growing rapidly and people are moving up the ladder, right? You're sitting amongst your, your cohort of peers and the boss walks in and he sees you on Facebook, alt tabbing over to the CRM when he walks by and Sally's beside you and she's on the phone cranking out deals, right? A week later,CEO walks by quietly again notices you're on Instagram you look over you see me all tab into the CRM, right Sally's bringing the bell book in another order. Who do you think is? He's moving to senior sales rep, right and so Next thing is they send you to the trade shows, your feet are sore. You're whining It's kind of slow, you sneak away from the booth for a few hours. Nobody'll notice there's enough people there blah blah blahwhat you need to be doing is going into the aisle, pulling people into your booth so the boss can see it. When the, when it's slow, you want to be talking to the executives that are at the show with you, figure out, Hey, what makes, what are the five things I need to know about your product? Why are you here? What's so great about your stuff? What, how do I, how do I dominate and kill it? Right. And always be, always be making a good, first impression because that every impression is an impression and it's there,And so, and, and that's how you go from being a tow motor driver in the warehouse to being the CEO 40 years later. And there's many examples that we see all the time in the news and whatever of people that started in the warehouse and ended as the CEO of a major fortune 500 company or huge company, right?Mark (19:44)Yeah, very cool. All right, let's final finalize with our last question here. And what's that one sales habit or practice that you do every day or week without fail?Glenn Poulos (19:50)Sure.well, one of the ones would be, yeah, never fax the facts and never ship the shit. Right. And so if somebody asks me for something, and of course I made this up in the eighties, right. And so now I have to argue with all the other people like, well, don't think it's a fax machine. Yeah. So I'm like, well, whatever email doesn't rhyme with facts. Right. And so, but when someone calls me up and looks for something,KK Anderson (20:11)What the fax with you?Mark (20:13)Yeah, yeah, yeah.Glenn Poulos (20:21)I try to turn that into an opportunity to go visit them. Now, of course, I'm the president, I'm in the head office and I, United States is a big place or whatever, but it's, but generally speaking, it's a philosophy, right? Like if, if they're within driving distance and the guy from Duke energy asked me for something, I'm saying, you know what, I'm actually going by Duke and in a couple of days, can I drop it off?And so I never fax the facts and they say, we need a demo. Can you ship it in? I go, no, no, we're not allowed company policy. We have to deliver all demos. You have to set them up, plug them in and make sure you can push the buttons. Then we'll leave it with you. Right. And so, because what ends up happening is, is that you ship those demos. And oftentimes when you go to pick them up or they ship them back, your, your packing tape wasn't even opened. Right. And so never fax the facts and never ship the shit.Yeah.Mark (21:09)Great.Well, Glenn, this was a pleasure and thanks so much for taking the time with us. Thank you again for joining. Thank you, KK, for being my co-host and thank you to our incredible audience for being here every week like you are. All the best.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Glenn Poulos joins Mark and KK Anderson to break down what truly drives success in complex enterprise B2B sales. With over 40 years of experience selling technical solutions across telecom, wireless infrastructure, and power utilities, Glenn shares the practical frameworks behind building trust, mapping decision processes, and creating repeatable sales performance.Drawing from his book Never Sit in the Lobby and decades of hands-on leadership, Glenn explains why buyers in complex sales are not simply purchasing products. They are buying safety, trust, and confidence that their decision will not backfire. The conversation explores how to slow down early, uncover real risk, build consensus across multiple stakeholders, and implement disciplined follow-up that keeps long-cycle deals moving forward.If you are leading an enterprise sales team or looking to scale predictable revenue in complex markets, this episode delivers actionable insight you can apply immediately.What You’ll Learn:• Why complex buyers prioritize safety and trust over price and specs• How to build trust early by slowing down and asking better questions• The importance of mapping decision makers and influencers in enterprise deals• How to prevent deals from stalling due to unseen stakeholders• The habits that create sales repeatability and predictable results• Why disciplined follow-up is a competitive advantage• How to coach sales teams before, during, and after every call• Glenn’s philosophy of greed-based learning and how it accelerates product masteryKey Topics:• Trust-driven selling in high-risk B2B environments• Mapping enterprise decision processes• Mutual action planning and consensus building• Sales discipline and behavioral consistency• Curiosity, preparation, and active listening• Scaling sales teams through repeatable behaviors• Coaching frameworks for enterprise sales leadersGuest Spotlight: Glenn PoulosGlenn Poulos is an award-winning author, sales expert, and serial entrepreneur with more than four decades of experience in complex B2B selling. He is the co-founder of Gap Wireless, which he scaled from startup to a multi-million dollar distribution business serving North America’s mobile broadband and wireless infrastructure markets.In 2022, Gap Wireless was acquired by the organization, where Glenn stayed on as Executive Vice President and General Manager to help integrate and grow the combined entity, now operating as NWS Canada.Today, Glenn serves as President of ProgUSA, supporting US power utilities and service firms with electrical test and measurement equipment. He is also the author of Never Sit in the Lobby, a practical guide to winning and sustaining success in complex sales environments.🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping enterprise sales, go to market strategy, and revenue growth. Subscribe wherever you get your podcasts.Mark (00:31)Welcome to today's episode of Selling the Cloud podcast. I'm excited to welcome Glenn Poulis, an award-winning author, sales expert, and serial entrepreneur with over 40 years of experience in complex B2B selling. Glenn is the co-founder of Gap Wireless, which he built from startup to a multi-million dollar distribution business serving the mobile broadband and wireless infrastructure markets.KK Anderson (00:57)and the infrastructure market.Mark (00:59)of North America. In 2022, GAP Wireless was acquired by Network Wireless Solutions, NWS, a portfolio company of green management. stayed on as the executive vice president and general manager to help integrate and grow the combined entity, which is now NWS Canada. Today, Glenn is president of Prague USA, a company that supports US power utilities and service firmswith electrical test and measurement equipment. Thanks so much for joining us here, Glenn, and welcome.Glenn Poulos (01:31)Thanks, Mark. Great to be here.Mark (01:32)Cool, so today we'll explore four critical themes. First one, the core of complex B2B selling. How deals really get done and when the product is technical and the risk is high, how do you make sure that you build very strong efficiency into your selling model? Building sales repeatability. The habits and systems that make results predictable.Scaling and distribution business. We're gonna go a little deeper in that than we normally do. But really from startup to exit in the telecom and technology sectors. And then AI and technology and sales. Using tools without using the human connection.Topic one, just start with the B2B selling model as a whole. Glenn, your book, Never Sit in the Lobby, is full of field-tested wisdom from 40 years in technical sales. When you're selling complex products, whether it's wireless infrastructure, equipment, or power utility testing solutions, what fundamentally determines whether a buyer says yes or ultimately walks away?Glenn Poulos (02:32)Great question. So, and we're talking about complex sales, right? So, right. Okay. Yeah. So, you know, complex sales is a little different than just, you know, box selling or when you're just selling commodities like printers and computers or something. And, you know, when, when someone's buying something that's complex, right, they're not really buying a product.Mark (02:36)We are. Yes.Glenn Poulos (02:52)I always like to tell our people they're buying safety and solutions, right? Like they've got a problem. It could probably be solved in many ways with a complex solution, right? And it, and they're buying the safety that it, the, that decision will work, won't blow up in their face. No one's going to get fired. That's where the old, nobody got fired for buying IBM or Hewlett Packard came from, right? And that someone will stand beside them when things get hard, right? The specs matter.but trust matters more, right? That's the most important thing is the trust. And if a buyer doesn't feel safe saying yes, price doesn't become an issue, product doesn't become an issue, you're kind of dead in the water. And that's just a little,Looking back, it's like that's why a lot of times people would say to them, so I can't believe I didn't get the order. Like I had the best product, I had the best price, I had the best delivery, but they didn't trust you. rather, and again, I love saying, nobody got fired for buying IBM, right? They knew IBM was going to be there even if they were twice the price. And it's like, you know what? I'm going to buy IBM. Then I don't have to worry about it. I can say, Hey, I bought IBM. What do you want from me? Right? So that's kind of my first part of it.so the question is like, how do you build safety and trust, right? That's the key, you know, and so one of the key things that I always say is, you build it by slowing down early, right? You got to ask better questions.Listening more than talking the old God gave you two ears and one mouth you do the math, right and ⁓ the so listening more than talking, know, and you want to you want to be open honest and upfront about the risks, right and Challenge them with the risks a little bit so that they're out there and you're discussing the real risks that are in play and when the buyer you were trying to establish report to the point where the buyer feels feels you're helping them and not pushing them to buyRight. And so that's, that's, that's one aspect of it. Right. And, you know, some of the biggest mistakes people make are, you know, pushing price too early, trying to dive into specs for bigger, faster, wider, deeper, 20 % cheaper, you know, all those kinds of, you know, salesmen kind of things. Right. And pitching before understanding. And yeah. So.KK Anderson (04:53)So in a complex sale where it could go on for six to nine months and there's lots of dollars at stake as we were just discussing, what are some tricks or ways that you teach or talk about building consensus as you go through the sales process, as new people are added on into the conversation, as complexities increase?you know, everyone's got a different opinion. Like what are some ways that you build, build consensus, if you will. ⁓Glenn Poulos (05:20)Okay, soor get to the order or whatever, right? I guess is yeah. So first, you got to understand the risk, right? Like that's the you got to present it to the customer, you got to present what the risks are to them and getting the job done. And you have to understand what the risks are to you and presenting your product at like your solution. You know, as being the as being the solution, right, you have to always remember early on and throughout it that buyers are not afraid of the price.And that proves itself out by just looking on the road and there's people that are driving Toyota Corollas and people that are driving Mercedes Benz S-Class, right? And so clearly some people just want to spend more on a car, right? And so they're afraid of being wrong, making the wrong decision. So you got to ask questions that uncover ⁓ what failure would look like if they make the wrong decision and who gets the blame if it happens, right? You're trying to identify that kind of stuff, right? And then second,This is so important, right? You wanna map the decision process, who influences, and there's many models and sales strategies out there. I don't teach these, but like the challenger model and what have you, where you're identifying the technical buyer, the financial influencer, the key decision maker and what have you. But you need to know, ⁓ especially the way I explain it to people is you have to look at the dollar value of the solution that you're selling.Let me, it's 50 K 500 K 5 million, 50 million. Right. And you have to say in the company that I'm selling it to who's signing that check, who's signing the PO, the authorization, the final, where does the buck stop? Right. Because if you're selling something that might be, you know, let's say, you know, 250 K and it's a $5 million company, it's probably the owner that's signing it. Right. But if it's, if it's a 250 K deal, but it's a $5 billion corporation.with offices around the world, chances are some vice president, regional manager, finance guy, whatever you need to map out and know exactly where you got to go to, find out why and where it's stuck. Right? So you're mapping the decision making who's the influencers, who decides and who could stop the deal. And, you know, and most of the time the complex deals fail because you ignored.the person you didn't know about or you were surprised late in the game who that was and that you never talked to. And sorry.KK Anderson (07:32)I think the key wordI'm hearing you say, Glenn, here is mapping. And we are huge fans of the idea of a mutual action plan or map, right? And so, and what's great about that is that not only are you mapping out the strategy of what's going to happen over the next six to nine months and who needs to be involved and who can say yes and who's going on vacation when, so you don't, you're not shocked at the end of the quarter when you're not getting a signature because you'reGlenn Poulos (07:42)Nice. Yeah, good. Yeah.KK Anderson (07:58)You know, the signer is in Barbados, right? But the trick I would think is, and I believe, is making sure that it's mutual. And so to the extent that you can really build trust by saying, hey, here's our plan, you know, when you have a champion, I think that action of creating a mutual action plan helps to really build that trust and build that relationship. And then as you're bringing new people in,it becomes easier because you're all singing from the same song sheet.Glenn Poulos (08:23)yeah, for sure. The there's a funny story in my I always like to say shameless plug for the book, right? But in my book, right, there's a story about a guy that sells high value tow motors, right? Like our forklift, some people call them. And these things are massively expensive machines, right? And $120,000 or whatever. And so, in the stories about a guy who shows up, he and he's trying to sell a companytow motors, right? And he works for Toyota. And so he looks at the organization and he says to himself, so they need like four machines. That's like half a million dollars. It's probably the CEO that's gonna, that could be the CEO that signs off on that, right? So what does he do? He calls the CEO and he says, hey, it's Glenn from Acme tow motors, right?You know, we want to show you the, these tow motors, they, know you're using Kawasaki, but you know, we'd love to get these in for a trial or whatever. the guys, what are you talking about? Glenn? says, I don't get involved with tow motors. the vice president of warehousing is responsible for all that stuff. That's Jack. I'm like, all right. Okay. Yeah. Fine. No problem. Let me give Jack a call. So call Jack.Jack, it's Glenn. was just on the phone with the CEO. He told me I really needed to get your attention. We've got these tow motors, right? We know you're looking at a few, you know, know you're a coil stock user. We want to show you the Toyota. says, Glenn, stop wasting my time. says, I don't get involved in that stuff. Right? I've got a director of warehousing. That's Bob. Right? Why wasting my time? Bob, Bob, I've been on the phone all day with the CEO, the vice president. They told me if I don't get these machines in front of you, you know, lickety split.Mark (09:41).Glenn Poulos (09:53)He's going to have my head. Right. And so, and he's like, glad, come on. I'm a director. I don't have time to look at tow motors. You got to talk to the warehouse manager. You know, that's Jack. Right. So Jack called Jack. Yeah. Of course, Jack refers you to the shop steward or whatever the floor manager or whatever. And before you know it, you're bringing in the tow motors. You say, look, I've been on the phone with the CEO, the vice president, the director, the manager, the, you know, the foreman. And now, you know, here they are. Right. So then you bring the machines to the, to the work.The whole idea behind that story is that at any point you can call anyone in the stack and figure out where the deal's stuck, right? And so, and one of the things I always like to do, and again, this is a metaphor, right? But it's very valuable and I've used it my whole life, right? Is he call the CEO and you say, look, I know you don't get involved in this stuff, but I got to, you know, I know you're putting half a million dollars of machines on the floor. got my machine down here and we're doing circles around Kawasaki right now. Like you need to come down here and have a look at this. And he's like,I need two minutes. That's it. And you know what the guy's saying? I'm tow motor ripping around my warehouse, brand new, whatever. I'm going to come have a look. And the CEO walks in and the, you know, all these people are like, what the heck's the CEO doing here or whatever. Right. And, but at any point you can call the CEO and say, why is my deal stuck? And then he says, well, Glenn, he says, I forgot to tell you, know, we have a deal with the national deal with Kawasaki and it doesn't expire until 2027 andAnd I mean, you want to figure that out from that guy as soon as possible. And hopefully before you delivered a demo or whatever. And, ⁓ but I like to try to give people real world examples of how it plays out and, what happens on the opposite side when people don't do it right is, you know, your sales guy says, ⁓ I, you know, I got an appointment to do the demos and it's now with the powers that be. Right. He, gave his report to the powers that be.He sent it upstairs, right? And all that stuff. I'm like, when salesmen tell me that makes me want to like blow my brains out, right? I'm like, who's the powers that be? You know, the people upstairs, right? And I'm like, no, those are the people that are buying your competitor. And you're going to come to me in a few weeks and tell me you lost, right? If you don't know that everyone in the chain and you can't call them, then you blew it. And the problem is you have to start at the top.and go down because you can't like start with the foreman and then he gives you the old powers that be and then start calling up the stack and alienating the guys below, right? You want to be pushed down, not up, right? And because, you know, it's like, how dare you call my boss, you know? And, and so that's like a real world ⁓ scenario of how it can play out in a way that people can relate to, right? So, and ⁓ yeah.And so I kind of got a little off topic. The other thing was, you you were asking me about, you know, how do you, how do you ramp it over time? Right. And, know, you, you always want to make sure all the trust is built before the brochures in the, and the pitching and the, know, you want to be sharing your insights and then you want to be playing to what you've learned. And you want to, you want to demonstrate and, and prove out only to that. Cause oftentimes mistakes I see guys make.is like a good example would be myself, but don't make the mistake of using yourself as marketing data because you'll probably be wrong. But when it comes to cars, I love Mercedes-Benz, but Mercedes-Benz is known for the speed and the AMG ⁓ motors in the car, and there's a lot of ⁓ very fastand very powerful cars, but that's not why I like Mercedes, right? I don't drive them fast. I mean, I do whatever the, whatever the proportional amount over the speed limit I'm able to drive is that's what I set the cruise at. And I, and I never, don't, you know, I'm not worried about dropping it down into third and going, you know, I'm what I like is the luxury and the comfort. I don't care about the speed. So, but most salesmen would start laying on 500 horsepower, dual torque, overhead cam, dual turbos, you know, new zero to 60. don't care.I'm already lost and I already know that you've not built rapport with me. Right? So how is it, he's not presenting to, you know, to sell $120,000 car to someone, you know, in the right way. Cause he didn't figure out what part of it's important to me. I don't even need to hear about the speed or the motor size. I don't actually care. You know, and it's the same with many, many things, you know, and, but people arethey're scared and nervous. And so they kind of like want to drop back to like the training, the bullet points they learned in the training class. You know, we do this, we do this, we do this, we do this, right? Whereas you want to be stopping talking and start listening. What is it you need to do with these? Why am I here? What is your biggest problem you're trying to solve? You know, is it quality throughput, timing, speed, you know, power, you know, accuracy, know, resolution.Whatever, you know, so sorry, I rambled. I said it.KK Anderson (14:40)makes perfect sense. It really does. Andlike it, this kind of is the perfect bridge into our second topic, which is around building sales repeatability, right? And the habits, you talk a lot about habits. As a matter of fact, on LinkedIn, I reposted one of your posts this morning around the habits and the systems that make results predictable. And so in your book, you outline57 winning sales factors and that's a lot of variables. And so when leaders hear that, their first reaction is probably something along the lines of how do I make 57 factors repeatable? So if you had to distill it down, are there three to five that are the most? Yeah.Glenn Poulos (15:07)Yeah.Sure. Yeah. I love him. Yeah. Yeah, sure.Yeah. yeah. And so, and just to touch on the 57 and the number, and I mean, obviously I'm not gonna run off 57 of anything on the show, but the...KK Anderson (15:31)Yeah.Glenn Poulos (15:34)But these are factors that cover the whole litany of things you have to do during the day and throughout your career in order to be successful running the business and in sales, right? And so it's selling and so it's how to get act and stay in front of your customers and be a pleasure to do business with always, right? And yet you have to be a pleasure to do business with because most big customers are repeat customers. And so it's not a one and done, right? It's not like, you can be cranky with them and get the deal and then you're good because you got the deal becauseAll the customers I work with, they're 20 year investments of time, right? They buy with for me forever, right? And the company Gap Wireless, I started in 2007 and the first call I made, you know, was a lady named Arefa and I was still making calls to Arefa the day I left, 20 years later, 18 years later, right? and so the...And so then another insight into the 57 is these are rules that I always follow. I don't break my own rules. Right. And so, and the book never sit in the lobby. That's one of them never sit in the lobby. Right. And we can talk about that later. If there's time. Why, why I say that. but the habits to be repeatable, I guess would boil down to as first as you want to be prepared. Right. And so you've done your research, you know, you're selling this kind of a system to this kind of a company.What does this company do? How does this company make its money? Because they don't care about your system, right? They care about whatever goes out their back door and with the invoice and what they get paid for doing, right? And so again, a quick story. I always like to put this in the real world so people understand, well, what do you mean, right? Or it's not just hyperbole that I'm saying. It's like Xerox, right? You're calling on Xerox, right? Well, Xerox makes photocopiers.And so I need to figure out about, you know, how they can make better photocopiers. No, that's actually not what they do. They're a bank, right? They're a finance company. They make all their money, you know, on either one leasing you a machine or two, selling you costs per page, right? They don't come and tell you that that photocopier is 40 grand. They tell you it's four cents a page, eight cents a page, nine cents a page, minimum thousand pages per month, you know. And soYou need to understand how the company makes money. So you want to be prepared, right? ⁓ You know, so, and you want to keep and always be prepared, right? Second thing in the repeatability stack is, you know, discipline follow up. And so this is where people get scared, lazy. They're just averse to it. Right. And so, so often you say to him, like, did you follow up? And he's like, yeah, I, I, I call them.And okay, did you call him? Okay. Did he answer? No. I left the voicemail. Okay. Did he, what'd you say on the voicemail? And you know, maybe he says it and again, there's rules on leaving voicemails in the book, but, then I'm like, okay, well then what'd do? He says, well, I sent him an email. Okay. Okay. Did he reply back? And no, no, he didn't reply back. And so I'm like, okay, so let me get this right. So you emailed the guy, didn't reply. So you call them, left a voicemail. He never phoned you back. And so, so basically you'd never talked to the guy.Right? Kind of thing. But you have to, you have to be able to figure out ways and means to be able to follow up and stay on top of it. And what ends up happening is, is, know, you call him, he doesn't answer. So you send him an email and then you say, follow up Monday, right? Monday comes at a fight with your spouse. You're not in a good mood. You didn't get enough coffee. You don't really feel like making the call. You snooze it to the next day. And then the next day you have meetings. You're like, I didn't do the call. Damn snooze it to the following Monday. Now you're two weeks away.Right? Like, I mean, that's not discipline, it's avoidance and it happens like a thousand times over every week with a thousand salespeople. Right? And so you want to be disciplined. and whatever that means. Right. And, you know, and the deals are always one after the meeting. Right. And so, third, you want to be taking good notes. You want to be, and then reflecting on what's happened, what's happening.you want to be reviewing sort of the conversations and then looking insights. And that's where I teach, sympathy, empathy and compassion, right. And trying, trying to put yourself in the customer's shoes, figuring out what they're dealing with, et cetera, right. And applying the right technique at the right time. and you want to be reflecting on those conversations, like I said, and taking the notes and following them up. Right. And then, and so those are sort of the keys, but some of the other elements, you know,was curiosity and ⁓ you never want to assume, you know, there's the horror story where I in the book about me assuming something about a guy and I just made him so mad by my assumption. And I was just very difficult to establish rapport after that. Right. And and you want to be consistent. Right. You want to always be a pleasure to do business with, even when they say you're not getting the order.because you'll get the next one or you had the one before or you want to be called back in a year from now because you don't want them to not call you because they know they upset you and they're scared of you, right? It's like, I'm not calling Glenn. Pardon my language. He snapped the last time we, you know, we couldn't buy from him because of a, you know, a minor issue and, you know, a technical anomaly or whatever, right? So that's how I beat repeat. That's how I build repeatability.Mark (20:22)Yeah.Perfect, good, well, yeah, those are some good thoughts and ideas. So Glenn, you've built multiple companies and have hired and managed dozens, maybe even hundreds of salespeople over the years. When you're trying to scale a sales organization, when you're trying to bring these principles into a team, how do you transfer what's in your head and in your book to the team? How do you make your processyou know, more easily teachable.Glenn Poulos (20:50)So.Well, you know, how do I transfer? mean, you have to break it up into the behavior that you want and not just the talent, right? So repeatable behaviors create talent of itself, right? That's why when you look at sports people and all that, they're always doing the basics, right? You know, it's like, they're like NFL players. Why do they have to keep doing that same thing with the running with the legs and the tires? And because, you know, because they're building, they're building the talent through a set of behaviors, right?So, and you you wanna be teaching what you do before, during and after every call, right? So we're gonna go in there, we need to figure out what it is the problem is, know, da da da da. So then you're trying to coach them during the call. And then after the call, you're like, Jack, what went wrong on that call?Right. ⁓ I was talking too much. didn't, I saw there was an opening. didn't take it. You know, we could have got a referral to that. You know, he kind of deflected that it was another team was involved, but you didn't get any names, you know, so you want to be, you want to be, coaching before, during, and after. Right. and you know, I always like to say, you know,Like the methodologies are the frameworks, but the winning factors are the behaviors that you follow. And you can follow a methodology and still lose because you, I would say you ignore the basics like respect, timing, preparation, follow up, what have you, right? And they all build on each other and compound into being more of a disaster the more you fail at that, right?And so, you know, and then you're like, then the question is like, how do you pass, how do you teach people and how do you pass it on? Right. And so one of them, that's a highly personalized ones, it's from the book, right. It's my, my philosophy of greed based learning. Right. And so, and again, I hope, hope I'm not going on too far if I'm spending too much time on each one of these topics, but, greed based learning is the key to how I've sold technical products for 40 years. Right. And I, and I realized that.you know, a long time ago and, and I allow it to, I allow it to, to work in my day to day, you know, behaviors, right? So what greed based learning is, is that, and again, I use an analogy, I love to use buying car analogies because everyone has a car. And soLike I told you earlier, I don't care about the horsepowers and stuff on cars or whatever, right? And don't even actually care. I just want to be comfortable in a nice car and whatever with the gadgets and the cruise and all that. Right. But, you know, and so I don't really know a lot about cars where other guys know every spec off the top of their head. Right. But every four years, you know, I get a new car or something like that. Right. Well, you can bet for the, for that very small snippet of time. And for me, I'm probably going to be looking at, you know,Mercedes, BMW, Volvo, something like that, right? And you think I can't go home and talk to my spouse and spout off every speck of those cars that I'm looking at off the top of my head with little need for memory, right? And it's a thing that I call, that's why I call it greed-based learning because my greedy little nature knows I'm getting a car at the end of it, right? And I'm able to absorb those facts painlessly and effortlessly.Right. Because I'm getting something at the end of it. Whereas if someone just said, here's a 40 car manufacturers in the, or, car companies in the U S right. Learn all the, learn all the facts about all these 40 cars or whatever. be, it would be categorically impossible for me. There's no win in it for me. Right. And so, what you want to do is you want to sort of defer your learning until it's relevant to something where there's something in it for you. And then it becomes effortless. Right.You're selling a million dollar system to a company you can bet that you're going to be able to remember the facts because you know what your commission is on it. Right. And so I show these guys how to allow greed based learning and gals to in their, in their career. Right. And so it's just a little, a little gamification on the, on, on learning that I do. Right. and if I have an important call with an important piece of equipment on a company and I don't really know the box,And whatever I'll call the manufacturer, I'll call the product manager. I'll say, give me the five things they need to know in order to be a rock star with this product. And if I get stuck, I'll call you from the, from the customer site. And, and they're like, well, it's this, this, this, this, and this, right? And I'm like, look, I'm not the expert, but these are the things, you know, and then you're again, you're probing and learning and what have you. Right. So, that's the basics of it.Mark (24:52)No, thinkSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Mark Petruzzi and KK Anderson continue their discussion with Jason Baumgarten, diving deeper into how boards think, govern, and evaluate senior sales leaders once they reach the highest levels of leadership.Jason unpacks why boards care less about confidence and more about clarity, learning, and diagnosis. He explains how CROs must evolve from operators into enterprise leaders who understand risk, governance, succession planning, and investor expectations.The conversation also explores what executive vetting really looks like at the senior level, how boards assess integrity and credibility over time, and why understanding context behind results matters more than headline numbers. This episode is essential listening for CROs, CEOs, and revenue leaders aspiring to board seats or the CEO role.What You’ll Learn:Board Governance for CROs: Why sales leaders must understand how boards think and operateInvestor Empathy: How understanding investor pressure builds trust and credibilityLearning Over Bravado: Why boards care more about why results happened than confidence aloneRisk Awareness: How governance thinking changes how CROs evaluate decisions and tradeoffsSuccession Planning: Why boards expect leaders to plan for a future beyond themselvesBoard Readiness: What boards actually look for when recruiting sales leaders as directorsExecutive Vetting Reality: What senior leadership evaluation really includesIntegrity Signals: Why honesty about misses builds long-term executive trustKey Topics:Board governance through a sales leadership lensOperator mindset vs investor mindsetRisk management and risk of inactionStakeholder alignment beyond compensation plansSuccession planning and leadership maturityBoard selection criteria for sales leadersExecutive search and forensic referencingEthics, credibility, and long-term reputationContextualizing revenue performance and growthPreparing for CEO and board-level rolesGuest Spotlight: Jason BaumgartenJason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he advises boards, investors, and executive teams on leadership selection, succession planning, and governance. He has led more than 250 CEO and board transitions and brings deep expertise in evaluating executive readiness, integrity, and long-term leadership impact.Resources & Mentions:Spencer StuartHarvard Business Review: How CEOs Build Confidence in Their LeadershipBoard governance and executive succession best practices🎧 Listen now and follow Selling the Cloud for deeper conversations on executive leadership, governance, and what it truly takes to move from CRO to CEO.KK Anderson (00:31)Let's talk about board governance for sales leaders. Jason, sales leaders are, as we've talked about, they're heads down. They're working on pipeline. They're working on deals. But investor expectations are ultimately what shape the pressure that's behind the number and behind the quarter. so talk to us about why.should sales leaders care about board governance? What changes when they start thinking like the investors instead of thinking just as operators?Jason Baumgarten (00:56)So it's hard. I don't have a perfect one size fits all question because obviously every situation is different and every sales leader and company is in a different position. But I would say going back to this concept of empathy of the individuals, if you're an investor that has to return to your LPs, you've got a job to do. You're showing up and trying to explain how this investment is going to drive LP returns. And I think the first and foremost thing is for people to understand that individual connection that somebody showing up in your boardroom has.Like why does it matter to them? what's driving their anxiety, their pressure, their sense of, combated and this at times or, or, skepticism that you're doing good job. So that's one. think the second thing is really bringing that mindset of what have we learned, not just what have we achieved. the problem is half, I would argue frequently sales leaders when they are successful, they have no idea why.And when they are unsuccessful, they have no idea why it's like I walk into a CEO's office and they say, look, the stock price is up. And I'm like, why? It's a good rumor going around. So I think the reality is it's really important to hit your numbers. It's even more important to know why you hit your numbers, because that allows you to do it again. And when you don't hit your numbers, your board and your investors are going to be disappointed. But the critical question is, can you understand why?and articulate what you're going to do about it, even if you don't have the perfect solution, you can bring them into the problem with you and say, here's what we believe happened. Here's now what we're trying. If you have other suggestions or people that can help us unpack this, we're all ears. I think the people who often lose their boards are the ones whose confidence overpowers curiosity or humility. And they come in just sort ofclaiming that they're going to hit their numbers next time. Because the problem is, if you succeed, great. But if you miss again, you've now lost the confidence of the group. And the problem is, you don't have perfect control over your outcome, right? You could walk into a market that's falling, and you haven't figured out that it's falling yet. So what are you going to do to sort of unpack that? Now, you know, listen, at the end of the day, nobody likes to be told that the numbers aren't good. But they want to they want to understand why too, because they don't want to be surprised.if it's a bigger problem or it's a structural problem that they don't understand. And salespeople are often the tip of the spear because that customer intimacy, they understand. But for example, are you seeking out that information? Are you trying to figure out what went wrong? if you were sure you were going to close a deal and you didn't, are you really honestly asking what went wrong so that you can diagnose it? Or are you trying to explain away the miss?And I think people get caught up in the game of ⁓ performative explanation of like, let me look good explaining the miss as opposed to being genuine and saying, I put the wrong person on the deal, or I was overly optimistic and I didn't realize we actually had five competitors well positioned and I thought we had won or our pricing was a total miss, right? Whatever it is,really being honest about trying to figure that out, I think goes a long way versus trying to, use bravado or confidence to convince them that it'll just be better next time. Because if you're right, great, but you don't really build your case as an executive. Whereas when you can really bring them into what happened and what you've learned from it, what you're going to try differently, what the team's trying differently, you build an enormous amount of trust and confidence that you're on.that you know what you're doing and you're ready to tackle it again.Mark Petruzzi (04:13)So Jason, what does thinking about governance actually mean for a working CRO? How does it change how you run your organization?Jason Baumgarten (04:22)So it's a really good question and it depends on the governance of company, but I would say there's probably three things that should circle in your mindset from time to time. One is risk. Most sales leaders don't think a whole lot about risk. They think about missing a number, but they don't think about what is the risk of that? What is the broader risk? What is the risk of serving a particular customer? What's the risk of a hire? So first and foremost, it's,part of the board's role is to think about what could go wrong and how do we mitigate that. So I think when you start thinking about it with a governance lens, you do temper some of the things you might do and say, that actually could be risky. We, something bad could happen to the company if we pursue that approach. So I think that's one is just this mindset that risk matters. By the way, there's another side of that, which is the risk of inaction, right? The risk of not doing can also come back.So I think that's one. I think the second thing is that it does get you in this stakeholder mindset of beyond the incentive plan, beyond the annual comp structure, beyond the value of your equity in the secondary market right now. What is the bigger picture of what's going on here? And what am I really solving for? There was a book years ago, probably 30 years ago called How to Become a CEO. And I always remember this line from it. said,Your job is to make your boss look good and your boss's boss look even better. And, one of the things sales leaders should think about is, you know, the board isn't ideally is not there to pass judgment and be critical. They're actually there to help you be successful. There's nothing they want more. So how do you think about, your role in all of that and how it ties into the broader trajectory of what the company is trying to do again, so that you can connect those dots and you can, you can be a more holistic leader.And then I would say the third thing that board spent a lot of time thinking about, and I think is helpful for sales leaders to think about is succession planning. And the reason it's important is if you've got a lot of aspiration, you're hopefully thinking about what you want to do next. But it also helps you think a little bit more about your team and how you're developing your team. And I think boards think about that because it's one of the things that, you know, probably stresses them out more than anything is notif it's going badly, but when it's going well, that somebody is going to walk out the door or something's going to happen. And so I think showing that maturity of planning ahead and planning for, Hey, what happens when I'm not around? You know, who's gonna, who's gonna run the play.KK Anderson (06:32)Well, speaking of that next, getting to that next level, a lot of sales leaders say that they themselves aspire to sit on a board one day, And few understand how boards actually select members when they're looking to add a director and specifically one with a revenue background, right? Talk to us about what boards are looking for when they're tapping asales leader, someone with sales leadership experience to sit on that board. And then how can the sales leaders today, in succession planning, I suppose, right, but for themselves, like how can they begin to prepare and plan toward that ultimate goal of being able to sit on a board?Jason Baumgarten (07:10)Yeah. So I would say that there's a couple of things. One is there's, venture boards, there's private equity boards, there's distressed asset boards, there's public boards, a lot of different kinds of boards out there. So the first thing is, they're not all the same. And they're not all transferable skill sets. The more established the board, the more it's about governance, the more the board is, you know, maybe for a smaller company, then often the board is a little bit more aboutI would say it's the team you can't yet afford to hire, right? It's the folks that are just, you couldn't bring them on to your executive team, but you want their assistance, you want their help, and you want them rowing on your side. So the first thing is to really understand that those are all different boards or different selection processes or different approaches. Within that spectrum, I would say the smaller boards are looking at you as more the person who's a step ahead, right? Who's seen a movie they're about to go to and they want the advice and counsel.And in that case, it's really just about being a excellent near day job and be showing up knowing you don't have every answer and there's other people in the room are going to have good answers. And, you're there to be of service to the, to the management team and to the investors, typically investors, as you get more seen, you know, as you get more, to the established boards, either very large private equity, a pre IPO or a public board, it is a little bit more about governance. And then the question is, you know,The way that those boards operate is typically they've a very, very defined spec. They'll come in and say, we need a, CFO who has experience in Latin America, specifically Brazil, who has also worked in Japan and who has deep channel experience and Revrec, with Revrec and channel experience. They don't come to us and say, need a good person. Right. And soThe first thing is recognizing that just because they're seeking a board member doesn't mean it's you. The second step is figuring out, when they do need a sales leader, what are the kinds of topics they're often dealing with? And how do you best position yourself as somebody who's thoughtful, who is advancing the state of the art in sales leadership, in revenue leadership more broadly, in the industry you're in more broadly, so that people see you as an expert.a little bit beyond your current, domain or your professional experience. And then also recognize that part of the role on the board is not just to bring your expertise, but especially as you get to the bigger boards to be thoughtful about risk, ⁓ &A, succession planning, all of these other topics that boards are responsible for. Even understanding that those are the topics boards talk about. I mean, I always say to somebody says, I want to be on a board, I'm like, do you know what's on a board agenda? And they're like, no. And I'm like, well, that's a good first step, right? Like,KK Anderson (09:32)YouJason Baumgarten (09:34)And not in a bad way, but like, go to your own board and figure out, go to your board members and ask them if what they would advise, right? Do they see you as somebody who can contribute to a board, get to know your own board as a first step. I think then really thinking about the then really thinking about how do you bring that perspective because they don't, they're not interviewing you for how excellent you are at meeting a quarter orMark Petruzzi (09:34)Thank you.Jason Baumgarten (09:57)breaking into a new account because that's not your job as a board member. They're probably going to interview you about, if they're if they're contemplating in organic growth, they're going to say, great, how have you thought about the big picture integrating sales teams at scale? How have you thought about that? Or how have you thought about advising a team that's that's, you know, going through a business model transformation or a pricing transformation? They want to see that you can think at a more strategic and advisory level versusbeing a great operator. you know, and I would say, I get asked a lot about executive classes and about trainings, they will not help you get on a board. But they may help you sound like you know what a board does. And they may make you more capable if you are lucky enough to get on a board. At a minimum, find a book about boards and read it. They're usually not the most scintillating reading to warn you ahead of time, there's no blockbuster movie about governance.said to anyone ever. But there is, you know, there's some wonderful books that take you through the legal responsibilities of a board. And if you're serious about it, you should you should do that again, not because it helps you get on a board, not because anyone's going to select your resume, because you added your LinkedIn that you read the ABA manual on boards. But because when you're talking to a head of non gov or an investor, they're going to go, this person actually sounds seems to understand what we do.Mark Petruzzi (11:11)Excellent. Well, Jason, I can't finish up here without having you go a little more general on all this around, landing your next role, topic four. what really matters at the senior executive level. So, you've also said out there in some of your publications that salespeople think they can BS their way to better gigs. But at senior levels, reference inreferencing gets really intense. for those who haven't been through a significant vetting process, what changes at that next level?Jason Baumgarten (11:44)And by the way, I wish that was only sales leaders. think many, many leaders think they can talk their way through the next role. The reality is, I mean, just to give you a perspective, for a senior executive, typically a company, you know, working with us, for example, may take 20 to 25 references. They may do a four to eight hour assessment. They may do a psychological assessment on top of that.Mark Petruzzi (11:50)HaJason Baumgarten (12:07)They are typically going to do a background investigative check that doesn't just say that you had a job, but they will be sending representatives to call on every courthouse in every city you've lived in to make sure there weren't cases that were dismissed that didn't make it to the digital databases. They will screen your social media posts for inappropriate comments. They will look for any shred of evidence that you have done things that are unethical.or that will cause risk or challenge to the organization. All of that, and then there's the bevy of actual interviews. And then typically a case study or a working session, typically a few dinners or lunches or breakfast. So by the time you're done with that process, most likely they're going to find out what they're going to find out. So that's a couple things. One is how do you get a great gig be excellent at your current gig?Second, really try to build bridges along your career. And even if you don't like somebody, don't make a big deal of it because it'll come back to get you. Third, be really upfront with anyone trying to hire you about what didn't go well and why, because they're going to find out. And so it's much better to say, hey, you know what, that job that was two years, it actually was not a success. I learned a ton. Here's what I learned. I had a boss that just was oil and water. Here's what happened. Because if you try to position it asNo, no, was really successful. And I do 15 references and everyone says you were an ogre. It's not explainable because then it's an ethical lapse. It's an integrity lapse. So that would be, kind of what the process looks like. Now, there are plenty of roles where it's, I called a buddy and the buddy vouched for me and I got the job. And, you that's awesome. That still happens. But at the more senior levels, I would say, generally speaking,expect that level of scrutiny and process. Certainly for a CO role, if not a CROKK Anderson (13:47)Wow.Yeah, that sounds exhausting.Jason Baumgarten (13:51)Yeah. And by the way, even customers, I have had numerous examples in the last decade plus where somebody says, I built the so-and-so account. Well, guess what? If that CEO is a good friend, which chances are we know them or our clients know them, we're going to call on them. If you're not working right now, we're going to just ask them flat out what the story was. But if you're working,One of the most powerful reference questions is, hey, Mark, you get called on by a lot of salespeople, a lot of software companies. Who do you make time for?Boy, don't make, I now know you didn't mention Johnny, but Johnny's told me he's your best friend. So now I'm saying, well, Mark, you sounds like you've done a lot with these four or five companies. Is that true? No, you don't mention Johnny's company again, strike two, strike three. Well, I know you're not mentioning, XYZ company, but what about Johnny, Chris and Mary? You seem to know them all on LinkedIn. they people you really, I don't even know who that person is.Well, now you've lost me at the company knows me. I'm important to the company and I actually have personal relationship and don't underestimate those calls that will happen, particularly investors. They will do forensic referencing where they'll take that. They'll go through your resume and look for every connection you've ever every client you've listed, every connection, everything you've done. And then the other is probably goes without saying, but the other Holy Grail is just never, ever, ever mistake.published document, I mean, in any format, but particularly anything that is, you where you're really putting your name to that, that you did that, whether it's a degree, a job title, we've, found this recently, where people are being a little loose and fast with job titles, just stick to the facts. You don't need to elaborate. Don't put a, don't put a, P and L leader, if you weren't one, don't put a general manager, if you're really not one, don't elaborate becauseYou may not be thinking about it now, but in 10, 15 years, that'll catch up to you. We had an executive years ago who overstated something probably 20 years at a company, but in his official biography with the company, he had overstated something and he didn't even remember doing it. It was when he was like, you know, in his twenties and years and years later, he went to switch roles in a very, very senior role and this became a real issue for him andhis entire career almost unraveled because of this thing he did 30 years earlier. And he didn't even remember, I mean, it wasn't like he got anything from it. He wasn't trying to obfuscate down the road. He just did it unthinkingly as a 23 year old, you know, guy filling out a corporate form and it caught up with him.KK Anderson (16:14)Wow. So speaking of the resume, you know, and sales leaders, you know, lot of, a lot of sales executives are going to lead with the numbers on their resume. So when what firm like yours is starting to dig deeper, like what are you really wanting to understand about those, like how those results were achieved? Right? Like what, what do you want? What do you want? How do you want the sales leaders to show up and talk about those results and those outcomes?Jason Baumgarten (16:37)Yeah, there's a few things. First of all, what was going, what was the context, right? What was going on around that industry? Are you actually showing me the best numbers you have, but they're the worst numbers of any of your competitors? So the more you understand the competitive landscape and your peer group, the better. The second is what was the momentum when you caught it, right? If it was going up 30%, now it's going up 20, you can tell me how amazing you are that you hit 20, but actually you decelerated the rate of growth. So I want to understandwhat happened because that's actually a story of negative, you know, negative impact, even though it's a positive number. The third thing is do you seem to understand what you did to achieve those numbers? Right? And that's a recurring theme that you'll hear from me. But, you know, do you have clarity as to what you did? One of the most common things is people who are in jobs for very short amounts of time, but the numbers were good. They're like, Oh, yeah, I was there 18 months, but wow, we crushed it.crushed it so amazingly, I could go on to the next role. And I'm like, let's unpack how you crushed it in 18 months, because it took you six months to find out what the name of the people what, where the bathroom was, and what the names of everyone on the team was, and what the products were all called, and blah, blah, blah. Any human being, takes months just to normalize. And then it probably took you three to six months to find your next gig. So in that short time, you were actually working enough to speed, what did you do?And if the answer is kind of fuzzy, it's not that I worry that they didn't have a great 18 month tenure, I worry that they're so busy trying to tell me that they did something they didn't, that that demonstrates how they show up as a leader, and how they show how they show up as a as a colleague on a team. And that's way more concerning than that they didn't have an amazing 18. Anyone who's at somewhere 18 months, and probably it wasn't an amazing run. I mean, the odds are good that if you're there less than two years,Something went wrong, whether it was up to you or not. Something probably went a little off. That's fine. Just own it. Just be like, hey, that wasn't so good. Or it was so good that it led to this next thing coming out of the blue. But also have the humility to be like, I inherited a great situation, didn't screw it up, as opposed to saying I did everything and I'm amazing, because things just take time. I mean, in 12 months, you can't turn around that much.Mark Petruzzi (18:41)Jason, and thank goodness that companies are doing this and focusing and figuring out how they can get senior executives that are ethical and honest and trustworthy. Because if not, who knows what our general economy would look like. ⁓ Because it's one thing if you hire a sales rep who maybe is a little unethical, you figure it out, you you...you move on that individual. But if you hire your CEO, CRO, and Chief Operating Officer with those kind of backgrounds, it's going to come out. It's going to show up at some point. so I'm really glad to hear the, I've experienced it myself in the vetting process, but to hear you articulate it takes my understanding to an even greater level.Okay, we just have a couple minutes left. We love doing these rapid fire questions that we do with our guests and I'm really interested in hearing your responses on these. So what was the first product or service you ever sold?Jason Baumgarten (19:43)I sold jewelry. I bought jewelry wholesale and sold it at street fairs.Mark Petruzzi (19:48)I like that.KK Anderson (19:49)That is so cool. How old were you when you did that?Jason Baumgarten (19:49)And you learn a lot selling jewelry.I was like 14.KK Anderson (19:52)Really cool, wow. You knew you would be going to Stanford at that point. The entrepreneur at 14. ⁓Jason Baumgarten (19:57)⁓ I knew I loved business. I knewI loved business.KK Anderson (20:00)Jason, who's your favorite CEO or business leader that you've worked with over your career?Jason Baumgarten (20:05)You know, I have so many, this one's really hard. I actually find that I learned so much from so many of the CEOs I work with and they're all amazing at certain things and they all have ⁓ foibles. I think that rather than share the person, I'll share the story. A CEO that has had an unbelievable career. He always takes the time to learn and get better. AndHe's got coaches, he's got advisors, he's got, but he's just a learner. you know, he's one of these guys, it's a household name, but you reach out to him and he says, I'm busy. sitting down with a 24 year old to learn about how to do better prompting. I'm like, you're retired. What are you doing? He's, I got to get good at this. It's really important. And I just, I think there's a amazing, the CEOs who keep wanting to get better are just really inspiring.Mark Petruzzi (20:51)Yeah. So a resource every aspiring board member should use.Jason Baumgarten (20:55)their network.Mark Petruzzi (20:56)Excellent.KK Anderson (20:57)That's a good one. Okay, my favorite question is not listed here, so I'm gonna go out on the limb and say it anyway. Jason, what advice would you give your 21 year old self?Jason Baumgarten (21:07)Take more risk. I think that's the thing that we underestimate when we're young is that you can recover, can do, you can get a do over. People are very tolerant of youthful, ⁓ you know, behavior. don't mean behaviors in a social sense, but you know, just try to start your own company, try to join a startup that's a high flyer, try to, do something that's risky, because when you get older, it's much harder to take risk for all kinds of reasons.So do it when you're young and within whatever is relevant to you. You might be the most risk-seeking person out there But you know, would say I think most people when they're young They squander good risk They take a lot of risk in their personal lives and not a lot of risk in their professional lives And I'd say take some professional riskMark Petruzzi (21:47)Excellent. Well, Jason, thank you so much for your time, your great analysis and answers. We will add for our audience here, we'll add a bunch of show notes and make sure you get to read some of the good stuff that Jason has put out there and learn some more about him as well. yeah, so thank you, Jason. Thank you to our amazing audience.We so appreciate you and thank you to my co-host, KK, as well.Jason Baumgarten (22:16)You guys were fabulous. Thank you.KK Anderson (22:17)Thanks, team.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level.Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as they move from execution to enterprise leadership. The conversation explores founder-led transitions, boardroom presence, customer lifecycle thinking, and why sales excellence alone does not guarantee executive readiness.This episode is essential listening for CROs, founders, and revenue leaders who want to move beyond quota and operate at the highest levels of leadership.What You’ll Learn:From CRO to CEO: The mindset shifts sales leaders must make to be considered for top executive and board rolesBoardroom Credibility: How sales leaders can show up as strategic business operators, not just revenue ownersFounder Transitions: When founder-led selling breaks and what must change to scale the organizationSystems Thinking: Why understanding the full revenue and customer lifecycle matters more than pipeline aloneExecutive Readiness Signals: What boards look for when evaluating senior sales leadersHiring at the Right Time: Common board mistakes when transitioning away from founder-led salesKey Topics:Evolving from sales operator to strategic executive CRO presence and influence in the boardroomFounder-led sales versus scalable go-to-market systemsRetention, lifecycle metrics, and long-term growth signalsBoard governance and leadership transitionsWhy sales is not always the answerGuest Spotlight: Jason BaumgartenJason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he leads executive search and board advisory engagements for companies ranging from early-stage ventures to multi-billion-dollar enterprises. He has advised on more than 250 CEO and board transitions, with deep expertise in founder-led technology companies, succession planning, and board effectiveness.Before joining Spencer Stuart, Jason was an Associate Principal at McKinsey and a Program Manager at Microsoft. He holds an MBA from Stanford Graduate School of Business, serves as Chairman of the Board for IslandWood, and is a frequent contributor to Harvard Business Review, including his article How CEOs Build Confidence in Their Leadership.Resources & Mentions:• Spencer Stuart• Harvard Business Review: How CEOs Build Confidence in Their Leadership• Mark Roberge: The Science of Scaling🎧 Listen now and follow Selling the Cloud for conversations with leaders shaping the future of go-to-market, executive leadership, and board-level decision making.Mark Petruzzi (00:37)Welcome to today's episode of Selling the Cloud Podcast. I'm thrilled to welcome Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stewart. Jason leads Executive Search and Board Advisory for one of the world's premier leadership consulting firms. He's completed over 250 CEO and Board Transitions.across companies ranging from early stage ventures to multi-billion dollar enterprises. His expertise spans CEO succession planning, board effectiveness, and leadership transitions, particularly for founder led technology companies. Before Spencer Stewart, Jason was an associate principal at McKinsey and a program manager at Microsoft.He holds an MBA from Stanford's Graduate School of Business and serves as chairman of the board for Island Wood. His thought leadership appears regularly in the Harvard Business Review, including a recent article, How CEOs Build Confidence in Their Leadership. What makes Jason's perspective uniquely valuable is his vantage point. He's interviewed thousands of sales leaders and observes whatseparates those who successfully transitioned to CEO and board roles from those who just can't get there. Today we'll explore four critical themes. The sales leaders evolution from operator to strategic executive. Founder transitions building a leadership capacity beyond the go-to-market motion. Board governance for sales leaders. Why thinking like an investor makes you better at your job.and landing your next role, what really matters at the senior executive level. So I guess a couple of things there. You really don't work hard enough or really haven't accomplished most in your life Mano man, Jason, what an amazing career you've had already.And I'm sure you're not going to be slowing down anytime soon. So thank you. Thank you for joining us and joining us here on Selling the Cloud podcast.Jason Baumgarten (02:40)Well, thanks for having me. And I felt a little tired listening to it, but it was all fun in the moment and delighted to try and share some learnings from the many, many, interviews and board discussions and CEO discussions with your listeners.Mark Petruzzi (02:53)Yeah, and Jason, we have an audience of mainly CROs, some of the best in the business. And, you know, there's a number of them that I've already prepped to make sure that they've watched this because they're looking at the things that you do. ⁓ And I have many CRO friends who join us as well that have made this transition. So I love the, I love where we're going here and excited.to dive in. Topic one, the sales leaders evolution. How do you evolve from somebody who's great at sales to configure out management and understand leadership, and then they really have to move to the next level as a strategic executive, often without the background, not to say an MBA or a more prominent type of... ⁓educational background gives you all the recipe to do it as well, but many of them, you know, just they feel like they don't have that. So in your interviewing of thousands of sales leaders, what fundamentally distinguishes those who you feel can successfully transition to the CEO role or to board roles from those who just you feel maybe we'll struggle with that?Jason Baumgarten (04:04)Yeah, it's a great question, Mark. I mean, first of all, it sounds perhaps silly, but I start with do they really want it right? And the reality is not everyone really wants to be a CEO once they learn what that role is all about. ⁓ And so you have to start with not wanting it for ego reasons or control reason, but really do I want to do that job more than the job I'm doing today? So that's sort of step one. It's important. A of people breeze right through it, but I'm like, no, actually, do you really want it? And why do you havethought out reason why. The second thing is, you know, sales, ultimately, I think have a sales leaders have a couple of critical advantages. One great sales leaders have real industry and customer intimacy, and great organizations are built around solving customer needs. And so if you can really lean into that proximity, that superpower, that's super helpful. The second is most sales leaders are great people leaders.And so if you're really thoughtful about how do you lead a team? How do you lead people? That's another thing to lean in. What are the areas they tend to be less good at? Well, the first is genuine curiosity, right? One of the challenges with sales is one can become quite transactional. How do I hit my number? How do I move the sale along? How do I move the conversation along? How do I get what I want done, done? And the reality is great leaders are deeply curious. They're deeplyinterested in learning about other functions, other aspects of the company. So the first thing I'd say is tap into your innate curiosity to learn about what's going on in finance, what's going on in legal, what's going on in product, what's going on in marketing, what's going on in customer success. So that as you evolve your thinking, you understand more about what's happening in other functions. The third thing is actually rising up.and doing two things. First, think as a systems thinker about how do all the pieces of the puzzle fit together to make revenue and profit happen and get knowledgeable about that system. And then two, ensure that you are not coming across as somebody who believes sales is the answer or the cause of all problems or solutions. So those are a few of the things that I'd share. We can go into more depth on any of them.But there's some of the high-level things if I had to add a final one, I'd say humility I always laughed that if I interview all the top sales leaders at a company that revenue will beat will go up at least a thousand percent from the interviews alone when you just add up all the numbers and of it is there's an amazing quality of confidence and You know that a lot of sales leaders have but recognize that when you're interviewing for a CEO role or for something else you've you've got to temper that a little bit withMark Petruzzi (06:24)Yeah.Jason Baumgarten (06:40)that empathy, that curiosity, that humility.Mark Petruzzi (06:42)KK, I think you're on mute.KK Anderson (06:43)Well, that's a first for a podcast to land. Jason, really interesting what you're saying. And you've said that board members can sometimes be like Christmas lights. Like, you know, they turn on once a year, right? And so for a CRO walking into, you know, a board meeting, like, and thinking about how, how...Mark Petruzzi (06:46)Yeah.Jason Baumgarten (06:46)Yeah.KK Anderson (07:05)What advice do you give? Maybe they're not aiming to be CEO, but what advice do you give them around not just being seen as a salesperson? Talk to me about that. Talk to me about a CRO walking intoJason Baumgarten (07:15)Sure. Youknow, first and foremost, it's think about your stakeholders and most salespeople do this really well. So think about who's around the board and what matters to them. What are they thinking about? What's their what did they show up worried about or excited about in that board meeting? And I don't mean conceptually and for all time Memorial, but like in that meeting, what's on their mind? What's going on in their companies? What's going on in their investment groups? If it's a public company, what's going on in their day jobs or their other boards?What is the context? know, are you, are they walking into a new product launch being announced at your company? Are they walking into a bad quarter? So the more you start with who am I presenting to, who are these people on the other side, not just in the singular dimension of them as your board member or investor, but also the rest of their lives. So that's sort of step one. Step two is to your question of how do you appear as more, you know, how do you present a more holistic perspective? You know, I thinkIt really comes from that ability to connect the dots between what's going on with your customers and the market, you know, competitive point of view, you know, customers need shifting product evolution, technology evolution. So that's one. And then the other is being able to connect the dots inside the company. You know, we did this thing on, ⁓ our customer support initiative. It had this impact on renewals. This then led us to be able to change the way we're going after new logo.The more you can stitch together narratives that are multidisciplinary, the more they start to see you as not a one-trick ⁓ answer. And the other thing I'd say is know when the answer is not sales. One of the most powerful things any functional leader can do is to say, that's a great question. I actually think the answer is in marketing or is in HR or is in finance or is in customer support.You could give us more resources and sales, but that would be the worst place to put the capital to solve that problem. Because showing that shows that you are stepping out of your functional role to really think about what's best for the company and how you as a systems thinker would apply that capital or that resource.Mark Petruzzi (09:15)Jason, so in general, when should a CRO start thinking about building the capabilities beyond the pure sales, execution, sales leadership side? What's the signal?Jason Baumgarten (09:27)So I think there's two things that are working in tandem. One is their ambition, right? Do they have ambition to do more bigger, more complex, even sales roles or CRO roles that are broader than sales? And then have they mastered where they are? So at a very simplistic level, do they feel like they've kind of got the, you know, the training wheels off in their current role? You know, do they have sales ops team leadership, you know, forecastingKK Anderson (09:37)it in thatJason Baumgarten (09:49)all those key skills down, if they do, it's a perfect time to now start to think about how do I broaden? If you haven't got those mastered, you know, probably need to spend time there. But if you feel like you've got your quote unquote day job in good order, it's only going to make you better in your day job. And that's I think one of the things people often forget is they think, I'm doing this to become a CEO or to become a board member, or to take on more, it will actually make you much better in your day job.because you'll start to think about ⁓ other levers you can pull with your colleagues to help move revenue beyond what's in your control. And that influence in your leadership team, you will be more effective because you won't be seen as somebody lobbying for your team's resources, but for solving, know, every function wants more revenue, more profit. So when you start solving for that, you become an enlightened sales leader who,everybody wants to pull into their opportunities, their, you know, their initiatives, et cetera.KK Anderson (10:46)Isn't that the truth? Yeah. Jason, let's move on to the second topic and talk a little bit about founder transitions and building, as you've been discussing, that leadership capacity beyond just the go-to-market motion. And you have worked with many famous founders, ⁓ and you've had the ability to see a lot of these founder-led companies up close. And so I would love to hearyou know, maybe a story or two about some of your, your favorite famous founders that you've led. and then specifically like when, when they stopped becoming the primary salesperson, right. And the company starts to scale. I'm curious, like what usually breaks first, right. And just talk, talk us a little bit about some of your, favorite famous founders.Jason Baumgarten (11:30)So I think I've worked with almost all of them in some form or fashion. ⁓ You know, I would say that what tends to break is sleep. If I'm realistic, it's, it's the thing is you just only, no matter how amazing somebody is, they only have so many hours in the day. And so that's one. I think the other thing is that, you know, and you know, this as well as everybody ⁓ who really is an expert in sales, the one-on-one connection of an individual can only scale to so many people.KK Anderson (11:36)Okay, there we go.Jason Baumgarten (11:54)And so I think what starts to happen is that while they typically are doing more of a business development motion, more than a real scaled sales motion, they start to realize, I need some channel sales. need some indirect sales. need some marketing driven conversion. I need more tools in the basket. And then they start to build a sales team beyond them. Now, I think the early sales leaders of many companiesare individual contributors themselves. And so there's almost two evolutions. There is the first, you know, it's the founder being the salesperson, and then there's the first salesperson being the only salesperson. And then it's you as a sales leader kind of going to the next level as a ⁓ building a team, building a, you know, a model of sales. So I think that's often the trajectory these companies go through. I would say the other watch out isMark Petruzzi (12:28)ThankJason Baumgarten (12:42)founders who have a couple of really good early deals and think, boy, this sales thing is easy. And then they start to scale it. And they realize that that was just friends and family. And people thought it was great. Or they got some early pilots and it's not easily replicable. And so I think when you really ⁓ move from founder stage to a growth stage is when you can replicate that journey, when you know that you can hand this to someone else and Mark can go sell.just as well as I can. Founders are always going to have a special edge, right? The reality is if a founder calls a company, they're always going to have a little extra time. It's a little easier to get through to an executive, but until you can replicate it, you really don't have a repeatable sales process. ⁓ You know, I would also say that what we're seeing now is a real evolution in how people are thinking about it, because you are also seeing ⁓ much more complex sales motions.And in some cases that's complex because we're seeing them look more like consumer sales motions. And in some cases, much more like consulting or professional services. So we're seeing more bifurcation than for a while we were into the fairly low complexity SaaS sale, you know, and that is on the edges starting to fray a little bit in terms of just the complexity of, the heterogeneity of all the different types of products and services we're seeing in technology.So maybe avoiding a particular person, but, you know, I think everybody goes through that wave and, you know, I worked with one leader who his startup was in the sales technology space. And that was perhaps the most incredible cause he was one of the best salespeople period. And he was one of the best salespeople for that company, even when they were at, you know, several hundred million dollars in revenue. But he realized he had other things he had to do. And if he spent all his time selling,So what he started doing was spending more time teaching and making sure the right process was in place to scale as opposed to saying, I could do that better. Because of course, but he also couldn't do everything. had to, he had to pick what he was spending his time on.KK Anderson (14:38)Especially if he wanted to sleep, right?Mark Petruzzi (14:40)Now that Jason, that is spot on. So in some of your publications, articles that I've read, you mentioned two critical dimensions. Building the right go-to-market engine as one aspect of it. And then at the same time, readying the organization for when it's not founder led sales anymore. And they're not spending 50, 70 % of their time on sales.How should boards in particular approach these transitions? What responsibilities do they have in all of this?Jason Baumgarten (15:13)Yeah, it's a great question. It does depend on this on the type of board and this, even for startups, what's the type of startup and the ambition of the startup? You know, I think the thing that boards should spend the most time on is what is the theory of the sale? Like what is the theory of the sales system that the company is starting to move towards when it goes from an individual to a system? Second, based on the data, you know, the early returns early data,is that hypothesis or theory holding true, right? So for example, if we say, we're going to sell into this ⁓ type of executive, we believe it's get a demo, show the demo, do a pilot, you know, whatever the the march you're taking people through, is that actually proving out in the early data? And then the third thing is, is the company continuing to appropriately experiment and test whether they have the right model? Because I think it's probably the mostdangerous thing is to very early and we see this when an executive comes in and says well I've heard it I know the way to sell is XYZ and I'm gonna bring that into this startup and it isn't the right model right something is off either the ideal customer profile is off or the literal ⁓ you know Approach is off or the pricing is a little bit off Something in there is a little off and instead of catching it early. They catch it really late That's really bad for that sales leader, but it's also really bad for thisfor the company. so board members can really try to make sure there's a crisp hypothesis as to here is how we're going to sell. Here is the data that's going to show us that we've got the right model. And then three, are we seeing reinforcement that we picked well, or lessons learned that maybe we've got something off and what are we doing to adjust. ⁓ And then you can start to diagnose what's going on if you're not hitting or beating your expectations, you can say, we had something wrong. And that's okay. I thinkThe worst thing is to double down and say, we just aren't trying hard enough. It usually is a strategy or a process problem, ⁓ not a try harder problem. You know, unless people are just flat out lying about what they're doing, but I don't find in, especially in startups, people are usually pretty excited to grow the company. And so they're showing up, you know, trying to kill it. The other thing is not recognizing that whatever works early is probably not the forever model. AndFor example, there was years ago, an enormous number of SAS companies that had very low cost direct models. And they realized that that wasn't going to scale that they needed to get a more enterprise motion. And yet they built teams that were so well oiled for a particular model that when the when the growth rates started to slow down, they didn't they weren't as quick to transition or try new things. And that's a failure. The know, it's a failure of the leadership team. Buteven a failure of the board because the board should have been asking those questions earlier than the executive team because the board's role is to try and look ahead of where the executive team is is reacting to right now because the executive team might be You know 70 % reactive 30 % planning the board should be the other way around and should be able to say hey I think this is going to come and hit you in a year or two years. How are you prepping for it? Now? What are you doing now? How are you learning now? So that's how I think about that board interaction early onKK Anderson (18:14)You know, we were just interviewing Mark Roberge this morning on the release of his upcoming book, The Science of Scaling. And he was talking a lot about, you know, an early, you know, indicator of retention around, you know, customer success. And so for a sales leader, you know, they are a CEO might be thinking like, hey, just get us more leads, you know.get it, we just need more pipeline. Pipeline will fix everything, especially in these early stage companies. And Mark's argument was actually, what you really should be focusing on is your retention. Like, are you hitting those benchmarks that show that people, your customers are staying and you have, you know, product market fit, you have go-to-market fit, your customers are there and they're coming back and they're renewing. So, you know, talk to me a little bit about kind of your perspective onon that idea and what are some, like when you see founders, you know, start to show maybe a lack of leadership or like you're like, I want to coach them to increase their acumen as their companies grow and scale. And you need to take into consideration things like, you know, the retention metrics, you know, more so than the sales metrics. And you said earlier, recognizing that sales isn't always the problem.Like what does all of that make you think of? what's your perspective there?Jason Baumgarten (19:24)Yeah.I mean, first of all, I think he's spot on and I'd go so far say, you know, you want your metrics across the whole consumer lifecycle, you know, the whole client customer lifecycle, because it may be showing up in retention, it may be showing up in a lack of cross sell, it may be showing up in different areas. And the point is not to say we did a good or bad job, let's understand what's going on. It may be that you're got great conversion, but with all the wrong clients. And the real issue is you're going after the wrong clients, the wrong customers.not ⁓ that you are incapable of turning those leads into opportunities. So I think the first thing is I'm a big believer in capture the data across the whole life cycle so that you can understand what's going on with the sales approach, you know, depending on the type of product we're talking about, the, you know, the onboarding, the services side, the customer support side, et cetera. So I think that whole life cycle is critical. I think that when, ⁓You know, when founders are finding themselves stuck, usually the answer is go talk to people who have done who are a little further along in the journey than you are and ask them for advice and counsel about what worked for them. And don't take one person's advice. Don't say, well, you know, one investor told me the answer is this metric. So I'm going to go chase that metric, triangulate different people, get a good kitchen cabinet together.and ask different people and don't just ask peers, don't ask other founders alone, don't ask other CEOs, ask people who are in CRO roles, ask people who are individual salespeople, ask people who are in other parts of the ecosystem so that you're hearing perspectives from, you know, the person who might be junior entitled to you, but much higher than you in scale. You know, I always laugh, you can be CEO of your own business, just pop a magnetic sign on your truck and drive around and Mark's got Mark and Co.He's a CEO done. You don't, you don't need to actually have a company to be CEO. Same thing with the sales person, right? If you're selling lemonade, you're a sales person. But if you're, you know, you could be a very junior person selling millions of dollars in a very complex way for an enterprise SaaS company, or you could be a founder who's got a big title and a lot of sense of importance, but you're selling half a million dollars. And that doesn't make you more sophisticated as a sales strategist and the person who's aMark Petruzzi (21:09)Mm-hmm.Jason Baumgarten (21:36)senior manager at a big SaaS company. So don't just think about your peers. Think about, you talking to people in different roles and different scope and scale? And to me, that helps you understand what's going on. It also gives you empathy because when you start thinking about things like incentive plans or how to inspire the team, you also are thinking about, wow, how does that work when you've got 40,000 people?I've got five, how does it work at 40,000? So I think the more they can get out of their own atmosphere, it helps a lot.Mark Petruzzi (22:08)So Jason, I'd like to take you back to the board perspective for one more question here. So what mistakes do boards typically make in the timing and structure of hiring professional sales leadership as they move from a founder led selling motion?Jason Baumgarten (22:26)Well, I think that I think the two biggest mistakes I've seen is they don't do it early enough. Right. There's a sweet spot. If you do it too early, you don't, you don't have product market fit. There's no point in bring on your professional sales leader. If you wait too long, things get pretty calcified before somebody has a chance to think about your incentive design, your partner design, your channel design, all those things. I would say the other piece of the puzzle is hiring somebody who is going to bring theAnd if you don't, you know, you can either start with a very open mind, you know, classic beginner's mind and say, I don't know what model, but I'm going to use this recruitment to help figure that out. Or you can do the work to say, we've actually figured it out. I figured it out or your team has figured out. And we now know what kind of sales leader you need, because if you believe your PLG and you're really not, you can hire the absolute wrong person. And that's not good for anybody. And I'm a big believer that there's, there'sthere's not good and bad sales leaders. There's not good and bad leaders is actually people who are the right fit for the right time. And so you need to make sure that the fit of that sales leader is what you need. ⁓ The third thing I'd say is sometimes they just over, ⁓ you know, there's a desire to sometimes signal a Rolodex and get somebody who's got a big Rolodex. And maybe because I'm in the Rolodex business, I always laugh. like, listen, if you've got a product that's solving real problems,getting access and the Rolodex will be the least complicated thing. And people want problems solved. And so if you really have a good solution, you will find a way to those people. That is probably the least value in most industries. That's probably the thing I would not get hung up on early. And yet I think a lot of founders think that's the magic unlock. The reality is most human beings at best,best have 100 to 150 relationships. And that's actually overstating the real quality of most of those relationships are ⁓ not preferential. Meaning if you and I have the same product and we both go, I'm not going to win it just because I have that relationship. It's really going to come down to who is the better product. And so I would say don't over bias to that concept of access.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Cherilynn Castleman joins Mark and KK Anderson to unpack what strong CRO leadership looks like in a time of rapid AI adoption and constant go-to-market change. As every team claims to be AI-first and tech stacks continue to converge, Cherilynn explains what truly differentiates leaders who drive real results.This episode dives into how curiosity with AI, disciplined daily usage, and protecting selling time translate into cleaner pipelines, shorter sales cycles, and fewer end-of-quarter surprises. Cherilynn also shares practical guidance on modern operating rhythms, how to run meetings that actually matter, and which metrics prove that change is working now, not quarters from now.What You’ll Learn:Building AI Fluency as a Leader: Why modeling curiosity, transparency, and experimentation matters more than mastering toolsAI as a Daily Discipline: How consistent usage creates confidence, clarity, and better decision-makingProtecting Selling Time: How CROs can reduce meetings and increase seller productivity from 10 hours to 15 to 20 hours per weekHumanized Outbound at Scale: Using AI for micro-segmentation while keeping messaging personal and relevantRunning Meetings That Matter: How 30-minute meetings, no slides, and clear ownership tighten pipeline executionProving Change with Metrics: The three numbers boards and CFOs care about to fund and support transformationKey Topics:CRO leadership in an AI-saturated GTM landscapeModeling AI curiosity and transparency across revenue teamsStop chasing tools and start building the right mindsetExact meetings, executive engagement, and decision-maker accessMicro-segmentation by persona, industry, region, and generationModern revenue operating rhythms and pipeline hygieneMeasuring cycle time, executive involvement, and multi-threaded win ratesGuest Spotlight: Cherilynn CastlemanCherilynn Castleman is a sales and leadership advisor who helps revenue teams adapt to modern buying behavior and post-pandemic selling realities. She is the author of Post-Pandemic Selling, a top Amazon bestseller that has been recognized by Salesforce as one of the top sales books for modern leaders. Cherilynn is also an active LinkedIn voice, hosting frequent LinkedIn Lives where she shares practical insights on sales leadership, AI fluency, and authentic connection.Resources & Mentions:Book: Post-Pandemic Selling by Cherilynn CastlemanWebsite: postpandemicselling.comRecommended Book: The Untethered Soul by Michael A. SingerLeadership Voice to Follow: Bill Green, former CEO of Accenture🎧 Listen now and follow Selling the Cloud for more insights on AI-driven leadership, modern sales execution, and building trust across today’s go-to-market teams.Mark (00:30)All right. Let's move to topic three. Leading as a CRO in a time of intensechange. So every team nowadays says they are AI enabled, they're AI first, and everyone's sales and marketing stack just looks very similar. So from the seat of the CRO, what actually differentiates leadership right now in your opinion? Could you give us two or three weekly behaviors you expect to seein the numbers of a CRO that is leading well.Cherilynn Castleman (01:04)Yeah, so a couple things. I think that if a CRO is demonstrating curiosity with AI, they are using AI, they are sharing with their team, this is what I did. I was working with the CFO for a huge company recently and they do a pricing exercise. And they normally would sit down for a couple weeks and work on this pricing exercise. And I challenged them to open AI and pull their data into their proprietary system.And in 30 minutes, they had done the entire exercise. And so it was like, wow, everybody's going to be impressed. I said, no, it's transparency. Tell them you used AI to do it. Demonstrate, model that you're curious. If you fail, talk about that. So number one, they're modeling curiosity. Two, it's a discipline. They're using it on a daily basis. They're talking about it on a daily basis.There are somewhere between 50 and 200 new AI tools every day. There are, when you look at go-to-market tools, there are somewhere between seven and 10 new tools every day. There's no way you can master the tools. Stop chasing the tools. It's a mindset. It's about confidence and clarity. The next thing that I would say is that ⁓ protect the selling time.Look at your meetings and make them very efficient. Get them down to 30 minutes. The goals is most sellers sell about 10 hours a week. You want to get your sellers to 15 to 20 hours a week. And so where you're going to see this, are you going to see a cleaner pipeline, you're going to see higher exact meetings. And so those are things you want to measure is not just meetings, but exact meetings, decision-maker meters. It will shorten the sales cycles and you'll have fewer surprises at the end of the quarter.KK Anderson (02:43)So good. was just on a coaching call just before this podcast episode actually, and was coaching a new seller that was joining the team and was asking about the hustle and the grind and around hunting. And so we popped open Chachi BT and we put in the overall team's average deal size, average win rates, know, sales cycles. And he...figured out that he needs to make 6,700 calls in the first six months to be able to get the number of opportunities in his pipeline to be successful. And he was like, what? 6,700 calls. But you break it down into a daily rhythm. And you break it down into who you're targeting. And you can use AI for those things to get smarter and hone in on offers based on personas and POVs. It's interesting.Cherilynn Castleman (03:24)Absolutely.It is. And the other thing is thatthe goal, and so I think Mark mentioned this, we're opening emails and we're like, yep, AI wrote that, yep, AI made it. And so what I challenge people to do is, yes, you have to do your volume, but what if you spent 15 to 30 minutes every day sending a couple better emails? Where you actually, you know, and so, then, yes, if you sent a humanized email, I love it when every once in a while I get an email and I'm like, yes.KK Anderson (03:50)humanCherilynn Castleman (03:56)this lands. We all know what those feel like. We'll learn to send those kind of emails. And if you're not sure, I tell people, email them to yourself and then open it on your phone. If you won't open it on your phone with the subject line and the first sentence, why would anybody else? So send it to yourself, look at it, and yes, get your numbers in, but spend time figuring out how to craft.better emails and micro segment because once you've done your micro segmenting, you can do emails to Gen Z, Gen Y, Gen Alpha. You can do it by title, can do it by industry, West Coast, East Coast. AI will do all that. Do all your micro segmenting and then you're now doing a more humanized outbound and I promise you, you'll hit your numbers and make fewer and send less noise.KK Anderson (04:43)meaningful, more meaningfuloutreach, yeah. Okay, so you said something a second ago. You said when Mark was asking about the CRO and leading well, you said less meetings and the meetings that are, having the meetings that are meaningful. And nobody likes a meeting, everybody hates a pipeline call, we know that, right? So like what in today's day and age, like what is like,Cherilynn Castleman (04:46)Yeah.KK Anderson (05:05)What are the non-negotiables, but what gets cut and what changes and what, talk to me about that operating rhythm, is it changing?Cherilynn Castleman (05:11)So I think it is. I think that, so what I encourage people to do is do 30 minute meetings because of AI and technology and Facebook and Instagram and everything. The 10-minute spans are very short. So do a rapid 30 minute meeting. Revenue review, focus on what are blockers, what is getting in the way. Focus on owners, deadlines, next steps. No slides, no noise, no operational.I used to call them my quick stand up. I taught my team the rule of three. They had to come in and in one minute or less give me three things about this deal that I needed to know and then end with, so it's a bottom line up front. Bluff is a military phrase, bottom line up front. Three things, one, two, three, and then conclude with here's what I know, here's what the so what is, or here's a call to action. People come in without slides.and give you those updates, you're gonna see your pipeline tighten up. And you're not gonna have surprises, you're gonna have that transparency. And then every meeting must either build a skill or make a decision. How many times you sit in meetings and it's just updates and it's updates and there's nothing. Either we're going in to make a decision or we're gonna build a skill. And like I said, I would do a 30 minute meeting, that, teach me something in five minutes at the end.KK Anderson (06:18)Excuse. Excuse. Excuse. Yeah.Cherilynn Castleman (06:27)So everybody is learning something every week and I have teach me something AI. And again, if it rotates, know, KK is going to teach us her best AI tip this week. Mark's going to teach us next week and next week I'm going to teach them. Everybody's best practices and people are going to learn things so they can teach them.Mark (06:39)andKK Anderson (06:42)it.Mark (06:43)Great. So we all know boards and CFOs fund what they can measure. funding is a big part of ensuring that you really are able to build the type of capabilities you're looking for and keep those skill sets building. So what three numbers belong on a page one to prove that change is working? And what targets would you maketo ensure that you can be confident that the program, the leadership you're bringing to the table is gonna create the lift now, this quarter, not quarters from now.Cherilynn Castleman (07:20)So the three numbers that I would look at, one is cycle time with a warm sponsor versus one without. So if you're doing this right and you're leveraging AI, it's very simple. You just want to say, here's what our cycle time is with a warm sponsor. We're seeing a lift in this. Number two, executive meetings by stage. So when do the executives join and what stage are you at? And being able to track that.and the win rate on multi-threaded deals. those are the three things. And what I think you're looking for is somewhere between a 10 and 20 percent quarter over quarter. That is proof that you are driving change.KK Anderson (07:56)Amen. That is proof. Okay, Sherlyn, we are gonna go to our favorite section of the podcast. We call it rapid fire. And Mark, I want you to kick us off so that we land on my favorite question on me. You go first.Cherilynn Castleman (07:58)atMark (08:07)You gotit. I'll start the first one. What is the first product or service you have ever sold?Cherilynn Castleman (08:15)Mark, I've been in sales since before Girl Scout Cookies were 50 cents a box.Mark (08:18)my goodness. Excellent.KK Anderson (08:19)did you do, Roscoecookies?Cherilynn Castleman (08:20)Every girl's got cookies. And I mean, I was probably in the first grade. Okay? And yeah, I was in the first grade and my brother would pull the wagon and then there were no order forms. They just gave you cookies and you went and sold them. And I would stand there and I just would say, you know, they freeze well. What's your favorite ones? And oh, and if you tried this, this is, know, and I'm telling you, you put them away, you freeze them, you'll have them at Christmas. And I just up-sold and I was...I a top salesperson and I just loved it. I was probably six years old.KK Anderson (08:51)That's amazing. Okay, who is one of your favorite sales or leadership voices that you like to follow?Cherilynn Castleman (08:56)So I have always followed who he was known as the client success guy and that was Bill Green, the former CEO of Accenture. He's just made such a change in the way I sold and Bill always said two things that stuck with me. One, if you criticize people, you raise their defensiveness. If you challenge people, you raise their game. And so that's why I coach and I challenge people.And the other thing he said, Sherrilyn, three C's. Competence, be damn good at your job. Be great at what you do. Confidence, just have confidence, have courage. And the last one, which I repeated here, is give a damn. Care about your clients, care about your industry, care about your product. He said the three C's, well, that is what makes you a great leader. And so I've read and listened to everything that Bill has done.Mark (09:48)right on. So one practice you believe every sales manager should adopt this quarter or maybe even this week.Cherilynn Castleman (09:56)I say curiosity. AI lets you be curious. ⁓ I was read in a couple of places that they say curiosity is the KPI for 2026 for sales leaders. So I think if you're going to leverage AI and build your AI fluency, curiosity, curiosity, just keep asking questions. What can I do better? And also one of my favorite prompts is what did I miss? What could I have done better?So even though you've done the prompt, you've done the analysis, stop and say, okay, what did I miss? What am I not thinking about? How can I do this better? So curiosity.Mark (10:28)So this may be one way that humanity is evolving a little bit, because they used to say curiosity killed the cat. And now it's not going that way anymore. And think about it, with AI, there's so much power in curiosity. So I really love that one. Thank you.Cherilynn Castleman (10:39)You knowYes.KK Anderson (10:46)So good, okay, and my favorite question. Okay, Sherrilyn, what advice would you give to your 21-year-old self?Cherilynn Castleman (10:52)So I would tell myself to trust my voice, trust myself earlier. I would tell myself, if given a choice, Sherrilyn, always choose kindness over being right. And the final one is always, always have the courage, regardless of what anybody else says, just have the courage, have the kindness, and trust yourself.Mark (11:13)All right, well, I'm gonna close this up with, and I'm really interested in this one with all the great stuff we learned about you during this call, Sheryl Lynn. What is your favorite non-business book?Cherilynn Castleman (11:24)The Untethered Soul. I read it every year. It makes me pause. It makes me spend a little more time on my rug. It is about self-reflection and choosing love over fear. And I've been reading it every year. I don't know, probably since it came out. I'm a voracious reader, but that is one book that I read every year. I love The Untethered Soul.Mark (11:28)Wow.And I love that idea of like reading something every year. I've never really, it's not like I haven't read books again, but the idea of having something that's so impactful and rereading it every year is really cool. Well, so.KK Anderson (12:02)Wait, when areyou going to release your book, Sherrilyn? Surely there's one coming.Cherilynn Castleman (12:05)Well, so I have a book. It was actually top of Amazon's best sellers for women. It's been recognized by Salesforce, actually one of the top 10 best sales books and link. You can go to post pandemic selling.com.And that's, you'll find out it's also on Amazon. It talks about a lot of things we've talked about coming out of the pandemic, why we had to connect with people, why people need us to be authentic and us to be curious and how to connect with people. It's called Post-Pandemic. It's what's in the cards. Post-Pandemic Selling is the name of it. Again, you can get it at postpandemicselling.com. You can also find it on my LinkedIn page orSherrilynCalfsman.com or just connect with me on LinkedIn.KK Anderson (12:48)You're right.Mark (12:48)Very cool.Cherilynn Castleman (12:49)Thank you.Mark (12:49)Well, Cherylin, thank you so much for taking the time with us. This was really a pleasure. And thank you to our amazing audience. I hope I remember that every single time. I don't know if I do, but we want to thank them as well, especially as we're moving in and through the holiday season. So again, Cherylin, thank you. KK, thanks to you as well.Cherilynn Castleman (13:12)Thank you, KK. Thank you, Mark. And thank you to your listeners and your audience.KK Anderson (13:15)Make sure to check the show notes and to catch Sherilyn's LinkedIn Lives. They're awesome. Almost every week. Okay. Thanks everybody.Cherilynn Castleman (13:20)Thank you, Kate.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams.Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy.This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise.What You’ll Learn:AI as a Daily Sales Discipline: How a simple 15 minute daily AI prep routine helps sellers develop POVs, anticipate change, and continuously improve.POV Development at Scale: A repeatable framework for triangulating industry, company, and persona insights using AI.Making AI Revenue Relevant: Why leaders should evaluate AI through insights, context, and business impact instead of activity metrics.Trust in the Age of AI Noise: How better questions and deeper listening create credibility when buyers are overwhelmed with automation.High Connection Discovery Questions: How to use AI to reframe discovery questions that trigger trust, openness, and buyer engagement.Prospecting Without Pitching: Why offering value through insights, case studies, and tools beats asking for meetings.Navigating Modern Buying Groups: How to adapt when new stakeholders like CFOs enter late-stage conversations.Financial Fluency for Sellers: Why precise numbers, not rounded estimates, matter when speaking with executive buyers.Key Topics:AI fluency as a mindset, not a toolsetDaily AI routines for sellers and managersPOV creation using LinkedIn profiles, 10Ks, and industry analysisRelationship selling and the science of trustDiscovery questions that increase buyer confidenceAvoiding buyer defensiveness and ethical AI useExecutive conversations and CFO expectationsFinancial storytelling with insight, context, and impactGuest Spotlight: Cherilynn CastlemanCherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops.Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles.Resources & Mentions:Course: Smart Tips Sales – Master Relationship Driven Selling via AIBook: Post-Pandemic SellingResearch Reference: Dr. Jane Dutton on High Quality ConnectionsConcepts: AI fluency, POV selling, high connection discovery, financial storytelling🎧 Listen now and follow Selling the Cloud for more insights on modern sales leadership, AI-driven GTM strategy, and building trust at scale.Mark (00:31)to Selling the Cloud. Our guest today is Cheryl Lynn Castleman, an enterprise sales leader turned strategic coach and Harvard instructor as well. She helps teams become trusted advisors with practical AI fluency and relationship skills. She also builds accessible learning at scale as a new to me creator. Her course, Smart Tips, Sales,Master Relationships Driven Selling Via AI is super highly rated and available versus a via Udemy business. Her programs focus on outcomes you can see on Monday morning. Better discovery, cleaner deal strategy, clear next steps. She has coached thousands of sellers and leaders, lifted promotion rates through hands-on coaching.and built a large learning community through weekly live sessions and workshops. She teaches simple operating rhythms that free time for customer conversations rather than adding more dashboards. And she's on a mission to equip 1 million women in sales and leadership with the fluency, confidence and playbooks to thrive. Here are three topics we'll cover today. AI fluency as a daily mindset.How to use AI to amplify strengths and turn prep into a repeatable routine that shows up every day in results. Relationship selling and the science of trust, the questions and behaviors that build credibility fast with modern buying groups, and leading as a CRO in a time of extremely rapid change. How to focus to team, communicate change, improve impact without adding any additional noise.Sherlyn, we're so happy and proud to have you here. Welcome to Selling the Cloud.Cherilynn Castleman (02:13)Thank you, Mark. Thanks, KK. I'm thrilled to be here today.Mark (02:16)All right, we're gonna take you right into our first topic. And our first question is, you frame AI as an amplifier for what sellers already do well. If a CRO asks you to install AI fluency in 30 days, what would reps and managers need to do each day and each week? And what early results would you expect by say week four?Cherilynn Castleman (02:38)So first of all, I would start with a 15-minute AI prep session for every rep. I would have them spend 15 minutes asking AI, first of all, one, to develop a POV, a point of view, which I know we're going to talk about a little bit later, for each of their clients. It's something they can do very quickly to triangulate and develop their opinion, because as you know, state of sales reports from LinkedIn and Salesforce told us that 87 percent ofB2B buyers expect us to show up as trusted advisors, meaning we have to have a POV. So use AI to develop your POV. Second of all, spend five minutes using it to look around the corner. Where is my industry going? Where is my product going? Where is my company going? If you ask those questions every morning, you're going to get insights. And the final thing is, what can I do better? What can I, what am I missing? How can I, so for example, I'll say,How can I be a better coach? How can I connect better with my audience? What is a new training insight I can try? What's a new engagement I can use on Zoom? I am every day getting better. They spend 15 minutes every day amplifying what they already do. They're going to accelerate deals. Number two, I would encourage managers to add to their weekly minutes, teach me something in five minutes. Have every rep teach something to the rest of the team.once a week. That means by the end of four weeks your team has learned five AI insights. Over the course of a year they will learn 50 AI insights. And I had a client who was in the middle of the pack as a manager for a Fortune 100 fintech company and she became the number one sales manager of the year within six months just by doing that one exercise. That will free upAnd what you will see is you will see about 30 minutes a day freed up from your reps. That 30 minutes, if you have 50 reps and they're doing about $100,000 per deal and they're doing one deal a month, if you take that math out, that will give you an additional $4.5 million in new revenue that and no additional headcount.KK Anderson (04:44)Wow, it's really fascinating when you put it that way and you break it into numbers.Cherilynn Castleman (04:47)Yeah, and that is one of the biggest takeaways, I think, that sales leaders and chief revenue officers can look at is when we first started using AI, people were talking about how to use it for email and how to ⁓ sound better. And what the most recent research is coming out is you have to ⁓ apply what I call ICB, insights, context, business impact. How is it driving revenue?How is it saving you money? How is it increasing operational efficiency? How is it increasing your ROI? Those are the questions that leaders want to start asking every single week. This is what my reps are doing. How is that making me money, making me more money, or saving meKK Anderson (05:28)And it's interesting because you need the leaders, the L1s and the L2s asking AI those questions and using the data to get smarter. But the sellers as well, like you said, use it to look around the corner, research your competition, your customers. And we know and have known for a long time that our customers are much smarter when they get to us. They know more about our product than we probably do.Cherilynn Castleman (05:48)It used to be there were a ⁓ couple of months ago we had about 79 % usage today. B2B sellers are 98 % using AI. Customers are 100 % using AI. So your customers are using AI and 100 % they know your company, they know your competitors, they know your product. They probably have done more research than you have. So that's why you have to show up.Mark (06:02)ThankCherilynn Castleman (06:12)with a POV, you have to connect with them, you have to build trust with them. People want to do business with people they know, like, and respect. Period. And we can leverage AI to do that.KK Anderson (06:24)And so where I was gonna go next was, I actually, I kind of thought people were getting over this idea that AI is cheating until I was in the car with my kids of all people. And one of my daughter's friends was like, AI is cheating, I can't believe AI, it's just not fair. And it's interesting, do you hear that still in your trainings and your classes that people feel like it's a cheat?Cherilynn Castleman (06:47)And with a lot of women, Harvard did it. There was an article that was recently said how AI is impacting women's career. And they discovered that women use AI in business 10 to 40 % less than men. And when they asked them what was the real reason, women said, because it's cheating. And so I tell people, just reframe it. I said, take what you already do well.What is your superpower? What is the one thing that you're better at that AI will never replace? AI will never replace your authenticity, your ability to care, ⁓ your ability to connect with people and ask AI to help you elevate that, to amplify that. Take 15 minutes in the morning and say, I'm a great listener. How can I be better?I ask great discovery questions. How can I do better? I'm meeting with this client. We don't seem to connect. How can I connect better with this type of client? My client's very analytical, very amiable, very expressive. A trick that I tell people is write a simple email and then ask AI, rewrite this for an analytic, rewrite this for an expressive, rewrite this for a driver, and rewrite this for an amiable. They're different as night and day. That alone will help you connect.with your clients, just reframing that. Another example is if you go to LinkedIn, go to the three dots, and it says PDF this profile. PDF the profile, attach it to the AI tool that you're using, and say reframe this email specifically for this person. And it will say, they're very innovative. They're very amiable. They're very analytical. And it will reframe it. You will connect with them. That's the power of AI and connecting with people.Mark (08:24)All right, well, that's very cool. So please help us to make this a little more Monday ready. Let's say a rep has a discovery call this afternoon with a new account. Walk through the 15-minute AI assisted prep that produces in your mind the most useful point of view for the call and how you coach them. How do you coach them to bring that into the conversation? We've discussed a little bitthis here, but take us a little deeper if you would.Cherilynn Castleman (08:51)Absolutely. So what I always coach my clients to do is to triangulate your POV. It's something that AI, generative AI tool does so well. So first of all, research your client. Pull down their LinkedIn profile. If they're an executive, pull their bio and that's number one. So you want to triangulate. want three things, industry, company, person or persona. So if you can't find the person, do a persona.Pull down several CFOs in that industry. Pull down, if they're a Gen Z, pull down Gen Zs in that industry in that job role. So the better you can micro-segment, if you can't do the person, do the persona. That's number one. Number two is company. My favorite company document for publicly traded companies is a 10K. The Form 10K, as your listeners know, I'm sure, comes from the Security Exchange Commission. You can get it onthe investors page of any publicly traded company, and the third one is an industry analysis. My favorite place to get it is Value Line. Value Line is free on every public library. If you work for a large enterprise company, they have this information for you. They have an industry analysis. They have company analysis. Pull it in and ask AI to triangulate this for you.and it will pull the three together and develop a POV. And then you just say to somebody, Mark, if I said to you, I have an idea I want to run by you, what would you say? People say, yeah, nobody's going say no to an idea. And that's all it is is an idea. Even if you're wrong, you get credibility because you showed up with an idea. So show up with an idea. This takes 15 minutes. This used to be an eight-hour workshop that I did on howMark (10:15)Yeah.Cherilynn Castleman (10:31)to research and how to read a 10K. Value Line has the ratios in there, so it can pull it and it has the ratios in there for three years. It will do a financial analysis POV, it will do an expressive one, any way that you want it. Fifteen minutes.KK Anderson (10:46)And then you take that information and you turn it into a value hypothesis for what outcomes your customer wants to achieve and what's going to get in the way and how you can help.Cherilynn Castleman (10:54)Yes.Right. So if it's a first interview, those are the three things. If it's a second interview, I include the discovery document with it. And whether you are going into a meeting and saying, have an idea to run by you, and you're starting your meeting that way, or you're sending a follow-up email, or you're going into your solutioning, or you're doing a demo, it doesn't matter. You always want to show up with your opinion. I'm the trusted advisor. I have an opinion.And that's what it is. And you could say, how does this land with you? Or this is what I'm discovering in the industry. How does this resonate with you? You're asking their opinion, but you're showing up with somewhere to start other than just with open-ended questions.KK Anderson (11:35)So let's, we could stay on this topic forever. Let's move on to the second topic though, relationship selling and the science of trust. And what's interesting is I was listening to a podcast just this morning about how, thanks to AI, right? And if you, I mean, you see it every day, you scroll LinkedIn and it's like emojis and dashes and it's just a bunch of chatty-bitty trash, noise. Let's call it noise. I wouldn't say all of it is trash, right?And so, and people are used to seeing that now. And so it's like the trust continuum is getting longer than it used to be. Like it used to be, like if you had a really slick website, you know somebody dropped 10 grand to build a really slick website or way more than that, right? You you used to be, and now an AI tool can turn that on and you know, 30 seconds flat. And so it's harder for people out there to know who they can trust and what's real and what's not real. And so,you teach that trust shows up in what we ask and in how we listen. you know, AI is making that harder. Like how, like, how do you balance that? Like how have you added that whole dynamic and that change into your teachings and your coaching?Cherilynn Castleman (12:41)So the first thing that I do is I ask my clients to pause for a second and tell me what is it about their client that they really care about. You have to give a damn about your client. There's no AI tool out there that's ever going to do that. And that's where you start. So if you really care about your client and you pause and say, what is it you care about? What is it that's important to them? And if you don't know, that's the first place you start, because that's what you have to start from.is you have to care about your client and what's important to them. Once you care about them, you can craft discovery questions that are high connection questions. And for example, and AI can help you do this. again, it's a tool to amplify and elevate you. So Dr. Jane Dutton at the University of Michigan has done a lot of research on high quality connections, HCQ. If you go in and ask AI,to reframe your discovery questions as high quality connection questions, what you're gonna do is you're gonna trigger what I like to call the love hormones. It is the oxytocin. It triggers the hormones that makes clients trust you, like you, want to do business with you. For example, I had a client who was in the financial services industry.And she used to ask her clients, tell me about your insurance policies or your insurance that you have. you how you feel when somebody asks you that. Her second appointment rate was around 17%. When she asked AI to refrain that, the question was, what is it about insurance that scares you? Can you see that just that little switch there makes somebody connect with you? I have another client, she's a career coach, and she used to say, tell me where you want to be in three to five years.And she was coaching women and AI suggested that she ask, when was the last time you cried at work? Because if you're a woman and you're going to look for a coach, it's probably because something is upsetting you to tears. And so you can ask little questions that just connect with people. have a client that she sells ⁓ data to, she sells data andAll of her clients are data scientists. And she said, Sherrilyn, data scientists don't have feelings. I can't ask you questions. And I said, hear me. Just for one week, let's just try it. She came back, and her clients now know her as a data therapist. Because she started asking them, what does it feel like when your company asks you to change the algorithm real quickly to come up with something? And this frustrates and angers, and they don't have the right data. And so her solution helps.resolve this and she's like now all my clients want to start with how they feel every time we meet. So she connects with them. She was able to renew more accounts than she ever has just by starting asking those types of questions. ask better discovery questions. Two of my favorite ones are either first or finance. What was it like for your first podcast, KK? Can you remember your very first podcast?KK Anderson (15:38)Yeah, the instant emotions, instantCherilynn Castleman (15:39)Okay,you see the emotion, you see what happens? Versus telling me about what's it like to have a podcast as a first question. Or if I asked you, Mark, what was your finest podcast? So first and finest questions are great connections to connect with people. You can make these very technical, very financial, very industry specific, but an AI can help you do that.KK Anderson (16:01)And I know Mark's gonna jump in here, but I gotta ask one more question. That's brilliant, by the way. I absolutely love that, first and finest. What about in prospecting, when you're trying to get the meeting? How are you breaking through the AI noise and building trust?Cherilynn Castleman (16:15)So just bottom line, offer value, offer value. Offer case studies, offer assessments, offer checklists. People are doing research. People want knowledge. And so I say leverage social proof. AI, anybody can go out in AI and say, I am a great coach, or I am a great podcaster, or I'm a great ⁓ strategist. Use.LinkedIn or whatever platform you use or emails or whatever, however you're doing your outbound to demonstrate that you can prove you do this. So offer social proof. Here's a case study where I helped a client like you do this. Here's a checklist that I use with my clients. Here's an assessment that you and your team might want to take. I have an AI assessment tool that I give out and I'm constantly saying, do you want to see where your team is for AI fluency? Take this AI fluency assessment. It is just a free tool.Here's a handout on how to prompt like a pro. Give value. Once you give the value, then I always say, if you have more questions about this, jump on my calendar. People know how to book meetings today. You don't have to book them. You can wake up every day with new clients on your calendar by offering value and insights. I ended up with ⁓ a huge client from a major retailer who said,KK Anderson (17:19)Yeah.Cherilynn Castleman (17:27)She just, she used all my free resources for six months and finally she's like, okay, now we gotta bring Sherrilyn in.And she just got on my calendar, so we want to hire you. It's just that quickly. so what it is. The trust is there. Here, give value, give value. Stop saying, hi, I read your post and let's have a meeting. never, don't ask for meetings. Just give value. And again, if you can't think of what to give away, AI can help you come up with tools, resources. You have case studies. I've got clients who've gotten job offers.and ended up earning six figures more than they ever had just by posting case studies on LinkedIn. Here's what I did with a client anonymously. Here's what I did with the top 10 airline. Here's how I helped them and the percentage I helped them did the case study. And I had a woman, the chief revenue officer called her and said, I want you to come in and be my head of sales ⁓ and went around HR and didn't even look at a resume. It's like, whatever you did with that client, I want you to do that for us.Because it's proof, it's a social proof, a lot helps you do that.Mark (18:29)Right on. Sherilyn, that's so you've taken us through some of the things that you want to say and things that add value to the full discussion early on. Let's talk a little bit about things that that you want to make sure you don't say or things that could actually trigger things like buyer defensiveness. And in general, like what two behaviors that do you see thatyou know, that you can then do the lower that threat and increase that openness right away.Cherilynn Castleman (19:01)So one of things that I call is don't be cringy, okay? There's so much information out there. It is so easy to take someone's information and abuse it. Don't do that. Just treat people the way you want to be treated. So number one is don't be cringy. Don't take the data, don't share somebody's information. Be respectful, be kind if given a choice betweenYou know, right and kind, choose kindness, just always be kind. I always say a fool with a tool is still a fool. There are fools out there with AI. Just because you have AI doesn't mean that you have to abuse it. Be ethical, stop and think about does this make sense? Is this ethical? The other thing is you will know if you're not triggering the trust and the love hormones, you're triggering their amygdala. And what happens when you trigger their amygdalais you see fight, flight, fawn, or freeze. If you're seeing any of those with your clients, they're fighting with you, they're arguing with you, they are freezing, they are not showing up, they are stalled, they are fawning. You ever ask a client a question and they sit there and they look at you? Well, they are fawning. just, you know, that's where they are. Or they just ghost you. Any of those say, okay, I've done this, it's time to stop, and AI is a great tool. I tell people,open a Word document, dictate just in your own voice what happened and ask AI to help you analyze it and say, what did I do wrong? What could I have done better? What made my client freeze? And learn from it. Another thing I see is that you mentioned it. So people try to sound ⁓ more intelligent or more technical. And how do you feel when you're around people with pretense? How do you feel when you go to that Thanksgiving or holiday mealand your in-laws or somebody has a girlfriend or boyfriend with them and they're just putting on airs. Everybody knows it. They can't stand it. Well, we don't want to do business with people like that. So the best way to be authentic and have your authentic voice come through is to just dictate. I use Word because it's not intimidating. I tell people just go into Word, hit the dictate and just dictate the email. Dictate the script. Dictate what you want to do and then drop it in. AI will use your words.they will use your intonations and you will sound like who you are. So those are a couple ways to avoid triggering the amygdala and have somebody go into fight flight freezer form for you.KK Anderson (21:27)I'm a big follower of Rory Vadin. I don't know if you know him. He runs Brand Builders Group and he wrote the book, Take the Stairs. And he says, my gosh, I feel like I've been quoting this every day. He says that in today's age, your humanness is now your uniqueness because everything else is,Cherilynn Castleman (21:34)Okay?KK Anderson (21:46)AI generated, like you have to leverage your humanness as your uniqueness. That's, that authenticity is still, is now even more than ever, you know, paramount. So buying groups are larger, they're complex. Very often, in these times, leaders who used to have decision-making authority now have to get the CFO involved and, and, and they're.Cherilynn Castleman (21:51)Yeah.It is.KK Anderson (22:09)more constrained than they've ever been. And so how are like, on this theme of building trust and authenticity and triggering the love hormones, I love that by the way, how do you do that when you've got like a buying group that's constantly changing? Like you're halfway through your sales process, you're on a, you have a meeting to negotiate or talk about terms of something and then next thing you know, boom, the CFO is there and you've never met him before. Like what are your kind of tips on that?Cherilynn Castleman (22:36)So a couple things. So first of all, I always ask at the beginning of any meeting, whoever's there, because like you said, buying committees are much larger. They used to be three to five people. Today they can be 12 to 18 people on a buying committee. Regardless of how large the buying committee is, at the very beginning, always go into the meeting asking each and every one, if you could get one thing out of this meeting, what do you want out of this meeting? Because...That may change the direction of the meeting. So you don't want to guess where the CFO, the CFO could be there because they're looking for operational efficiency, cost savings. They could be there because they're looking to drive revenue. They could be looking to improve the pipeline. You don't know why they're there. And so ask, and so I always ask, even if there are 15 people in the room, I'll take 15 minutes and say, real quickly, what's one thing you want at this meeting? And I note those down. Now I have the direction of the meeting. That's number one. Number two.Do your homework and do like I said, so do a POV for the chief marketing officer, do a POV for the CFO, do a POV so that you have those. So you're not changing the agenda, you're just changing the lens. And number three, executives want to talk about numbers. Develop your financial fluency. Understand what the key numbers are. Are they interested in what's driving revenue?and be able to tell stories. And the stories, again, is the insight, what is the number, what does this number mean, and where is this number going? How will it impact us in the future? So is it the cost of acquisition? Is it the cost, is it the life, the cost, the client life cost of, you know, of maintaining the lifetime value of that client? So.Know those numbers and be able to speak to them. And one other tip I always tell people when a CFO is in the room, take your numbers out three digits. Never say 50 million. Say 47.2 million. Know your numbers by three digits. CFOs will dismiss you if you round your numbers as a salesperson. So know your numbers. I'm sorry, what? Yeah, if you talk to CFOs, they'll tell you, I hate it when somebody says 15%.KK Anderson (24:33)That's a good tip.So that's a good tip.Cherilynn Castleman (24:42)Because nothing is exactly 15%. It's 14.7 or 15.2. So know your numbers, know them out three digits, know your numbers and tell financial stories with them where you can talk about the insight from the numbers, the context, and what it means to the business. And be able and have a financial point of view in your back pocket so that you're just changing the lens, you're not changing your agenda.Mark (25:07)Well, you know, Cheryl Lynn, that is also it's like speaking with someone who's bilingual and, you know, speaking in the language that they may be struggle with the whole time and maybe touching it for a second. You know, CFOs, are they are bilingual. And one of the items is numbers. It has to be. So that makes a lot of sense.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Mark Roberge joins KK Anderson and Mark Petruzzi to go deeper into what happens after product market fit is achieved and why going too fast too early can quietly break a business.Mark breaks down the transition from product market fit to go to market fit, explaining why these stages must be earned in sequence, not pursued in parallel. He outlines what real go to market readiness looks like, how to design a buyer centric sales system, and why retention and unit economics are the true signals of readiness to scale.The discussion also tackles sales process design, hiring profiles by stage, and the common mistakes founders make when front loading headcount after a fundraise. Mark closes by sharing a disciplined pacing model for growth and why predictable scaling beats vanity growth every time.What You’ll Learn:• Why product market fit must be proven before optimizing go to market execution• How retention serves as the strongest signal of long term product market fit• What defines go to market fit beyond revenue growth alone• The core components of a buyer centric go to market system• How to build a sales process that mirrors the buyer journey• The difference between discovery driven selling and pitch driven selling• How sales hiring profiles should change across product market fit, go to market fit, and growth stages• Why aggressive headcount expansion often leads to future layoffs• How pacing hiring and spend creates predictable and durable growthKey Topics:• Product market fit versus go to market fit• Retention as a leading indicator of success• Founder selling and unscalable early motions• Go to market system design• Ideal customer profile and buyer journey alignment• Discovery, qualification, and modern selling principles• Sales hiring by company stage• Scaling headcount responsibly• Unit economics and growth pacing modelsGuest Spotlight: Mark RobergeMark Roberge is the founding CRO of HubSpot, where he helped scale the company from zero to IPO. He is a Senior Lecturer at Harvard Business School, co-founder and managing partner at Stage 2 Capital, and author of the bestselling book The Sales Acceleration Formula. His latest book, The Science of Scaling, distills decades of research into a practical, stage specific roadmap for sustainable growth.Resources & Mentions:• Book: The Science of Scaling by Mark Roberge• Book: The Sales Acceleration Formula• Organization supported: McLean Hospital• Opportunity to download the first chapter via Mark’s website• Pre order The Science of Scaling with proceeds supporting mental health research🎧 Listen now and follow Selling the Cloud for more insights on building durable go to market engines and scaling the right way.Mark (00:31)I do wanna go deeper into the topic three here, go to market fit. Before I do that, Mark, is there anything you definitely just wanna cover?in addition to what we did already on product market fit. If not, I've got another question for you.Mark Roberge (00:44)Not at all. Like so far we have is like, you need to try product market fit first. We're quantifying that as retention in the long term and defining a lead indicator retention in the short term. And we created a framework for that. And the famous Paul Graham says, the founder of Y Combinator says, do unscalable things early. We're not worried about a scalable demand gen channel, a scalable sales process. We're doing founder selling. I don't even need to optimize price at this point. And I prefer to pay my salespeople with equity and not industry commission. Let's just get to success.KK Anderson (01:06)I mean, stop it.Mark Roberge (01:12)Once we have that, we move to go to market fit. We can't do them at the same time because you risk optimizing the go to market on the run market. If you don't prove product market fit first, but we moved to go to market fit and that just tells us that we can create this value profitably as measured by unit economics. And this is the stage where optimal quota price, demand, gen channel and sales process come into play. That's where we're at right now.Mark (01:32)Yeah, right on. Okay, topic three. So go to MarketFit. We want to go deeper into the process, the hiring, the demand, the pricing side, the compensation side. This is where I think a company gets to run and increase their productivity the fastest of any other stage. So you define go to MarketFit as generating customer success and revenue consistently and profitably.Starting with process, so starting with process, what should a codified repeatable sales process include at this stage? And where is the line between useful structure and a little bit of bureaucracy that slows deals at the end of the day?Mark Roberge (02:12)yeah, sure.Okay. Framing out one step. talk for a decade now around the go-to-market system design. This is what we teach at Harvard Business School. And so trying to move away from sales is just an art form. Let's give our salespeople a bunch of leads and let them do what they do best and go close business. Now, like we have a system for our finances. We have a system for our product development. We need a system for our go-to-market. So we call this go-to-market system design.The go-to-market system sits on top of obviously your first target market, your ICP, ideal customer profile. On top of that is a definition of how those buyers buy, the buyer journey. And on top of that is your sales process, which just helps them buy. There's two inputs to the system, the salespeople you hire and the demand that you create. And then the system runs by how you coach and pay them. And it spits out in sequence, sales activities like meetings and demos that lead toa forecast that lead to revenue. That's the system. And so within that system, Mark is a process. So it depends where you're like, at the very bottom is the ideal customer profile, which we can talk about. It's just really who we've proven to be able to sell successfully and make them successful. And so I mentioned like on top of that is a buyer journey. This is a part that's often skipped in sales process development. I think founders think that their sales process is a pitch deck.think like a good meeting is like, I went to the meeting and I got through all 27 of my slides about the problem I'm solving and how my product works and the awesome case studies we have. It went great. And there's a million studies that we know that shows that that is suboptimal selling. I can't find a study that says it's good. We know that in the first meeting, the less that the seller the better. And so what's happening in there isYou're qualifying and discovering. You're discovering what the buyer perceives as their biggest problems and how they're thinking about it before you tell them about your product. And you're qualifying to see if you can make them successful, if they're in a position to buy your product and be successful with it. That's our objective. And we can't do that unless we understand a buyer journey. So the buyer journey is really just like sequentially how the buyer comes to terms with purchasing your product.They don't wake up one day and be like, where's that contract? need to buy that product. They wake up one day saying, I have a major problem. And that's their first stage is it's just like the awareness stage is like, is this a problem? Is it a big problem? Yeah, it is a big problem. Why is it a big problem? How do I think about this problem? How do I frame this problem? Then they start considering solutions. how do I fix this problem? Do I delegate it to someone on my team? Do I hire a consulting company?Do I buy a software product? And then once they've decided how they're going to solve it, they choose a solution. I'm going to delegate it to Mary. I'm going to hire a seller in the cloud. I'm going to like, you know, I'm going to buy this software product. Right? So like, no matter what you do as a seller, that's what they're going to do. So if we understand that and frame it in that way, and we look at our sales process, not as going out andMark (04:45)ThankMark Roberge (05:01)pitching the world on everything we've built. But instead going out and discovering how people are perceiving this problem and qualifying whether we can help them and help them make a good purchase, that's modern selling. That's buyer-centric selling. with that in mind, the components of your sales process is your ICP definition, it's your buyer journey, and then it's how you take that, how do you run that first meeting, which is often called the discovery guide.And then once you've done your discovery and qualification, whether that's in five minutes or five meetings, you usually move on to some sort of a presentation process on how you explain how we're a fit. ⁓ then once we're, you know, hopefully the outcome of that is a purchase and we get to a onboarding and customer realization process. like, you know, obviously within there is negotiating contracts. It's like, there's a lot of different steps, but those are generally the components of the sales methodology.KK Anderson (05:52)You are preaching from the AGS playbook the framework that we talk about a lot at AGS, we call it the two sale mentality, which is taking, I feel like I say this every single day actually, whether you're selling Girl Scout cookies or you're selling multimillion dollar software.Mark Roberge (05:56)Yes, exactly. KK. I figured.Mark (05:57)⁓KK Anderson (06:12)every sale is really like two distinct sales. And the first one is getting the customer to articulate why they need to change. And it has nothing to do with what you're trying to sell. It is why, this is a problem, why is it expensive? why getting that and getting them to say it right. And the second sale is why you and why now. And, and one of the things that we do a lot of our competency assessments where we'll, we'll take a sales team and we'll give them,the assessment we use objective management group, and we'll be able to see that they're really low on that discovery, those competencies on the discovery end. And then the second sale, they're like aces. They're selling value is like 80%. They're really good at presentation approach. Like they're really good at selling the second sale. And that is like the immediate recognition of, my goodness, you know, our sales process is not matching our buyers journey.Mark Roberge (06:48)Yeah.Yes.KK Anderson (07:02)And that's, that's, love everything you just said there. So go ahead.Mark Roberge (07:05)KK. I mean, to your point, it's like you have to meet the seller where you are and that's what you all preach. It's just like, okay, we're selling Girl Scout cookies. Like, where are they at right now? Like, thing is like, are they even hungry or not? Like, if they're hungry, I'm gonna pitch them in a different way. I'm like, did you already have...KK Anderson (07:18)youMark Roberge (07:24)Lunch? Yes, I did. Would you like a treat then? Yes. Now I just have convince them that my Girl Scout cookie is better than the candy corn or the dark chocolate. It's a very different pitch versus if they're not even hungry, I can still sell them a box, but my pitch is different because it's like, are you going to be hungry later? And would you like to support a co- like, you know, it's just, it's a very different perception I'm leaning into. So, but like, you know, many founders come out of the gate. I've never sold before.and they just think this is about getting through the 27 slides.Mark (07:52)Yeah. And Mark, though, the one problem with that is that being hungry has nothing to do with when I eat a Girl Scout cookie. It just pretty much is when it's accessible and then I just start eating them. So complicating fact for our sellers.Mark Roberge (08:00)Yes.Right. Just looks really good.KK Anderson (08:06)So I have a quick question though before we keep going. This has just been so fascinating. So let's say you're in go-to-market fit, you've got your go-to-market system down. What are you looking for in those first five A's that you're hiring? How do you know you're gonna get someone that can sell to their sales process?Mark Roberge (08:28)And you're raising up another, I think important abstract point that we take away here, KK, which is at this point, we've got a clear definition of how we move through the readiness to scale from product market fit to go to market fit. eventually we get into the growth stage. What we haven't covered yet, and we have also discussed the go-to-market system, that this isn't an art form, just like we have a finance system and a product development system, we have a go-to-market system.And we've talked about the components of those, you know, our ideal customer profile, sales methodology, our sales hiring, our demand gen strategy, and KK is asking about the sales hiring component. Now what we haven't talked about this important point, which is the optimal design of those components is contextual. have discussed that a little bit. Like don't...Don't be bringing like an AI cyber product to market in 2025 and copy what HubSpot did in 2010, bringing a marketing product to small businesses. Like these optimal designs are contextual to the product you're selling, the buyer who's buying, and nuances of your own business in terms of stage and culture and all that kind of stuff. But another contextual driver is what stage we're in. Product, market, fit, go to market, fit, growth and moat. For each thing.including KK's question of the odd deal sales hire. I will tell you, if you are bringing a new product to market and you're in the product market fit phase, the absolute worst hire you can make is the number one salesperson at workday right now. The number one salesperson at workday is a genius. They are like the Michael Jordan of sales. They make millions of dollars a year.and they will destroy your company if you hire them during the product market fit phase. Because like when they joined Workday, they went through a month of training with all the objections, the entire playbook. Their manager was there coaching them through. You don't have any of that. You don't even know if you have the right product. Right, so like.The optimal hire at the product market fit phase is kind of like half account executive, meaning they can talk about commercials and do a little discovery and all that kind of stuff, but half product manager who can like reflect on the 10 conversations they had with the market this week, summarize the patterns and talk to engineers about them. That's what we need. When we move to go to market fit, which is specifically where KK is asking is, okay, we feel like we've got product market fit now.Now we need to build the process. So we need a couple salespeople probably, and one of them has to be really good at sales methodology development, which the number one rep at Workday has no clue how to do. Okay, so we need a process builder. And then finally, when we get on the growth phase, that's when we got the number one rep from Workday come in. If they're the right hire, again, like the optimal hire for Workday is probably different than the optimal hire for us. But at this point, it's more of as if I can quote the sales learning curve, a coin operated salesperson.that's going to take the pitch deck, it's going to take the comp plan and it's going to sign up a bunch of healthy customers for our business.Mark (11:16)Excellent. Okay, so let's move into our final topic here, growth and mode. So when teams set the growth and mode stage, you warn against front loading, hiring and pushing vanity growth. What pacing model do you like for headcount and program spend and which board level guardrails keep an honest quarter to quarter? And I'd like to really take this deep, just kind of...Mark Roberge (11:24)Mmm.Mark (11:39)reminding myself even how brilliant our audience is and how this is an area that they don't often get guidance on because most of these, whether it's podcasts or things that are written for sales leaders, doesn't go into the level of just execution and structure that I'd love for you to go into in the few minutes we have left here.Mark Roberge (12:03)andyeah, just to frame it, I every quarter I run into this story.You know, whether the company is at like a million trying to go to 10 or if they're at 10 trying to go to 100 or whatever.it's like, just had this one happen. Some founder was pitching me and they're like, yeah, we'd love to raise around and we're gonna go from 1 million to 6 million this year. And that's possible without headcount with like a PLG type distribution, but this wasn't a PLG distribution. I was like, how are you gonna do that? And they're like, well, we hired 15 salespeople last month.And I was like, How many salespeople did you have three months ago? And they said one.And I was like.They're like, what's wrong? I'm like, you're going to lay off 12 salespeople in like eight months. And that's just what I know why it happens. I know exactly why. Well, first off, why does this break? Okay, this breaks because you're just not ready to hire, ramp and enable that many salespeople that fast.Mark (12:47)without question.Mark Roberge (13:00)And there's no appreciation of what that takes. Let's just start with the recruiting muscle. Like I, let's, I don't have like raw data on this, but I know that if you are, generating for each hire sales hire, if you generate 40 candidates and screen 20 and interview 10 and hire one, that hire is going to be better than if you generated one candidate screened one person.interviewed one person and hired one person. It just is. And you just don't have the recruiting muscle to even attract that high of a quality talent bar and interview them. Nevermind you don't have the demand gen formula on how they're going to get meetings. And you also don't have a proven process and you don't have a management layer. Cause the average manager ratio right nowFor outside is six to one and for inside it's like eight to one that will probably change with AI, but we're not there yet. So there's just all these like very obvious reasons why this is going to fail. and so I know why they do it. It's just that they promised their VCs this massive valuation and the VCs bought it. So now they promised this massive growth rate and they just opened up Excel or a Google sheet and divided by the expected revenue divided by.the quotas and that's the number of reps they have to hire next month. And that's what they think of scale pattern is. And so let's go get more leads. So we triple the burn now. So anyway, the easy fix in our final two minutes here is don't think about scale at that point as a one-time event at the beginning of the year or after a fundraise and then absorption over the year of those reps. Think about it as a pace.KK Anderson (14:14)And that's why the CROs are saying, get us more leads.Mark Roberge (14:34)So don't think of it as like we're gonna hire 15 reps in January of 2026 and cross our fingers and try to hit our number. Think about it as we're gonna hire three reps a quarter.And so like, let me just, to finish it real quick is there's gonna be signals every month and every quarter that will tell us if we're going too fast or too slow. It's really the leading indicators of retention and the leading indicators of unit economics. And so if we make those three reps and we go through the ramp and like, we look at this two quarters later and it's like, wow, things are good. Then we go to six reps a quarter.And then it's like, if it breaks, we'll fix it. We'll know a way ahead of everyone else and we'll fix it. It might take a week. It may take a month. It may take a quarter, but we'll fix it. And then we'll go to 12 reps a quarter. And then we'll go to 20 reps a quarter. And then we're a unicorn. And we did it in a very predictable way.KK Anderson (15:18)That sounds amazing and like a strong game plan. If only it were that easy, right Mark? Real quick before we wrap up, I love that you're donating 100 % of the proceeds from this book to McLean Hospital. Why is that important to you? Tell us a little bit about.Mark Roberge (15:24)Exactly.Yeah, I just think like I don't know the last proceeds to an awesome for sales acceleration form at bill.org. That's another really big motivator for me writing a book. You know, you never want to do badness with tech. We always want to make the society better. never want to see that's that's the cause right there. That was awesome. So you never want to. Nice. I love it. I'm feeling the joy.Mark (15:49)got to ⁓KK Anderson (15:51)Yeah,that's my senior finishing his final.Mark Roberge (15:58)You neverwant to do badness with tech. I think like mental health has been a little bit of a negative ramification as we've gone through various variations and I've suffered dramatically myself. I've had severe anxiety and there's a stigma out there in the world around mental health. If you find out that a candidate is a cancer survivor, a job candidate, I think that elevates your perception of them. If you felt like they hadsevere depression and we're hospitalized for it, you have concerns and that's not right. They're both diseases. I've had that and I've been fortunate to be blessed with things that people perceive as successful so I can speak openly about this without massive concern. We're getting better with each generation ⁓ but we need to do even more and I think McLean is the global leader around that.In addition to helping with your skill pattern, just know that you're also helping with the great societal cause as well.KK Anderson (16:50)Well, that is incredible. And so the Science of Scaling is available for pre-order now. It releases on February 2nd. And Mark, if it's okay with you, we will leave a link in our show notes to where they can go to your website and they can download the first chapter. will get you there.Mark Roberge (17:01)Great.I'd loveMark (17:04)Yeah, and we should also includea link to just the donations at McLean. So we will add that as well.Mark Roberge (17:11)Yeah, and you can pre-order the book now if you want to do it that way. That'd be helpful. But thank you, Mark. Thank you, KK. It's an amazing platform to be a part of.KK Anderson (17:19)Thank you so much.Mark (17:19)Pleasure, thankyou as well, Mark.Mark Roberge (17:21)All right.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Mark Roberge, founding CRO at HubSpot and author of The Sales Acceleration Formula, to unpack why most companies scale at the wrong time and with the wrong signals. Mark introduces a stage-specific, data-driven framework for moving from product market fit to go to market fit, and explains why managing to readiness and retention beats chasing top-line revenue alone.Mark breaks down how founders and boards get trapped copying outdated playbooks, why product market fit is often misunderstood, and how to define it through value realization, not just revenue. He also shares a practical approach for finding a leading indicator of retention, then translating unit economics into clear operating KPIs that make scaling repeatable, profitable, and measurable.What You’ll Learn:Why scaling “scientifically” requires managing to readiness and retention, not just revenue growth.The difference between market-message fit and true product market fit.How to define product market fit using retention and value realization.How to build a leading indicator of retention using a simple “P percent do event every T time” framework.Why startups should delay scalable processes until product market fit is proven.What go to market fit actually means and how unit economics define it.How to translate LTV:CAC targets into practical KPIs like quota, close rates, and meeting volume.How to diagnose pipeline problems as readiness issues vs volume issues using conversion patterns across reps.Key Topics:The danger of copying borrowed playbooks from past unicornsReadiness pacing vs hiring based on fundraising timelinesProduct market fit as value creation, not revenue milestonesLeading indicators of retention and early customer success signalsGo to market fit and unit economics as the profitability testTurning unit economics into a repeatable go to market formulaQuick tests for pipeline issues: lead quality vs sales executionWhy small funnel improvements compound faster than single big swingsGuest Spotlight: Mark RobergeMark Roberge is the founding CRO at HubSpot, where he helped scale the company from zero to IPO. He is co-founder and managing partner at Stage 2 Capital, a Harvard Business School senior lecturer focused on sales and go-to-market strategy, and the best-selling author of The Sales Acceleration Formula. His newest book, The Science of Scaling, distills decades of research into a stage-specific roadmap for scaling with measurable readiness.Resources & Mentions:Book: The Science of Scaling (pre-order available)Book: The Sales Acceleration FormulaConcept: Product Market Fit vs Go to Market Fit vs Growth and MoatFramework: “P percent of customers do event every T time”Example: Slack’s activation benchmark (high-volume team messaging)SaaS Metrics: Retention, Leading Indicator of Retention, LTV:CAC, Payback PeriodReference: Winning by Design and compounding funnel improvement🎧 Follow Selling the Cloud for more episodes on building durable GTM systems, improving sales execution, and scaling revenue with confidence.Mark (00:00)Welcome to Selling the Cloud. Our guest today is Mark Roberge, founding CRO at HubSpot, who has helped lead the team from zero to IPO, a beautiful IPO. He's now the co-founder and managing partner at States2 Capital. He's a long time Harvard Business School professor of sales and entrepreneurship and go-to-market. And he's the best-selling author of the Sales Acceleration Formula. Mark's new book,the science of scaling distills 25 years of research into a stage specific data driven roadmap for moving from product market fit to go to market fit and ultimately to growth and mode. Personal note, Mark and I have known each other for a few years here and he is a great person to know as a friend and certainly as a business colleague with all the incredible success he's had throughout his career.So let's jump into the four topics we will cover today. also just to remind us all to make sure we cover a little bit of the amazing things that Mark does for McLean Hospital and for mental health and in general throughout our country and the world. Four topics, why scale scientifically? The failure patterns leaders repeat and how to replace borrowed playbooks.with a measurable readiness model. We're go deeper into product market fit, defining ICP, instrumenting a leading indicator of retention that proves value creation and learning how to run fast learning loops within your organization. And then what does it mean to go to market fit and deeper there, how process hiring, demand gen, pricing and compensation.evolve to make revenue consistent and profitable. And then the dream, the growth and most, when you're pacing head count, choosing scalable channels, raising price with confidence and appropriateness, and running a metrics cadence board, an approach that drives trust throughout the entire organization. Mark, thanks so much for joining us. Welcome to Selling the Cloud.Mark Roberge (02:14)Hey, thank you, Mark. Thanks, KK. Appreciate all the preparation in that wonderful intro.Mark (02:20)Beautiful, thank you, Mark. So yeah, topic one, why scale scientifically? We see teams copy a hot playbook, know, ramp up spend, and then they learn six months later in many cases that renewals are soft. So they kind of work on the first side of the equation, but they really don't do the right planning and approach in making sure that they're really able to build long-term client relationships. The science says,manage to readiness and retention, not just the top line. We all know that companies are feeling that for the first time in a number of years as we move from the pandemic to a little more of a specific focus on making sure the growth is there and also that we get to profitability with many of these early stage SaaS companies. So what changes when a founder manages to the readiness and retention?instead of just revenue only. And what is one decision you would stop immediately when the data is noisy and contains more clutter than signals?Mark Roberge (03:25)Yeah, there's a lot to unpack there. So really a lot of the origination of that question comes back to my time after HubSpot before starting stage two. I had this interesting five year period where a lot of this work was originated. ⁓ I honestly did not intend to write another book, but sometimes you do a speech or write an article that⁓ becomes something bigger, I suppose, and people want more. And then you can start to see the timeliness and also the abstraction by which some of the framing could be applied. And so at the time I was teaching full-time at HBS, but also had a lot of time to participate in the startup ecosystem. As a board member, angel investor, advisor, I basically chose one company every quarter.to spend a day a week with and help them build out their opening sales org. ⁓ At the same time, I was a senior advisor at BCG and I was working with these massive global conglomerates on launching new products to drive revenue, top line growth and EBITDA. And I just found in both situations that there was an unnecessarily high failure rate because this concept of like,when you were ready to scale, like you got your product, you got your beta, you got your whatever. And like the time that you were ready to scale and the pacing was not analyzed strategically well enough. And that's what made me kind of start to reflect on these things on like ⁓ how can you use your own data to figure that out? In the startup arena,Pretty much it was aligned with like when they raised capital. They just happened to convince ⁓ VC to give them some capital and then that was the time that they were ready to scale supposedly because they had capital. And the pacing was essentially like copy whatever some other unicorn that just went public. What did they do 10 years ago the year after they raised their seed round?Mark (05:47)ThanksMark Roberge (05:47)Which like is, it doesn't make any sense. The contextual differences are so, so off. And then on the, on the big company size, it was like, Hey, we're going to launch this new product and engineering, you build it. We're going to launch it at our customer event in nine months and marketing, change the website and get the collateral going and sales, train all the salespeople and customer support, get all your scripts ready. And then they launched and wasted tons of sales motions on a product that didn't haveproduct market fit. So it's like two different diagnoses with the same issue. And that's what led to the research and understanding why some of these went, some of the companies that I'd worked with did an IPO, a billion dollar outcome, some went bankrupt. And what was the difference in their plan? And it was this three sequence framework of product market fit, then go to market fit and growth and moat is whatOver last decade, we've been coaching people to at State Shoe Capital and my work at Harvard Business School with my founders to have a more scientific approach to that. Now, to your point, Mark, you're asking about a focus on customer value creation. And I said the first step is product market fit, which isn't like profound. Normally when you go into like a classroom and ask like a bunch of 30 year old founders, how do know when you're ready to scale?they'll say product market fit, which is a great answer and a term that didn't exist in the year 2000. I think it was popularized by Eric Reese at Lean Startup or Steve Blank. it's like, the term caused us to progress as entrepreneurs. It's fantastic. But what's weird right now is when you turn around and ask those hundred entrepreneurs, what is product market fit, you get a hundred different answers. And half of them are like correlated to revenue and customer count.we have product market fit when we hit a million in revenue. We have product market fit when we have a ton of inbound leads. We have product market fit when we have 15 customers. Mark KK, we all know that like great sellers can sell ice to Eskimos. They can. ⁓ But Eskimos don't need ice. You know, when you can sell, you have market message fit. It just means you're going out there, people get interested and they buy.Mark (08:02)Yeah. Yeah.Mark Roberge (08:12)But the essence of product market fit means that whatever you promised them came true. It means they realized the value. It means they succeed with your product. And in a lot of the businesses that we work in, ⁓ that's best quantified by customer retention. Right? So that's really the backstory mark on your question of like, you know, why do we have to root the opening stages here in customer value creation and retention as opposed to top line revenue growth?And it's just because like acquiring a customer, generating revenue is just a step in the end process ultimately to get to the value realization.Mark (08:51)Mark, you've given us so many things to unpack here and we're gonna dive into all of those. Before I do though, I wanna make sure I cover one item you mentioned there that really, so many things hit me, but this one hit me directly. This concept of like taking the last similar company that went public or had a great exit and trying to replicate the plan there. That would be like Harvard Neuroscience researchers.saying we're going to start a new study, but we're only going to use information of 10 years old or longer. We're not going to look at anything in the last 10 years or five years. We're going to start from there. And we all know where that would bring us, and really not bring us in.Mark Roberge (09:33)And even worse thanthat, Mark, it's not just like someone doing a neuro study today and copy what was done in 2015, but also that they were in the potiatry department in 2015. That's really the fair analogy is like the context is so different. It's like, oh, we are bringing, you know, a cyber security AI agent to finance departments today.Mark (09:46)Yeah, that's a better one.KK Anderson (09:47)youMark (10:02)Right.Yeah.Mark Roberge (10:03)So let's copy what HubSpot did in 2010 as they brought marketing software to landscapers.Mark (10:11)Perfect, that is perfect. That is much better, love it. All right, KK, let's take us on. We're going upward.Mark Roberge (10:12)Ha ha ha ha ha.KK Anderson (10:19)First of all, Mark, thank you so much for giving us a pre-read of your book. I can already tell that it's going to 100 % become a Bible in our industry. I was just reading the other day that I think just this year alone, there were something like 2000 AI businesses that started up. So it's very timely. A lot of founders.Mark Roberge (10:22)You bet, KK.KK Anderson (10:39)starting up and they're going to be going, as I was reading this, was thinking of our clients and thinking, I wonder if Mark will let me forward this onto our clients because it's just, it's on the mark every step of the way. ⁓ retention, you talk about retention, I couldn't agree more. But that's lagging, you that's a lagging indicator. And so we need an early signal thatMark Roberge (11:01)Yes.KK Anderson (11:05)that actually helps us kind of figure that out. And so you talk about in the you know, that the framework and figuring out that that leading indicator of retention. So what is likeTalk to me about how you figure that out. It's a chicken or an egg. You need revenue, but you need retention. How do you, in those early stages, how do you do that?Mark Roberge (11:19)Mm-hmm.Yeah, that'sa great tee up on where we left off here, KK. So, you know, what we've got so far is like, okay, that makes sense. I have my product and I need to figure out my first North Star. And we're arguing so far that like, don't get in front of your company and say, we got the product. Let's get to a million in revenue. We're saying we got the product. Let's get to dozens of customers using this and being successful. Let's have our percent conversion fromsign customer to successful customer would be really high. And we're measuring that with retention. To your point, KK, like we can't, like a lot of times we don't really have a sense of the retention on the customers we signed up this month for like a year. You know, like, or at least like many, many months. And that's just too much time in startup world. So we need to pull that measurement back to right now.And that's where we come up with the term leading indicator of retention. this is a term that's been talked about for 20 years. I think we probably framed it at State Shoe Capital in this way. I think in sort of the B2C to B PLG ecosystems, they talk about it. was like the aha moment, even in like some consumer environments. ⁓ and what this is essentially, what can we observe of our customers experience with our product in the first month? That if we observe it.In the long term, they'll be with us forever. And if we don't, they're a significant risk of churn. That's essentially the leading indicator of retention. And I go so far to, I haven't found that there's a universal right answer, like wow, Dow ratio, weekly active user to daily active user ratio, or like time and product, like lead, you know, there's all these different ways of measuring. We can speak about how to come up with it for you. And this is one of those cool, like creative.elements of entrepreneurship is like you get to find this unique thing about your business that's magical. But let's talk about a framework around it. We talk about as P percent of customers do event every T time. So P percent of customers do event every T time. So now we just have to work on three variables. All right. So Slack has a famously documented example. Eighty percent of their customers send 2000 team messages every month.Wonderful. Right, like just imagine like the early days of Slack, there's like 10 people in the room, mostly engineers and designers, and the CEO says, we did it, we're launching. The first goal is to get to a million in revenue. You can imagine like what actions occur. Higher salespeople generate tons of leads, but versus the first goal is to get 80 % of our customers to send 2000 team messages every month.It's just such a healthier foundation of the business. And hopefully through that narrative, we understand that like how we can pull this back to measure this on a week by week, month by month basis. So we can go at startup pace. Now to your point, KK, there's this tension between maximizing revenue and maximizing customer success. This is not necessarily the same.We certainly like, I bet if the CEO of Slack stood up and said, let's get to a million in revenue versus let's get 80 % of our customers to send 2000 T messages every month, they probably would have gotten a million dollars in revenue faster, but it's highly likely that that customer base and revenue base would not have been as healthy. And that in the former situation, they probably would have ended up with a churn rate somewhere between20 and 40 percent. But by rooting it in the leading indicator of attention, they end up with a churn rate of five to 10 percent. So if I had to choose between getting to a million in revenue in two quarters, but ending up with a 30 percent churn rate versus getting to a million in revenue in three quarters with five percent churn rate, that's a no brainer.the latter's better. And so it just helps us like find that trade off is like revenue growth is critical in the success measure of a business, but it has to be healthy. And we have to have the right guard rails in there to check it.Mark (16:00)Yeah, very, ⁓ very cool. So, okay, so when a CEO says we're missing our number and the first thing they do, CEOs, even boards, we need more leads, we need more pipeline. And you've said in the past that that's rarely the right fix. And it's often this issue is that the system isn't ready to convert the leads it already has. How do you quickly test if that's true?Mark Roberge (16:14)Haha. Yeah.Mark (16:30)And if you can give us a few examples, stories of some fast checks that you use or any founder can use that they can run this week to decide if the problem is readiness versus volume.Mark Roberge (16:37)Yeah.Yeah, okay. So that progresses our discussion to the next phase of go to market fit. Okay, so what we have is like, we have a clear understanding, duh, the first thing we need to do is to get product market fit. But we have a much clearer definition of what product market fit is. I think if you go into Wikipedia and Google, know, or JackGBT, you know, product market fit, you get like a lot of like, it's just a feeling you know.So hopefully now we've like really quantified it and we know what we need to achieve. However, when we're sitting here and it's like the third month in a row and we've closed 10 customers and nine out of 10 customers have hit their leading indicator of attention, we are calling success on product money fit. Are we ready to scale? No, because of what Mark just asked. All we've proven is that we're gonna sign up 10 customers and 90 % of them are gonna be super successful in our product.We're not ready to add 10 salespeople because we still have a lot of questions. Like what's the process? How do we feed them? ⁓ What's the quota? What's the price of the product? I actually don't care that much about these things during the product market fit phase. I just care that these people are taking it seriously and they see success. But like now we have to figure out all these things out, like what Mark is saying around like, is it the lead flow of the process? So we call that go to market fit.Right? like product market fit is I'm, I'm confident that when I sign up a customer, they're going to be successful. Go to market fit as I can do that profitably. Now, when we talk about profitability here, we're not talking like gap accounting profitability out of your income statement, because that accounts for like your entire business, your, your, your office, your, your C-suite. These are some of these things don't necessarily scale with revenue. We want to isolate profitability here.to what scales with revenue and we often in our world talk about that as unit economics. So we need good unit economics. There's a lot of ways to measure unit economics. People that are listening here, you might say LTV to CAC. Lifetime value divided by customer acquisition cost greater than three. That's been a popular one for the last 20 years in SaaS. You might say payback period. How much does it cost to acquire a customer divided by how much do they pay us every month? There's burn ratio.There's a bunch of different like you and economics. And so like, let's just talk about LTV to CAC greater than three. Technically when a salesperson joins your company, picture a 27 year old account executive joins your company. And like, what's my job? The perfect answer is to generate an LTV to CAC greater than three. That would cause a 27 year old account executives had to explode.Like what, is that? How do I do that? So that's where we have to do the work. And we've kind of implicitly done this is we have to algebraically extract that target back to more understandable KPIs. Like how much is the contract? What's the close rate on leads? ⁓ how many, how many leads, how many meetings per month do I need to generate? Right. So that's, that's, you know, we can do that algebraically, you know, to extract it back to like, okay.Cost per lead, number of leads, close rate on leads, et cetera, et And so that's what our go-to-market formula becomes. And now all these things become important of like, how much are we charging for this thing? ⁓ What is our sales process? Do we have a scalable demand gen channel? I don't need one during the product market phase. I do need one now. And that's really what Mark's asking about is trying to get that like math and formula down.KK Anderson (20:29)really what we're asking about terms of.Mark Roberge (20:34)⁓ So now we're like through that process, we've got three or four salespeople. We have a quota. You know, we're generating, each of them is like either each salesperson is either generating or marketing is helping or SDRs are helping, but they're ending up with like 10 new meetings a month to start off. But the close rate isn't high enough to get to their number. How do we know if it deletes or the sales? That's what Mark's asking. That's really tricky.⁓ when you're at greater scale, it's a much easier answer. And this is an area that very few boards look at, which is individual rep performance and conversion rate. Cause if I have a team of 10 and four salespeople are constantly achieving a conversion rate of 30 % on their qualified meetings and other salespeople are converting 10%, then I know this is a sales process issue.Now, put aside like to changes in territory and all that kind of stuff, you got to make it fair for everybody. But like that helps me understand that it's, it's some sort of lead, you know, it's a sales process issue versus if I have 10 salespeople and they all have relatively the same conversion, despite probable variances in their skill sets, then, ⁓ you know, we probably have a lead volume or quality issue. And that's where I'd look, but the bottom line is like,You kind of attack both. know, our friend, Jaco at Winning by Design, like famously talks about like, you can do a 10 % improvement in every stage of the funnel. Like it's like, it's not like we're either going to double lead flow or double lead conversion. We, let's attack both and we're probably not going to be able to double both, but we probably can increase one by 10 % and one by the 20 % and the cumulative impact is massive.Mark (22:31)Incredible, incredible.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Amy Weber joins KK Anderson and Mark Petruzzi to go deeper into how modern revenue leaders should think about AI, outreach, hiring, and coaching. Amy challenges traditional sales motions like cold outreach and rigid playbooks, and explains how AI should be used to personalize engagement, free up seller time, and enable more meaningful one on one conversations.The discussion also dives into assessment driven hiring and coaching, unpacking why resumes are a poor predictor of success, how to identify true talent signals, and how leaders can reduce friction by understanding identity, motivation, and communication styles across their teams. This episode is a practical guide for CROs who want to build revenue teams that perform, scale, and adapt in a more human centered, AI enabled world.What You’ll Learn:Why cold outreach is losing effectiveness and what CROs should prioritize insteadHow AI can personalize messaging without removing the seller’s individual voiceThe right way to define ICPs based on engagement and impact, not volumeWhy playbooks should act as flexible frameworks, not rigid rulesHow assessment driven hiring reveals true talent signals beyond resumesKey differences between hunter, farmer, and CSM profiles and why misalignment hurts performanceHow leaders can reduce friction between managers and sellers through better coaching and communicationWhy understanding identity, emotional resonance, and motivation matters more than process aloneKey Topics:AI powered personalization in sales outreachICP refinement and engaged account strategiesFreeing up seller time for high value conversationsAssessment driven hiring and role fitCoaching frameworks for sales managers and leadersManaging conflict between sales leaders and individual contributorsIdentity based leadership and communication stylesPositive intelligence and managing saboteurs in high performing teamsGuest Spotlight: Amy WeberAmy Weber is a strategic advisor to growth stage and enterprise revenue teams and the founder of VEDA Sales Consulting. She specializes in aligning people, process, and purpose to drive measurable revenue outcomes. Amy works closely with CROs and executive teams to improve hiring, coaching, and leadership effectiveness using assessment driven insights and practical operating frameworks.🎧 Listen now and follow Selling the Cloud for more conversations on building modern, revenue focused GTM teams in the age of AI.KK Anderson (00:31)if I could kind of double click on that a little bit, what's one of your favorite starting points? Like if you're gonna recommend to a CRO, I know it's obviously where they wanna focus, but what are just some examples of where you would have them start first?Amy Weber (00:46)Yeah. So I think that of the first pieces of it is that, look, I don't think cold emails work anymore. I don't think cold outreach works anymore. think it's figure out your ICP who is already engaged and then how do you automate some outreach to them in a way that makes is impactful to them. So using AI tools to be able to take that outreach and instead of a ⁓ rep,doing what you're saying, making a thousand emails a week or a hundred calls, kind of automating that outreach, whether it's through, and maybe it's a multifaceted approach, right? Getting more information out on LinkedIn. One of the things that I hated when I worked for big companies was that they wanted, like they wanted to silence your individual voice and they wanted it all to be very static and documented. Well, then you're getting the same message over and over again.Mark Petruzzi (01:28)Hmm.Amy Weber (01:34)Using AI to take that static message, but to personalize it based upon who you're going after is a real tool and trick today. And so you're getting out in front of more people and you're getting your message out in more ways. The second part is, like I said, figuring out what your ICP is and what's impactful for them. And then leveraging those AI tools to kind of create a outreach that is not generic.and is not just cold, it's taking the people that you know today that you want to talk to and making it more important to them, you know, in that capacity. ⁓an understanding really kind of that the goal is to free up more time for them to meet with these individuals one-on-one. So automating the things that are getting your message out in a content personalized manner so that the AEs and leadership is getting freed up time so that they can actually engage one-on-one because look,The other thing I think is ridiculous, again, I may get in trouble for saying it, a playbook should just be a framework. If you think there's one answer to how to be successful in sales, you're going to fail. Because you have to understand the client and their business need, and not every need is the same. It doesn't matter if you're selling the same product.or the same service, it's how that product or service is going to impact that end user in a new way. And you can only do that if you actually get in front of them and understand what their business or challenge or issue is, how that solution is going to play.Mark Petruzzi (03:12)Great, well let's move to topic three, which is assessment-driven hiring and coaching. And again, something that's near and dear to AGS's heart and what we do, and we're learning a lot as we've gotten to know Amy ⁓ over the past couple months. So how should a CRO use assessment insights wisely and the most productively? Who do they need to assess?Amy Weber (03:35)Yes.Mark Petruzzi (03:36)what two to three signals matter for this role and how do those signals translate into the right interview questions and then most importantly, the coaching plan for that new hire.Amy Weber (03:48)Yeah, like I said, I'm a huge proponent of this because I do think we hire people or we have historically hired people based upon their resumes. That might be the worst possible thing you could ever do. Now, the resume might get you into the door to talk to the recruiter, to the team or get into the interview process, but it shouldn't be indicative of how successful you're going to be in this role. 85 % of millennials will tell you that they are in the wrong role, but they're afraid to change.And so they're just going to keep taking jobs because that's what they did in the past. It doesn't mean that they're in the right role. And scientifically, 1 % of your past success will dictate your future success. So when we do this, we assess people in three different ways. We assess them during the interview process. So you get through the initial screening to say, ⁓ I think they might be a good fit.What are their really, their talent signals? And you're not gonna figure that out just by interviewing them. Because so many people will interview someone and say, I think there'll be a good culture fit. I like them. I'd like to have a drink with them. Great. That means they're a good person. But are they, do they have the right skills to do the role? Right? I'm glad you like them, but are they going to fit the role? like, you know, talking about the hunter, a hunter needs to have a really high driveand desire to go out and be with people and meet people and drive impact and outcomes. Whereas a CSM needs to have a really high precision to say that I can execute on a vision and I can track and make sure that all of the steps are going, that need to be in place for this person to, their rollout to happen in the right timeframe or their,you know, we're engaging the right individuals from their team on a weekly or bi-weekly basis to ensure that everything is going as planned. Those are different people. so understanding those key characteristics, even your emotional resonance, how you deal ⁓ with emotions. And if somebody has, and we can test for that, if somebody has a really high ER and you put them in a hunting role,it might take them a long time if they lose a deal to deal with the fact that they lost that deal. If they have a lower ER, they're going to be like, okay, I lost it. I can move forward to the next piece. And then we customize through the tools that we work with the interview questions to really pull out those key characteristics and those key identity markers because they're different based upon what you're looking for. From there,Once you've hired the people and you've got your team, then you need to determine who your leader is and kind of what their core identity is and how they individually need to understand managing people. That's going to reduce the conflict. And we build out custom management plans for each of those individuals. So we say either here's your team, here's all your benefits. Here's how you should look at your team overarchingly. And then if they have specificissues with a certain individual, whether they're like, I don't feel like I'm getting the most out of them, or we've got some sort ofconflict for the use of a better word. How do I address this? Because I really want this person to stay and be successful. We build out specific plans for them in that regard.KK Anderson (06:58)Yeah. Well, and kind of where my head is going is around that conflict, like what you just said. Like there is, and even kind of pivoting more toward that coaching aspect of making sure that the new hire is successful. There's very often just natural friction, especially in the sales world, right? When you have sellers who are entrepreneurial,you get a lot of friction between sales managers and individual contributors. And like some things that come to mind are, a sales manager may, be insisting that you're multi-threading and talking to different stakeholders in a prospect where the individual contributor is like, no, I have a champion. I've got this under control. I don't want to go around them. So deal strategy, right. Or, or there might be, like communication style issues, right. Where.Amy Weber (07:38)Correct.KK Anderson (07:43)A manager is wanting to review the pipeline and have those laborious, sounds like a broken record meetings every single week. And the individual contributors like would rather just, you know, eat nails. And so like when you have, when you have this kind of friction, like what are, are some ways that you can, you know, that you help alleviate it? Like what's it, walk me through like what you would do.you know, trying to.Amy Weber (08:05)Yeah. So,like I said, number one, when I work with clients, I figure out, I do these assessments and I figure out kind of who the people are that we're working with and what their, what their identities are and then how those are impactful to each other. Right. Because you're right. Look, when you are a driver and you're going out and you've got maybe a manager that was really successful and they want you to do it the way they did it, you're going to have conflict because they have to understand that.that ⁓ they can give an outline or framework, but that if they are trying to say, mandating that you have to do it in a certain way, you're gonna probably lose some of your top performers because those top performers are going to, they thrive in chaos. They're going to figure out the best way to work. And they do maybe have that champion and understand the relationship better. It again is going back and looking at opportunities as individuals, not as⁓ just repeating the same process over and over again. So I figure that out and then I go in and figure out where the tension lies. Is the tension a communications issue? Is the tension a conflict of you've got two really strong opinions and so they're just butting heads? And then it's not so much about changing either one of them, but it's changing how they communicate with each other.It's changing the language. Honestly, what we talk about in business works in parenting, right? You can have two different children that are very different people and maybe how you communicate to one is going to be different than how you communicate to the other. The same is true in the workplace. And you have to think about it from that perspective. If you've got someone who does have a really high empathy level,and so that means they're going to take everything in more personally, then you have to address that problem or that conflict with them in a different way than somebody who has a really low one and you can say, hey, I don't like how you did that change, right? Because they're not gonna take it personal. So we go in and we try to figure out really each of those core components.and then create frameworks for those leaders and those executive leaders accordingly so that they know based upon their core how they should address the different people on their team. And like, I don't think that you should have a team of people who are just clones of yourself. I think that diversity is important, but it's understanding how to manage that diverse environment and where based upon that diversity.you may sometimes falter. We learn as much from our failures or maybe more than we do from our successes. And so if we fall down with somebody, we need to figure out how to pick it back up. And that's just educating ourselves on who we are and who those people are as well. I'm a huge proponent of positive intelligence. I don't know if you know anything about that. Positive intelligence, it's a book, it's been a course.And it says that all of us have ⁓ our saboteurs and, you know, high achiever. Everybody's got the judge and it's trying to figure out how you get to your sage. And that's what we try to coach people on is that it is okay to be hard charging, but understand that you need to take that pause before you just treat everybody the same way.understand who you're talking to before you make that comment. That works, by the way, with your clients as well.So it's just a framework and figuring out where to go and what it's signaling. And then like I said, you also may determine that you just have the wrong people in the wrong roles, be that the individual contributor or the leader.Mark Petruzzi (11:27)Yeah, very good stuff. Cool, all right, well let's move into our final segment here and that is our rapid fire. So real quickly, first product or service you ever sold.Amy Weber (11:38)long distance and you can put an asterisk there for anyone under a certain age to tell them what that means.Mark Petruzzi (11:42)Exactly.KK Anderson (11:43)Likelong distance phones, like services.Amy Weber (11:44)Yep,door to door to evaluate people's ⁓ long distance bill and sell them on a lower cost solution. It was hilarious and it was really good at it and it was probably I had no.Yes, long distance for businesses. It did.KK Anderson (12:03)It started you on your career in sales, that's for sure.Yeah. Okay. So who is a, like a chief revenue officer or a CEO that you love to follow?Amy Weber (12:11)I follow several, lots of them, and some people I've worked for in the past and other people. When I sit down and think about it, there's a few that come to mind. Like, think Mark Cuban is phenomenally interesting to listen to, just the way that he drives companies forward and as a CEO and his mindset and the fact that he is very open to giving his opinion. I'm going to mess up his name, but Satya Nadella at Microsoft, I think is really fascinating today because heHe has taken a very different approach. worked for Microsoft and trust me, he is a very different leader than the leaders I had when I was there, because I think he looks at it from a people perspective. Alicia Tillman at Delta, she's more of a CMO, but she's taken a real people approach as well. So I think her conversation is interesting. And then there's a guy now that's the CEO of a water company that is very active on social media. name is Jay Williams.And he kills me because a lot of what he puts out there is not related to business at all, but he is increasing his following and his brand in such a creative way. I mean, it's water and people are engaging with him at huge rates. you know, I was in Nashville recently and it's kind of like what the guys at Liquid Death did.KK Anderson (13:26)Yeah.Mark Petruzzi (13:26)Excellent. All right, one leadership habit more sales leaders should practice.KK Anderson (13:30)What a great conversation.Mark Petruzzi (13:32)Excellent, thank you again, Amy.KK Anderson (13:34)All right, and thanks to our amazing audience.Mark Petruzzi (13:36)Of course.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark and KK sit down with Amy Weber, founder of Vetta Sales Consulting and strategic advisor to GrowthStage and Enterprise revenue teams. Amy specializes in aligning people, process, and purpose so strategy translates into real performance. She shares why many revenue organizations stall not because of tools or plans, but because of role confusion, misaligned talent, and leadership gaps.Amy breaks down how to design roles that reflect reality, how to hire and coach based on true behavioral identity, and why companies must stop promoting top reps into leadership without assessing desire and capability. She also explains how AI can power a stronger customer experience by removing low value tasks and freeing sellers to focus on discovery, executive access, and relationship building.This conversation hits the core of modern revenue growth: the right people in the right roles, operating in a healthy, human selling system.What You’ll Learn:The three fastest tells that your people or role design are brokenHow to distinguish hunters, farmers, and CSMs without relying on personality stereotypesWhy top performers burn out in “Frankenstein” job descriptionsHow to test for core sales behaviors using identity based assessmentWhy leadership is not a reward and should not be given based on quota attainmentHow AI can support human selling by automating research, follow up, and content prepHow to create operating rhythms that ensure AI actually frees time, not adds more dashboardsKey Topics:Role design and talent fit for revenue teamsBehavioral identity vs personality in hiringMisaligned promotions and the manager IC divideWhy customer success is undervalued and misunderstoodModern client experience and relationship driven sellingPractical, tool agnostic ways to use AI for research and personalizationOperating cadence changes that make AI adoption realAvoiding analysis paralysis when implementing new technologiesGuest Spotlight: Amy WeberAmy Weber is the founder of Vetta Sales Consulting and an advisor to high growth revenue organizations. She helps CROs and CEOs fix the people's side of revenue through role clarity, talent fit, and leadership development. Her work replaces outdated activity goals with clear rhythms and systems that actually change behavior, increase productivity, and create healthier teams. Amy also advises organizations building AI for talent decisions.Resources and Mentions:Cisco sales story on customer experienceMedium content repurposing with LLMsTalent identity and psychometric assessmentsOperating rhythms for revenue teamsRelationship led selling frameworks🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders driving the future of revenue. Subscribe wherever you get your podcasts.Mark Petruzzi (00:31)Welcome to Selling the Cloud podcast. Today we're joined by Amy Weber, a strategic advisor to GrowthState, Stage and Enterprise Revenue teams and the founder of VEDA Sales Consulting. Amy's work centers on aligning people, process and purpose. So strategy turns into the most powerful performance. She's known for helping CROs fix the people side of revenue, writing roles that match reality, hiring for fit.not just overall pedigree, and coaching managers to run simple weekly systems that actually change behavior and drive the highest level of productivity. Amy Kevin Lee serves as a strategic advisor to organizations building useful AI for people decisions. And she's led transformations that replaced the old fashioned ad hoc activity goals with clear operating rhythms.This allows there to be a freeing up of more human time for discovery, executive access, and relationship building. Her lens is tool agnostic and outcomes first. What should change on Monday morning and how do we start measuring it? We'll cover three topics today. People and with the focus on them being greater than tools, roles, fit, and real leadership.Why growth stalls when the wrong people sit in the wrong roles, and how leaders create clarity and accountability. AI plus a strong experience culture, freeing time for human selling, using AI to take low value work off the team's plate so sellers could spend more time with customers, and assessment-driven hiring and coaching, really tool agnostic but practical ways to use talentdata to hire coach and fix manager IC friction without turning it into a tech commercial. So most people who know us and are on this ⁓ podcast with us every week know that's all things that are near and dear to KK and my heart and to what we do at AGS as well. So in another way, we're bringing an opportunity to get a...a different perspective or another perspective, but I think we're going to agree on a lot of things here based on the stuff we know about Amy already. So Amy, thank you so much for joining us and welcome to Selling the Cloud.Amy Weber (02:43)Thank you both. really appreciate it and I'm looking forward to the conversation today.Mark Petruzzi (02:46)Excellent. Cool. So first question, lots of teams have the right strategy and plenty of software, but the people role fit isn't right and results off install. As a CRO, what are the three fastest tells that role design or fit is the real problem and that it's not the plan or the overall tech as well?Amy Weber (03:04)Yeah, it's great because everybody steps back and they're like, what tool can I put in place? What new playbook can I roll out? What's our strategy? But they forget about the fact that the number one thing that they need to determine is do we have the right people in place and are we managing them correctly? So number one is, are your top performers miserable? Are they out there driving sales, but they are updating their LinkedIn? They're telling you that they're unhappy. They show up and they are on Monday mornings.you can just see that the energy is drained out of them. Because they're driven individuals, they're going to go out and they're high achievers, they're going to go focus on success, but you can just see that they're deflated. So number one, top performers are just absolutely miserable. You the second thing I see is that you see the same mistakes over and over again. You're providing individual or team coaching. You're giving a...guidance, you're rolling the playbook out, but you're seeing that the mistakes are just compounding. That's just repeating themselves. And then really the third one is we're promoting people incorrectly. So promotions are causing problems. I tell people that leadership is not a reward, it's a responsibility. So we're taking top sales performers. We're like, oh my God, they killed it. They were 300 % of their number again, and they've made club every year. So we're going to make them the manager.a director. And they may be a phenomenal sales individual, but they have both not the desire nor the actual skills to lead a team. And that desire component is really important. You could be the best sales rep in the world, but really not have the desire to want to manage, train, create empathy, you know, in other situations. So for me, those are the three glaring ones that I see that when I go into organizations, I'm like,They say we can't grow or we're stagnant or we've got a lot of they say culture problems. It's it's not culture. It's people you people problemsKK Anderson (04:56)That's so interesting. what we see with our clients and sales organizations is that the quote unquote job description for the sales roles, I mean, they're conflicting. You've got this mandate to go out and hunt and prospect and build new business, must hunt. And yet they need to be also an account manager and running projects and programs and keeping the relationship of the...keeping everybody happy, right? And then, you know, some of them are also part-time analysts. And so it's just like a lot of conflicting roles. And I think that probably leads to what you described with that burnout almost, right?Amy Weber (05:37)Exactly.I call those Frankenstein job descriptions because they're like, I want a self-starter who's a good collaborator. And I'm like, what? You know, I need somebody who's going to really go out and drive revenue and has the executive relationship that's good at doing the research. OK, well.KK Anderson (05:41)Yes.Mark Petruzzi (05:46)Ha!Amy Weber (05:54)They're just, they're putting together these, what they think the requirements are and they really need to hire for the key components of what they're looking for. A hunter role is different than a farmer role. A customer success manager, and sadly we see that get cut from companies all the time. It is cheaper to maintain a good client than it is to find a new one. And I could repeat that over and over again, but people don't understand it. And they're like, well, they,Accounting executives as Hunter can be the CSM as well. You know what? They probably don't have the right skills because a good CSM is going to be somebody who really wants to be a collaborator, can hide behind the scenes, is very detail oriented, likes to follow a process, right? A good salesperson thrives in chaos. There's somebody who goes out and can just drive opportunities because they're listening to the business needs.and they can kind of pivot and determine how to pitch the right solution, but they're not following a step one, step two, step three mentality that a good CSM really needs to do. That's why I don't think, and I get in trouble all the time, and I'm going to say it and just throw it out there. Most SDRs are not salespeople and should not report to sales. SDRs are operations people. They are good at following a script and setting an appointment, but they're not doing the key coreKK Anderson (06:53)Right.Amy Weber (07:10)attributes of sales, is listening to the business problem and creating a solution.KK Anderson (07:14)Right. So I follow up on that real quick though. So once we get those kind of roles rewritten and we figure out like what are the real core behaviors as you said, that that job demands, do you have any tricks on how to like test for those behaviors in interviews and specifically, know, a hunter, right? It's a very hard role to hire for. And they may think, for example, thatMark Petruzzi (07:15)Great.KK Anderson (07:38)because this person is an extrovert that they're gonna be really good at picking up the phone and making connections and calling people, not necessarily true. So talk to our audience, if you will, a little bit about how do you like kind test for behaviors.Amy Weber (07:50)soI actually do test and I leverage psychometric analysis tools in that regard to really determine people's core identities. So the irony is this, look, I've been in these roles 30 plus years now, which I like to tell people that means I was 12 when I started because I sadly do not want to acknowledge how much older I've gotten. But ⁓ we took this personality test from the time I was in college.KK Anderson (08:07)That's right. You were.Amy Weber (08:16)and your personality changes as you grow and as you meet new people and things, but your core identity doesn't. So somebody who is a self-starter should really have a high drive of influence. And there are specific questions that you can ask during an interview and or a promotion stage and or as a sales leader to determine if they have that true drive, right? If somebody is saying, talking about the influence that they have or that theythat they've had in a deal or with a specific executive, you know that they're a high influence type individual ⁓ versus someone who says, work really well and I like when people bring ideas and I like to brainstorm those and I like to work in a group to determine that. That is not somebody who's going to go out and be impactful from an influence perspective. They're going to be good at working behind the scenes. Someone who's a good influence person is going to kind ofbe a strategic thinker and then you need those people with the lower influence to implement that strategic vision. The same is true on like, I don't care if they're an introvert or an extrovert. Some of my favorite people I know are incredible introverts that can turn on that extroversion because they're passionate about the solution or the product or the service that they're providing. But once they've done that, then they...they'd master that Irish goodbye, they can just leave. They don't like that small talk or that networking where, it doesn't matter. You don't have to be that extrovert, but there are, there are solutions, there are tests that you can take that really get to the core of who you are. And then there are interview questions that we coach people on asking to really understand kind of where they are from a influence, sociability, consistency and precision perspective.Mark Petruzzi (09:35)Ha ha.Amy Weber (09:56)to model out who makes sense in these different roles. Like I said, I had a young lady who worked for me. She was fabulous. And her previous leader was like, I would fire her. And I'm like, okay. So I interviewed her and when I was bringing her onto the team and I laughed because they had her a ⁓ hunting role. She was a farmer. She was very precise. She was very good at maintaining clients and getting them to buy new products.She did not like the aspect of going out and building new relationships every day. She wanted to take a relationship and grow it. That is a farmer versus a hunter. And you have to understand as a company, what are you really looking for and where are you putting those people? And then coaching them and managing them per their identities versus everybody's the same.Mark Petruzzi (10:40)Amy, those are all great insights and I'm going to bring us back to a point you made earlier where you were saying how, there's all these companies that are cutting customer success and the value and the cost of driving a new deal, finding a new one, hunting a new one versus the concept of just, you know, keeping clients, keeping them happy, keeping them expanding.I've always, I am always saying that to my clients as well. And there's a couple thoughts I have behind that. And in the first book that I wrote, Selling the Cloud, I have a whole chapter around how in general, I believe women are better sales reps and sales leaders than men on average. That's just the nurturing.Amy Weber (11:07)Mm-hmm.Mark Petruzzi (11:25)perspective, the empathy connection, all those things are so valuable. Even grit, I think women have more grit on average than most men I know, including myself. So with that in mind, this concept of like hunting being more valuable than farming or customer success is something I fight about every day. And I think it's a bit of a machismo type of mindset that we all know.most CROs or sales leaders over the last 20, 30 years are men, not women. And luckily and thankfully, that's changing. But when we look at that concept, it all kind of comes down, guess, this. Nobody celebrates the person who comes back with a, a bucket of fruit or nuts and something they just cultivated and brought back into a village.but the person who has a deer or some other animal on their shoulders and they're carrying it back, they get a big celebration when that happens. So how do you think you change that mindset when it really comes down to it? How do you make companies just understand that it doesn't matter. A dollar of revenue is a dollar of revenue.Amy Weber (12:34)Yeah, you know, I've got a specific story I'll tell you. Back when I was a young sales rep, I walked into an account, literally walked into it. The receptionist wasn't there and I just wanted to figure out what the company was doing. I'd never heard of them. And I met the CEO. Luckily, he didn't just pitch me out of the office, which he could have because I was well.I had inappropriately entered their building. And I ended up having this great conversation with him. He's still a friend of mine to this day, so I think it's hilarious because I just walked in and knocked on his door and I said, hey, what do you do here? And when he got done laughing at me, he's like, how did you get here? And I said, well, no one was at the front desk. But the long and the short of the story is that they were a growing company and they were a small business when I first met them and they are now a massive provider of technology.Mark Petruzzi (12:54)Yeah.KK Anderson (12:54)That'smy thing.Mark Petruzzi (13:05)youAmy Weber (13:16)and he's no longer the CEO there, but across the country, across North America. And they said, I was working for Cisco at the time and they're like, you're too big, you're too expensive, we won't need you. And I said, okay, that's your opinion, but really I just wanna hear what you do. And they appreciated kind of the fact that I just wanted to learn. So they invited me into a technical meeting. Long story short, they had zero Cisco when I took them on.When I left Cisco all those years later, they went from zero to 95 % of their footprint was in our product. they, whereas they were never going to spend any money on us, 95%. And it was because we listened to them and we helped them determine ways in which they could leverage the technology. They became a reference of look out. They were a multimillion dollar customer for us. Right. When I left Cisco and I was no longer the rep at that time, I had moved into leadership and other aspects.But I had stayed engaged with them. People did not keep that relationship going. And they moved off of all of that platform. So they went from zero to 95 to back to almost nothing again, because I had built the relationship, I had listened to them, but I had supported them not just when we needed a PO. I had supported them when they were growing or they had ideas and we went and talked. It wasn't about justcelebrating their success when they were spending money with us, it was helping them figure out what their plan was for the future. And that's why I say the number one skill in sales is listening. And then it's that customer engagement. I'm kind of, you know, I talk to people about, getting back to that point where that client experience is going to be the key. And whether you are a retailer or atechnology company or a restaurant. I was down in Miami for a holiday weekend recently and we went to this fabulous restaurant and it was a Michelin star place and they could only seat 16 people at one time. And you're having this curated prefix menu experience. And I whisper basically to my significant other, I'm a little chilly. And within seconds, cashmere pashmina was draped over my shoulders.That is a client experience. I never said a word. And that is what we need to take to our companies, that idea that when we're talking to them, that we understand their needs, even if it's just that they're cold. Right? And so it's really just taking that step back and figuring out kind of what we need. And what we need is client customer experience to go out and ensurethe client is continually taking care of. We need the account type reps that aren't out for the big kill, that they're not looking for the next elephant, but that they understand that they can take their current client and continuously grow them. And then you still need the hunters that are gonna go out and find new business.KK Anderson (16:00)So I love that story. And it's actually the perfect segue into our next topic, talking about AI and really kind of this customer experience culture that you're talking about. And what you described, is just so human. And that is the human part of selling that will never be replaced by AI.Right? It will never, it will never be replaced. Now that said, that's, that's what's critical. And you're right. and we talk about this a lot on our podcast. The pendulum has swung from everything being process heavy tool, heavy, you know, send 5,000 emails a day, make 100 calls a day, being able to use technology to just,increased productivity, even if it's not productive, right? Or effective, all the way back to, wait a second, people buy from people they trust and relationships are what matter. And Mark, maybe that's why women tend to be so effective in sales roles because that's paramount, you know, in our hearts and in our minds is that relationship like you described.Amy Weber (16:53)Correct.KK Anderson (17:06)Knowing and appreciating and 1000 % agreeing that the relationship and the human activities and the experience are paramount. How can a salesperson use AI for the other things? Like what are some things, specific tasks that they can do that you've seen your customer or clients doing to give them the time to have that human experience?Amy Weber (17:23)Yeah. ⁓Yeah, it's great questions and all of that I agree with as well, right? I think that one of it is ⁓ that research and account prep. I don't want a rep to ever go into a meeting that they don't know the answer to the questions that they're asking, right? They should have done, there's so much information out there, but instead of them spending time, I mean, I remember being a young rep reading when it was a publicly traded company, I was reading the financial reports. And thankfully I have a degree thattaught me how to do that, but a lot of people don't, right? And so using AI to do that research and that account prep to really build out kind of a portfolio and the tools are so good at that and kind of reaching out across all the different platforms, know, is the person you're meeting with, are they active on LinkedIn or socials or are there blog posts? What's interesting? So that you build that connection. So that's one. And then being able to take that information andpersonalize the content that you're sending back to them. Whether it's the communication from you speaking to them, whether it's the emails that you're sending, whether it's you you see an interesting article that you think would be good for them, that content personalization. And then post meeting intelligence work. So being able to automate all of that. So that you're not spending time doing the mundane tasks of the follow-up.and those repetitive outreach type solutions, automating that through AI and having that process put into place. One of my clients is actually, they've ⁓ got an individual that has been writing on Medium for like the last 11 years. And so his voice is really interesting. And he is, instead of him continually having to write and post because he's really busy,they're now using, they built in their, LLM to be able to go out and kind of pull segments from what he said in the past so that they can then automate it to repost it on the social channels in different ways. And that's fascinating because you're taking his intellectual property and AI and you're putting it together. So his voice is still being heard, but in smaller bite-sized pieces. So there's a lot of really different.cool ways to leverage AI that what it's then going to do is free up time for me to be out in front of the customer more. I think we spent a number of years back in front of the video camera like we are now. I think that now we are pivoting back to, we want to be out in front of the customers and clients and talking to them one-on-one and listening and understanding and engaging in group discussions and all of that. And AI will free up our time to be able to do that.because it's going to just take away those repetitive tasks that we don't need to be handling or doing. The tools will do that for us so that we can get back to the real interaction of the human engagement.Mark Petruzzi (20:14)Good stuff, Amy. ⁓ Teams say that we use AI, but at the end of the day, nothing really changes in our calendar. What weekly operating changes, cadences, coaching, or metrics ensure AI actually creates more customer time, more selling time, and not just a lot more dashboards or new processes?Amy Weber (20:35)Yeah, analysis paralysis is kind of the mindset that comes to me, right? That they just keep linking on additional tools and instead of thinking, how is this providing benefit to the teams or to the organization? So I like to think of it as stop trying to boil the ocean, pick one tool that's going to make a difference, implement that, and then move on from there. So have a plan.If there's multiple tools that you want to engage or that you think might be good and you're testing them, pick the one that you think is the most impactful first, deploy it, and then execute based upon that tool, right? Automate one task out of the gate instead of all the tasks. And then measure the time savings that you're getting from that tool, not just how many people in the organization are using it. we tend to, organizations are like,I've got a 50 or 75 % adoption rate into this tool. But is the tool really giving the people back more time or is it just another tool that they're using, right? Then layer in the next piece of automation and analyze that behavior and just follow that routine. Because that's how you're going to determine, am I really getting any results from this versus just investing in multiple tools and multiple components.So it's stop trying to boil the ocean, pick one thing, focus on it, do that well, and then move to the next step.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Drew Sechrist, CEO and co-founder of Connect the Dots and longtime Salesforce veteran, joins Mark Petruzzi and KK Anderson to unpack what it really means to build a relationship intelligence layer that changes how your team goes to market.Drew shares why his own career win stories at Salesforce led him to build Connect the Dots, and how mapping real relationship strength can turn stalled enterprise deals into closed revenue. He breaks down the nuance of activating networks at scale, aligning incentives around introductions, and embedding relationship data directly into the existing workflow so new processes do not die on the vine. From Monday pipeline reviews to executive access and stuck late stage opportunities, Drew explains how the best revenue teams treat relationship intelligence like the air they breathe.What You’ll Learn:Relationship Intelligence Fundamentals: What it really means to build a relationship intelligence layer and why it is a different go to market motion than cold outbound.Incentives and Activation: Why simply seeing who knows whom is only half the game and how incentive alignment, compensation, and context determine whether relationships actually get activated.Workflow, Not Side Quest: Practical ways to embed relationship data in tools like Salesforce, Slack, and email so managers naturally coach around it in pipeline reviews.From Story to Playbook: How one trusted introduction at Salesforce unlocked a seven figure deal and how that kind of magic can be turned into a repeatable team playbook.Modern Deal Strategy: How to use relationship maps and heat maps to unblock late stage deals stuck with finance, legal, or executive signoff instead of just hoping the contract gets approved.Key Topics:Building a relationship intelligence layer for GTM and revenue teamsThe nuance of relationship activation and incentive alignmentWhere relationship intelligence should live in the RevOps and sales tech stackUsing Salesforce embedded views, alerts, and APIs instead of forcing new UI and heavy change managementDesigning Monday pipeline reviews that start with “who do we know” and “have we connected the dots”Why LinkedIn connections alone are noisy and how signal based relationship scoring changes the gameMoving from manual “who knows who” exercises to scalable, AI powered relationship mappingGuest Spotlight: Drew SechristDrew Sechrist is the CEO and co founder of Connect the Dots and a former Salesforce executive who rose through the ranks during the company’s hyper growth era. His experience closing large, relationship driven enterprise deals at Salesforce inspired him to build a platform that operationalizes the power of real networks for modern revenue teams. Today, Drew helps companies turn hidden relationship capital into measurable improvements in win rates, cycle times, and deal size.Resources and Mentions:Company: Connect the DotsConcept: Relationship intelligence and relationship heat maps for GTMBook: The Tipping Point by Malcolm GladwellPlatform Ecosystem: Salesforce, Slack, email, and RevOps systems as primary surfaces for relationship data🎧 Listen now and follow Selling the Cloud for more GTM, sales leadership, and AI driven revenue insights from leading voices in enterprise growth. Subscribe wherever you get your podcasts.KK Anderson (00:31)And this really feeds into our second topic, which is around building that kind of relationship intelligence layer. What you've been describing, right? That is, it really is a different approach to like, to go into market. And so like, and if you think about like, let's say we do, you do this 90 day plan, it's working, like your team is,show this team that you're piloting this with is showing success. You build kind of the playbook and the process for how you could repeat it or scale it. Does this become something then that your managers start coaching? Does your pipeline meeting sound differently? What happens then?Drew Sechrist (01:08)Absolutely. So do anything except use our network to go to market. That's it. That's all we do. I can't actually say it's entirely true. It's like we do some events. We'll go out. I was at Dreamforce last week. We hosted the Salesforce alumni reunion. So we do things like that. But that's also kind of relationship based as well. But we don't do anything else. So we're kind of like this purist in this new motion.So the answer is absolutely yes. But I will say we don't have it all figured out yet. We have some of it figured out. The challenge, think, is really like.The challenge is a lot about protocol. Protocol and aligning incentives for everybody. Just because you can see everybody that knows everybody in the world and how well. Just imagine there's some magic way for you to see everybody that we collectively as a company know and all the people that they know and how well they know them so that we could say, great, Mark's got this really strong, looks like he's got a strong relationship with the CEO of this.Fortune 500 companies, let's leverage Mark to get to that person. How do you do that? Like it depends on, there's a lot of nuance. Who is Mark? Is Mark one of our senior executives? Is Mark an investor? Is he an advisor? Is he just a friend from the gym? Is he my neighbor? What are his incentives aligned with us? Is he a customer of ours? You know, like all of this.those things play into the, how do we activate Mark's relationship with this person? Just because we can see that it exists. That's, that's like, call it 50 % of game. But then the other 50 % of game is how do we actually activate this in a way that Mark feels good about that's going to be effective. That's going to, know, he's going to facilitate the introduction. one of the big challenges I think on this is like, the incentive alignment thing, like, let's just talk about compensation here.Let's talk about compensation for a moment, if I can take it that direction. If you really want to unlock the network, then everybody's got to be compensated somehow. Now, I don't want to be too capitalistic about this. I don't want to be too capitalistic because many moons ago when I was starting my career at Salesforce, it was around that time.I read Malcolm Gladwell's The Tipping Point. you've read it, KK. Mark, have you read that? Yeah. So deep in our brains, right? And I definitely identify it as a connector, even at that young age. And I was like, I'm a connector, and I love this. And so no surprise that years later, I started Connect the Dots. And I do make connections for,Mark Petruzzi (03:09)I certainly have,Drew Sechrist (03:25)Many like Matt, vast majority of the connections that I facilitate in my life are not, I'm not expecting any kind of, know, compensation for that. let's say certainly not any monetary compensation. might like, would, I might like, Hey, thanks a lot, Drew. That was really nice. You helped me out a lot here by introducing me to this person. I like that. makes me feel good. So.But if you want to do this at scale, you got to figure out like, what is the compensation that everybody's in the network is going to have? and it could be straight up, just, you feel good doing it. Like I'm a connector and I do feel good doing it. KK, if you wanted to get to get to somebody, let's say, totally random idea. Like you're, you're going to go to Dublin and that came up and you're like, I really wish I knew great.whatever pubs in this little town outside of Dublin, cause that's where I'm going to be. like, you know what? know somebody from that town. Let me introduce you to, I'd feel good. You go to some cool pub and have a great time. And that person that I connected you to probably would be like, yeah, that's kind of neat. Somebody's going to my town. And so my compensation on that one is, you know, it's, basically, it's a dopamine hit. I feel good that I've connected to people and their lives are going to be a little bit better because of that connection. But KK, if you hit me up like.40 times a day, every day for introductions to various people, for various reasons. At some point I'll break and I'll be like, KK, I got a day job, I'm sorry. You know, like I can't help you with, you know, 40 introductions a day. Now, if you hit me up with 40 at and say, Drew, I'd like you to make 40 introductions a day for me. And these are the introductions I'd like you to make. And it's good for the person that you introduced me to.And by the way, Drew, for every introduction that you make, I'm going to give you $10,000. I'd be like, hmm, all right, KK, you only want 40 a day? you like 50 a day? Would like 60 a day? I'll see what I can do. Right? So incentive alignment and compensation are important here, it's so nuanced. mean, think about it. Like, you're getting paid to make an introduction to somebody, you're a friend. That doesn't feel...KK Anderson (04:58)Yeah, or 400. Yeah.Mark Petruzzi (04:59)YeahDrew Sechrist (05:14)Right? Does it? You know, it feels, that feels wrong. Like if, he's, if KK you say, Hey, Drew, could you introduce me to one of your friends who is a good prospect for us? And if they buy, or even if they don't buy, I'm going to give you a thousand dollars or something like that. then I don't know. just, it feels weird. that feels weird. Now, if I were an advisor for your company, KK, you're CEO of company andYou say, Drew, it looks like you've got a great network into the companies that we want to sell to. would you be an advisor for us? We're going give you some equity and we'd like some advice from you. We'd like you to open some doors for us so that we can get in and sell our product and get feedback and grow and become a successful customer. That doesn't feel bad in the same way as getting paid with cash, right? so there's a ton of nuance here.Candidly, we don't have it all figured out yet. I think this is like this whole space is taking shape right now. It's like there are tools that are making it possible to leverage networks at scale like never before, but you got to figure out how to, how to activate those relationships and make everybody feel good about it and also incentivize.KK Anderson (06:05)Yeah.What's old is new. Relationships are old as time and here we are, right?Drew Sechrist (06:14)Mm.Mark Petruzzi (06:17)Yeah, so that makes perfect sense. this is, I love where this discussion is going. So let's just analyze a little bit. So everything we're talking about for most companies is a new process. And the adoption of new processes, they typically die if you can't get it into the core workflow. So how do you build this in? Like where should relationship intelligence live in the overallstack and the overall rev-up and what you're doing there so that you don't need to drive any heavy change management in this process. So what's the latest weight setup that still moves the needle that you work with your clients on?Drew Sechrist (06:54)Yeah.Yeah, that's a great question. I think it should be kind of like the air you breathe. It's everywhere. So whenever you're in any place that you would need this information, it should just be there and you shouldn't have to go look for it. So for example, our customers have access to us inside of Salesforce. Not everybody wants to use Salesforce, if you're using Salesforce, then you're looking at an account or contact. We have ourrelationship, your relationship data visible to you inside of Salesforce. So as you're doing your account planning, now sales managers are saying, okay, did we connect the dots? Literally, they'll say that and they'll look and be like, well, why didn't we use this contact here? So we have our board member knows the CMO has a strong relationship with the CMO at this company. Have we connected the dots there yet? And if the answer is no, then you just click the button and you initiate that request.And it gets routed through, however, it should get routed, it might get routed through your CEO to, the CMO of that company or whatever. so that's, that's one, other places that people work or Slack, either email, getting notified via email that you've got a relationship that you should be leveraging for a deal that you're working on. We do that. we also, we're launching an API shortly where your rev ops team will be able to put the data anywhere that you want.whatever that is, if you have a list in sales law for outreach or you've got some other single pane of glass that is the thing that you look at to figure out what's your next action with your target accounts, ConnectedOuts can just be one of the pieces of data that's on there that says, hey, don't be stupid here. Don't try to go cold into this account. You can get a direct introduction fromYou know your VP of finance who knows their CFO. And so just do that initiate that. So I think that the best way is not to have any new UI. We do have a UI that's no are tool as a UI, but I think the best way to do this is just not have any UI at all and just be where be wherever the users are already working.KK Anderson (08:48)makes a lot of sense and that sounds, that would be amazing, right? Gosh, this time has flown by so fast. I'm gonna move us along to the third topic and I'm afraid we're gonna run out of time. But let's talk about stories and playbooks and how we can turn some of these connections into outcomes. so I love a little story time. So like what jumps right out at you when you think about kind of a,a story where a relationship, changed the game and because of a relationship, because of a connection, then boom, an intro was made, like some magic happened and like what changed because of that? Cycle time, win rate, deal size, like give me a story.Drew Sechrist (09:27)Yeah. one story, one story was, from, early days at Salesforce we hired in, there's a really important relationship I made in my life was with my new boss who came in then was named Jim Steele. So that was probably 2004, if I recall correctly. And I just saw Jim at Dreamforce this week, caught up a little bit. Mark made Jim interview with a lot of people before Mark Benioff hired Jim Steele.And I was one of those people. so I love Jim at that point. I love Jim today. it was such a great decision to hire him. So I gave him, thumbs up, to Mark and then Jim, saw later in the hallways, like drew, I you gave me the thumbs up. Thanks so much. What can I do to repay you? And I was like, Jim, I'm so glad you asked that. And then I pulled up a, like, here's my list of accounts. These are my, this is my territory. Who do you know at these accounts?Mark Petruzzi (09:55)Mm.ThankDrew Sechrist (10:11)That's how you can repay me. And, we found, I won't name the names, but we found there's a large semiconductor company there that he had a friend at who was a very senior executive C level exec. and he's like, I know this guy right here. and I said, great, let's see if we can get in. So Jim picked up the phone, called him and we were in that senior executive's office the next week. Now I had been trying to crack into that account.I don't know, for the years, I don't know, for some long period of time, completely unsuccessfully. And then here we are sitting in the C-level executive's office, you down in the peninsula in San Francisco. And, and then, they had a conversation and I was kind of flying the wall and, know, I, basically was the errand boy on that. And I took all the follow-up notes and knew what we we had agreed to do next. And, but those two kind of, discussed everythingAnd there was a high level of trust between them because they'd both worked together for long time in the past. and next thing you know, a couple of months later, we closed a very large transaction. I think it was a seven figure transaction. And, that was amazing. It was totally transformative and like blew out my number for that year. And it was a deal that would not have happened just zero percent chance that that would have happened. And that, and I wouldn't say it happened a lot for me.But it happened enough where I definitely, at some point I'm like, am I any good or am I just lucky that I'm surrounded by these people that have these relationships? And then I was like, what? I really want to be good, I want to be master of my craft, but I could also just continue to be unlucky and this is okay too. And the commission checks still cash. so that is,Mark Petruzzi (11:27)youDrew Sechrist (11:40)a big part of the reason why I decided to go start this company, Connect the Dots, because that magic is out there. It's just waiting there. It's just hidden. You can't see it, right? And if you can just see that that relationship exists, then you can manifest.KK Anderson (11:47)my goodness.You are best equippedto help the person you once were and those experiences that provided you that unlock is what you're helping others to achieve.Drew Sechrist (11:58)Yeah.Yeah, bythe way, thanks if you're listening, Jim Steele, thank you so much.Mark Petruzzi (12:06)Well, that's interesting. So next time I speak with Jim, I'm going to have to see if you have given him his 5 % of the equity of Connect4Dots because that sounds like exactly when you came up with the initial idea here one way or another.Drew Sechrist (12:20)Yeah.Jim made plenty of money from all the deals that we closed together. He's fine. That guy's totally fine.Mark Petruzzi (12:28)That's true. Yeah, and Jim wouldn't want it. So no, that's reallycool. Okay, so let's make this even more real. Let's go even deeper. So, let's say it's our Monday pipeline review in an enterprise SaaS company. And we've got all these late stage deals stuck with finance, lots of middle stage activity, and we need more executive access. what should we do?right after that, how do we make that happen? And what are the top three actions you'd put in motion right away when you're at that point? I'm sure you do every quarter with your own company.Drew Sechrist (13:04)Yeah, I'm sorry that you're just like giving me these layups about connect the dots, connect the dots. That's this company. I mean, the thing we do all day, every day is, is at every stage of our sales process, we are looking to connect the dots. that was, know, David, David Nitsky from, from Salesforce came up with that phrase back in the day, connect the dots meant, okay, who do we know at this company? How do we get into this company?Mark Petruzzi (13:08)No, and that's exactly where this one's gonna go, I know that.Drew Sechrist (13:29)How do we get hired in this company? And we basically built the tools like our dream tool for solving this problem. The problem is, we can't get in everywhere. doesn't, it doesn't work in every situation. You cannot assume that you always have an in at every company and, to be able to get to every executive, through your relationships. But it's definitely the first thing you should check. Cause if it exists, then that's it. That's your, that's your Trump card. Good play.Right now, play it immediately. Boom. ⁓ So, you know, first thing we do is we check to see if we know anybody and our heat map of the relationships is connect the dots. So we can, and we'll go into, we can go into Salesforce and see, do we have any relationships via our network and our network to sort of clear is it's all of our employees. You can see all of them are bored, our investors, our advisors, all of our customers happen to be on connected. That says you may.Be aware because they're using connect the dots. So we can see through all of those networks, anybody that knows anybody and all of those scored relationships. So if a deal stuck and you're at two weeks out from the end of the quarter and you've got a champion, but you've never gotten to that C level executive that is ultimately going to sign off on it. And by the way, we do this all the time. It's like happening today in the background right now. we're seeing, okay, Hey, we actually.have this former colleague who is now on the board of this company. And they're on the board. So they know the CEO who's going to be the ultimate decision maker on this this deal. Send them a text message. And just ask them, this is in, it's with your chief. It's with the chief legal officer of your company. It's almost done with red lines. It's going to be on the desk of your CEO for decision. Could we get your voice of support on this?Or could you introduce us to the CEO so we can have that conversation? And if you don't have those relationships, all you're doing is twiddling your thumbs and hoping that like, I don't know, when it gets on the desk of the CEO, they're going to say yes and sign it versus no for some reason. So that is what I recommend you do. You need to have that relationship map. We're not the only thing in the world that does this. We're the thing that does it the best.So, and if you're not using Austin, at the very least use LinkedIn. YouMark Petruzzi (15:28)you can see that, I've signed up about a month ago. I've been in the system. I was in it again last night and today. And yeah, it's a lot from LinkedIn, but it just makes the whole process move even more productively.Drew Sechrist (15:43)we didn't really talk about exactly what it is connected. That's does. So I should maybe I should say just real briefly what we do when a when a company turns on connect the dots, they plug connected out into their email server. Then we analyze all of the historical email across every email account that they've got. And we look at the metadata and we score the relationships of all the people that they have. So if they've emailed with anybody,ever, and it doesn't matter what job they were, we analyze that and we build a score for each person. And anybody who's outside the company that's already using Connected Outs, which is a lot of people now, so like, a lot of VCs are on it, a lot of PE firms are on it, your investors, your advisors, you see who they know. They've done the same thing. They've analyzed all their networks. So all you're sharing with each other is who I know and how well I know that person.But that's it. That's it. And it's super powerful. So what you get is now instead of with like LinkedIn, you just get this binary result. Like Mark and Drew are connected on LinkedIn or they're not. And in that world, you can't really navigate and figure out like, can I leverage Mark to get to this person or not? Cause the failure rate is so high on LinkedIn. There's such a high noise to signal ratio. And that's the complete difference on connect the dots and connect the dots. You can laser target and I can seejust the people that Mark has a strong relationship with and never bug him about the other 95%, right? Just the 5 % that he really knows well. And what that does is you scale it across a large organization. That means that you really now have a heat map that gets you directly to the people you want to get to. So that's why you can do it the old fashioned way. You can use LinkedIn. can also, the really old fashioned way at Salesforce was just asking your colleagues around, like, hey, didKK Anderson (17:19)Whodo you know at this company?Drew Sechrist (17:20)Yeah, holdingup the list. That's I've been in a super old fashioned way. So there's like, you know, V zero, there's V one, you know, and now we're on, CTD is like V eight or whatever. don't know. but whatever you do figure, figure it out. Like you do need to connect the dots somehow. and you can do it manually or you can deploy technology to do it, but that is definitely the hack right now. And that is in a, in a very noisy world where there are too many messages from too many people that you don't know.KK Anderson (17:46)Mmm.Drew Sechrist (17:47)Basically, the answer is to all that stuff. You just delete everything right? The things you don't delete are if it's Mark sending me an email. I know Mark. I'm going read it. That's it.KK Anderson (17:56)It's so true.Mark Petruzzi (17:56)Yeah, and you know what, we're running towards the end of our time here and we don't wanna ask for any more of your precious time, Drew, than we already started with. But here's an idea. Would you be open to doing a LinkedIn live session with us where we go just a very deep dive into topic four and really talk about with all your great sales and sales leadership experience.how you're leveraging AI into everything, your product, your processes, your company.Drew Sechrist (18:26)Yeah, I'd love to do it. Count me in.Mark Petruzzi (18:28)Yeah,KK Anderson (18:28)And that willbe.Mark Petruzzi (18:28)I think that would be great as well. And then we'll do our rapid fire then as well. So we're not gonna share that rapid fire with you and give you all this time to prepare, because we wanna really see your reactions to it.Drew Sechrist (18:38)Beginner's mind. Allright, beginner's mind, I'm cultivating it right now. I will go into a deep meditative state until we have our LinkedIn live session.Mark Petruzzi (18:48)no better way to prepare. So Drew, thank you again. Thank you for taking the time with us. I think this was great. And we're really looking forward to diving into this next topic with you as well. And I'm sure our audience will be as well.Drew Sechrist (19:01)Likewise, Mark. Thank you so much, Mark. KK, a lot of fun.KK Anderson (19:01)All right, thank you, Drew.Mark Petruzzi (19:04)Awesome. All the best.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Drew Sechrist, CEO and co founder of Connect The Dots and longtime Salesforce veteran, to unpack why traditional ABM motions and high volume outbound are running out of gas and what comes next. Drew shares how relationship intelligence, warm introductions, and network aware playbooks are giving revenue teams a durable performance edge over cold, volume driven tactics.Drawing from his experience leading enterprise teams at Salesforce and now building Connect The Dots, Drew explains how to operationalize real relationships at scale, how to reimagine the role of the account executive as CEO of the territory, and why senior sellers should lead the shift from spray and pray to relationship driven go to market.What You’ll Learn:• Why ABM has reached peak utility and where it still fits in a modern go to market motion• How relationship intelligence and warm paths consistently outperform cold outbound and one to many ABM• Why the best enterprise sellers behave like CEOs of their territories and how that model broke during the growth at all costs era• How to design KPIs that expose when your current motion is tapped out and ready for a relationship first rethink• A practical 90 day approach to shifting from volume based SDR motions to relationship driven plays led by senior sellersKey Topics:• The limits of high volume ABM and cold outbound as primary growth levers• Mapping networks, scoring relationship strength, and surfacing warm paths into target accounts• Dreamforce era relationship building and how those habits still drive enterprise deals• The return of the account executive as CEO of the territory, not just a cog in the sales tech machine• Using AI and systems like Connect The Dots to make relationship based selling scalable and measurable• Reweighting your go to market mix across ABM, intent, and relationships instead of relying on mass spray and pray• How SDRs evolve into behind the scenes orchestrators of introductions, routing requests through executives and board members without breaking trustGuest Spotlight: Drew SechristDrew Sechrist is the CEO and co founder of Connect The Dots, a relationship intelligence platform that helps go to market teams tap into the power of real relationships at scale. Before founding Connect The Dots, Drew spent more than a decade at Salesforce during its hyper growth era, rising from one of the first account executives to leading enterprise sales teams. His career has been built on leveraging networks, warm introductions, and trusted relationships to win complex, high value deals.Resources and Mentions:• Company: Connect The Dots• Event: Dreamforce• Topics discussed: account executives as CEOs of their territories, relationship driven GTM, shifting off pure volume motions🎧 Listen now and follow Selling the Cloud for more conversations on modern go to market, revenue leadership, and the future of relationship driven selling in an AI enabled world. Subscribe wherever you get your podcasts.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrain, joins KK Anderson and Mark Petruzzi for a compelling conversation on how modern sales leaders can use AI to coach more effectively, eliminate wasteful pipeline rituals, and build real self-leadership within their teams.Paul outlines how high-performing sales managers are shifting from performative metrics to meaningful enablement; using AI to flag risk, generate insights, and equip reps to close complex deals. He also shares how sales leaders can establish operating rhythms, drive accountability, and lead with trust; all while reporting to the board with metrics that prove the business value of relationships.What You’ll Learn:AI-Enhanced Coaching: How to pair red/yellow flag systems with AI insights to pinpoint stalled deals and coach with precisioCadence of Accountability: How to replace unproductive pipeline calls with actionable, written commitments that build trust and executionManager Enablement: Why coaching the coach is the next evolution in sales performance systemsBoard-Ready Metrics: Which numbers matter most to prove relationships and strategic selling actually move the needlePractical AI Use Cases: Where AI drives effectiveness now (e.g., summarization, follow-up, personalization), and where it still falls shortKey Topics:Operationalizing AI in pipeline reviews and deal strategyMoving from activity tracking to outcome coachingSystems for continuous manager developmentReal intelligence vs. performative sales theaterCRO priorities in the AI era: focus, trust, proofEnabling full-cycle reps with better content, follow-up, and insightsMeasuring relationship impact: customer engagement, strategic touches, lifetime valueGuest Spotlight: Paul FullerPaul Fuller is Chief Revenue Officer at Membrain, where he brings structure, strategy, and coaching to complex B2B sales organizations. A strong advocate for elevating leadership and execution within sales teams, Paul focuses on embedding process, insights, and AI into daily workflows to help reps and managers improve continuously.Resources & Mentions:• Company: Membrain• Book Recommendations:– The Greatest Sales Question Ever Asked by Brent Long– A Mind for Sales by Mark Hunter– The Speed of Trust by Stephen M.R. Covey– Mere Christianity by C.S. Lewis• Sales leader to follow: Matt Green (Sales Assembly)🎧 Listen now and follow Selling the Cloud for more real conversations with revenue leaders building tomorrow’s go-to-market playbooks.KK Anderson (00:31)So building on that, Paul, from a sales manager's perspective, let's say they're in a coaching call with the rep and there's deal after deal that's stalled. And we know that stalled deals kill quarters, right? And so what are some ways you see top sales leaders leveraging AI?or AI signals, to help coach through some of those common challenges that sellers have.Paul Fuller (00:55)we personally, do it by, coaches that managers that use our system and, are doing, but we have a really robust flagging system and a really robust ability to, look at a pipeline by a variety of factors.then you can start to layer the AI in top of it. So we've built a flagging system for years. So something has been in stage more than 15 days. Let's check this out. Let's understand it. Let's, let's figure out and based on the profile of the customer and the actions that we've taken, red, yellow, red, yellow, let's categorize those flags. where you start to get into the AI stuff is that AI can then start to deliver based on that framework, very specific things based onto other reps that have been successful and move things based on situations that have happened across the organization and based on that rep behavior itself. If you do things like tie in, tie in recordings and fathom and gong and those types of things. So you can do some really cool work there. What I found is it's best for the flags and the AI to bring up suggestions to a manager saying, Hey, here is threethree or four deals ⁓ that are specifically, let's talk these through, right? Bring up those flags. I do believe a hundred percent that it is on the manager then to dive in into those deals, understand them and human to human get that coaching on what are the barriers that are, are specifically in the way and how we're then improving.the skills, the who and the who of what we want to be and how we want to act. How are we improving that on ongoing basis? So we have a platform called Elevate within our tool set that is a, it's a cadence to coaching and cadence rhythm platform. So it ensures that we're doing the right work. we can set goals in that platform. It can bring insights from our pipeline. It can flag deals that we need to discuss.But if we don't actually have the meeting, I'm still a huge fan of that. Like we have to have those one-on-ones and dive in, discover and understand. And so for the sales manager, the most important thing data is about half of it. The other half of it as a sales manager is how am I improving as a leader in my ability to coach these deals? And they need to have a cadence on those. need to understand howCause information is not the, we need the information and we need to have it highlighted. But if there's not a rhythm by which you're continuing to improve your coaching skills and ability and dive into deals and those types of things, the sales manager, doesn't matter how much information I give them. because the sales manager in that, that is coaching a lot of times, we'll just do the same things over and over again. It's a man.why aren't you closing this? I would have closed it. that's a lot of the coaching that happened that happens today. Well, I would have done this. And that doesn't that doesn't cut it. So I think that that layer of those sales managers and those coaches really need to work on that skill.Mark Petruzzi (03:44)Right on. So Paul, let's kind of anchor this maybe around like a mini cadence. So if we're reviewing pipeline for 12 weeks at a client, you if you're doing it within your CRO role for your own company, what are the three weekly review items and the three actions that you'd mandate and who owns each and when do they need to be done?which are the ones that really drive behavior to become sticky?Paul Fuller (04:14)That's a great question. Do I have to limit it to three?Mark Petruzzi (04:16)You do not.Paul Fuller (04:18)All right. Well, again, I can only go from my experience.And, this is weird because we've been talking so much about, the who and the, core of the people that we need to become and those types of things. and then the processes, and I am going to give you an answer that I think is completely outside of that. and it's a very simple answer that I think doesn't happen, across just about everyone.I've seen there needs to be and I don't care what system you're using. don't care if you're using Excel. I don't care if you're using a membrane. I don't care if you're using a pad and paper, but on a weekly basis, every rep and every manager of that rep needs to have a full understanding and picture of an updated pipeline and the deals in those pipeline in that pipeline.And, again, our system makes this easy. makes it much more, much easier and gives the ability to do it, and flags and pulls information out of it and all that stuff. But that habit in and of itself on a weekly basis for a sales manager, is something that is skipped so often and it changes everything. second.is the cadence of, if you have that, then you can effectively coach and have a cadence and rhythm to that. And I call it a cadence of accountability. The cadence of accountability is just as important to the sales manager as it is to the sales person, as it is to the VP of sales, as it is to the CEO, right? It is.What are we committing to this week that we're going to get done for each other? And that goes back. It does go back to that who like self leadership and the ability to be a self leader, but that cadence of accountability is critical and it needs to be written down. It just, it just has to, Hey rep one, I'm a sales manager. I am going to dive in and review through your accounts and I'm going to do this for you.Okay, and I'll do it by Friday or I'll do it by next Tuesday.Do you know how you're in sales? So you know this and you're in leadership and coaching and you know this is that how frequently that gets missed and pushed to the side and in favor of busyness is, is crushing. It's crushing to a sales team. It's crushing to a sales leader and it's crushing to a forecast ultimately. All right. And the third thing that a sales, I would say that's incredibly, incredibly important.And again, we, going back to the basis, you could do this on a pad and paper is, what are the things that I am accountable to my prospects and customers for this week? My top five, right? And in, and I might, I'm going to complete those. I think just those three things, absolutely.It's why I harp so much on, the self leadership and I, what I call the real intelligence, the leadership, the service, the way if I have accepted and we've defined that together, those three things don't become necessarily easier, but they become something that I will commit to, as, a person and as a manager and as a sales team member. and they become so, so important. And so again,Our systems, everything is a glorified system around that, quite frankly, but those things are so incredibly important to make an impact and to move forward together, lead well, serve well, and to really ⁓ drive performance.Mark Petruzzi (07:28)Yeah, and you know what's really cool, Paul, about what you just walked us through is you really define what the items that are really important in the selling process as compared to things that we have done for so long. For example, we've relied on a CRM and we all know a CRM doesn't do anything to make a sales rep more effective or even more productive.And so, okay, so we spent a lot of time with a CRM process and we all know that most of the data is just really not good within CRM systems. That's a whole nother discussion for another time. But if you look at the, even things like a pipeline, what amazes me is some of the clients that I work with, when I first get in there, they love that weekly pipeline meeting and it can be an hour, many of them are an hour and a half.A few of them I've seen are two hours by the time they're done every week, just sharing all this mumbo jumbo jumbo and also just manipulation that sales reps end up doing because it's a good way to do it. So when you could put a process together in the ways that you're describing it, that takes a lot of that out of the equation. And by the way, the business KK and I run, AGS,We're moving with some products that will allow you not even to have a pipeline call each week because the information is shared so closely and who knows, maybe some of those products we work with are good fits to coordinate and integrate with some of the great things you're doing with membrane. But you really hit me on some key items there.Paul Fuller (09:02)Yeah.Yeah, we don't have a pipeline call every week. which is fascinating. If I think about it, I do have a sales team meeting every week, but it's not a pipeline call. mean, pipeline is an individual that the reason people have pipeline calls generally is, I hate to say it. it's performative at this point andMark Petruzzi (09:10)Mm-hmm.Paul Fuller (09:21)that really is it like performing, but it's more for the manager than it is for the salespeople. It's like, and, so I have a call. I took a format from one of our partners. it's a, we call it unpack, but it's updates and I do ask for short numbers, but I can look at the number because our CRM is actually clean.And actually we have a process that's built into it that understand and the sales reps agree helps them close deals. They use that process. Sometimes they get outside of the process, which is fine. They can call audibles. It's, fine, but they use that process to actually work their deals towards success. And so I don't need to have a long call where everybody's talking about their, their pipeline and individual deals and doing it in front of each other.Instead, we can start to have discussions about, what are some things that you're doing that is helping you improve your win rate? What are some things? How can I help you? And, we have discussions like that and in our number eight and then I, could say, Hey, this is what I'm really seeing in membrane. This is what the numbers are showing me. Is that true? Like, are you guys feeling that as a true, is it, how can I help you get those up?So the two hour performative pipeline call where you're forced to come in and a rep is forced to, to essentially embellish. Cause that's what they do. They want to look good in front of their, their team members. I don't, I don't need that. What I can have is a, is we can start to have just a mature discussion. Cause we've agreed that we're going to be self leaders and leaders in the organization. And we have a process by which to do that. And we can, we can talk about what's actually going on.Mark Petruzzi (10:38)Yeah.Paul Fuller (10:52)but I do trust, they have to have, there is no question like it has to be updated. That is just a habit. Like if we're going to provide this and we're going to provide this system that helps you close deals more effectively, it does have to be. And there are some things that I do need as a manager to update, but most of this is for you, Mr. Mastrip. So, you're dead on with that, right?Mark Petruzzi (10:58)Yeah.Paul Fuller (11:13)How do we drive effectiveness, not performative nonsense?KK Anderson (11:18)So Paul, I'm to take us into our final topic around focus, trust, and proof, right? Specifically from the lens of a CRO having to report up to a board of directors. And let's just start with, there are so many CROs right now that are beginning to invest in AI. Some organizations are further ahead than others, butI would say nobody wants to be left behind, right? And so if you're like, what advice would you give to your fellow CROs that are out there? Let's say they are just starting to kind of dip their toe in the AI water and they're gonna have to go to their board and ask for funding. And we know they're gonna fund what they can, boards are gonna fund what they can measure. So like in this era, what would your advice be to them on where to start?And later on, you would, some of these concepts of real intelligence, because that's really what AI, as we've talked about in this episode, allows us to do is to focus on the real which is the relationships and the trust and whatnot. So where would you tell a CRO to start in their journey?Paul Fuller (12:20)The greatest help that I've found so far, and let's talk about this in the concept and I won't talk about it necessarily from a concept of a CRO. If I can narrow that concept to almost a VP of sales in B2B sales.because I don't want to jump to the marketing side right now. I, cause there's a lot of stuff that I would, I think is really important. AI does extremely well there. So if you don't mind, I'll narrow the focus and on what we've been really talking about, which is it's the best thing that I've seen it do. And where we're heavily investing and investing on behalf of our clients as well.is summarization of data and taking things out of a manual taking things that can be taken out of a manual workflow and more effectively done by AI and so very specific examples of that. mean, call recording came in early, the fathoms came in early. I think what a wonderful tool, right? So how do youBut how do you take that data and then systemize it in a way that you can say, ⁓ man, I am going to be able to give my reps back three hours after a really good call to systemize this and to improve followup and improve communication. Right. Amazing. It helps them be more accountable. It helps them drive better, better outcomes with, with reps.I love it. It's so good. where I would, I have struggled with this one as a, as a CRO is things like the prospecting, things like AI prospecting and those types of things. Cause I get so inundated with things that I guarantee that I know. and I've not seen anybody do it well. soKK Anderson (13:48)is based on the prospect.youPaul Fuller (14:00)I struggle with that piece and I'm still figuring that out. But I know the piece, emails, LinkedIn, everything. It's just the prospecting side of AI. People have sprinted towards that. Like they have really sprinted towards that side and how are we going to make that happen? And I have not I sprinted towards how I can make my full cycle reps more effective.KK Anderson (14:03)You mean inundatedPaul Fuller (14:23)in what they're doing now to drive impact for the customer and the prospect. Like if I can have AI helped me make a conversation more effective and give me a better chance of winning that deal, I'm going to do it. And that's where I've been really heavily investing and looking. I don't think, and this is just a me thing.AI has a big place in the prospecting and that type of stuff. just, the operationalization of it has not worked well yet. in, a lot of when it's completely responsible for creating the message, getting it out, trying to get a meeting, doing all those things. I have not put, and it's partially also cause of how we operate as a business. like I have a partner network.That's how I get most of our leads in. I love our partners. I love how they operate. So they connect and they drive leads to us. So I haven't had to look as closely. but that, that would be where I would highlight, just there's been massive enhancements in empowering a good full cycle rep that understands how to sell. it's just so helpful.to drive improved output, help with notes, help with proposals, help with all those. It's so good.Mark Petruzzi (15:28)So Paul, so boards typically fund what they can measure. And we touched on that before, know, just when you were driving how these, how do you prove these items that we just were discussing to a board, to a CFO, to a CEO. So they typically fund what they can measure. How do we go about and prove that relationships matter in this?Like what three numbers should be on page one of a board book that defines like example cycle time with or versus worth without a warm sponsor or executive meeting rate by stage when we lift on strong familiar paths and how do you can define that versus you know other processes and paths that get developed along the way as well.And what targets do you focus on to make sure that you can convince the board and the executive team that this overall program that we're discussing here today works and is more productive and effective?Paul Fuller (16:27)Wonderful question. I wish I had them all laid out for you in a specific presentation and could give you the one, two, three, four. That's a magic formula. Unfortunately, I can't. Fortunately, I can't. I tend to...I tend to look at history and our historical metrics so I can look at what our future metrics could be. So if I'm looking at ARR and I'm looking at customer lifetime value and I can then see, you know, what is it, what is the number of touches and strategic touches that we need to have with a customer to increase our, lifetime value of a customer and how we're doing that and what is the level of,operation we need to have with them. So you can measure that in number of different ways, meetings per customer, conversations per customer, strategy sessions per customer, customer engagement with support, those type of things. If I can start to look at those and then I can say, what is, what is our average rate for a really good growth? And then I can say, what can AI actually help me cut down on the human element, but increase the actual strategic impact? That's really helpful.I'm sure there's a VC term for that or VC stat on that, that I don't know. but that is really, really, and I think they call it replacement to those types of things, but, that is a measure incredibly impactful. And so it's really, do we, we have the same level of service or increased level of service that will help us increase the lifetime value. andWhat do we need to invest to make that happen? Cause I already, we have proven models for this. We have proven models for this and what our people have done on an ongoing basis and what other people, know, and the type of things that we need to create that work well. I'll give you an example. I just had a meeting yesterday with a guy that I thought was ridiculously good. and it, he was selling to me and he,he created a marketing strategy document for me in 15 minutes. after we had, a structured, a structured call that he recorded on Fathom, after he used AI to research our, our market and, and the things that were out there, he had set up a couple of, agents to do that. And then he delivered me a document. He said, and how he said it, he's like, this is not going to be perfect.This is our starting point, but, and, here you go. Right. But it was, it was customized. It was me. It used my language and it was incredible. Right. Like in terms of the sales process, like I really loved that. So that to me is an enablement piece that I could help my reps be more effective in market by delivering more effective materials that are customized to a person. And I know I need to do those types of strategic documents regardless. Right. They just,in our type of complex sale, need to do that type of work. hopefully that's helpful.Mark Petruzzi (18:56)Now that very much was and let's finish up We only have a minute or two here more and we want to make sure we don't keep with you past our committed time So we're gonna do an extremely rapid fire segment here. We're gonna try to do this in about 40 seconds So we love the rapid fire segment That's why we really want to make sure we still do this with you Paul So first question first product service you ever soldKK Anderson (18:57)it'syouPaul Fuller (19:22)Printing door to door in Arizona in the Tucson summer heat.Mark Petruzzi (19:27)⁓ I was hoping you were going to say maybe Flagstaff in the summer, not Tucson in the summer. But that's a tough one.KK Anderson (19:35)Paul, who is a CRO or a CEO that you love to follow?Paul Fuller (19:39)Matt Green from Sales Assembly.KK Anderson (19:41)So look them up.Mark Petruzzi (19:41)So what,yeah, we definitely will. One leadership habit that more sales leaders should practice.Paul Fuller (19:48)self-accountability.Mark Petruzzi (19:48)beKK Anderson (19:51)My favorite question, advice that you would give to your 21 year old self.Paul Fuller (19:54)motions lie.KK Anderson (19:55)There's a story there, huh?Paul Fuller (19:57)and cut back on the drink. Partying is not the way.Mark Petruzzi (20:01)Alcohol is not the way, right? Yeah, it's kind of hard to avoid in college, isn't it? Okay, favorite sales marketing book.Paul Fuller (20:03)Yeah.there's a new one out. It's called the greatest sales question ever asked by Brent Long. Amazing. I need to throw out two other shout outs here cause I do love a mind for sales by Mark Hunter and then, the speed of trust by Steven and Mara, Covey is, just, I, it's life changing book for me.Mark Petruzzi (20:23)Yeah, I'm two for three with those books, but I've got a new one here with the Brent Long one. That's great.Paul Fuller (20:28)All right, yeah, great book, great book.KK Anderson (20:31)Okay, and what about your favorite non-business book?Paul Fuller (20:33)Mere Christianity by C.S. Lewis. ⁓ C.S. Lewis is my favorite author in everything he's written. It just blows me away.KK Anderson (20:43)That's awesome. Okay, well Paul, thank you so much. We had so much fun chatting with you today and we've all learned a lot.Paul Fuller (20:48)Thank you for having me on. Hopefully I wasn't too long-winded and if I was, cut it out.Mark Petruzzi (20:53)No,KK Anderson (20:54)You are awesome.Mark Petruzzi (20:55)you were great.Beautiful. Thank you to our wonderful audience and everyone out there listening.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrane, joins KK Anderson and Mark Petruzzi to reframe how revenue teams win in complex, multi-stakeholder deals. Paul explains why many orgs over index on apps and one-off skills while under investing in operating rhythms, leadership habits, and relationship-driven execution. He introduces the idea of real intelligence as the who and why that guide the how, and shows how process plus AI inside the workflow can coach managers, focus reps, and change what happens every Monday morning.What You’ll Learn:Defining real intelligence: moving beyond tools to leadership, service, and wayfindingBuilding operating rhythms: weekly coaching, clean pipelines, and a cadence of accountabilityEmbedding insights in the workflow: checklists that coach, not just boxes to tickActivating AI where it matters: individualized multi-stakeholder follow ups and manager signalsProving what boards fund: focusing on measurable behaviors that move win rate and cycle timeKey Topics:Systems over one-off training for durable behavior changeProcess plus AI to guide day-to-day actions in CRMCoaching frameworks that reinforce who, why, then howMulti-threading effectively and right-sizing stakeholder engagementFrom performative pipeline calls to meaningful operating reviewsGuest Spotlight: Paul FullerPaul is the Chief Revenue Officer at Membrane. He helps complex sales organizations operationalize process, coaching, and buyer-centric execution so managers can coach and reps can execute without bouncing across tools.Resources & Mentions:Fathom and Gong for call capture and summarizationMembrane workflow checklists and coaching cadenceWINS framework for servant leadership based sellingBooks: The Greatest Sales Question Ever Asked by Brent Long; A Mind for Sales by Mark Hunter; The Speed of Trust by Stephen M. R. CoveyLeader to follow: Matt Green of Sales Assembly🎧 Listen now and follow Selling the Cloud for more GTM insights from enterprise operators and CROs. Subscribe wherever you get your podcasts.Mark Petruzzi (00:31)Today on Selling the Cloud, we're joined by Paul Fuller, Chief Revenue Officer at Membrane. Paul spent years helping complex sales organization operationalize process and coaching, bringing structure to multi-stakeholder deals while keeping sellers focused on what moves outcomes. At Membrane, he's championed approach that layers insights and prescriptive guidance inside the workflow so managers can coach and reps can execute.KK Anderson (00:40)youMark Petruzzi (01:00)without bouncing across tabs. We'll dig into Paul's thesis on real intelligence, the durable leadership practices that operate, rhythm sales teams need to thrive amid AI tool bloat and rising partner competition. We have three topics we'd like to cover with you today. From skills to real intelligence, why systems, leadership habits and operating rhythms be one-off training.Process plus AI, kind of day-to-day actions, putting insights inside the workflow so reps and managers change what they do on Monday morning and every single day of the week. Focus, trust, and proof. Leading in the AI era, keeping teams competent, and proving to the board, CFO, CEO, that relationships and systems move the numbers. Welcome, Paul. We're so happy to have you with us here today.Paul Fuller (01:50)Thanks so much for having me. really appreciate being here. I'm pumped. I'm excited.Mark Petruzzi (01:55)Beautiful. We love it, All right. Let me open with a question here in topic one. So Paul, you've argued that revenue orgs over index on apps and one-off skills while under investing in the systems and leadership habits that drive outcomes. In your words, what is real intelligence for a sales org? And how is it different from adding another tool or another skill module?Paul Fuller (02:17)Yeah, great question. And I think you've, everybody's been there. in terms of we love in the sales world to focus on the how, And how do we get things done more efficiently and quicker and better and put more numbers on a rep and make sure that they get, things done more appropriately. LikeThe whole revolution of the past 25 years has focused on that. Let's, make sales and manufacturing line. Let's get an SDR. Let's get to an AE to an AE that does, another thing at a sales engineer to the next, to the next, to the next, right? How do we make this more efficient? there's, there's an interesting concept though, that I I'm really finding that more and more as we, today's world and what we're dealing with.is we have skipped some certain things. We have skipped some of the fundamentals that it takes us to operate as sales professionals as a human and really make a continual impact in the market. We have skipped things and pushed them to the side. Things like relationships, things like how we work on those relationships together, things like a long-terma relationship that is going to drive impact for your business for years to come instead of, and instead in much of what we focused on, have you gotten a conversation and is there an opportunity? So when I talk about real intelligence and building that into a company, I'm focusing more on the who we want to choose to be. And then the why that we choose to be this instead of, and then move into the how. And I think that focuses on three things that we choose to be in sales.how we choose to lead, how we choose to serve. And I have a word that it's wayfinding, but how we choose to problem solve and find a way to work with companies and, do that core to who we are and define the, make those choices about who we want to be in those actions. We can always figure out the how another app, another thing. andSo many of us just focus on that. How let's just, my gosh, I got this, I got this for data. got this for this scraping. got this for this. And you focus on that so much that you've seen tech bloat. You've seen confused reps. You've seen reps promoted to AEs that just cause they know how to book a meeting, but they couldn't, they couldn't discover and ask a question for the life of them. Or they don't even know who they are and what a sales motion is. So that's what I.Mean when I'm talking about real intelligence.KK Anderson (04:27)So the real intelligence as my daughter would call it is like the invisible thread, right? That connects everything. It is the common denominator that must be there to be able to make a sale. And that's a true relation. It's a human-based relationship. that what I'm hearing?Paul Fuller (04:45)Yeah. Amen. and let's make it real with like one word that you hear a lot in sales today and you hear people throwing up their hands about accountability, right? I can't get my reps to be accountable to leadership or customers. And so how did most people solve that? Well, I'm going to throw, I'm going to throw test management at this. Right. I'm going to throw check boxes that they have to do in their CRM. I'm going to throw.And they think that's solving the problem. Well, the problem lies much deeper than that. Yeah, the problem is much deeper than that, right? The problem is that you haven't invested in your team and built leaders on your team that know how to lead themselves and lead others. So why don't you start? Why don't we start with core components of self leadership as a team and say, that's how we want to sell and what that means to us before we then create this in the line thing wall andKK Anderson (05:10)another box to click.Paul Fuller (05:33)of accountability, because you have so many see I was on a CRO forum the other day and they're like, I just can't get these Gen Z errs or whatever to be accountable. Well, quite frankly, look at the system they've grown up in look at a lot of things that has happened. I think you need to go back to the real intelligence part of this. Let's talk about what it means we want to hire leaders, have leaders in our culture and what that looks like for us here. Let's start there and how that can impact your life.Therefore, you know, so you start a little earlier in the cycle, get rid of that. You do the how, but start with the who.KK Anderson (05:57)Yeah.Mark Petruzzi (06:03)So Paul, where do teams get stuck in this? What's kind of a common anti-pattern? Something that looks smart, feels good, shiny AI, but doesn't translate into consistent behavioral change.Paul Fuller (06:17)well, I'll use, we, are heavily, we love sales process. I love sales process. I actually really appreciate, our, platform is built around sales process, and how we're able to do that. sales process is a wonderful thing. and, let's say it's created in the mind of, the sales process is created in the mind of the medic expert that knows everything and has been.been in there for 30 years and knows exactly the questions to ask and all of those things, right? And then I put that out there and I put it into an organization. I find out, why isn't this working? It should be. I mean, we had an expert design it. it was perfect. It's in a system, right? There are gaps in the people I think don't see where they say, okay, let's fundamentally go back to this. And I put this concept of real intelligence, butlet's go back to these fundamentals of leadership there that are embedded into it. Let's agree on those and gain agreement for our team that that's what we're to practice. And then let's look at that in the context of a sales process. What are the actions that we're going to do continually and how is that going to, how are we going to craft reminders of that initial who that initial agreement, who do we want to be? Right? How do we're going to craft those in the sales process that actually helps us execute?cause if we have our who and our why figured out our how, we can systemize that really well. Right. So I think people get stuck in the anti thing is, well, I'm just going to put it in a sales process. Okay. If, if you just do that, you're going to get a bump. You're not going to optimize unless you have a complete and total agreement and, and, and focus and help people drive their core and, their understanding of why they're doing this and helping them and coaching them to do that.then you can execute on the how really well.KK Anderson (07:50)Sorry, are you saying then that where people get stuck is that they are skipping stages of the sales process or accelerating faster or skipping critical pieces of it and that's why their deals are stalling or, you know.Paul Fuller (08:05)No, I'msaying they're skipping stages. I think we're skipping stages and expectations a lot of times in our sales team themselves. And so for example, I was just talking to somebody last week and they're like, well, I hire really good salespeople. Right?that's what I do. And so I don't, I hire good salespeople. I have this process here that's helpful forum and I asked them to follow the sales process, but I asked them to, I hire good salespeople and I just count on them. And, and it's like, great, that is a wonderful step. They can do that. But I, the, the core thing is then, how, but how are you empowering them to be the best salespeople out there? Well, I really don't. I hire the, I hire the best ones and I let them run.now I think there's a, there's a step there and that is missed, which is all your hiring. You're hiring really good salespeople, but the step is how are you, how are you working with them, coaching them and helping them develop things that we know are core to continually get better. their leadership and account, their self leadership and accountability, right? Back at the ability, how they serve people, how theyhow they help people find what it is they need, right? Those are not things that are necessarily natural to everybody. And even the best salespeople need that help. So how are you continually helping them do that? And then how are you helping put things into the how, into the process that remind them of that activity, of the things that they need to do to be at the top of their game?And so that's really what I'm talking about. I think a lot of times we skip the step we, and we skip it far too often. We expect too much of things like new hires or especially new college grads that are coming in young sales reps that they understand concepts that are inherent to sales leadership service and wayfinding. we don't even give them, we throw them into a ⁓ niche role and we never pay attention to that. And I think it's time that we shift that, especially with AI, cause AI can do a lot of the how now.I can do a lot of research for us. And so we need to develop the things and the skills and the leadership service, the way finding on that side, much more impactfully to scale a good relational organization.Mark Petruzzi (10:05)Right on Paul. So give us a quick before after story where shifting from train to skill to build the system plus leadership habit materially change win rate cycle time and or forecast accuracyPaul Fuller (10:20)Yeah. I have one, that's a very recent one that we've been working with it. We have a partner, that we work with and he dives in and he very specifically focuses on a servant leadership based, who, right? Who we are is, servant leaders. They define that's how they define sales. And then once you decide that and, and figure out, okay. And then each individual is figure out why they're coaching.or why they're selling, which is more of an individual goal. He was able to put in a process and framework. So he's got a framework that he calls wins. And it's an amazing framework. That's how we're going to have these conversations, how we're going to do this continually, how we're going to lead, serve and way find as a, as a team. And then that framework then led into the specific sales processes themselves. So this is the order of operations that we want to follow.Right. Just by doing that work, but doing the hard work first on defining, who we want to be, how we want to lead, how we want to sell, what sales is. Right. And getting that hard work done first that is often skipped. but by doing that in, then putting in the processes of the framework and the processes afterwards, he's able to see, I think the stats on the recent case study or something like a 20 % increase in pipeline development.Quality conversations has gone up with all the reps. So qualification is massive. So pipeline flow through is incredible because they're qualifying more effectively from a place of confidence in who they are and what they can do. and so I will pull up the specific stats for you, but it's been tremendous. And so we do this through our platform. Like he implements a part of this in our platform. but the core of it, it becomes way before that platform.Right? It's, really deciding on who we want to be and the core elements of the, call it again, the real intelligence assets that we want to dive in, how we want to up or who we want to be and why we want to operate as a team. Is that helpful?KK Anderson (12:10)I think this is going to take us into our second topic, right? Around process and AI and how it impacts day-to-day actions. And so I know you love process. I believe one of the reasons you love it is because you also believe that this real intelligence is insights. they have to live where the reps work. Like it has to be in the workflow.in the CRM in membrane. And so on a Monday morning, what does an AE actually see? how does this real intelligence show up?Paul Fuller (12:40)Yeah, great question. So membrane itself is we love process because again, process helps us do the job that we have, we can do to the best of our ability. That's, that's what it is. It's consistently it's a checkbox, right? now let's tie this in. Before I answer that question, I'm going to use an analogy, if you don't mind. I'm going to tie it to the medical profession,KK Anderson (12:50)consistently. Right.Paul Fuller (13:00)Medical profession has this defined pretty darn well and a lot of things that they do. They have that who we need to be and the critical components of that pretty well defined. They have a Hippocratic oath. They go through a ton of training to understand the type and form of doctor they need to be and really get that down and the person that they want to be operating in that system.skip forward to the checklist, the checklists are there for a medical for a doctor to go through and a process is like, so I don't make mistakes. So I can bring my best self every single time to the surgery that I have. And a lot of times I've seen some of those checklists, like my brother's doctor and, and he'll even make his own. And it's like, before I go into an appointment, I will X, Y, Z, right. I'll take a time, take a second to center myself. I will dodo the appropriate research on the client, on the patient that we have, and I will be able to head in. And then during it, they have additional checklists, right? So again, my thesis is that we're, and what the, is that we are skipping a lot of that stuff in sales that helps us define that who we want to be. Now, in terms of how we activate in that process and checklist, like very simple.a process and checklist that can score a pipeline based on whether or not you have a sales rep has actually had a prep meeting with their manager and gone through coaching on a deal to bring their best self to that sales meeting that they have. That's massive help. If you can score a check, if you can score a pipeline based on whether a sales person has actually gone inand reviewed, all of the core people in that deal has gone into their backgrounds and understands it, let's look at a certain stage of our pipeline understands how the, the vision, so understands the current state they're in, the vision state and the gaps. And you can then have that be a part of your process, but then also score your pipeline on.right and understand based on the actions that the sales rep is taking to be the best person that they can be in this thing, it helps and it also helps the reps. Like so many times CRMs just give data, they're like, just go fill out these six fields that you need to learn and go ask these questions. But they do nothing to help coach or guide and actually help a rep be really good. And that'swhat I believe a good checklist and a good process should do. Cause I mean, a pipeline is nothing but a lot of different sales processes, a lot of different checklists amalgamated into one view. And so what they did when they log in is, I'm just meeting them. Have we gone through, have we done our pre-call prep? we know, do we want to? Yeah, sure I can skip that, but I know if I skip that I'm going to be much less successful.And I can actually measure that have here are some suggestions based on AI and what we've had on questions based on our framework that we have and who we choose to be as a sales team. So serving that up right there in the context of where they're doing their job is so helpful. Instead of forcing them to go to seven different things or go back to a learning management system or call a coach or it's just really helpful to have it in one spot.KK Anderson (16:06)Makes a lot of sense. we talked a lot about kind of checking the box. And so I'm going to ask this question just because I'm wondering if others are thinking it. So we have a box. Did you have a pre-meet with your manager? But don't we run the risk of just having more boxes to check?Paul Fuller (16:22)Yeah, and I think that's the critical nature of, starting with who moving to why and then moving to how, right? And so we do run that risk. If you, and membrane can be abused like any other system, right? You can give a rep for 400 things to do, and say, check all these boxes and make sure you do them and measure them.That's just like any other system. where the difference becomes how do you define? And this is where I think a lot of sales leaders and teams skip is how do you define a process that actually brings in best practices and helps people? So if you, so for example, don't, don't give them a box to check and say, Hey, we defined, the org chart.in the organization and we know who people are and that it's a great box. could literally give a checkbox. I've done that. Right. Instead in the process, give them a way to actually do it. Well, right. give them a way to understand the organization and how they're operating, visually and easily and in something that helps them do it.We just did a big research study on the number of stakeholders in complex B2B sales and like the optimal number for deal success. And we found it hovers around four and a half, right? So between four and five stakeholders actually increase the deal success and above that decreases it. so if we're learning that and we're understanding thatKK Anderson (17:36)Hmm, interesting.Paul Fuller (17:40)And we've decided as an organization that we want to, be the best sales team out there. And that's the who, and we're going to put the work in and be accountable to each other. Then a tool like that within to map those four to five makes is incredibly helpful. just right there. And then we can have great discussions and coaching discussions on, who those people are and how they operate and how they're going to help us work a deal.we could say, Hey, are we talking with too many or too few? it's right there and we can see it and we can work it and it becomes a step, but it also becomes a critical part of it. It's a critical part of winning a deal, that, we know we needs focus. most people, like they'll set up a CRM with, know, here's your 17,000 fields that you need to fill out and do.What we argue for is what are the core things that are going to truly drive both enablement for the sales team and excellence in results. And so take that time and really work on that. So I hope that answers your question, but that that's a philosophy thing that comes out of a lot of years of doing this. It's like, where is the impact and focus on that.Mark Petruzzi (18:43)Yeah, that is very easy to follow. So thank you, Paul. So teams don't need to be prompt engineers when it comes to generative AI. For example, at the same time, how do you enable and engage your team into what they can be doing, should be doing, how they should be leveraging the AI component of this?So can you share two or three prompted actions or snippets that do the things that really matter, like reliably improve their execution, discovery follow ups, multi-threading asks, building up the sponsor relationship and going deeper and wider at the same time. And where do you surface them so that they're used often by the sales teams you work with as well?Paul Fuller (19:29)Awesome question. I have one very specific example that I love and this actually came, it's an innovation. It's actually going into our product pretty soon, but it's an innovation that the team made. And it's actually ties onto that stakeholder discussion that we just had. So let's say we, deal with a lot of complex sales, right? So B2B complex sales.You have the four stakeholders, five stakeholders on a on a zoom meeting. And, one of the great innovations is that let's just say it allows us to be a more effective, salesperson, also ties into our processes. I now have the ability to, to follow up individually so much better. So I don't need to send that, I don't need to send that.to every person, here's my notes. Here's the action items for all of us. I can take a fathom fathom integrates with membrane. I can take that and I can take a snippet and say, Hey, for each of these people, pull out their core questions, their core actions, and some key insights that we have for them. and help me craft an, an email directly for that.Whereas that would have taken two, three hours, if you're really going to do a really well on a meeting follow-up, to do previously, you can now have that systematically built into a sales process. If you have a meeting with multiple stakeholders, four, five, six stakeholders, right? you now have this tool in here that AI and you can have a very specific, we do have what we call snippets in the system thattakes that and says, help me craft these very specific email. And then, then it becomes an editing and execution point because we know that as if we decide on the who that we are, we are going to choose to be accountable and choose to be servants. know that the best way to do that is individually one-on-one with a core team. Let's make sure that they're getting the attention that we've given. The barrier to that has always been, why I can't spendthree hours, four hours on a specific deal, especially for us, like it's if we're get a $3,000 MRR deal, right? that's great, but is that worth spending time, that level of time? And so there was always that trade off. You can start to remove those types of trade-offs systematically and it actually empower reps to be who you want them and who they want to be.And that's the type I think is stuff is awesome. And we're also process like we're processing methodology based. So being able to query a thing like having, we don't, you don't need to be a, context engineer to, if you have developed your sales process, right. And we're, walking through that and we're capturing all the data in that sales process, the system itself.engineers the context, right? Here's where we are in the process and here's maybe some of the differences that we can... And then you can start to query AI ⁓ directly and say, any recommendations based on our methodology, based on our process and based on what we've heard from them, that can help us be better and query that directly. Because you're right, one of the biggest challenges is that context engineering. And we kind of tend to throw...KK Anderson (22:16)Thank you.Paul Fuller (22:25)throw stuff at the wall in terms of that. we try to figure it out. if so, our, that's one of things I love about our system. If we've really defined who we want to be, the methodologies that we want to act, the process we can, then we can leverage that framework really well for AI to bring actual knowledge to us that we can translate to wisdom and how to act.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this replay of Mastering Sales with AI, AGS Co-Founder Mark Petruzzi is joined by KK Anderson and Scott Stollwerk, Chief Sales Officer at Pest Share, together with Gabriella Koenig of Collective[i], for a lively and practical discussion on how AI is reshaping the art of selling.The conversation dives deep into what separates average sales teams from AI-empowered ones—and it’s not the tech itself. It’s the thinking. The panel explores how smarter questions, better hypotheses, and trust-driven selling can transform AI from a productivity tool into a true strategic partner.They share real stories from the field: how AI predicted buyer shifts before humans saw them, how teams replaced pipeline calls with signal-driven insights, and how great sellers now act like the CEOs of their own territories—with AI as their superintelligence.Whether you’re a CRO, RevOps leader, or AE curious about where to start, this session shows how to go beyond surface-level prompting and turn AI into an amplifier for strategy, trust, and results.What You’ll Learn:• Why AI transformation in sales is not about technology—it’s about better thinking and sharper questioning• The “value hypothesis” framework for creating AI-assisted prep before every customer meeting• How leading teams like Pest Share use AI to forecast, coach, and prioritize deals in real time• What happens when sales leaders replace pipeline reviews with AI signal reviews• How to coach teams to trust and collaborate with AI rather than resist it• Why the best sellers now operate like CEOs of their own pipelines—and how AI makes that possibleFeatured Speakers:• Mark Petruzzi – CEO, Accelerant Growth Solutions (AGS)• KK Anderson – Co-Founder, Accelerant Growth Solutions (AGS)• Scott Stollwerk – Chief Sales Officer, Pest Share• Gabriella Koenig – Moderator, Collective[i]Key Topics:• Prompting for insight vs. prompting for confirmation• From search to strategy: moving beyond AI as a shortcut• Trust, empathy, and human connection in the AI era• Smarter forecasting and self-coaching with collective data• Building AI-driven sales cultures that embrace change#SellingTheCloud #GetAGS #ReimagineGrowth #AIforSalesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of our conversation with Neil Graham, Chief Revenue Officer at Disqo, we dive deeper into how modern CROs must rethink their org design, marketing execution, and AI integration strategies to stay competitive in 2025 and beyond. Neil shares why curiosity, humility, and bias for action are now non-negotiables; and how his team is operationalizing those values inside a flat, fast-moving GTM system.From building AI-generated deal strategy sessions to deploying 24/7 agents on the website, Neil unpacks the real-world tools and team behaviors that are reshaping sales and marketing execution. This episode is packed with tactical insights for CROs leading through change.What You’ll LearnFlatter Orgs, Bolder Execution: How Disqo’s three-layer model speeds up decisions and drives alignment across marketing, sales, and delivery.Non-Negotiables in Revenue Teams: Why curiosity, humility, and action orientation matter more than ever, and how to screen for them.AI as a Revenue Multiplier: How Disqo uses AI for outbound personalization, content creation, and automated deal intelligence.Coaching in the AI Era: How Neil’s RevOps team leads enablement through data-driven strategy docs and always-on insights.Creating New Roles for the AI Age: Why Disqo now has a dedicated AI strategy lead embedded in RevOps, and how other CROs can follow suit.Key TopicsScaling outbound without bloating headcountRedefining RevOps to include data, process, enablement, and AI ownershipDesigning a leadership team that balances vision and executionThe future of SDR and BDR roles in an AI-enabled GTMUsing AI agents for 24/7 coverage and real-time buyer insightsBuilding culture through feedback, modeling, and EQ-based hiringGuest Spotlight: Neil GrahamNeil Graham is the Chief Revenue Officer at Disqo. A proven growth operator and revenue architect, Neil has helped scale iconic brands like Salesforce, Siebel, and Jive. At Disqo, he’s building a flat, AI-accelerated GTM machine that prizes speed, ownership, and alignment over legacy hierarchy.Resources & MentionsCompany: DisqoFrameworks: MedPick, DSF (Disqo Success Framework)Sales Tools: Gong, Clay, ChatGPT, AI agentsLeadership Inspiration: Carl Schachter, Eli Cohen, John BarrowsBook: Emotional Intelligence by Daniel Goleman🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.KK Anderson (00:32)to drill into this topic, topic three, talking a little bit more about the flat org and the expanding CRO role, we've had this conversation quite a bit on our podcast about how CROs are now...taking responsibility of the marketing org, of the customer success org, of the sales org, of the entire go-to-market revenue system. And one of the things we see every day in our customer conversations is how disjointed marketing can be from sales disjointed product and from product management as well. And soas marketing is kind of folded in under you and this kind of this new flatter org and you mentioned that the alignment that you're having with your SLT every week but tell me a little bit about how this is helping to kind of bridge that gap between marketing sales customer success like the whole go-to-marketNeil (01:24)So I am a big fan of the CMO role in today's modern company and organization and, I know the SaaS and sort of technology world really well. So I'll speak from that perspective.I can't really make a comment on other industries, but I am a big fan of, the CMO's role, and, sort of ownership of a modern AI driven marketing strategy. that said, we're trying to innovate quite a bit and do some really cool disruptive stuff and shift the focus of our marketing strategy here. And my CEO is a big vision behind that as well. And,hoping that I'm actually a pretty good impact on that. and we've got some great leadership on our marketing team that's doing an awesome job thinking big and bold and in a differentiated way, but also really good at execution. And I think, this is a little bit of a side point, but I do believe in, making sure that on your management team, you've got a good, portfolio of leadership skills.from vision to execution oriented people. So you can do both. And we've been really careful to kind of put together our leadership team on the marketing team and the sales team. I don't own the success side of the business here, as you mentioned. We've got a whole, Chief Customer Officer owns all of our post-sale delivery and customer success functions, implementation consultants, all that kind of stuff. But doing a great job there.creating a leadership team that spans between visionary and execution oriented and has skills and that can kind of augment each other and kind of take both to market. That said, in marketing, I think what we've done a really good job at especially the last nine to 12 months, is shifting the focus to data-driven ROI creation activities and initiatives and making sure that everything thateverybody's focused on has proven results when it comes to lead creation and continued pipeline development of those leads into high converting opportunities. Right. And so we look at the data constantly in terms of how many leads, how many stage one pipeline deals were created, what conversion rates are going on and how much closed business happened from the marketing activities we're doing and dropping the stuff that doesn't have higher ROI.And for us, some of the traditional things that most people in this industry think drive a ton of output are things that we've actually cut. And just from a perspective keeping our own sort of information and strategies a little bit behind the scenes, like I'll just leave it at that, butin a pretty severe direction from less inbound and more outbound pipeline creation strategies with our marketing team and our marketing skill. that's been a lot more focused on demand gen, content, sales-facing, market-facing content, and overall product marketing.And those are the skills that we've really built out on the team. because, you know, getting into like the final subject a little bit, but we can dive deeper into AI. But I mean, because of AI, it's like, it's allowed us to do this. there's mass personalization that we can do at scale, truly. And people have always said, you know, mass personalization at scale. like today with the tools that are available in the market for us to understand the ICP.that we're focused on, our ideal customer profile and the key personas at those companies that have challenges that we solve for in a unique way. That data is all now massively in our CRM and with other tools, it makes it easy to augment a message to those people at those companies based on specifically what they care about and specifically what the business issues and challenges are at that company at scale.so we can get out the best prospecting that the most senior BDR and or sales professional would do because they know this account and they know these people and they've worked with them the last 20 years, that's starting to happen at scale in an automated AI based way. So we can get a message out there to the market that's hyper contextualized for the person in the company that we're targeting.And create awareness and pipeline that way. So mass personalization. The other thing we're doing in marketing, like creative content factories, like we're getting with AI, we're getting five, 10 times the output and a consistent brand voice.through creative and through content creation than we did before. And it's all kind of wrapped around what I'd call before that curiosity culture, that experimentation culture, getting a lot of velocity there with, auto-generated hypotheses and variants and insights into how to create better content, have better creative, do better outbound at scale. And that's what the whole marketing team's focused on right now.Mark Petruzzi (05:58)Excellent. Neil, very cool.Mark Petruzzi (06:02)So Neil, what are the non-negotiables?Neil J (06:05)The non-negotiables. All right. Quick question back. Are you talking about what non-negotiables exist in terms of how I run my business, my team, the operation itself?Mark Petruzzi (06:14)Yeah, I mean, would say kind of yes, yes, yes, all three. Just what are the things you have to do for success in this business?Neil J (06:17)Okay,KK Anderson (06:18)as well.Neil J (06:21)Ah, that's a great question. I think they all, to me they all ladder back to, and maybe this is for other leaders too, they ladder back to the core values of the company that you're at. And hopefully as a business you've done a good job or as a business or a business leader flushing those core values out and making them applicable to the unique attributes of your culture and your company and the space you're in and all that kind of stuff. Because they shouldn't just be words that are up on a wall, right?here we've got four core values at Disco. I'm not going to go into each one of them. They're actually on our website. They are up on a wall, but at other companies they've been slightly different. And I think about, I go back them quite a bit in the way that I lead, in way that I help my leaders lead the organization. If we keep kind of connecting things back to, as we talked about before, the DSF, the overall objectives of the company, for us it's our Disco success framework. Or if it's...the core value of the employee experience and the culture itself, right? One of ours is together, win together as one team. Another is pursuing outsized impact. So delivering exceptional results, being relentlessly all in as a third. There's more, but I think those are really impactful for, especially for a customer facing organization that are driven by numbers and that have clear objectives in terms of what good performance is and what it isn't. Like having those three things be.kind of non-negotiable to me and the rest of our core values non-negotiable and we try and bring things back to that quite a bit, right? We do a lot as a business to really rally around that. There's some other things too. I just think that, you know, I think about attributes in terms of how we deliver results every day and how we behave and operate. I've mentioned the word quite a bit already in this discussion, curiosity.I want my team to be genuinely curious. I don't want people to like try to manufacture it. We're living in a world where AI is reshaping how we work. And when people lean into that and experiment and ask questions and figure things out, that's a real competitive advantage. And I think curiosity drives innovation and it's just non-negotiable for the skills of the people that are around my organization and how I lead.A couple others that come to mind, one is humility. I think we all make mistakes, but what matters most is owning them. And I tell my team, over communicate, fall on the sword for your teammate or your customer, do it naturally. Again, needs to be natural. It needs to be part of their core instincts and their core kind of makeup. You can't force humility. It's too obvious. I think when leaders model this kind of...behavior and they look for that in employees that they're bringing into the organization and they help reinforce it along the way. It really builds trust and unlocks a culture where people step up and support each other. And then I'd say the third kind of major attribute that is non-negotiable for people in and around the go-to-market operation that I want to be a part of is problem solving and sort of taking action. You can call it action orientation. You can say, youproblem solving kind of mindset, but people that don't wait for permission, they take charge. we're in a flat company as we've talked about where it's small, it's nimble. We can't wait. We got to go make things happen. We may fail, but that's okay. Use data, evaluate the scenario, make a decision to move forward and then don't just bring problems. You know, what frustrates me as a leader is when we get into a meeting or I have a one-on-one and it's like, you know, data dump of all the problems that are going on. Okay.That's fair. There's always challenges, right? But what I try to coach and enable my leaders and the people that roll into my leaders are working with them and I am every day in terms of here's an issue I'm seeing that impacts our number one or number two priority. Here's the data that I'm looking at that calls this issue out. Do you agree with this data? Let's talk about this. Do we all agree it's an issue? Okay, cool. We agree it's an issue. Here's my idea is to solve for it. What else is there?help me out team, help me out Neil, whatever it is, Versus just bringing problems, right? So I think that kind of shift in people's approach to the market and how we're gonna move forward and communicating internally and also with customers and prospects is like something that's just non-negotiable. It's like, you either have that skill, sure, we're always tweaking it and developing it, but you either have that kind of mindset in how you operate. And if you don't, not a problem solver, if you're not action oriented,If you don't have humility, if you don't have a ton of curiosity, then we try and figure that out upfront and not bring those people in.Mark Petruzzi (10:26)Yeah, and those items are just far less coachable. So I totally get it and all great stuff.Neil J (10:31)That's a good one too.Yeah, people talk about EQ quite a bit, right? To me, there's that emotional, I think the Q was quotient, but it was like emotional intelligence, right? And that kind of sums up a lot of this self-awareness and self-management and just having a focus on relationship management and taking action. So I think that's a, it's a buzz term, but you got to like know what you want out of EQ and make sure that you're seeking that out. When we interview, we...Mark Petruzzi (10:40)intelligence, yeah.Neil J (10:57)we ask scenario-based questions to flush this kind of stuff. Like, how would you act in this situation? And if you're not doing that, it's just so powerful. And so I think you gotta sit with your leadership team based on the role in the JD that you're looking to bring someone in on and make sure that you agree on the types of questions that you ask and where you like to see the conversations go to flush out those things like humility and curiosity and action orientation. Because the stories,that people tell you will tell you if they are or not. And so I think that's a real way to be careful in terms of bringing people in that have the right skill set and the right approach to the culture and the DNA that you're looking at.KK Anderson (11:36)Let's dig into the AI conversation a little bit more. You've said that you've experimented with Gong, Clay, Chatubi-T, even building your own AI. Where are you seeing the most value?Neil (11:47)a lot of what you just said from a technology perspective. I think the disruption opportunities in marketing, I called some of them out already, like the, outbound personalization at scale, kind of creating these content factories. call them creative and content factories where you can.KK Anderson (11:50)Mm-hmm.Neil (12:04)really get higher output and get a consistent brand voice and create content and impactful creative at scale. I think there's a lot of automations just within marketing there and those disruptions, we have the always on personalization that we're, that we're able to have based on some of the tools that you mentioned and also through some of the tools that we're using on our websitewith chat bot and through the tools that we're using with our outbound strategy. But think about the AI agents and go to our website and you can now interface through an agent and they handle the questions and the objections better than a human and they're always there. And so we've been able to use agent technology to actually create more leads into the organization than we had before covering it 24 by seven when before we were kind ofwith higher propensity leads on our website, our chatbot interface would fall over to a human being. And we're able to cover that with an agent now. So we're able to kind of save a headcount or two just in one little process within business development. In sales, there's a lot of disruptions around mass prospecting, as I said.We're doing deal intelligence and deal strategy sessions with those tools that you mentioned ⁓ to surface multiple data sets of information into one document.and we're running deal strategy sessions for our top pipeline opportunities without the reps having to put anything together once a week. And we're typically getting through six or eight deals within about an hour and a half time. And the rep doesn't have to put anything into it. Like previously it would be, sales professional, let's do a deal strategy review with the team. Here's the PowerPoint template. You got to go fill all this stuff out. This data already exists.in Salesforce and in Gong and all these places. Today, the AI can just pull it all together into one place and use something like a traditional framework like MedPick or value selling as a methodology or whatever you have, whatever your flavor is as the basis for that strategy doc.let's say we use MedPic here. So walk me through this opportunity from a perspective of what's the pain points investigating the pain that the customer wants to try or the customer wants to solve for? what are the metrics that they have in terms of their business issues and challenges? And if they could solve for this pain, what's it going to drive their business? D, what's their decision criteria? Other D, what's their decision process?So AI can take all that stuff in and around a framework like MedPic and surface it all into a document that we can all come onto a call together and go through really quickly. but the information's all there and nobody has to put all the information together like you used to have to do.So things like that, deal intelligence, deal strategy sessions. If you think about customer success, QBR templates, customer success, health scoring, generation of QBR, support triage, support knowledge base, auto updates, all that can be kind of augmented and enhanced with the use of AI. So everything, marketing, sales, success, it's like we're seeing 510x improvements in efficiency through the use of AI, being able to kind ofbring the base level of information up into one place and allow us to be more strategic and talk about how do we win, not what's happening,Mark Petruzzi (15:05)that makes perfect sense, Neil. So you've questioned whether the whole concept of SDR, BDR functions will survive in this world here of AI. In general, how do you see AI reshaping early stage prospecting?Neil (15:20)I think like any technology change, there's going be massive job creation, not job loss. anything in history. whether it goes back to, the industrial revolution to the creation of the wheel like, we don't, it's hard to envision.exactly what the jobs are going to be. But we all know that the information is there and it's up leveling the value that humans bring to the conversation. but we still need humans. we're gonna like the, roles of humans in the world of, which istechnology, solving problems for businesses, communicating that, executing on understanding their needs so we can solve those problems and show them how we're going to do it and then implementing it and being there to support it. Humans are going to have to be involved in all that stuff. What they bring to the table is just quickly being up leveled and the job creation is going to be massive around the future. I think in the short term,There's efficiency gains. Like for example, we on our BDR team, because of some of the automation we put in place, we didn't have to fulfill on a head count that we had planned in this year. But that's just such a super in the moment tactical small point in time of what's going on. Ultimately, I think that, organizations are going to thrive with more and more job creation through the use of AI.than job elimination, like any technology ever in the history of mankind.KK Anderson (16:48)It's almost as if we don't know even what those drops might be. it's moving so fast that there could be a whole new role in sales that we haven't even identified yet, or that hasn't even become mainstream yet. Right?Neil (17:02)Yeah. It's smart because people smarter than me. And what I mean, one job that we did just create in the last six months is like on my rev ops team, just this, like we've got a really talented person who's super curious, super innovative, very good at collaborating cross departmentally that rolls into my VP of rev ops and has been more on sort of the system side of our revenue operation.Our rev ops team, like a lot, and maybe not everybody's as familiar with this, but our rev ops team is data and process and enablement, right? And so they're constantly looking at the data. They're, constantly using what we find in the data to drive new process. And as we roll out new process and tools and strategies, we have to enable everybody. So there's an enablement strategy and plan. There's resources in all those areas,our team of...people that are managing the tools, really talented individual there that we took and we promoted to be the head of our AI strategy from a tools and data model perspective. And I've practiced some other sales leaders that have this role on their team now. And that person has been in charge of understanding the potential use cases across. the entire go-to-market.pipeline generation, to execution, to ongoing customer success and adoption and renewal. And they're identifying the use cases across these constituents and narrowing down the platforms of which we will use to enable those use cases. And some of those tools that you mentioned are going to be, or are already our major platform for AI enablement going forward. So we've taken like 30 different technology potential ideas that we're kind of bubbling up either in the form ofbeing used, being POCs, they're being evaluated across our go-to-market. And we've narrowed that down to about three platforms, maybe four. And we're excited about that because generally speaking, we can go tell our employees, go get creative with AI. You've got these platforms that will lead with AI in everything you do. Be creative, be curious, and lead with AI. And they're coming up with the use cases. We don't have to go solve for every use case. We just know thatWe've picked platforms that holistically help us enable use cases around a really solid data model.Mark Petruzzi (19:09)So Neil, unfortunately we are coming to the end or towards the end of our time with you. Can we do a quick rapid fire and a few questions here to finish this up? All right. All what was the first product or service you ever sold?Neil (19:19)Sure.man, you're catching me off guard. Product and service I ever sold. T-shirts. Junior high. Made a few thousand bucks and realized, wow, you I can be an entrepreneur and I can actually sell and win and pay for things. So at that time I bought my own motorcycle and then I ended up buying my own car, it was powerful.Mark Petruzzi (19:28)He searchedI love it.KK Anderson (19:39)awesome. Okay, favorite CRO or CEO that you like to follow?Neil (19:43)My favorite CRO is a gentleman that's not a CRO anymore, people aren't going to know him. Just a great coach and career mentor of mine, guy named Carl Schachter. Maybe they'll know him. Some people will know him. Carl, you know him.Mark Petruzzi (19:54)Yeah, I think more will know than you think.Yeah, I know. Sure.Neil (19:58)In fact,funny, because I met with a client yesterday, a gentleman in New York who worked with Carl at their previous endeavor where Carl was CRO. And he and I hit it off. And I'm like, yeah, we both commented on the fact that he's been a great and this gentleman was a engineering leader. But he's like, Carl taught me how to sell anyways. Great leader with us in the early days. was even he headed up some of the alliances teams at Oracle back in theIn the 90s, in the 2000s, I got to work under him at Salesforce as we scaled that company from 12 million in revenue to two and a half, three billion over about 10 years. This gentleman went and ran the Japan operation, went and ran part of Europe, but I got the fortunate experience to work for him and still call on him for coaching and assistance and all that kind of stuff.Couple other people, really, and this goes back a little bit to the Salesforce ecosystem, but people that I'm big fans of, and I think some of the people here will know these people. Eli Cohen, who's the CEO of a company called Saleshood, an amazing leader, an amazing innovator. John Barrows, the CEO of company called JB Sales. I've used John and his methodology as almost like an extension of our selling team.He has a methodology around just lightweight methodology on how to prospect really effectively for BDR organizations and how to go win for sales organizations. And it works. It's easy. It's logical. And the energy and the culture that he and his team bring to organizations when you partner with them are worth it. Outside of the methodology, it's just like an extension of your selling culture. And so really big fans of those people as CEOs of their companies.small business.Mark Petruzzi (21:33)Yeah, youyou put out some great names there and I hope the audience does look and research some of them.Neil (21:40)no affiliation. Hopefully that helps. No,KK Anderson (21:42)HahahaMark Petruzzi (21:43)All right, well, Neil, thank you again. This has been fantastic. I guess real quick, where can people find you? What's the best way to connect if they'd like to?Neil (21:52)LinkedIn.I'm a big fan of being super real on LinkedIn reach out to me on LinkedIn, tell me what you need, and I'll be direct with you and let you know if I can help.Mark Petruzzi (22:01)Excellent. Beautiful. Neil, thank you again and to our incredible audience. Thanks for joining. All the best.Neil (22:07)Awesome. Thank you.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, we’re joined by Neil Graham, Chief Revenue Officer at Disqo and a seasoned revenue leader whose career spans Salesforce, Siebel, Jive, and Telem. Neil shares a ground-level view of what it takes to lead, scale, and modernize revenue organizations in an era where traditional sales playbooks are no longer enough.From breaking out of funnel-stage rigidity to building flat organizations that prioritize curiosity, Neil walks through the changes CROs must embrace to stay ahead. He also shares how Disqo is rethinking GTM structure and leveraging AI to drive personalization, speed, and operational clarity; without drowning in tools.What You’ll LearnWhy the Playbook is Obsolete: What Neil really means when he says the old models no longer work, and what replaces them.Lightweight Rigor at Scale: How to build process and alignment without slowing teams down.From Bottoms-Up to Top-Down TAM: How Disqo blends relationship selling with TAM-led targeting for scale.Curiosity as Culture: Why curiosity is a non-negotiable leadership trait in flat, fast-moving GTM orgs.Leading Through Change: How to coach teams to self-govern, move fast, and stay mission-aligned in a no-layer org model.Key TopicsBuilding sales organizations without bureaucracy or bloatAligning marketing, sales, and success teams around business outcomesUsing AI to power real-time customer insight and hyper-relevant outboundFlattening GTM structures for speed, ownership, and clarityCreating cultures where experimentation and impact are rewardedGuest Spotlight: Neil GrahamNeil Graham is the Chief Revenue Officer at Disqo and a proven sales leader with decades of experience scaling GTM organizations from Series A to post-IPO. Known for his ability to bring structure without red tape, Neil has helped some of the most recognized B2B SaaS names balance scale with agility in high-growth phases.Resources & MentionsCompany: DisqoFramework: DSF (Disqo Success Framework)Sales Tools: Gong, Clay, ChatGPTBooks & Influence: MedPick methodology, Salesforce early days, AI-led sales enablement🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.Mark Petruzzi (00:33)Welcome to today's episode of Selling the Cloud Podcast. We're excited today to welcome Neil Graham, Chief Revenue Officer of Disco. Neil is a proven revenue leader who has helped scale organizations at Salesforce, Siebel, Jive, Telem, and now Disco, the best name of them all. At Disco, Neil leads a go-to-market organization of about 45 inside a nearly 300-person company.KK Anderson (00:33)Thank you.Mark Petruzzi (01:00)His career spans taking companies public, guiding series A to series F growth, and balancing early stage venture backed and private equity operating models. Today, Neil will share what it looks like to lead and scale revenue organizations when the old playbook is obsolete, which pretty much is all the time nowadays. Covering agility,operational discipline, and why CROs must embrace a new approach to building revenue in 25 and beyond. Here are the four themes we'll explore. First, when the old playbook is obsolete. So when these old legacy models no longer fit, no longer work, how do leaders adapt? Scaling from 10 to 100 million, that sweet spot, especially in the SaaS and ISV world.And then, the concept of lightweight operational rigor, like how to combine a sleeves rolled up selling model with really good process and tools, but not too many process and tools slow How flat orgs need to be structured and how they work and how that really puts more pressure and responsibility on the CRO.and also sprinkling AI into the go-to-market mix. How Neil is experimenting with AI to augment productivity and rethink traditional roles. Neil, thank you so much for joining us. Welcome to Selling the Cloud.Neil (02:26)Thank you, Mark. Appreciate it. Thanks for having me.Mark Petruzzi (02:30)Happy to have you here. All right, topic one, when the old playbook is obsolete. So, Neil, I've heard you say, don't even know what the playbook is right now. It's all getting disrupted. Tell us a little bit about what you meant by that.Neil (02:43)thanks for the introduction. That was great. look, privileged to be at a lot of great companies through the years and hopefully caught on to a little infrastructure and kind of prioritization through the years in terms of how I approach things. we're in a really unique age today.the traditional playbooks from the last, I'd say 20, 25 years in a way, are going out the window in a way they're still there. And I think if you think about what's happening with AI and with how that impacts operational structures, go to market strategies, people and process skills.And overall playbooks, it's like you really have to kind of reconsider the way you're operating at every step of the way yet continue to operate and make sure that you put one foot in front of the other and execute. And so what does that look like? we've spent a lot of time. I think about the back in the days at Oracle in the early days and then at Salesforce, where we really scaled some organizations from small to large.the playbooks that we created around, marketing and sales and customer success became kind of a standard. And it's like, if you think about the processes from lead development, MQLs to SQLs to, early stage pipeline and the sales process from stage one to being selected at stage four or five and getting into a negotiation, the process of value selling along the way where you identify.the customer's business issues and challenges, you map your solution to that. You think about trying to position how you're unique against the competition or the status quo and quantify that, that value and articulate that really well to the client. A lot of that was put on our people and we would train and enable around these processes and these plays, try to roll out frameworks like, every part of the sales process, dissecting it.providing people visibility and information into what it takes to be successful, whether it comes to discovery, whether it comes to running a great demo, whether it comes to positioning the differentiated value prop, whether it comes to building the business case of the impact that you're going to make at the organization in terms of driving business outputs, whether it comes to scoping and professionally delivering a plan to make the customer successful, whether it comes to the negotiation, the objection handling, the competitive intel.All that stuff's still there. And our customer facing people and processes need to execute flawlessly on that. At the end of the day, it's just that the information is so readily available and we'll talk more about it later with AI have to do everything that I just said, but it's so flat in terms of being able to access that information, position that information on the fly.and make it part of your cadence that some of the traditional models of the playbooks and the enablement plans and the objection handling frameworks and all that kind of stuff literally go out the window and they become kind of almost in the moment. So I don't like at the end of the day, I think the old playbook being obsolete, I don't know. I think from my point of view, customer value still wins,the modern model starts with the customer's business case, knowing their business issues and challenges, understanding the pressures and constraints they have, and your people being able to flush that out and have that information at their fingertips when they come into a conversation. Then being able to articulate how the solution that they bring to market is differentiated and tie that differentiation to the measurable outcomes.It's just doing it in a more productive and higher impact and flatter and faster way. But every interaction that you have should clarify, how you come back to the business issue and challenge the customer has. So I think second, the AI tech that's out there puts these answers within reach and, we're able to have this information quicker and faster than ever before. And then I think third, just creating a culture and sort of a overall.go-to-market system that is rooted in curiosity. So your people and your processes continue to evolve quicker and faster than the competition is really important for every company.KK Anderson (06:30)I echo everything you said, Neil. this morning, as a matter of fact, I pulled out my phone and I wrote it in my notes thought exactly what you just said. The activities, what's changed now is that the activities aren't the work. Going into CRM and working in CRM, that is what's obsolete. Right? You can't do the same things every day and expect to have a differentiatedcustomer focused, customer obsessed approach, right? it's all about leveraging all of this super intelligence, leveraging AI, what's at our fingertips to do the hard. And so sales, in my view, is going back to what it was originally, the beginning of the sales profession, right? Where it was all about solving problems asking great questions and getting to know people and relationships.And then we had all of these years of playbooks here's what you do, here's what you say, here's how you handle this objection, here's how you position this, here's how you differentiate this. And it's almost now, like the second something gets turned into a PDF, it's no longer relevant, right? And so it is interesting. All of this is allowing sellers to do the hard things, which is if you go a day or a week,God forbid, and you don't feel that anxiety of what am I gonna say on this call or how am I gonna approach that person, then you're not doing the hard things. Ticking off tasks is old school. That's the old playbook, right? Anyhow, so as you think about this kind of seismic shift that's happening, what are the principles that are guiding you as you lead today? If you're going back to basics,back to you were just talking about, like what are those principles? Like how do you lead through this kind of a change?Neil (08:04)Yeah, look, first of all, think, it goes a little bit to the second kind of area of discussion. It's sort of how do you create this lightweight operational rigor, especially as you scale companies I've kind of been at a few companies now that are series A, series B. there's a disruptive technology that's solving for a problem uniquely in the market. Doing it, it's a better mouse trapthan what was there before. And because of this unique model, the unique data set, the cloud, whatever it is, it's able to solve the problem in a more effective, more efficient, more holistic, better quality way. The company I'm at right now is disrupting the marketing media effectiveness measurement market, the old stodgy providers that are out there that weren't as innovative and disruptive.We're disrupting that. I'm entering into a company, I've been here about a year and a half, where had, a better mousetrap than the competition, that a company could build on their own. Companies want a partner, they don't want to kind of be in the core competency of doing what we do. so we've been taking share from the competition.in the early days as we built the product five, six years ago and started to take it to market, we hired some good people from the competitors and knew the space and they brought their book of business and their relationships and it was a lot of hard work. Don't get me wrong, but at the end of the day, we were able to take share where we had relationships and where we had knowledge and sort of the bottoms up, right? And now we're moving more towards what I'd say is understanding the total addressable market.aligning our skills and our people and our organization around that, picking our bets on where is the biggest total addressable market, what can we take on right now as we scale and grow and we get past 50 and 100 and 150 million, aligning our skills and resources, training and enabling, getting the right people, hiring the right people, all that kind of stuff to go take the market more from the top down. Having that bottoms up, but also that top down where...We know this is the right place for us to aim the arrow and shoot. And we're going to put a lot of emphasis behind where we shoot and make it really impactful, improve our win rates, execute more flawlessly from marketing to sales to success and do a great job serving that market. So as we look at doing that and things are at the same time getting disrupted by AI, I've kind of run this play before where you're taking a company from 10, 20, 30 million to hundreds.and have the playbook and kind of like know the motion, right? You build in some process, you bring in world-class tools, you align your people and your skills to the market opportunity, you help limit the distractions on stuff that's not within that market opportunity that's the biggest bang for the buck. However, you still have to be nimble, you still have to kind of pay attention and pivot at the same time.And so there's a lot of art and science to rolling out lightweight process and tools and enablement and skills, yet at the same time, not over engineering it so we can go execute and we don't get in our own way and we don't have a lot of bureaucracy and there's not a lot of layers. And I think we've done that really nicely here. It's like I kind of came into an organization where we had a marketing team and there was a bunch of different pockets ofweird reporting structure. And we quickly fixed that where it's me to my heads of marketing versus like in demand gen versus product marketing versus PR and comm and then they have teams, right? And then on the sales side, we did the same thing. We kind of had a one size fit all motion for the salespeople and they were kind of going after the market based on what they all knew. We layered in where do we need to be and what skillsand tools do we need to have in order to go attack that market? Let's bifurcate the sales team because we saw two plays going on in the market. And we did that. We aligned the right people with the right opportunity. We hired the right people coming in to grow into these two opportunities. And we've rolled out playbooks and processes and competitive packages and, objection handling frameworks and all that kind of stuff for all the people that are in these two swim lanes in terms of how we go to market. What's been really cool in the last12 months is we've embraced AI to just do all that bigger, better and bolder. Right. And so, answering your question, I think first, leaders need to get out there and be in the market, especially at this size of a company. can't, more so than ever. It's, like, you have to be in the field. You have to be with your customers. You have to be with your teams. If you're not spending 50, 60, 70, 80 % of your time.even as the CRO is the operational leader, executive part of the executive committee, all that kind of stuff. If you're not out there in front of the market, then something's wrong, right? So that's number one. Number two, just building this culture of genuine curiosity, I think is critical. You have to hire then promote and exit people based on curiosity or a lack thereof.And that's in everything you do. It's if people aren't asking questions, if they're not genuinely curious in front of the customer, in front of their own internal teams, if they're not innovating and trying new things, and if they're continuing to be focused on delivering the results, right? Like we have OKRs here. We call it DSF, the Disco Success Framework. My marketing team knows exactly what's expected out of them when it comes to the specificoverarching business goals, the key metrics to achieve those goals on a weekly, monthly, quarterly basis, and the initiatives that they have to go solve, to go generate those key metrics that they continue to evolve around. We're kind of continuing to tweak our initiatives every month, every quarter, to make sure that we're hitting the actual metrics in alignment with our objectives. And if you don't have people not only being curious and being innovative, but also keeping their eye onHey, is this an alignment with the objective and the key result that I'm trying to drive? And if it's not, what the hell am I doing? Let me stop doing that, right? And allowing people to be informed around that, have the information be very clear so they can almost self-govern because as you create a flat organization, there's a lot of greatness with that, but there's a lot of challenges that come with that as well. And you have to allow people the power to kind of understand, does this map back to the key objective and...desired outcome that I'm working on. if it doesn't call an audible, let's get the hell out of here and let's stop doing this. Right.Mark Petruzzi (14:07)Well, Neil, you have me thinking and wishing this was an investor presentation rather than a podcast. And what I mean by that is we, get to a fair amount of opportunities to hear CROs like yourself when they're looking for funding and, get to get excited about that or not excited about that. And you actually made me put together a thought that has happened in the back of my mind many times, butnot as clear as today. And that is when we're doing this podcast and a CRO or a CMO gets on and, or a CEO gets on, they start talking about their approach. And I start to just think exactly that of, this should be an investor presentation because I, want a piece. So that's very impressive. As you know, I hear these things and we have podcasts every week as well. So I love the way you, positioned all that and you went,radiant to this direction, but I'd like to have you tap a little bit and go a little deeper.Neil (15:03)it kind ofa little bit of the, how do you build in this operational rigor, but also like, how do you do it in a flat world? So, I mean, feel free to drill in there because it was kind of two of those.Mark Petruzzi (15:14)Yeah, nowthat's great. And I also like, you described how these some CROs are clinging to these old cadences and funnel metrics and SDR handoffs and the whole process of lead generation. What do you feel are broken about these models and a little bit on how do you fix them?Neil (15:31)I don't know if it's broken. I mean, look, don't get me wrong. we still have operational metrics that we look to kind of the leading indicators on a weekly and bi weekly and monthly and quarterly cadence. And still one of the objectives is an objective around, MQL and lead creation, right, that my marketing team owns andSQL and down funnel lead, qualification that the BDR team owns and SAO generation, which is our stage one opportunity that the BDRs and the AEs and the CS team own in terms of creating net new pipeline. And we have a certain amount of pipeline that we got to create every week, every month, every quarter. And, we're trying to be in front of it with key initiatives that we're rolling out to improve our outbound motion.And we're looking at Salesforce dashboards and summarizing all this stuff up.just take the sales team, for example. We've got about 20 sellers and I've got three SVPs. And so our sellers are director and VP level, our SVPs are managerial level and they report to me. And so we flattened it those three layers. In marketing, it's three layers across the whole organization.on our success and delivery teams and our product teams and our engineering teams, we've gotten it down to three layers. I think that's really helped us as a business. Our CEO drove that and...made it a mandate and not everybody kind of understood the why. And we did a lot on our all hands calls and our internal communications to help people understand the why behind all this. And over a period of about a month, month and a half, we got the company that flat. And the goal was to get faster information flow and get quicker, better decisions and have more experimentation and fail faster and succeed faster, right? And just have.higher organizational ownership and impact, have impact be visible, versus lost in silos. And if you can really then build your, internal compensation and promotion and recognition system, which we do a lot there, we do stuff on a quarterly, biannual and annual basis around those subjects. If you can build it around impact.And make it impact based in alignment with your goals and objectives back to your OKRs and promote the people that are having high impact. Those are going to be the people that are the most curious. Those are going to be the people that are experimenting the most. And, if you do this the right way, you'll start to set those examples. And pretty quickly within about a year and year and a half, we've weeded out a lot of people that aren't curious. we've kind of weeded out people that aren't trying to make an impact.Now the challenges with that is when you have that flat of an organization, it can really blur decision kind of ownership and there can be competing initiatives and there can be some accountability gaps and it can overload some of your managers and your leaders. I'll give you an example. It's like my CEO and I are very tight at the hip on working with the marketing team andThere can be times where my CEO will grab people that roll into me and send them in a particular direction. And it's like, he and I have to be really well aligned on what are we trying to accomplish here? What are the goals and objectives of the company? And let's make sure that we're pushing people towards the same outcome, because if there's any competing interests, it can get confusing for our employees.And so just the communication and the collaboration and the work that we do, have at this company, we've got about two hours set aside every week for SLT alignment. that for the executive team to meet, to go through all the key initiatives and strategies, everything from people to process, to tools that we're using, to the outcomes and the initiatives that we have, and making sure that we're all in alignment.in this flat culture, we get everybody kind of pointed in the right direction. So hopefully that helped a little bit, it can create an opportunity, but there also can be a lot of challenges with it as well.KK Anderson (18:57)You know.Really, really insightful, Neil. Thank you for that.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of our conversation with Josh Hoffman, we explore the leadership mindset required to thrive in moments of high-pressure change, like mergers, long enterprise cycles, and AI-driven disruption.Josh shares how sales teams can stay grounded in customer value, build trust through co-created plans, and lead with consistency; regardless of who owns the company or what the logo says.We also talk about the real-world impact of AI on sales effectiveness, onboarding, and go-to-market readiness.What You’ll Learn:Leading Through Change: How to stabilize culture and focus teams during M&A, leadership transitions, or high-stakes GTM shiftsMutual Action Plans that Work: Why aligning around a co-created calendar is a simple but powerful tool for accountability and momentumConsistency Over Chaos: How sticking to your core value proposition helps drown out internal and external noiseReal AI Use Cases: How Josh and his team use AI for onboarding, writing, analysis, and market research—without replacing human judgmentLeadership in Modern Sales Orgs: The behavioral traits that inspire performance, loyalty, and resilienceKey Topics:Sales leadership in high-pressure, transitional environmentsUsing backward-planning and mutual calendars for deal velocityStaying aligned on value across long sales cyclesCultural consistency across internal and client-facing teamsAI for productivity, market intelligence, and GTM strategyEmbracing humility and continuous learning as a CROGuest Spotlight: Josh HoffmanJosh is Chief Revenue Officer at Totus Rx and a long-time leader in B2B revenue organizations. He’s built and led sales teams across tech, telecom, and compliance industries, with a focus on building high-trust teams and delivering real value to customers. Josh is known for his practical, human-centered leadership style, especially in complex, high-stakes environments.Resources & Mentions:Book: The Challenger SaleBook: SPIN SellingLeaders Mentioned: Mark Anderson, Russ Reeder, Todd Abbott, Mike Jenner, Joe BurtonFollow Josh Hoffman on LinkedIn for more insights on sales leadership and culture.🎧 Listen now and subscribe to Selling the Cloud to hear more from enterprise GTM leaders shaping the future of sales.KK Anderson (00:31)our third topic is around leading teams in a time of change. And so where I wanna take us. All the pressure of a change. You know, it can be a pressure cooker. All the accountability, which we know sales is famous for. The behaviors and the mindsets and the relationship and the building trust. All the things, right, that go into being an exceptional salesperson. Like when you're...going through like some of these acquisitions or mergers or whatnot, people are under the microscope, like how do you get your reps to believe and act the right way on the same side of the table in these high pressure environments?Joshua Hoffman (01:07)It comes back to me to the word consistency. You have to maintain a consistent value based approach on what you're delivering to your partners and clients. That shouldn't change. Even in times of mergers, acquisitions, whatever they might be. I don't know that I've been through any of those situations where the value proposition of the company changed at all. There might have been something added to it.There might have been something taken away from it based on that. But the general value proposition, if you believe in the organization that you're a part of, who owns it doesn't really matter. If the value of what you're delivering to your client or partner has remained the same, the rest of it is noise. And you have to remain focused on the outcomes. I really can't think of a time that I've been forced to say, oh my gosh, the value of our organization or the value of what we'rewhat we're providing to our clients has changed so dramatically that we've got to make a shift in who we are with them. Now, there may be other shifts that take place inside the organization. There's changes in leadership, there's changes in locations, there's changes in potentially having another strategy that has to come into the business because two things are coming together. But what doesn't have to change is that your approach with your clients and partners, it's still the same.you're still there to be a part of a team that's driving an outcome. And if you can remain consistent in that approach, you can help people remove the noise from the system and say, you know what? I don't have to worry about that. I don't have to worry about whether our company name changed. I don't have to worry about whether headquarters is in Dallas or Michigan. ⁓ It doesn't matter because I'm still doing the same thing every day. Now that's a lot easier, I think, for salespeople.than it may be for others in other parts of the organization. I don't want to paint it that it always works the same way, but for the pieces of the business that I've been the most part of over the years, sales, sales operations, marketing, very much consistency is an opportunity to make things a lot smoother and a lot better for people and to make sure that culture remains a consistent, strong, positive force in people's lives.Mark Petruzzi (03:11)Very cool. so let's talk a little more process here for a few minutes. What kind of role does a mutual account plan or an action plan that you may create with your team, what did they play in making sure both seller and customer are aligned and accountable? How much do you use them? What kind of value do you get out of them? And are there times thatthings like that are a distraction and not really productive.Joshua Hoffman (03:37)so first of all, I'm a little nervous answering this question with you because you've literally written the book on some of these things. I feel I might be a little bit on my heels, but let me try and answer the question as best I can. First of all, the idea that you're sitting on the same table with a client, with a partner, with both of them simultaneously, by default, that should mean that you have a mutual action plan. It should mean that you have a mutual calendar that you're working off of.It should mean that the outcome that you're trying to drive is identical because you've coordinated that you've co-created it. You've, but you know, back to my co words, right? You have co decided what those things should be. Now, whether you're a value selling person, a challenger salesperson, maybe even a spin selling person, there's all of these different models that are sitting out there. there are some attributes that those things have that are in common.And I always like to quote one of my favorite people. So I had this person in my life for a long time named Marcel Brunel. And Marcel was at this organization that did great work when it came to helping people work through the process of selling. And one of the focus areas that Marcel brought to me, it was a learning for me at the time, and that I've carried with me throughout these years, is about having that calendar in place. And for me, when I talk to aclient or partner, it's about having a backwards-facing calendar. And so let's start at the end. Where is the end here? What is the date? What is the outcome? What is the goal that we share in? And let's work our way backwards and establish goals and milestones that are going to help us achieve that. And then let's hold ourselves accountable to that. And as soon as we have alignment on the end of the line,it becomes much easier to fill in everything that works backwards. And if you miss a date, you need to catch up and you need to come up with a co-created action plan to do that. And that kind of collaboration, it really solves not everything, but it solves an awful lot. And it's not that things don't go wrong, things do. But if you build the action plan the right way, if you build the outcome the right way, you also try and provide yourself with the opportunity.for things to potentially not go the way you expect. You build in a potential buffer. Maybe there's an extra day or two here. Maybe, depending on how complex it is, there's an extra week that's baked into that that allows you to still achieve the outcome. And so that kind of planning is something that I talk about consistently, whether it's with a person on our team, whether it's with somebody that's working inside of an organization that's actually delivering the product or service or with a partner or client.Let's start at the end and let's work our way backwards and make sure we're in alignment.KK Anderson (06:16)it occurs to me as well, especially if you're in any kind of a, you know, complex sale where, or a longer sales cycle, right? Where you may have different people coming in and out of the sales process. If you have a mutual action plan or mutual account plan, whatever you want to call it, you can always lead with that outcome, lead the conversation with that value that everyone is synthesized there together to accomplish. And whoever's new to the call just falls right in place.Right?Joshua Hoffman (06:42)That's right. You get onto a call of you. If you had that co-created action plan and you've decided on the outcomes and the dates and you're having, you know, let's pretend it's a longer sales cycle, so to speak for that. And maybe it's a two month sales cycle when you're having that series of meetings to get there. The first slide should be that calendar. What have we agreed to already? Are we on track or are we not on track?and let's make sure that we're in this together. And that way, when new people do enter the conversation, they walk right into a framework that allows you to be successful, that allows you to introduce other people into the process.KK Anderson (07:18)What allows them to have the confidence that the conversation has been effective and aligned so that when you're at the wire and procurement comes in and starts asking questions, you've built the value. So you don't need to worry about getting slashed in negotiations and whatnot.Joshua Hoffman (07:30)That's right.Well, and partof it is even is making procurement legal, whoever else needs to be engaged in that process. Part of it is making them part of the team. If they're part of the team that's creating the outcomes and the decisions, then you don't have those surprises. Now, candidly speaking, look, there's always a surprise. A lot of times there's still a surprise.But the more you engage in that model and the more you broaden the team that you're working with, the easier this becomes because everybody's in alignment. I know what the outcome is. I know what needs to happen to get to that.Mark Petruzzi (08:08)Perfect. Well, so I guess we're even now. You made me blush with your last comment and KK made you blush. So we gotta get KK to blush at some point here. You got anything?Joshua Hoffman (08:19)Well, the blushing trifecta. Look, I tried to do it at the beginning of the conversation because I have seen KK's work. I have seen the impact that that you have had on people's lives by helping to make them better. I've seen the modeling that you've done. I've seen the outcomes of the not only the analytics associated with it, but the coaching that comes along with it. And I've seen the relationships that you've built and and that kind.of thing goes a long way because you not only bring your shining personality to this conversation, you bring credibility to the conversation. And so if that doesn't make you blush, kick it. don't know what I'm So ⁓KK Anderson (08:55)You got me.Mark Petruzzi (08:56)Now, let me tellyou, that was beautiful. I have seen it all firsthand as well. So I echo everything you say. But yeah, that'll make you blush too. Okay, so last question within kind of topic three that I have at least is, so what leadership practices have you found? Do all these things that we're describing, like,KK Anderson (08:59)You made my day! Even it's Friday!Thank you.Mark Petruzzi (09:24)build that trust, that loyalty, that long-term performance inside a sales team, and again, with the clients that you work with and prospects that you work with as well.Joshua Hoffman (09:35)so the things that I've brought up already sort of round some of those things out. Look, you have to care. You have to have compassion. You have to want other people to succeed. You have to have humility inside of this. You have to own up when you make a mistake. And gosh knows I make enough of them. And so I do my best to own up to them every step of the way. You've got to make sure that hierarchy is not really a part ofthe culture, at least for me, it's not. I would rather be viewed as a teammate than be viewed as a CRO. We're, the same way that I portrayed the company-client-partner conversation of being on the same side of the table. I like to view myself as being on the same side of the table with all the people that are part of the internal organization, too. Look, it doesn't always feel that way. I know I'm not perfect at it, but I do my best. AndIf I don't make it happen again, I try and own up to it and say, look, there's a chance for me to be better. And I talk about behavioral change in the context of not just people on the team, but about myself and being humble about that and being sort of true to myself that I'm still learning after, you know, I hate to call it the number of years, but after this many years that I'm still learning every day, I want the same for everybody that's in the organization. I want the same for our customers.We learn together, we grow together. It's a constant force.KK Anderson (10:52)try to remind myself whenever I'm in any kind of a conflict or a difficult situation that it's okay because I'm going to be better on the other side of it. Right? It's gonna, we're gonna get stronger.Joshua Hoffman (11:01)Yeah.Yeah, it does. ⁓I don't want it to, yeah, that old phrase, if it doesn't kill you, you know, makes you stronger. don't necessarily want anything that painful, but I've tried to make it work to my advantage.KK Anderson (11:15)So let's go to our last topic, which is the audience favorite always. And this is the future of go-to-market in the age of AI. so you have said that your mission is clearly helping others find careers that they love. You're very passionate about that, about caring for the individuals and helping them achieve things that they once thought were aspirational. Just like how you started out in the manufacturing floor at and look at you now.Right? So how do you see AI supporting that mission of yours for the next generation of sellers? What's going to happen in our world?Joshua Hoffman (11:47)look, AI is a game changer in so many ways. And look, I don't know that there's such a thing as an AI expert right now. And, Mark, you might be as close as the one that I know of. So again, you've written the book. And so I'm to be careful about how I how I answered these questions. Everybody's still learning right now. And I am part of an AI driven organization right now. We use AI.in how we deliver our services to our clients. AI reads evidence, AI scores evidence, and we still have to have people because we're an audit and compliance company and there's still people engaged. But we do use AI as part of what we do. And I get to see that every single day, the power of what it can do to save time, save money, save stress. I've also seen that you have to use caution because AI is not always right. The concept of hallucination is real.And you have to be careful and you have to make sure that you're using other sources to validate what you're getting out of AI. Now, I've also seen it in sales and marketing where you have the capability of not only getting information in a faster way than you did before, but having that information be more complete and having that information help guide you through a process. Using AI to learn about yourclients, your partners, the industries that they're a part of, understanding the relevance of what's important to their outcomes is a very powerful thing. And it's not cheating. I think some people have viewed it almost like, oh man, if I use AI to give me the answer, I'm not being true to my own creative self. Well, the reality is that you should use it to make you better. You should use it to make you more complete. You should use it to validate the other work that you're doing.It does come down to one thing that's, well not one thing, there's many things, but a thing that's really important is your ability to write the prompt. And your ability to ask the right questions of AI is what will deliver an outcome that's going to help everybody be more successful in that. I watched my wife's business use it. She's actually far better at AI than Igive her great credit. I don't think there's a night that goes by that she's not watching or learning something about AI. And we have had many conversations in our organization about how to use it effectively. But it does come back to prompt writing when I'm using AI, where I'm trying to teach myself is what's the right prompt? Not am I getting the right information all the time? And the better I get at that, the more useful it becomes.And it does help us solve problems. AI will come back with answers that I haven't thought of. I love to think of myself as being super brilliant, but the reality is I'm not as brilliant as what AI can go uncover in not only the universe of information, but the universe of context. And I find it to be incredibly valuable.Mark Petruzzi (14:31)and I kind of look at it like Josh is if you're going to go play some golf or play some tennis and do you want to go out there with the old tools, a tennis racket from 20 years ago or do you want to go out there and find something that is using all the state of the art technology? It's kind of what AI means to me at the end of the day. every we're kind of sick or at least I'll speak for myself.I get really touchy on acronyms and things like that, maybe because I've been in a number of the largest consulting firms and everything's an acronym and, everything's an acronym kind of built to get clients to spend more money. And so I look at those things and I say, OK, yeah, I'm not loving that side of the old eco AI ecosystem that we live in now. However, Ineed to shake that off and I do shake that off because at the end of the day, it's incredible. The things you can do and the productivity improvement you can bring in is just incredible. And we can't miss the opportunity to grab that and leverage it every step that you can. So with that being said, kind of share your perspective on that. how are you using AI today?Joshua Hoffman (15:37)That's right.Mark Petruzzi (15:43)How are your teams using it? I'd love to see what you're taking advantage of.Joshua Hoffman (15:47)Yeah, so let me use a couple of examples. You know, one of the examples is in trying to understand ⁓ value proposition and understanding what else is going on in the marketplace and getting context for the kinds of problems that people are trying to solve and how you go about solving that problem. And so from that, you can actually get great information about how you can best position something so that it's heard the way that you want it to be. You can get guidance along the way.If I'm in a situation where there's a new client that's coming in or a new partner, the ability to use AI to understand not only the data about those folks, but also about contextually how it fits into their vertical marketplace, what problems they're trying to solve, what problems are they most often faced with? What are the typical solutions that they use to do this? What are the pitfalls of those? These are things that you can work with AI to understand at a better level than you could before.And you can consistently figure out how to synthesize that information. so being able to bring that, boil that information down is another value of AI. doesn't have to be 20 pages long. You can figure out how to get that information into a much more concise manner, and you can help use it to teach you how to communicate it effectively. And I think that there's so much opportunity there.Now I do use AI for things like analytics and so I absolutely try and use it to help grade my work so to speak. Am I looking at this problem the right way? Am I using the information the right way? I certainly use AI every day on my writing. So I am not the best writer and giving it an opportunity to help hone in on the message that I'm trying to deliver is a constant force for me. As a matter of fact, I think that I use grimm really at times.And so every week I get my message that, no, no, I think I'm in the top 3 % of Grammarly users. Part of that is because I'm terrible. The other part of it is because I actually believe in the power that ⁓ there is this thing that knows more than I do. And I'm willing to listen and learn. It's changed the way that I write, being candid. It's literally changed how I go about things. And so there's other pieces of process that are important to me.Look, I happen to work in a very complex environment right now. The environment of compliance, audit and security, these are three things that require an enormous amount of technical capability. I'm in awe of our delivery team and what they're able to do. Sometimes the best way for me to understand it is to actually use AI to help explain it to me because I'm not an engineering level technical person. Even though I've been in tech for 30 plus years.There's so much that I don't know. And so it does give me the opportunity to learn more on the fly.Mark Petruzzi (18:28)Very, very cool. All right, let's do some real quick rapid fire questions and I'll just pop off. So what was the first product or service you ever sold?Joshua Hoffman (18:34)Sure.carpet cleaning a boiler room environment with a guy literally throwing phone book pages at me. Things that shape you, I romanticize it now, but it was awful at the time. And I know exactly how not to be.Mark Petruzzi (18:38)I love it.So were you the wolf of carpet instead of the wolf of Wall Street?Joshua Hoffman (18:57)I was terrible. By the way, I was a miserable failure with a miserable attitude. It was, it couldn't have been worse. And you know, my next two sales jobs were just as bad. I sold copiers and I, well, actually I should say I didn't sell And I sold, I tried to sell copiers. I don't even think I, I don't even think I'd ever sold one. And I sold insurance door to door.Mark Petruzzi (19:14)You tried to sell copiers, right?Joshua Hoffman (19:22)And you talk about three experiences in a row, it's no wonder I went into manufacturing. But it didn't help that I failed either. So I didn't make any money on top of being miserable.Mark Petruzzi (19:32)Hey, again, what doesn't kill you makes you stronger. So that's cool. Do you have a favorite CRO or CEO that you like to follow or read about?Joshua Hoffman (19:36)That's right.I do my best to stay up on what people are doing, learning and providing using things like LinkedIn, using things like Forbes, and reading as often as I find the time to do so. And so I don't necessarily have one favorite, but we talked about some of those leaders before that I've had the chance to be around, whether it's Mark Anderson or Russ Reader or Todd Abbott orMike Jenner my current CEO Joe Burton who was the CEO at Polly for most of my time there I love reading what he writesMark Petruzzi (20:13)Josh, again, thanks so much and we appreciated you taking the time with us today.Joshua Hoffman (20:18)I really enjoyed it.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, we sit down with Josh Hoffman, a seasoned go-to-market leader who has guided sales transformations at Dell, Avaya, Poly, Datto, and now ControlCase. Known for his “sell-with” philosophy, Josh shares what it really means to drive symbiotic outcomes, where sellers, partners, and customers win together.He unpacks lessons from decades of leading in high-stakes environments, including mergers, market pivots, and rapid scale, and makes the case for consistency, humility, and emotional intelligence in modern sales leadership. From shifting away from zero-sum thinking to building customer-aligned mutual action plans, this episode is a masterclass in outcome-based selling and team-driven success.What You’ll LearnSell-With vs. Sell-To: Why Josh believes the most successful sellers don’t “close deals”, they solve problems alongside the customer.How to Build Mutual Action Plans: Practical ways to bring partners and clients to the same side of the table from day one.The Role of AI in Sales Coaching: How Josh’s teams are using AI for prompt writing, context synthesis, and deal prep, without losing the human element.Coaching Through Change: Why consistency, not charisma, helps teams thrive through high-pressure acquisitions and pivots.From Manufacturing to CRO: Josh’s story of going from putting screws in motherboards at Dell to building global GTM teams, and what shaped him along the way.Key TopicsTransforming sales cultures from transactional to consultativeTeaching sellers to ask better questions, and when to talk lessWhy top sales leaders reduce the distance between themselves and the AECoaching through ambiguity and building career-defining momentsWhy consistent behavior builds trust in times of changeUsing AI to augment, not replace, frontline coaching and prepGuest Spotlight: Josh HoffmanJosh Hoffman is the Chief Revenue Officer at ControlCase and a proven sales leader with over two decades of experience building high-performance teams. With a track record of leading in moments of transformation, Josh is passionate about coaching sellers to exceed what they thought was possible, through shared success, customer obsession, and scalable systems of growth.Resources & MentionsBook: The Qualified Sales Leader by John McMahonBook: FYI: For Your Improvement by Korn FerryCompany: ControlCase (compliance & audit automation)AI Tool Mention: Grammarly, prompt engineeringLeadership Inspiration: Todd Abbott, Mike Jenner, Mark Anderson🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.Mark Petruzzi (00:34)Welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Josh Hoffman. Josh has built his career leading sales and go-to-market strategies at some of the most iconic companies in tech. He started in Dell's early inside sales organization and went on to senior leadership roles at Avaya, Poly and Datto, often stepping in during times of transformation.Along the way, Josh has become known for his self philosophy and his passion for helping people build careers and outcomes they once thought were completely out of reach. At the heart of that philosophy is symbiotic growth. The idea that sellers and customers succeed together. Instead of pushing a deal across the line, Josh frames selling as sitting on the same side of the table with a customer.tackling the problem on the other side and building shared wins that last. We'll cover four themes today. The sell with era that we feel like we're in today, lessons from a career across Dell, Avaya, Poly and Dotto, leading times in a time of change. We certainly have that world amongst us today. And the future of go-to-market in the age of AI and ecosystems.John, us again, welcome to Selling the Cloud.Joshua Hoffman (01:47)Thank you so much for having me here today, Mark. I'm so appreciative of you and the team and all that you've done to help us all grow. And so it's a pleasure to be here.Mark Petruzzi (01:56)Excellent, thanks again. All right, Josh, so you often talk about creating symbiosis in selling. What does a sell with model look like in practice?Joshua Hoffman (02:05)That's a great question. For me, it's about helping people understand that we're not here to pick up a PO. We're not here to get a credit card number. We're here to solve something together. We're here to deliver something that's gonna help all of the organizations be better off. And in a lot of those environments, I've worked in direct sales, I've worked in partner sales, and I've worked in hybrid sales. They all have a slightly different meaning.But when I think about it the most, you described it at the beginning. It's about making sure that all of us that are solving the problem together, we're all on one side of the table. Sales is not combat. Giving somebody a product or a service that they need is helping them be successful. And if we all focus on what that means, if we're all laser focused on the outcome that we're trying to deliver, then we're all in it together. We're all with each other in that.KK Anderson (02:56)could not agree with you more, Josh. And my question is, so how do you help your sellers make that shift from quota-driven, transactional, I need to educate, I want to talk about my product mindset to one where they are the problem solver sitting on the same side of the table. How do you do that?Joshua Hoffman (03:16)Yeah, Kristen, thanks for the question. I appreciate it. There's a couple of things. First of all, I do want sellers to be quota driven. I do want them to be successful. They have goals to meet also. And part of leading a team is making sure that everybody succeeds company, people, internal, external companies that you're working with. And so there is definitely a part of me as a leader of revenue that says that we need to make sure that they are quota driven.But the shift comes when you help people understand that the more that they listen and the more that they ask questions, the better they're going to understand why are they in the room today? ⁓ Why are they a part of this conversation? And if you can get them into that mode where they care in a way that allows them to open themselves up to different possibilities. And I know that's a very EQ set of statements.but you want them to be sitting there thinking that I'm here to help somebody else succeed today. And the way that I phrase it, for example, with partners is if I focus 100 % on your growth, then it's going to work out. If you grow, we grow. If you succeed, we succeed. And getting that mindset to take place.It's a big shift for people, especially people that have come out of a transactional sales environment or have come out of something that's maybe a little bit more cutthroat. I live and breathe this idea that consultative sell with strategies make a difference. they not only build a better business for the client, for us, for the partner, it does help us build a better world. And that might sound a little bit kind of hippie-ish.But the reality is that I do want the world to be better. And if we all work together, it's going to be.KK Anderson (04:56)It reminds me of, you said hippie-ish, I love that, my Austin, keep Austin weird roots, but one of the things, one of the tactics that I've used in my 20 years of sales training has been, as soon as you feel the compulsion to start talking about your product, ask another question.Joshua Hoffman (05:11)That's a really interesting way of phrasing it. know, Kristin, I've had the benefit of seeing the outcome of the good work that you provide and how you help enable other people to get better and grow. And that goes a long way. It's really well put.Mark Petruzzi (05:25)And with both of those examples, we're hitting on things that I hold near and dear to my heart. And we're living in a world that's not really built that way anymore. Everybody kind of looks at things. We look at it in politics, for one, that you have to win. And then you really have to make somebody else lose, too. And that's not the way I look at it.I've always been someone who's used the term win-win and that's something I always want to do. And then it's nothing in what I do, at least in sales. Maybe there are parts of sales that is closer to a zero-sum game. But when you're looking at the value you can bring for clients and the return on investments and the business cases you can build for your clients, that's not zero-sum. You really can look at it from a solution standpoint.and allow that to really hit home and work to your advantage, not against you. So we love stories here at Selling the Cloud. So can you give us an example, a story, where this approach has created an outcome that wouldn't have been possible in a traditional sell-to model or just a mindset of win-lose?Joshua Hoffman (06:36)I have a lot of stories and so I'm going to generalize just a little bit so I don't name names, but I'm going to use an example where there was a partner engaged as well, where we were the provider of the product or service, but there was a partner that had a client that was involved. And the way that things had traditionally operated at this organization is that the sellers were consistently focused on selling to the partners.You've got to buy this. You've got to buy this. And then you got to go sell it. You've got to go figure it out. You need to internalize and ingest all this information and data. And you got to figure out how to go make it happen. And we changed our approach dramatically. One of the first things we did is we actually brought partner salespeople and SEs into our new hire training. And we said, you're part of the team. we're not trying to sell to you.And sure, you might actually be the ones writing the PO for it, but we're in this together. And so we're going to enable you the same way that we enable our people. We're going to speak the same language. We're going to talk about the same benefits. We're going to learn together. We're going to grow together. And as that shift took place and people started to see ⁓ their cohorts that were on the other side of the table before, I'm trying to get a PO from you.Now they're saying, OK, we're on the same side of the table right now. We're in this together. And once we had crossed that chasm, we now had the opportunity to say, you know what? There's another chasm to go across. Now let's get the customer to be a part of this. Let's get the client to be a part of this. Let's put them on the same side of the table with us. And let's take the approach that we're here to deliver an outcome. And we're going to co-strategize. I'm going to use the word co- bunch right now.We're going to co-strategize, we're going to co-create, we're going to co-decide what the solution is. And when we get to the end of the line, we're actually sitting in that mode of getting a PO, getting a check, getting a credit card, whatever it might be, given the different organization. We're not closing a sale. We're solving a problem. And that became a constant driving force.in the approaches that, that candidly I was able to take, but really organizationally that we were able to take, because we're a team. It's not just me. ⁓ Whether it was at Palo Alto networks, whether it was at Avaya, whether it was at Datto, Poly, whether it's here at Control Case, where we view things the same way. We're here to solve a problem. We're here to create an opportunity. We're here to create an outcome together.and having a collaborative environment makes all the difference in the world.KK Anderson (09:08)win together, right? And I know exactly who you were talking about, Josh. And you're right, you get to a point where all of a sudden your customer is calling you and saying, hey, I've got this client call. Can you help me prepare for it? And then you're building pipelines.Joshua Hoffman (09:10)Yeah.That's right.multiple organizations. I've had the chance tell our team, look, go put on their shirt for the day. You don't have to wear a Control K shirt. You don't have to wear a Datto shirt or a Palo Alto Network shirt. Go put on their shirt for the day. You guys are part of a team. And that team mindset, it solves problems so much faster. And that's what we're really here to do. As long as you're working for a company where you believe in the product or the service that you're selling,KK Anderson (09:34)Put on their shirt. I love it.Joshua Hoffman (09:47)and you're not working for something that's trying to gouge people or trying to do something nefarious. I happen to have been fortunate, the companies that I've worked for for my entire career, maybe minus one or two at the early part of my career, we were really trying to solve something important. And it was something that I believed in. That's an important part of that as well. You've got to and I tell this to people all the time, you got to be happy. Part of being happy is making sure that when you go to work every day, it doesn't always feel like work because you believe in what you're doing.KK Anderson (10:14)Yeah, 100%. And it absolutely applies in the COCEL environment, but even in direct B2B, you at Control Case, are you more direct B2B, or are you more channel partner?Joshua Hoffman (10:26)we do business in 73 countries right now. Not every country has the same kind of partner model. so depending on where we are in the world, it could be direct sales. It could be consultancy partners. It could be referral partners. It could be technology partners. And in the case of one of the missions that we have, it's using MSPs and ITSPs. So I have a vision thatMSBs and ITSBs should be a bigger part of the compliance journey. It's using partners that are actually part of the technical journey that the client's about to go on. so depending on where we are in the world, it could be any one of those things.KK Anderson (11:00)But you know it's one of the ways that we met previously Josh I've got a lot of experience in assessing sales organizations and going through this whole you know sales effectiveness and improvement process and almost always out of hundreds of organizations almost always the sellers come back as they're good at hunting getting the meeting and thenthe next best skill that they have is presentation approach or going into like sell value. And I think they get so comfortable in learning the value proposition, learning the talk track, learning about the features, advantages and benefits of the product that they're trying to sell. And they get that word sell so stuck in their mind that I'm a salesperson, just Mark, we were earlier talking about that very thing.There are so many people that don't even like the word sales. And so it's almost transitioning their mindset from I'm a salesperson to I'm a problem solver. So my question for you, Josh, would be like for the CROs that are listening, and that's probably most of our audience, what's one thing they can do now to help start to drive that culture of ask more questions, solve more problems?Joshua Hoffman (12:05)Well, part of coaching is spending time with people. And in any sales leadership role, you see people get their time pulled in multiple directions. Should I be working on this Excel spreadsheet? Should I be working on this report? Am I spending time in an operational meeting? Am I spending time doing X, Y, or Z? When one of the biggest opportunities that people have is to spend time with people in the environment where they're talking to customers or partners.and having the chance to talk about it afterwards, to talk about what went well, what didn't go well, what would you keep, what did you change, what did you learn? There's all kinds of cliche phrases around that. But that kind of coaching environment is what helps people get better. Now, of course, you have to be a sales leader that believes in this model, and not every sales leader does. And so you have to be a little careful about that. But assuming that you do, that time that you spend with people is one of the most valuable things you can do.The other thing that you can do is model behavior. And I'm the first one to say, look, I screw things up all the time. I'm not perfect. I don't always get it right. But what I do try and do is when I'm sitting inside of that environment, when I'm with the client, the partner, the salesperson, the account manager who's leading that account, is I do try and model that behavior and make sure that they're seeing what, at least what I hope good looks like.Again, said with a little bit of humility, it's not always great, but I try and be very consistent in my approach and it served me well. That's the advice that I give, spend time with your people. there's nothing more valuable than that. That's how you help people get better. And one of the ways that I've branded myself throughout my career is that helping people find a career they only thought aspirational.is a motivator for me, helping people learn and grow and develop into something that they never expected. And you can't do that if you don't get to know your people, if you don't get to spend time with them, if you don't get to coach them along the way.Mark Petruzzi (13:56)Very, impactful. Everything that you just said there. All right, let's switch over to the second topic. know, and this is a perfect build on where we've started, like lessons from a career in tech. So you have been through multiple transformations in your career and transformations within the companies that you've worked within. From being within Dell's Inside Sales team,to intern CRO at Poly, Dorn, what turned out to be a very turbulent year. What experiences has shaped your leadership style the most?Joshua Hoffman (14:29)good gosh. Let me start with, I feel so blessed because I have been shaped more times than I can count. I've been shaped by great leaders. I've been shaped by great situations of growth. I've been shaped by times of, as you said, turbulence where things are not always going well. And I've done my best to learn from each one of those situations.Picking one out of the group is a little bit challenging to consider, but I look back on my early career at Dell. My first job at Dell was putting screws in motherboards. Candidly, I had tried sales, I failed. It wasn't going well for me, and I said, I'm gonna go do something different. And getting the opportunity to walk into an environment at Dell is probably 1992. They said, the phone's ringing off the hook.We need more people in sales. came onto the manufacturing floor. Who wants to come to sales? me, so they chose about 25 of us raised our hands and me and Rick. So Rick knows who I'm talking about. We were the two that were selected and we end up, sitting on the phones for four hours a day and going back to our manufacturing job or vice versa, depending on what day it was. And I got to be part of an environment that wasgrowing like a rocket ship that was also going through challenging times. This was the time of the exploding laptops. And so not exactly one of the best moments in that company's history. And I got to learn from some amazing leaders. Now that carried on. I had leaders at Dell consistently, actually throughout my career, I could probably call out 10 leaders easily that have made a difference in helping to shape who I am.Almost all of it leads back to a common theme, which is being given the opportunity to step into a situation and learn on the fly. I wasn't always put into places where I knew what to do. I wasn't put into places because I had the experience. I was put into situations where I had the opportunity to learn, to grow, to be creative, and to help come up with what are we going to do to solve this.And I give a lot of thanks to people that were willing to put trust into me at various points in my career. And that's what's shaped me the most. That's the consistent theme throughout all of those organizations is let's let Josh do it, which by the way, wasn't always perfect. It didn't always succeed, but I've been fortunate more times than not. It's been a successful.KK Anderson (16:53)You need to screw the tight, the screw is a little tighter on those laptops so they don't explode.Joshua Hoffman (16:57)Yeah, well, okay. It's a funny story when you look back on it now. It was unbelievably stressful at the time. Dell grew so much over so many years. when I started, it was a thousand people. When I left, I think it was 70,000. And, but they gave me opportunities to go learn on getting to move to China, getting to move to India, getting to lead the first services organization, doing things thatKK Anderson (17:05)totally agree.Joshua Hoffman (17:21)that I hadn't done before, but also that the company hadn't done before. And so we got a chance to make things happen along the way. It was pretty spectacular.KK Anderson (17:29)Really cool, and I like what you were saying about trust. That's so important. So you worked under our mutual friend, Todd Abbott, and he's such a strong, awesome leader. I know that he had a strong style and impact on you. What would you take from that relationship specifically, just out of curiosity, that influences you today?Joshua Hoffman (17:37)did.⁓ look, I love Todd. I had this amazing experience with him. I think it was three years or so that I had the opportunity to work for him. And ⁓ during that time, I got to experience a different type of rigidity and approach that I had experienced other times in my careers, but never with the clarity that Todd uses to set expectations.to create an environment for people to succeed, to approach things both analytically and with creativity at the same time. He was a champion of the people on his team and you always knew that Todd had your back. And by the way, I have actually been very focused in my career of finding people to go work with and for that are like that.that provide that kind of environment. It's not always easy, by the way. My CEO today, Mike Jenner, has many of those same qualities. And he has other great qualities too. So it's not like Todd and Mike are twins, they're not. But Mike provides that same kind of environment. And I feel fortunate to be in a place where accountability is sacred. And there's never a moment that you're confused aboutwhat needs to happen and what the outcome needs to be. I've worked for other leaders in my career where there was ambiguity all the time. And candidly, that's really hard to be a part of. And I do my best to make sure that I'm modeling that behavior that I get out of folks like out of Todd, out of Mike, out of other folks in my career. Mark Anderson at Palo Alto Networks is a great example. Earlier in my career, David Lockett at Dell.with somebody that had that same approach. And I've had other leaders too, so I could probably name 20 names and so forgive all the people that I didn't just mention. But these ones jumped to mind because of that approach and combining analytics and behaviors is a lot of what leading a successful revenue organization is about. You have to have both. And so thanks for asking that question. So I'll make sure and call Todd.Mark Petruzzi (19:44)Yeah, you described that really well. So Joss, through many of your companies you've worked with, you've lived through significant change and cultural shifts as well and acquisitions and putting companies together. What did you learn during those times about keeping teams motivated and effective during times of change?Joshua Hoffman (20:04)Well, there's a couple of things. Now I have been fortunate. Most of those times of change have been about rapid rocket ship kind of growth and how that impacts an organization. I know that one of the lessons that I've learned and one that I try and live, although again, not always perfectly, is my behavior doesn't change ⁓ almost no matter what the situation. The message may change. The requirements or the outcomes may change.but my behavior doesn't change. Nobody has to worry about schizophrenic Josh. There's an opportunity to know that there'll be a level of consistency there. The other thing is about making sure that people understand that change isn't necessarily bad. If you go back to the days of like corn fairy and FYI and the introduction of these competencies into the corporate world, I got to live through being one of the guinea pigs for that.One of the competencies was dealing with ambiguity. And getting the chance to teach that, to share with people the sort of the pieces that fit into dealing with ambiguity ⁓ is helpful. And giving people a future that makes sense to them, that change can lead to better things, you have to be consistent in that message. Now,by the way, there's times where change doesn't lead to that. I've been parts of organizations that did layoffs. I've been parts of organizations that were bought. And maybe that wasn't the best thing in people's eyes at the time. But it doesn't mean that the culture of the organization has to change. Candidly, everybody has to be a part of that. And that's one of the other key messages is that change doesn't have to happen to you. You can be part.of what makes things better and that you should feel empowered, you should feel emboldened, you should feel like you have a voice, you should feel listened to. And the other skill that I think comes with that is having compassion. You have to have empathy to be successful in any leadership role. If you don't have that, one, you gotta go find it. Two, you really do have to be able to put yourself in their shoes and say,What are they feeling based on this message? What are they thinking right now? How do I answer questions before they're even asked? And the more you can get ahead of things, the better off things will be.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of our conversation with Max Elster, Co-Founder and CEO of Minoa, we go deeper into how sales teams are actually operationalizing outcome-based selling; at scale.Max shares how revenue teams at companies like Vanta are moving beyond founder-led, feature-centric narratives, and building scalable, repeatable playbooks rooted in customer outcomes, business impact, and data-backed storytelling.Whether you’re leading a 10-person sales team or a 1,000-person GTM org, this conversation will help you reimagine enablement, coach for value, and build business cases that win over CFOs.What You’ll LearnVanta’s Transition from Features to Outcomes: How CRO Stevie Case transformed Vanta’s narrative, and drove shorter cycles, higher win rates, and stronger executive engagement by focusing the team on value-led discovery and storytelling.Why Business Cases Shouldn’t Be Optional: Hear how teams went from building 10 business cases per quarter to over 500, without hiring hundreds of SEs, and how that shift boosted win rates by up to 15 percentage points.Teaching Reps to Think Like CFOs: Max explains how the best sales teams equip champions to model ROI and outcomes with buyers, not for them, and why the strongest business cases are co-owned with the finance team.How AI Accelerates Discovery, Coaching, and Differentiation: From call summaries to intent signals to customer benchmarks, Max shows how LLMs and predictive tools are giving reps the context to build relevance at scale, without losing the human touch.Key TopicsFrom founder-led sales to repeatable revenue enginesVanta’s shift to value-led selling, and what it unlockedBuilding outcome plans that close deals fasterWhy the CRO’s best insights come from AEsCoaching for customer outcomes, not product demosHow AI is reshaping forecasting, discovery, and enablementThe real future of revenue leadership in an AI worldGuest Spotlight: Max ElsterMax Elster is the Co-Founder and CEO of Minoa, a revenue platform helping companies scale value-based sales across the deal cycle. With a decade of experience in AI and B2B SaaS, Max works with companies like Vanta, Cognite, and others to operationalize value intelligence, from discovery to renewal.Resources & MentionsBook: The Qualified Sales Leader by John McMahonCompany: VantaMax Elster: LinkedIn | Email: max@minoa.io🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts. Stay tuned for next week’s episode!Mark Petruzzi (00:36)So let's move to topic three, stories from the field, moving from features to outcomes. So I have heard you say how you've worked with Vanta's CRO on shifting from feature led to value led sales. Walk us through that story.Max Elster (00:52)Yeah, I think it's a great example. Stevie, who is Vanta's chief revenue officer, she came from Twilio in the past and came to Vanta's organization, around probably somewhere between like the 20 and 40 million AR range. like basically Vanta is a good example, right? They initially were, basically kind of building this idea around a trust management platform and compliance and the importance of security and compliance with startups.And then they expanded over time. one important thing was that as they have more competition, they need to differentiate themselves. they basically, one way of differentiating is to focus on value, right? So Stevie came in and she talked about this publicly as well, many different times where she said that one of the most important things that she drove as an organization was evolving the company from a feature led organization, the initial founder led sales days to...basically focusing the company on value selling and moving away from feature to an outcome led and value led story across the board, pre-sales to post-sales. And then of course it starts with changing your narrative. It starts with changing the decks that you're creating. It starts with making sure that every single seller can talk about the business case and the value that in this case, Vanta provides different than their competitors are oftentimes against StatusCrow, So why should I do anything about the specific initiative here?And they have seen great success, And actually making that transition, but ultimately I would put it even into a larger scope. any successful company out there, whether you look at the old days, the SAP is the oracles, or whether you look into modern companies, Databricks, Snowflake, many of the other kind of modern go-to-market tech organization, like go-to-market teams, they all rely on the value principle and they all operationalize their thinking around how do we make sure that everybody can speak to.value across the board, not just pre-sales but also post-sales. And Vant has a good example where Steve done a great example at also articulating that a way. And yes, I think they're a great customer of ours. We're very happy to have them then kind of go take the ride with them. But I think they're just a great example of how they have transitioned. And the outcomes are incredible, rent rates go up, sales cycles go down.You can actually make sure that everybody is more proficient at articulating the value that you're driving. So even thinking about discounts, especially in very competitive markets where you want to avoid discounting every single deal, And if you can uniquely position value to a procurement team, that's going to help you actually have that conversation over your competition.KK Anderson (03:01)And all of that is stemmed from having outcome plans and business cases in that kind of value intelligence layer as you describe it. that the sellers are talking to outcomes and talking so that they can then derive the value to lead the sale.Max Elster (03:15)a good example of company, a couple thousand employees where have actually measured that they built mutually created over 500 business cases a quarter. And before it was almost basically 10 to 30, In a quarter where individual SEs were building business cases to support the sellers. In a future world, basically every seller will be able tobuild a business case, have that being automated and have it readily available to them for every single deal. So what happens was that actually we saw that VIN rates go up six to sometimes even 15 percentage points for specific segments, which was incredible. And it's less because you bring a business case late into the deal and you try to justify the value to a procurement person. It's more of there's a process and a guidance for an SDR or a seller or an SE to talk about value earlier. It's almost liketeaching a kid kind of basically ride the bike. If you give them a little bit of a guidance of how to start with, they will do it themselves. And it's similar, in value where if you teach them that the end result will be you driving the bike or you actually closing more deals, they will kind of think backwards and think about, if I just need to get to a final business case that includes a few different questions I need to ask, but that will help me and the customer and the champion have an internal story they can tell to their buying committee.I can do that, I can make sure that every single discovery call has these like three to four questions that would help me then shape a better narrative as we go along the sales cycle. And then it's becoming a routine and a habit, right? And as soon as it's a habit, it can actually get scaled and be successful across the company.Mark Petruzzi (04:43)So Max, how did these stories resonate differently with executive buyers like CFOs who we all know scrutinize every purchase?Max Elster (04:52)looking at, have a few CFOs in our advisory board and I always say the CFOs will do it themselves if you don't do it for them. So they will run internal projections and internal business cases themselves. And if they don't believe in it, then they are the ultimate gatekeeper and they can just say, no, I don't believe in this. So as a seller, you're either destined to keep it up to them and you can't control it or you do it yourself. And you can control the outcome plan and the business case you're presenting to them.or equipping a champion ideally to do that. And we have a couple of interesting stories where sellers have actually reached back to us and said that the executive, whether it's a CFO, it's a CSOR, whether it's a CIO, they actually came into the application and they almost modeled the assumptions to the base minimum. So they came in and tried to understand if we almost have no success here, what is the minimum value? And they compared that internally to other initiatives and projects that they are currently exploring.And it resulted almost a CFO to have ownership and accountability on the business case, Because they actually control the assumptions and the narrative and they're doing it based on the framework that the vendor provides to them. And it just changes the dynamic. I also say,I don't think a CFO is kind of this alien on the other side that doesn't want to talk to you, But they want to see that you can relate to them. They want to see that you have experience dealing with similar businesses and the more you can do that proactively, the better. And yes, I think I had CFO conversations where I presented them a business case and they said, I don't believe in this number. And then I went back and said, okay, then tell me what you believe in. And then I think like you almost opened up the room and you have a conversation about a mutual goal that you're trying to go after and you find a good solution.It brings everybody closer together. think that's the ultimate desire of running a good sales process.KK Anderson (06:25)Really, really interesting. Okay, let's move to topic number four, which I know is a really hot topic with our audience. And that is the future of revenue leadership in an AI world. So I've heard you say in a previous conversation that many CROs, and I agree, fear their jobs because of AI and how quickly things are changing. And I just.I want to get your perspective, but do you think that is?Max Elster (06:50)Uncertainty is always a difficult thing for us humans, Some get excited by it, but the majority of people get afraid of uncertainty and not knowing what the future beholds. And I think that's the scenario right now where things are moving so quickly and it's hard to estimate where it's going and how you potentially react to it or how your competitors potentially are reacting that you're missing out on, right? That I think a lot of people either start almost freezing, And they startNot to move. that's a risk or they start to move too quickly. they make like, test a lot, but they don't make fundamental decisions about which AI solutions or strategies do I deploy and what's the underlying reason for that. think a lot of people are just trying to move and make a decision, but they actually forget about what I'm actually trying to solve in, my process and, kind of my day to day execution with my teams.And which solutions and vendors and strategies and data plays do I want to run in order to make sure that that can actually get accomplished? AI hasn't really changed that, ultimately it's going back to kind of yourself first and thinking about which problems do I want to solve for my revenue team? And then how do I apply the right AI solutions to that? I do think though that the quality of LLMs today give us an enormous opportunity to tap intounstructured data sources and data sources that have previously been so messy and so complex to analyze that it's going to open up a lot of more opportunities to improve your day-to-day work, whether it's one individual seller, or whether it's a CRO trying to almost run better analytics around the idea of, for example, why do we win? Why do we lose? Why do think there's so much data there that actually has never really been tapped into that now is possible with LLMs? But I would sayIt's going back to the fundamentals of thinking which strategies do you want to change? What are the underlying solutions and options that you have? then deploying and testing the ones that feel most suited for that particular purpose. And I think you will be successful, it's just probably give it a bit of time to, have everyone adjust it. But then it's a new reality that we all work with. I'm sure you too see it with your clients as well every single day, Where you help them have those conversations internally.KK Anderson (08:48)see AI reshaping all of these different roles of the direct level team members? So the sellers are obviously on chat, GPT all over the place. They're using AI inside a gong. They're using generative AI. The leaders are using predictive AI.AEs, SCRs, like what are the big ones that stand out to you?Max Elster (09:10)I mean, we all become more intelligent, right? think that's kind of, we all essentially, we have ourselves and then we put an additional intelligence layer on top of that, which is gonna make us a smarter seller. It's gonna make us a smarter advisor to our customers. It's gonna make us more credible, more relatable because we can actually tell stories that are similar to what others have seen. So think that's very tactical. think sellers start to tap into those resources of previous deals, previous conversations. So do think about,Gong or the respective call recorder that you're using in the past, you didn't have an opportunity to get an account level overview of 150 plus conversations, Of like what actually is kind of the underlying executive summary around this particular account. Now it's possible, right? Because you have all those conversations that can feed into Gong summaries or kind of other tools that you're using in order to help prompt yourself for a business case, help yourself prompt for a better...code outbound, you're sending whatever you're doing in your sales process that can actually get leveraged by those individual call recordings. what we're seeing is that a lot of the forecasting providers are starting to open up their signals to more and more data points, which is interesting. If you think about your forecast, maybe in the past, it was limited by how well your Salesforce fields were filled out. think nowadays you can tap into many more signals and data sources around an individual account. Not just the conversations that you're having, but alsoDid they fire executives in the past two weeks, right? That could potentially impact your deal, right? Or it could risk the forecast. And all these different data points can now be merged and made accessible in your day to day, whether you're a chief revenue officer that runs the forecasting process with your sales manager. So whether it's an AE trying to become a more intelligent seller and more credible seller and advisor to your prospects. I think that's where AI is just getting started,started my first company back in 2019 where we built speech technology with natural language processing. And I remember back in the days that we were competing with Google and AWS on some first speech models. And it was incredibly difficult and almost hard to actually transcript a meeting. Nowadays, we talked six years later and we have almost perfect transcripts for almost every single language in the world. We can take those data points and put them into other sources, ask questions around it. It's pretty crazy, but also pretty exciting.I think opportunity for go-to-market teams to truly advance and be even more customer oriented than what they were a few years ago.Mark Petruzzi (11:23)So Max, what happens when every company has great AI building tools? What will still allow differentiation amongst the best revenue leaders?Max Elster (11:34)listening and building strong relationships. we're to go back to, core human strengths and qualities where we were social animals, And we want to come together and learn from each other. And I think that's what AI gives us more opportunity to not do cumbersome work that you would otherwise be spending a lot of time on and actually focus on how can you drive.better conversations with customers and how can you potentially show up more often, Maybe take that flight and just be with your customer and spend time with them, get to know them and make sure that you bring all the information that would be helpful with you. But all that information is there, You just need to tap into that and then you can focus on the actual conversation and trying to understand the other side better. it gives us an enormous ability to actually be closer to what we're supposed to be doing and not just typing letters on the computer.that's a great opportunity, but also it's a big opportunity will be to almost let the team run a little bit. Everybody's worried right now that teams are using chat, JBT and other systems. it gave everybody a first stint of what is possible with AI. And I often suggest to let people run and explore themselves. And at some point you grab everyone together and say, let's talk about the kind of individual projects that you've always tried out at home, On the weekends, during the week, like what are the things that have been, been working for you and how can we.now build a system around it that we can scale across the company because otherwise we're to be running around like headless chicken and everybody's going to be doing their own thing. But it's actually not solidified in one neutral story that you can execute on. And I remember a few years ago, everybody talked about great customer experiences. And I think we kind of come back to that again now where everybody had some internal runs on AI technology. And now it's probably getting everyone back in the room and thinking about what actually works. What do we want to deploy? What do we want to scale?KK Anderson (13:09)But after work, what is the point?Max Elster (13:11)I think that's kind of phase two of the AI go-to-market story right now.KK Anderson (13:15)I feel like AI is going to help the sales profession get back to what it originally was, which was building relationships and trust and credibility and having the time before we had all of these tools and technologies and everything had to be inputted into CRM. And, there was so much admin, before those days, was, your Rolodex and who you knew.And it was the relationships and that was the value, the value that you had as a salesperson. And now with AI being able to take so much of the busy work back, it's like you can focus again now on relationships. I always, mean, shoot, you can even use different generative AI tools as like your assistant, like your strategist and ask questions like, Hey, I'm thinking about this customer. I'm thinking about this challenge they have.Max Elster (13:56)Mm-hmm.KK Anderson (14:01)What are some questions that I can ask? what are some, just ask questions as if you're talking to like a sales coach, right? That's too.Max Elster (14:07)like different projects in ChatGBT and other tools where I kind of built those individual projects for me, I have a product coach who's advising me on how do I best navigate a new product idea. I have basically almost like a company coach that's helping me think about culture and strategy and then have a sales coach, That's helping me on some more tactical piece on go-to-market.And I'm kind continuously building that out as, we speak, I have an investor kind of related one where it helped me craft a good investor update. So there's many different sorts of these like micro projects that you can build. And you bring up a good point though of like, ultimately it's about the relationships. And I often compare that with what happened in coding, Which is actually moving at a faster pace right now as go to market, essentially what engineers are doing now is they work with cursor in order to automate some of the work around.writing code, And what happens is they come back to their core strengths, which is thinking about engineering problems and thinking about product problems and talking to your peers about that. And then the actual writing of code can be automated or at least partly automated, And you can have more time thinking about the solutions and the scoping of that, which is a more important task and the actual writing of it, So I think that's going to be an interesting.time where I coding kind of you can see that that's almost like a little bit of a headwind they already had of time and then go to market will follow. And it's going to be built around the relationships as you said, specifically in go to market, it's going to come to the core strengths of what the individual kind of people are actually doing in their function and department. Hopefully, I mean, that's maybe I'm an optimist hopefully in this regard.KK Anderson (15:33)the engines that you're using are selling the cloud listeners and reading our newsletter and recommending that you come and be on our podcast. We're so glad that you're here today. And I know that you have been a listener as well. So for the CROs that are listening today, what's the one thing, and it's gonna be hard to boil it down into one, but what's the one thing that they can do to future-proof their role?Max Elster (15:44)Thank you.KK Anderson (15:59)in the age of AI. The first thing they should do.Max Elster (16:01)I would say the first thing that they should do is I would pick 20 sellers and I would like the first thing I would probably do tomorrow if I would be a chief revenue officer right now, I would go into like a channel and say, Hey, I'm actually curious to learn from my team, whether it's 20 people or 50 people. What are the AI applications that they've built at home during the work time and have 15 minute conversations for every single one of them.and learn what they're doing and why they're doing it. And note every single action, note every single problem that they're trying to solve and then aggregate it at the end and think about a strategy that you can then deploy to everyone else. Because I think a lot of sellers are already doing something and they would love to, tell their story of what they have been experimenting with through the chief revenue officer and the chief revenue officer can future proof themselves to build a strategy around that, but also then guide and lead the managers below them to execute on that strategy.Often it's talking to the sellers. They're the ones that are testing a lot. I think actually reducing the width between the chief revenue officer and the AEs would help them get more future-proof and understand what's actually possible with AI. So that's probably what I would do tomorrow if I were a chief revenue officer.Mark Petruzzi (17:03)That's great. Well Max, this has been a great discussion. Do you mind if we jump into a few rapid fire questions? Our audience loves them Cool. So what was the first product or service you have ever sold?Max Elster (17:12)Of course.It was actually a ticket management software that was sold to event organizers and clubs in 2015.Mark Petruzzi (17:24)Nice.KK Anderson (17:24)Okay, who's your favorite CRO or CEO that you like to follow?Max Elster (17:29)That's a good question.I'm a big fan of Patrick Olsen at Stripe. I think they've done an incredible job building the company, the culture, the go-to market as well for a company that initially was built out of almost like a one bedroom apartment and now became, I think, is it now, 50, 60 billion company, Fintech. great company. The person that I admire for the work he has done in the team.Mark Petruzzi (17:51)What about a leadership or go to market practice that you believe every sales, marketing, executive leader should adopt?Max Elster (17:59)principles of the qualified sales leader. I've re-read it again, John McMahan's book. I think it's kind of the Bible and the principles for a lot of the thinking that we have building our product, Thinking about value and outcomes and making sure that it follows through. But the best go-to-market organizations have applied some form of the qualified sales leader's principles that John McMahan and the team.in the early days of BMC and Blade Logic and some of those companies have initially built and it still stays true today. he's on the board at Snowflake, Building the next $100 billion company plus and it stays true. So I think that's a great principle. would definitely read the book or take some summaries in order to develop our thinking.KK Anderson (18:38)I can't wait to check that one out. We'll put it in the notes as well. my favorite question. Advice that you would give your 21 year old self.Max Elster (18:44)I would probably say is to ask a lot of stupid questions and learn from others. when I look back over kind of the last like 10 years or so, think it's, I always try to kind of reach out to different people that were great in their qualities. And I try to just say, hey, I'm a person trying to learn about the field that you operate in, and I have a few questions and usually people are actually very happy to talk about themselves and in a good way.I think they, if you ask the right questions and they can tell about their stories and how they made decisions, they will open up and they will become mentors. They will become friends. And I think that's something where, if I think about the probably thousands of conversations I've had, think oftentimes it's just being curious and asking more questions that will help you become more curious about yourself, but then also you learn from others and you can apply those tactics in your day to day, whether it's on a professional or on personal site. AndPeople are very open to help, you just need to ask for it.Mark Petruzzi (19:31)Excellent. Max, this has been so informative and so enjoyable. Thank you for taking the time with us. Where can our audience find you if they're looking to get in touch, learn more about the company? What are their best ways?Max Elster (19:46)Yeah, LinkedIn is great. So I'm available on LinkedIn, maxelster, or if you want to send me an email, it's max at minoa.io. So pretty easily accessible there. Just send me an email and happy to find some time.Mark Petruzzi (19:56)Perfect, thank you again, Max.Max Elster (19:58)Awesome. Thank you too. was great and incredible questions.KK Anderson (20:01)Thanks Max.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Max Elster, Co-Founder and CEO of Minoa, joins co-hosts Mark Petruzzi and KK Anderson to explore what B2B revenue leaders often miss: a clear, consistent understanding of why they win.Max introduces the concept of a Value Intelligence Layer, a data-driven framework that links discovery, business cases, and outcomes into a single narrative that everyone from SDRs to CROs can use.Drawing from years of experience across SaaS and enterprise sales, Max shares how leading GTM teams are moving away from feature pitching and toward outcome-led selling, especially in a world where AI has made building software easier, and differentiation harder.From strengthening discovery questions to creating scalable outcome playbooks, this episode is packed with tactical ideas for revenue leaders rethinking how they sell in the age of AI.What You’ll LearnThe “Why We Win” Blindspot: Why many sales orgs still can’t answer the most important question, and how that gap leads to poor qualification, forecasting, and deal execution.From Features to Outcomes: How modern buyers evaluate value, and why understanding customer priorities matters more than your internal product roadmap.Creating the Value Intelligence Layer: How to unify customer impact, product usage, sales stages, and discovery insights into a single GTM operating model.Scaling Outcome-Led Playbooks: What it takes to align SDRs, AEs, SEs, and CS teams around a shared value narrative from day zero to renewal.AI as a Differentiator (Not a Replacement): Why the best teams use AI to personalize engagement, not to automate it, and how AI helps surface deeper buyer context.Key TopicsWhy most GTM teams don’t know why they winBuilding discovery questions that lead to business casesEmbedding outcomes into CRM and sales stagesCreating a “value intelligence” system across teamsHow AI and call data can power more relevant sales motionsTurning post-sale value into pre-sale advantageAligning playbooks across SDRs, AEs, SEs, and CSMsGuest Spotlight: Max ElsterMax Elster is the Co-Founder and CEO of Minoa, a SaaS company helping revenue teams operationalize their value story. With a background in B2B software and product development, Max built Manoa to bridge the gap between feature-led selling and outcome-driven growth. His team helps sales orgs unify discovery, use cases, and customer impact into one connected system.Resources & MentionsBook: The Qualified Sales Leader by John McMahonCompany: Minoa.io Max’s LinkedIn: linkedin.com/in/maxelster🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts. Stay tuned for Part 2 with Max Elster, dropping next week!Mark Petruzzi (00:36)Welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Max Elster, co-founder and CEO of Manoa. Max has spent nearly a decade in B2B software and AI. He co-founded Manoa to solve a critical gap he observed across SaaS and enterprise companies that most revenue leaders don't actually know why they win. Manoa helps teams uncover the valuedrivers behind deals, building what Max calls a value intelligence level, layer rather, that connects discovery, business cases, and customer outcomes into one system. Today, Max will share how CROs can shift from feature-led selling to outcome-led value selling, and what it means to scale revenue teams when differentiation and ROI storytelling are more important than ever.So we'll cover four themes today. Why the old sales playbook falls short, building the value intelligence layer, stories from the field moving from features to outcomes, and the future of revenue leadership in an AI world. Max, welcome to Selling the Cloud. Thank you so much for joining us.Max Elster (01:46)It's great being here with both of you. As you know, I've been an avid listener and kind of follower of your newsletter. So it's an honor to be here and speak a bit about Valley Intelligence.Mark Petruzzi (01:57)Well, it's an honor to have you here as well. So topic one, why the old sales playbook falls short. So Max, you said CROs often can't clearly answer why they win. Why is this such a big problem today?Max Elster (02:09)been particularly relevant, I think, over the last couple of years, right, when we came out of basically post-COVID world and everybody was almost adjusting to a new environment, a new set of buying, a new set of selling. And oftentimes what we see is that companies understand the what and the how. They understand which deals they work on. They understand their internal sales process. They understand the RICP. They understand the different stages, of course, in order toget a lead to a close one opportunity. But oftentimes what we see that actually they don't know enough about is why they win and why they lose. So what are the underlying criteria that helps the chief revenue officer detect whether an opportunity is truly qualified? what are the data, what's the previous data that actually helps you make a good call of whether a certain deal will close or not? And what are the underlying value drivers, use cases that you're selling and how do they relate to?the conversation around the outcome. you're trying to deliver and then how can you reverse that back to why your customer is actually buying or not? And oftentimes the, the why is not really clear to a lot of revenue teams, the what and the how it's pretty, pretty set and pretty default, understandable, but the why is often what's missing and what, what's the consequence of that is that sellers start to, start to basically just rely on more like deal heroics, right? They look into like previous deals, they feel rather confident about a deal, but they don't actually know.is this deal going to close because of actual factual reasons of why other customers that have been similar to this particular account have closed in the past? And that's a massive gap and more revenue teams are starting to ask that question of why do we actually win and why do we lose on a basis of understanding your use cases and your deployment of use cases better.KK Anderson (03:42)So that's really interesting. When I think of a huge misconception with salespeople that we have seen, every day for 25 years, it's that a salesperson believes that their primary job is educating about that product, describing the features and advantages of using that product. And it's all about how quickly can I talk about what I'm selling when reallythe primary goal of a salesperson is to listen and to understand and to figure out what are their outcomes, what are their business problems, what do they need to fix, do they have a pain they need to fix? And then, and only then, can you go into why you, why now, why this feature, why this benefit, et cetera. And so when I think aboutyou're right. All of these sales organizations have all of those tacticals in place and button down the process, the tools, et cetera. but they probably, those that are more successful are the ones that are selling to outcomes, right? The ones that are, answering or solving a problem with, and that's why they win. Right. That's, that's kind of where my, where my head is going. And so.When you see sales leaders who are relying on features and broad messaging and educating buyers, what gets lost in the conversation?Max Elster (04:56)it's great question. mean, we've, we've analyzed over like tens and thousands of different conversations, call recording data, but also business cases that are being built with customers, outcome plans, sales. Right. And I think a lot of the actual sauce that's missing is around the business priorities. Everybody talks about the features and functions, but when you go a level deeper or a level more like basically a level higher, you kind of uncover business priorities, right. And you can map.individual functionality and individual features to those business priorities that matter to that organization. And I think five, six years ago, you could probably still sell on feature and function and product. And having been a product kind of manager by background, right? I think that's kind of what drives an organization, right? It's features that are released. gets everyone excited about the new products that are being launched that you can sell to customers. But when you look at it from a buyer's angle, they don't care too much about your internal release thoughts.They care about their problems that they need to solve and then how your individual use cases map to their problems. And I think what specifically happened, I would say, in the last 12 months, and I think that's why this topic becomes more relevant than ever, is that a lot of revenue teams see that their competition is not sleeping either. And I think it's because of AI. It's becoming easier and easier to build. There's going to be an abundance of software in the future where essentially every...person out of a single bedroom is going to be able to ship a product and actually release it to an audience. And yes, there will be differences between you as an incumbent or you as a player that's been in a category for a long time, but you need to make sure that you can display and communicate your differentiated value drivers better than the person that's building a new software out of a kind of one bedroom apartment. And I think that's kind of what's becoming evident right now that a lot of the data that we are looking at.really showcases that the sellers that are performing better are first understanding the business priorities and then actually map them back to the individual use cases that map to their persona, that map to that individual use case and the industries that they're targeting. And ultimately in a world of AI, it's more important than ever to be more differentiated and understanding the business priorities and linking that back to your unique differentiated value is the only answer on how you can solve that problem because everybody's going to be able to build sooner or later.Mark Petruzzi (07:06)So Max, building a sort of a moat is gonna get more more important because you're gonna have to do it with your products, you're gonna have to do it with your processes, and you're certainly gonna have to do it the way you sell to your clients going forward. So what does it look like to move from feature function selling to outcome selling, especially at scale?Max Elster (07:28)Right. Yeah, mean, we work with companies that have thousands of employees, right? And they are spread across multiple different regions and languages and countries. I think scale is often the biggest question, right? Of ultimately trying to move away from individual pitch decks and individual messages that maybe sellers have put onto a spreadsheet and try and iterate on to something that can be unified across an organization. Essentially asking the question of how canEvery SDR to the AE, to the sales engineer, to the customer success manager, even thinking about account management, talk about the same language and talk about the same value that this organization is delivering to customers. And I think there are very tactical pieces of how you can change that. think the underlying theme definitely is that it is a change management process, right? You have to educate your team on a new narrative that buying is going to be different and sellers have to adjust to that new buying cycle and the way that buyers actually evaluate software.But on the other side, they're very tactical things that I think you probably also have an interesting perspective on that you can, you can build. One of them is how do you build better outcome led playbooks, right? When you're delivering and you do discovery, how do you make sure that before you even jump into feature and functionality, what are the discovery questions that are related to an individual persona that you're going to be talking to? How do you capture metrics as early as in the discovery and not just wait until you want to prepare a proposal to gather metrics that help you then.create a solid business case for the CFO, right? Like actually building those playbooks and almost moving everything early into the cycle and not just waiting until the CFO question comes around of, can you kind of make sure that I understand what am I buying here, right? What's the ROI? What's the outcome plan? What's the net present value in this opportunity? And making sure that a lot of those questions can be built into discovery playbooks where you already start gathering. And I always say like mutually lining on.the outcomes that you're trying to deliver. The champion on the other side is not an enemy, right? They have the same interests as you. If they're excited about the opportunity, they want to be part of the creation of understanding how your solution maps to the pain points and the priorities of the organization. And they want to help you with that, but you have to ask the right questions in order to get them there. And then I had a conversation this morning where I talked to a sales leader out of Europe. She manages a couple of ⁓ sellers that then have sales managers. And what she said is thatDiscovery starts in the outbound message, right? And how do you make sure that the data that you already have about the outcomes you deliver and the why of why customers renew and expand, how can you make sure that an SCR can talk about that, right? And if they talk to an executive in their outreach or they call somebody on a cold call, they want to have, make sure that they have those benchmarks and those data points available. And that's often where organizations are just under high scrutiny right now to just bring all that together.And of course the data economy kind of, think, gives the answer to that. There's so much in an organization at scale that people are not leveraging that they are considering as we speak.KK Anderson (10:15)Really interesting. So what advice would you give a CRO who has a sneaking suspicion that their current sales playbook is falling short? Where would you start? ⁓Max Elster (10:27)think probably thefirst couple of things that they need to be looking at is pick your first, like pick your most successful like top 10 deals over the last quarter or last six months and talk to those sellers and understand, okay, can you walk me through how did you position the unique value of our organization compared to the differential compared to status quo and let the sellers answer that question, right? And oftentimes there's a lot of ⁓ insight in how they positioned why.this particular organization is different than others. And ⁓ it's just making sure that those individual wins that have already had great success ⁓ or the specific expansion deals that you're working on, how can you make sure that you'd templatize that and build a playbook around it from discovery questions that you could ask and enable sellers to work on to the renewal conversation where you're trying to basically expand with somebody on additional use cases. And I would always start with kind of where do you win and where do you lose and make assumptions around that.and then make sure that you align the company on those individual success stories. And then it's a process, of continuously picking the winners every single quarter and making sure that you re-communicate again and again why this method is important so that the more junior sellers or the people that are just getting rammed can take those wins and the underlying ⁓ outcome stories and outcome maps that you've built for customers as an example for their internal processes and their opportunities that they work on. And that's just, of course, a very tactical piece, but I thinklooking at like, even like running reports and Salesforce and picking a few of your kind of recent deals and talking to those sellers often creates a unified story of what you can actually scale towards the rest of the team. And then I always say, when companies come to me and they ask, okay, how can we even get started? I always say, and sometimes it's companies that make like 50 to like a billion in revenue, right? Like 50 million to a billion in revenue. And they come to me and say, okay, how do we understand what are our value drivers?And I often say, what do mean, right? You have had some great success getting to 400 million in AR, right? And there's probably some, some KPIs that you're tracking well along that in order to make sure that you're delivering value and you've gotten to that point of time. But what a lot of organizations are I think overseeing is that the customer success organization and the account management teams, they are trying to renew with customers based on the value that you're delivering. And they are somewhat trying to tie the story between the outcomes the customer is interested in and your product and taking those and actually building playbooks for the pre-sales team.can be an incredible starting point because otherwise we wouldn't be renewing and expanding with customers.KK Anderson (12:47)You can even use that data with the existing team to figure out who are the right people they should be spending their time with. the old 820 rule, 80 % of ⁓ sellers are spending their time on the wrong accounts, right? So let's move on to the second topic here.Max Elster (13:03)Spot on. Spot on.KK Anderson (13:06)and kind of focused around building the value intelligence layer. So you describe the importance of creating a value intelligence layer. But what does that really mean in practice? Like, is that a tangible thing? Is it a process? What does that really mean in practice?Max Elster (13:23)Yeah, I mean, how we woulddescribe it and kind of the definition for the value intelligence layer is essentially trying to find a way to better map the features that your products basically have accommodated and map them to individual outcomes of customers and then relate them back to what does customer impact look like, right? And this could be even a simple, like you go into a spreadsheet, yours is a chief revenue officer. You know which products or which features are most popular within.kind of your individual user group, and you try to map them to the outcomes that you want your sellers to drive within your customers' accounts. And you refer that back to then, ideally, customer impact, right? How do these individual outcomes that map to the features actually help somebody drive impact within their companies? that's measurable on the post-sale side. That's measurable on, like, if you look at product telemetry data, right? Are people actually leveraging the features within your product that actually result indedicated outcomes across your organization. And that's, think it's essentially building that single source of truth in order to understand how does an individual feature connect to a customer impact and how do you make sure that when you talk to a prospect, you can go into a conversation and say, this is apparently the problem that you're trying to go after. This is the outcome that you're trying to go after. want to reduce costs in 2026. have.different use cases that accommodate that, right? That I would love to walk you through and understand whether that's helpful, right? Whether that's like the potential use cases that could be deployed in your organization. And you almost open up the room. I'm not sure if you've ever used a car configurator in the past where you can kind of configure your Porsche or the BMW or the Mercedes that you would like to explore. It's almost similar to that, right? You open up a shared space and you try to explore the future car that you want to buy. And you want to do something ideally with the prospect as well, where you talk aboutThis is kind of the value intelligence that we have built. These are the features that we have. This is the outcomes that we usually drive with customers. And this is the proof and the customer stories and the impact that we're succeeding with with customers. So it spans from pre-sales to post-sales. It's essentially this unified layer. it helps, that data layer helps to create better business case because every business case will not just talk about features and functions, but it will also relate back to the customer impact. It will help an outcome plan, right? Everybody talks about.mutual success plans on the wholesale side, they will not just be individual checklist items anymore, right? They will actually be basically deployments, right? Which use cases did we deploy and how can we make sure that we measure them quarter by quarter, month by month or year by year to say this customer is actually on track. We're not just seeing whether they're using our features, but we actually see whether they are delivering the outcomes and we're working with our customers to keep ourselves accountable.And I can tell a good story there. Actually, one of our customers, Cognite, is a leading software AI manufacturing company. A couple hundred million AI are a pretty successful category leader. And their Northstar internally is to drive customer value. And everything basically that aligns within the organization is around that principle of driving the Northstar, which is helping a customer succeed and deploy the right use cases and making sure that not justThe customer success manager can talk about the value, but also the customer can go internally and say, we deployed these four use cases with Cognite. That's how they operate. This is how successful they are. This is where we still see gaps. And you almost keep yourself and the customer accountable on a mutual story of how you are succeeding with them. And it's building a different narrative. You're almost handing over the relationship of customer impact also to the customer. It's not just a vendor.specific relation that you're trying to build. it's really vice versa. You're trying to mutually succeed and both parties have to understand how the feature usage relates to the impact that you can get from a vendor specifically.Mark Petruzzi (16:48)So Max, take us a little deeper in how do you pull data from systems like Salesforce, Gong, and general call transcripts to fuel this layer?Max Elster (16:58)Yeah, of interesting ones. So one big layer that we tap into are case studies and any existing successful stories that you have, right? Where you've essentially articulated the problem that you're trying to solve for a customer and the relatable metrics that go along with it. Some companies have a better case study system than others, right? Some companies are still very feature oriented in their case studies, but it's a good starting point at least, right? To then say, okay, this is what the case studies say. Another data point is Gong wherewe pull or like any sort of call recorder, right? ⁓ Where we pull call transcripts and make sure that we can map the talk tracks of a seller or an account manager to these individual case studies and the results that you have seen with other customers, right? So that's another big data point. The third data point is Salesforce, where a lot of organizations have some sort of overview on the medic or a med pic or a spiced scenarios of what is the problem we're solving? What are the metrics associated with that? Right? And all these different data points.are essentially fueling this customer value intelligence layer. And you could almost see it as like a small database, right? Like on a, that's not like where like all that information is gathered and summarized. whenever an SDR wants to send an outbound message, they query that database, right? And they can say, Hey, I'm targeting Kristen at a Pepsi at PepsiCo, right? And she's this persona, she works in this department. What should I send to her? Which relatable customer stories can I bring up in my cold email or in my cold call?that actually would relate to her job and the problems that she's potentially facing, right? Or there's another account manager that taps into that same quote unquote database where they're trying to now expand with an existing customer and think about what are the additional use cases I could deploy. And then that database will help to make sure that you can find your path in upselling and cross-selling the next use cases and the next products that you can offer. And essentially that, like those different data points are continuously fueling.the quality of your value intelligence layer, the more calls we have, the more case studies that are being released. Of course, the better the system gets over time and the better it can actually help organizations communicate outcomes over features.KK Anderson (18:54)So it's almost like a generative AI interface for your querying and asking questions. Is it also listening to the problems that your prospects and customers are telling you about? ⁓Max Elster (19:05)100%. I mean,that's the interesting part of the talk track of the seller, but then also the underlying pain points that the customer is articulating. ⁓ So it's both. It's of course the customer's pain and the way they articulate their problems and relating it back to your value proposition. ⁓ I often say it's essentially two contexts cloud. It's the context cloud of what is your value proposition if you put it into very abstract words, right? Like what do you deliver and how do you make sure that's measurable?And the other context cloud is the pains and the business priorities of your customer and essentially merging them together. And you're trying to align how do we, what's the, what's the similarity between everything that we do as an organization and the products and features that we've shipped and the outcomes that we deliver to the pain points that the customer has. you, you build a natural coherent mapping between both of them.KK Anderson (19:53)And does it also give information about, like in some kind of an LLM model, give information about the prospect or the companyMax Elster (20:00)you bring up a good point. think a lot of companies, they start to tap deeper into account research, right? So when I'm a seller and I'm trying to prepare for my next meeting, I'm trying to get a better understanding of what is this customer even about, right? And how do they make decisions? What are their current priorities based on what I can find from just like online research? The problem with that oftentimes is that it's generic and it's not tied to the previous value that you've delivered for customers.Right? Anybody can run a chat, you would see prompt and say, Hey, let me prepare for this podcasting interview. Right. But the people don't actually know what's what are the, the different podcasts that you've run in the past and how is my maybe unique value proposition in those types of environments. Or when I'm selling to somebody, how do I make sure that their specific challenges are tied to my individual value proposition that I can bring as an organization? And that's something where chat should be T unless it has a lot of context struggles to give you.a performant high quality answer, right? It can always guide you in some direction, but it doesn't have all the context about the value intelligence there or the outcomes that you're delivering to customers because it doesn't access your product data and basically the outcomes that you're delivering across the board. So that's where we see systems like Chatjibiti and others and typical LLMs struggle. Doesn't necessarily mean that we don't use them as a technology or our customers don't use internal tools for their technology, right? I think LLMs are a great starting point, but you...have to give them enough context and business context in order to really help you find the right path.KK Anderson (21:22)so I'm thinking about like if I were prospecting and I was in a prospecting motion, like having this single source of know value truth, right? How does that change the way I operate day to day? How does it differentiate me as a seller, as a prospector?Max Elster (21:36)I think very clearly, let's take an example. If I'm in an SDR at a software company selling to large FMCG companies, and I come in and say, we have built this platform with these individual features. And that's usually what individual users are reporting back to. this is what our platform does and the value it provides.it can get very generic, right? And everybody has hundreds of those messages every single week in their inbox of something that is platform and feature pitching. How this is going to differ and differentiate you is that you're going to come in and you're going to say, hey, Kristen and Max, I work at this company. We have worked with three different FMCG companies in the past six months around these two core pain points. And after six months, these are the relatable ⁓metrics that we have deployed, that we have basically mutually measured together with the customer, that we would love to see if that's also relevant to you. And if you are interested in solving similar pain points and you're interested in basically seeing similar outcomes for your organization. And it's less about the message itself, but it almost gives you more credibility as you're reaching out to these people and you're almost seen as somebody that actually understands their business, but alsocan give relatable examples from other companies, not just on a qualitative, this is what our product does, but on a deeper level of these are the benchmarks that we have deployed for this customer and this is the outcome that potentially we could build for you as well. And let's mutually explore it before we jump into a conversation.Mark Petruzzi (23:01)So Max, what's the one thing CROs can start doing today to better capture the why we win?Max Elster (23:09)Yeah, think probably, how would a good consultant do it, right? I think usually it's like, let's do an assessment today and see already what you're doing today. So I would probably look at every single exit criteria in my sales process and just see what are we actually tracking? Are we tracking whether metrics and impact and the business case has been built before stage three, stage four? Is that something that's already happening today? Or is there...almost like a free way for the seller to just continuously sell on features and function without actually getting any step in the sales process where you say, this is what we're going to do today, and this is kind of we make sure we measure that in the future.I think it's a tactical step. So I think that's something that I would probably recommend to everybody just thinking about exit criteria and making sure that you can align your thinking and the outcomes you want to drive to your sales process. That's oftentimes a good starting point. It drives immediate quick wins. You can measure it. You can keep yourself and the teams accountable. And it's an easy way to get started.Mark Petruzzi (24:05)Excellent, excellent.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of our conversation with Steve Smith, Chief Revenue Officer at Live Oak Fiber, we go deeper into how his team is scaling with both agility and authenticity—blending AI, community engagement, and a customer-first mindset to win in a highly commoditized telecom market.Steve unpacks what it really means to lead with transparency, build a culture that thrives across residential and B2B markets, and design a sales engine that delivers personalized value at scale. From t-shirt cannons to AI-assisted prospecting, it’s clear: growth happens when you meet your customers where they are—and actually understand who they are.What You’ll LearnCompeting Beyond the Product: Why the best way to differentiate is not what you sell—but how you serve.Human + AI Prospecting: Steve shares how Live Oak’s team blends digital ads, field outreach, and AI signals to achieve 80%+ MQL conversion.Leveraging Customer Context: How insights like home square footage and pool size help personalize campaigns—and why trust starts before the first call.Net Promoter as a North Star: The cultural and operational moves that helped Live Oak achieve a 76 NPS score—higher than Apple.Culture-Driven Growth: Why hiring “athletes,” not just resumes, is key to building high-performance sales teams in uncertain markets.AI Without the Hype: How Steve’s team uses AI practically—from outage alerts to upgrade prompts—without losing the human connection.Key TopicsGTM in both residential and business segmentsCreating “shock & awe” customer experiencesMapping Day 0 strategies with local event engagementDesigning growth systems that work across sales channelsUsing CRM, digital behavior, and AI for smarter targetingBalancing automation with local, white-glove serviceOperationalizing culture in sales teams and hiring practicesGuest Spotlight: Steve SmithSteve Smith is the Chief Revenue Officer at Live Oak Fiber, where he leads a people-first, tech-enabled go-to-market strategy across residential, MDU, and commercial segments. With more than 25 years of experience in telecom, Steve is known for his bold talent bets, operational creativity, and unwavering customer obsession.Resources & MentionsBook: Good to Great by Jim CollinsBook: Blink by Malcolm GladwellInspiration: The Savannah BananasSales Concept: “People don’t buy drill bits. They buy holes.”🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts.Mark Petruzzi (00:31)So Steve, we have a lot of audience members that are in the ISV market or SAS, Software as a Service. And really what you do is kind of telecom as a service, even though you guys were before all these acronyms like SAS. And it's interesting. We can all debate what a commoditized market really is.Steve Smith (00:37)Right?Mark Petruzzi (00:52)but some of them feel like their markets are moving into a commoditized market. So what advice would you give those CROs that trying to stand out as their market matures and does get more commoditized?Steve Smith (01:07)Well, will say it's a continual battle. there's no magic, there's no silver bullet, it's consistency, it's having the organization focus on it. But I would say don't compete on the product alone, compete on the experience. So focus on trust, transparency, and outcomes. If you do that, for instance, we have an outage, we post it online.And we'll say we're having an outage, sorry for the inconvenience and call us here if you need assistance. And sometimes we'll have outages or issues in an area because we're still under construction and we'll proactively give people credits and say, hey, we're sorry. We're sorry this happened and we'll reach out. If you focus on those things, then you'll stop being more of a commodity and you'll be more indispensable, so to speak.But people respond with that. It depends. it's a continual battle. In today's climate, everybody wants the best for the lowest price. if you focus on those things, trust, transparency, and outcomes. I have a friend that would say, people don't buy drill bits, they buy holes. So you talk about what they get out of it, not so much how you're doing it for them. Yes, we have fiber optic. Yes, it's in conduit, and it's buried, and we haveKK Anderson (02:04)Mm-hmm.Steve Smith (02:12)phenomenal connectivity and nodes and we have all this telemetry around our network, but they don't care about that. I mean, they care about is it going to be up. Last year in September, Hurricane Helene was one of the late storms in the season and it went to, we have a lot of storms, but this one went across Glen County. 80 % of the county was without power. And however, if you had live Oak fiber,Mark Petruzzi (02:27)Yes.Steve Smith (02:35)and you had service, lot of people had generators, you were able to watch the Alabama-Georgia football game and there was watch parties online and people were like, I've got live oak fiber, you come to the house and we're watching the football game. That's what they care about. They do not care about that, yes, it took all that that I described to get that experience, but they care about the experience and what the outcome was. So yeah, we're excited about that.Mark Petruzzi (02:43)youYeah.KK Anderson (02:56)Wow, yournumbers must have flown after that.Steve Smith (02:59)Yes, we always get a bump on the weather for sure.KK Anderson (03:03)That'sawesome. Okay. so we've sort of touched on the first couple of topics, but like I'd like the most, lot of our audience are B2B CROs and CEO. we know 80 % of your businesses in the residential sector, but talk to us about how you're growing the business segment. And then also like same thing, how do you decommoditize a commodity inwith your business customers what's working.Steve Smith (03:25)Well, I mean, at a high level, we want every type of customer that we pass to be able to experience our service. So the most passings we have are residential. So that's the foundation of our company. And it builds that brand awareness and scale. It gives us cash. We can build into neighborhoods. There's a lot of houses. We have pretty, we have a good machine, I would say, in assembly line on how we connect those folks. But.We balance that with business customers and multi-dwelling unit because that gives us density. Those are other kinds of customers on the network. The message, the philosophy, the ethos is the same. So it's not an either or. Like I mentioned, they complement each other. People ⁓ own a business, they also own a home and live there. And so there's that kind of crossover there. The motions are different on how you engage with them. We alwayswork with chambers and local stakeholders because that's a great way, especially in the communities we're in, that's a great way to stay ahead of the message. If there are issues that the community is experiencing or they have questions, these are the people, these are the leaders that are active in the community. And so we're engaged in those discussions. Our folks attend chamber meetings and they participate in those committees and that helps drive that. So it all works together, it all stacks, but it goes back to that basic principle ofI would say every door, every floor. Anyone on the network, we want them to be able to experience live-o-fiber.KK Anderson (04:41)love that every door, every floor. That's really cool. Okay. let's go into some sort of classic sales skills, if you will, and let's talk prospecting. that's an attempt at business development. And well, I guess across the three channels, residential business and your multi-family dwellings, what's working for you from a prospecting perspective?Steve Smith (05:02)Well, we have a recipe. I think we've nicknamed it shock and awe. And what we do is we have warm-up period. So we measure, we call day zero the ability to schedule a customer to install. And we work backwards and forwards from day zero. And we have an idea of how much time we need and what we need to do to warm up the market up until that day zero.And we want people to be aware of our brand, be aware of our offerings. And so when the time comes, we've had a couple of interactions with them, and then we can schedule. So we work that channel. I would call those pre-registrations or pre-registered leads, marketing qualified leads, depending on who you are listening. And our sales teams actively nurture those. They nurture them through outbound phone calls. So we'll use digital to drive in some demand. We will use direct mail.which is kind of like the percussion section of a band. You've to keep beating the direct mail drum. We'll use door hangers. We'll use a lot of stuff to generate this awareness over that timeframe, which is roughly, 60 to 90 days because people get excited about, you want them to get excited about having the service. And then from there, it turns into more of a, active conversion campaign. We convert about 80 to 85 % of those marketing qualified leads.The ones we don't convert typically have moved or they fall out. That's a pretty high ratio and we do that through these nurture programs. But how we prospect is very simple. Our business is address driven. So direct mail is one thing we do. We have a very great, great's not even the right word for it. Thomas Allen runs our marketing. We have a highly customer focused digital program.and we're running different kinds of digital ads as we get closer to day zero. And that helps as well. Anyone that interacts on our website, we capture bits and pieces of information. Maybe we only get your address. Maybe we get a phone number or an email. And all of those get collected. I'm a huge fan of that show, Gold Rush, when it first came out. If you've ever watched that show, everybody builds their gold machine differently. But essentially what they do is they turn through yards and yards of dirt.And they put it in those machine and it knocks out the big rocks and at the very end like it goes through all these different methodologies to get to the the pay dirt which is the dark dirt and the gold and it's like two guys and they're literally hand panning it out, you know in a tent. That's really what it is for us too. And you've got to go through that you got to go through and constantly fix that machine. Sometimes we do buy cold leads and at the residential level that's tough with Do Not Call.regulations in place. The other thing, we do a lot of events, we do a lot of localized events. We have a great local campaign on that. people come in. A lot of times now at this point, they're customers. We have customers show up and then we have future customers show up. So we get all that interaction. But anyway, we can kind of drive that consumer, but we start with the consumers because they have the most events around that.KK Anderson (07:25)Mm-hmm.Steve Smith (07:45)And then it just drives it into that machine that I talked about. And we just try to nurture them to that day zero and then we convert them. So today that's what we do. There might be some different things that we have to do going forward. It's continuous improvement. So I have to say this because it is funny, but when I worked at a company in Arkansas and we would go to a lot of events and you give out t-shirts.KK Anderson (07:55)Yeah.Steve Smith (08:05)And if you ever give it out t-shirts, people will show up to your booth and they'll say, I need two mediums and a large. And then the large isn't big enough, so they need the XL. it's not a very effective way to give out t-shirts. So one of our folks that worked there, her husband built things. And I mean like built things. And he said, I can build a t-shirt cannon. And I said, can you build it? So I gave him the specs off Amazon and I said, can you build one like this? And he built his t-shirt cannon.Mark Petruzzi (08:14)ThanksSteve Smith (08:29)Now, the difference was when we would go out with the t-shirt cannon, it didn't matter what size the t-shirt was. If we shot it out of the cannon, then people would knock each other over to get to the t-shirt. So I was like, we're going to need that at Live Oak. So in the original business plan, we had these really nice t-shirt cannons and we still have them. We have a blue one and we have a red one. Blue one stays in Florida, the red one's in Georgia for the Bulldogs. And yeah, we shoot them off.I may or may not have shot one off in the office in the last couple months and shot a hole in the ceiling tile. So it works. It'll put a t-shirt on a rope at 100 yards, but it's just fun. So those are different ways that we kind of, know, people like that and it's fun. So that's some of the stuff we do.KK Anderson (08:56)youMark Petruzzi (09:08)So Steve, have you shot at people that have not made their quota? Is that kind of how it works?Steve Smith (09:13)⁓ well, no, we haven't done that yet, But I have shot at new salespeople, testing, the trajectory in the parking lot. We have we have done that. And I think it's probably on video somewhere. Yeah.Mark Petruzzi (09:16)butwell, you see if their reflexes are quick enough to catch it. That's the, that's All right, well, let's go to topic four. This has been really, really enjoyable and let's keep it going. So I think we titled that leveraging AI and community engagement for growth. But I think I'd like to title it leveraging, technology and kind of anti-tech, before tech.Steve Smith (09:28)Yes, that's exactly right. Exactly right.Sure.You got it.Mark Petruzzi (09:50)because you're using a bit of old school here combined with all the power of GenAI. So what I love about your team does, and frankly even easier in the B2B space than it is in the B2C space, but your residential team uses a lot of creative local insights. They're analyzing Zillow all the time. It's all about maps.You mentioned about the home square footage and figuring out what that is. I even read somewhere you're looking at clients pool size to tailor particular offers. How does that improve conversations and how does that improve your Salesforce effectiveness as well?Steve Smith (10:21)Yeah.Well, I mean, it makes the conversation personal and not generic. We're not doing it to be, sneaky or anything. We're just trying to understand the customer. We've done our homework. So if we're calling someone, if someone's got a pool or, you know, a large backyard area, probably might have some, they might be spending some time outside. They might be inclined for like an outdoor wifi solution as an example. It just builds trust out of the gate that you know thatyou're asking them about their, you've got their address, so that's public information. You're just trying to have a better conversation. We've all been in those sales situations where the pitch is completely off and you're like, you didn't do your homework. I want my teams do their homework. So they try to have a very, as much as possible, an intelligent conversation, a casual, informative conversation. we're not just.banging through numbers to get to yes. We're having real conversations with people. So there's tools that have that. And then there are some AI tools. We do a lot of work around buyer personas in different areas. we look at words or messages that might ring true with some of those folks. For instance, in a lot of our markets, we have a real heavy DIY DNA.and a lot of people like to do so. we focus a lot of things around that. Messaging around, creating a gaming room or with our app you can basically kind of customize your home network. You can have a network for the kids to stream, one for kids to game, and then one for mom or dad to do online work or online school. kind of little different things like that. We're using technology. We do...AI is, I hear a lot about AI replacing people and maybe it will for certain jobs, but the way we use it a lot and we have kind of the standard kit that comes with your Microsoft license and then some folks will use different versions, Claude or ChatGPT. And I would say that it's an enhancement to the experience. It's never gonna replace the authenticity of a human and not yet. Well.You said season at the beginning. I definitely feel old when you say that. mean, it's old. maybe not as long as I have a say in it, because I think there's a personalization part that you can't get yet. But you could definitely get far ahead in terms of understanding your customer and their needs with these different tools. And some are free. So why not use them? It was our sales manager, Katie Robeson, whoKK Anderson (12:22)What are you doing?Mm-hmm.Steve Smith (12:41)She came from Louis Vuitton. She was the one that came to me with this like hey, we're doing this and I was like, that's fantastic I didn't even it wasn't my idea. I just encouraged it. So yeahKK Anderson (12:51)I keep thinking as you're talking about all of this data that you have, there's so many ways you can use AI to really leverage that data to be even more customer obsessed and meet their needs even more directly based on different data triggers. Have you guys looked into doing that yet?Steve Smith (13:07)We have a little bit of that. We have some of that on our digital side. So we adjust our ads based on weather and that's what that's automated. then we also have, but in terms of like kind of a CRM and loading that we're in the continual phases of making that work. Like where does that information reside? We look a lot at our customer experiences. We have systems that kind of things that happen to users. We know when people probably need an upgrade.and we proactively will text them and they're having, maybe they're hitting bandwidth limits.KK Anderson (13:36)And how doknow that? Because you're hitting bandwidth.Steve Smith (13:38)Yeah, we can see the user behavior. how much they're using, how many times they're kind of hitting peak, when they're hitting peak. Every ISP can pull this data, but we have a tool, a platform that we use through our CPE provider that allows us to get that visibility. So then we just action on it. So that's in play now. So the next step is kind of how you described is the more information we can.gather about our customer and their experience, can store it. It's not just the storing it, it's being able to action off it. Is it insightful enough or are we having to boil the ocean to get some answer?KK Anderson (14:11)with agentic AI, you'll be able to piece agents together to make workflows to just, it could really be incredible. Yeah.Steve Smith (14:13)Yep.It is. I'veit work too on the fiber design side. So there are softwares where we're designing networks and you can input all these different data sets, like where's the utilities, where's the streets, where's the public right away, and it will, generate a design, which might take a drafter, seven to 10 hours to do, and it can be done in 30 seconds or less. So there's tools like that that are helpful. Not that the designer isn't good, but where computers can crunch things.looking for correlations and data and things like that. That's super helpful. So we're thinking about it and we're startups, so we're still, you know, the old analogy, we're definitely flying the plane and enhancing it at the same time. yeah. Part of the fun, thank you.Mark Petruzzi (14:53)Aren't we all Steve, right? Great, all right, let's jump to our rapid fire questions that our audience loves so much. And I'm really excited to see your perspectives on this. What was your first product or service you ever sold?Steve Smith (14:54)Yes, that's right.Okay.Okay.I would say I was a paperboy for the Denver Post. I'm definitely dating myself. People literally bought subscriptions to the newspaper and the Sunday one was easy to sell because it had comics and it had the really cool sports section and of course it had the coupons. And as the paperboy though, you had to put all that stuff together in your garage. You got the Sunday paper delivered and you had to put it together.Mark Petruzzi (15:32)seven times heavier, maybe 10 times heavier.Steve Smith (15:34)⁓yeah, was, gone are the days you couldn't deliver it from a bike and just wing it. I mean, I couldn't. I didn't have the arm strength. We did it out of the back of a country Squire station wagon. And it was, you my dad would drive and my brother and I would, you know, chuck the papers two hands because the Sunday paper Denver Post back in those days was something to behold. But the upsell was the daily. So if you could get them to take the daily, then,that was the tough part. you try to say, oh, you know, again, this is pre-internet. So you're going to get the news every day. You're going to find out what the Broncos are or aren't doing in the off season or during the regular season. I think that was my pitch. So yeah.KK Anderson (16:10)I love it.Even then you were thinking about customer outcomes. favorite CRO or CEO to follow.Steve Smith (16:14)I was. Yes. Yes.I touched on him earlier, Jesse Cole of the Savannah Bananas. I follow that He's on LinkedIn. He has great content. He talks about the books he's read. He's fantastic. And it's enjoyable to watch. Yes.KK Anderson (16:25)That's right.Can't wait for him to hear this one. And Jesse,if you're listening, we want you to come on selling the cloud as well.Mark Petruzzi (16:35)Yeah.Steve Smith (16:38)You should come on Selling Cloud,Mark Petruzzi (16:39)ThereSteve Smith (16:40)Jesse. Yeah.Mark Petruzzi (16:40)you go. Okay, so a leadership or go-to-market practice that you believe every sales and marketing leader should adopt and you've shared a few great ones already. Is there one of those or another one that just goes to the top?Steve Smith (16:55)I'd say, I said it before, hire athletes. So hire people that can collaborate and thrive in adapting to change. You do this, you can fill a lot of roles early on. Even if you're an older legacy industry, you're gonna get really fresh perspectives if you hire people like this, because they can transfer their learning. So when I say athletes, I mean like a business athlete. Someone that's really good at, can be good at multiple positions within your company. Those are the people to get.KK Anderson (17:20)Love it. My favorite advice you would give your 21 year old self. Which was just yesterday. That was just yesterday, right?Steve Smith (17:24)there's a lot. yeah, itwas absolutely just yesterday. would, it's definitely not yesterday. I would tell my 21 year old self to bet on people sooner. Skills matter, but character and curiosity and grit, that's where you're gonna get the most out of life. Don't be afraid to take those big swings.You mentioned it, Mark, you're betting on people, you bet on people you trust and share your values. And that's where the wins come from. So I've always bet on people, but I would bet on people more sooner if I could go back in time.Mark Petruzzi (17:58)So I have a typical question that we ask every week that I'm gonna change a little bit to you. The question is, what is your favorite sales or marketing book? But then I wanna add on, when are you writing your book?Steve Smith (18:10)⁓ well not gonna write a book, I'm gonna write a movie. So that's my... Yeah, I don't know if it'll get made, but it'll... I have a lot of business...Mark Petruzzi (18:12)Even better. You make a lot more money with the movie, selling a movie script than you would with any book nowadays.KK Anderson (18:21)Hey, you need to talkto Mark. He's got a lot of movie experience actually.Steve Smith (18:25)Hey, we should do it. even have actors picked out for various characters. So we'll see. Hopefully I want it to be PG-13, but I'm worried it's going to be TVMA. Favorite business book is, I like a lot of them. I like Blink by Malcolm Gladwell because it talks about paralysis through analysis, trusting your instincts, which is hard. what I liked about the book wasMark Petruzzi (18:29)I love it.KK Anderson (18:41)andSteve Smith (18:46)People have natural, your human brain, AI is awesome, but the human brain can do so many things so fast that you don't even know that it's doing it and it picks up on all the subconscious behavior. Like I'm sure if the computer analyzed my facial expressions during this podcast, it would give you feedback on me. anyway, but it does this and people that can harness that, and it's hard, but that feeling you get like, have a good feeling about this or that, like why is that? And.KK Anderson (18:53)Mm-hmm.Steve Smith (19:11)learning to harness that, it's great. And it's an easy read. He's got great perspective. It just kind of flows. So I would recommend that one. It's my favorite.KK Anderson (19:19)Okay Steve, well thank you so much. Tell us where people can find you.Steve Smith (19:22)Well, you can find me on live Oak fiber.com. If you go there, you can follow us and we're on LinkedIn. We're on the gram. We're on the Instagram. We're on the X or Twitter or whatever they're calling it these days and Facebook and LinkedIn. So yeah, you can find us at live Oak fiber.com. if you're, if you're, yeah, if you're in Florida, if you're in the panhandle between Pensacola and Panama city beach, or if you're over there in Georgia,KK Anderson (19:36)And if you're in Florida or Georgia, then they can switch to you.Steve Smith (19:48)outside of Savannah, Tybee Island, or if you're down in Glen County, St. Simons Island, Sea Island, Brunswick, you can find us. You'll see our trucks everywhere. So yeah, follow us. Even if you're not living in those areas, you should follow us. We have great content. We run our own podcast. have a kid named, he's not a kid, well, he is a kid, Garrett O'Leary. That's the one that came, Garrett came, used to do social media for a soccer team in California, but Garrett runs our podcast and it's called The Fiber.and we have great local people on all the time. have some industry folks, so you guys should get on it one day. We'll have you on. Yeah, follow us there and watch our journey and cheer us on or throw tomatoes. ⁓ You can. There's a check availability button and just put your address.KK Anderson (20:20)would love to.Mark Petruzzi (20:21)We'd love to as well.KK Anderson (20:25)Well, please come to Texas. I'm ready to switch right now.Mark Petruzzi (20:31)Yeah,that's the only problem with that. We can't get you in our markets for sure. We'd love to. Yeah, we'll get there. All right, Steve, well, thank you again. This was really informative, really enjoyable. And thanks to our wonderful audience out there for joining us each week and enjoy that we're right before it. Well, this is gonna be coming out after.KK Anderson (20:33)Okay, done.Steve Smith (20:38)we're not there yet.Mark Petruzzi (20:54)after the Labor Day weekend, but I know we're all working pretty late here before the Labor Day weekend. So thanks again for doing that with us, Steve.Steve Smith (21:02)WeYeah, thanks for having me on to both of you and we should talk again.Mark Petruzzi (21:07)Sounds like a plan. Cheers.Steve Smith (21:09)All right,thanks y'all.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Steve Smith, Chief Revenue Officer at Live Oak Fiber, joins co-hosts Mark Petruzzi and KK Anderson to share what it really takes to stand out in a commoditized market. Drawing from 25+ years of telecom and GTM leadership, Steve reveals how Live Oak is building a “fiercely local” go-to-market model powered by customer obsession, simplicity, and a people-first sales culture.From recruiting talent outside the industry to treating broadband like a luxury retail experience, Steve breaks down how to differentiate when your product looks the same as everyone else’s on paper, and why NPS scores in the 70s are possible when you design everything around the end user.What You’ll LearnHow to Compete in a Commodity Market: Why Live Oak avoids tech jargon and positions packages around home square footage—because customers don’t care about speeds, they care about experiences.Hiring Outside the Box: Why Steve hires from Louis Vuitton and paddleboard shops, not just telecom resumes—and how that decision drives creativity and customer care.Fiercely Local GTM: Learn how a hyperlocal mindset builds trust, unlocks referrals, and builds brand advocacy—especially in overlooked communities.Customer Experience that Rivals Apple: How Live Oak’s white-glove service and full-time technicians boost NPS to 76 (compared to cable companies’ scores below zero).Product Simplicity That Wins: How pricing transparency and a “price-for-life” model inspired by the Savannah Bananas builds loyalty and eliminates churn frustration.Key TopicsBuilding a customer-first sales cultureDifferentiating when your product is a utilitySegmenting sales teams by audience (residential, MDU, SMB)Why most broadband companies have a bad reputation—and how to flip itLocal community engagement as a growth strategyMetrics that matter: NPS, feedback loops, and service consistencyGuest Spotlight: Steve SmithSteve Smith is the Chief Revenue Officer at Live Oak Fiber, where he leads go-to-market strategy across residential, business, and MDU channels. A veteran telecom executive with a passion for customer-first innovation, Steve is helping redefine broadband with a culture that starts and ends with people—both inside and outside the business.Resources & MentionsBook: Good to Great by Jim CollinsBook: Start with Why by Simon SinekInspiration: Savannah Bananas (yes, really!)🎧 Listen now and subscribe to Selling the Cloud wherever you get your podcasts. Stay tuned for Part 2 with Steve next week!Mark Petruzzi (00:31)Welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Steve Smith, Chief Revenue Officer of Live Oak Fiber. Steve is a seasoned telecom executive and growth strategist with more than 25 years in leadership roles across sales, marketing, and product. At Live Oak Fiber, Steve is helping to redefine how broadband providers can stand out in the world.where internet service is both a necessity and a commodity. Under his leadership, Vivo has adopted a customer first model from hiring outside the industry to building fresh perspectives that simplified billing and driving net promoter scores in the range of Apple, not in the range of many of their competitors. Today, Steve will share what it takes to build growth cultureand differentiation in a commoditized market, lessons that apply well beyond technology to any CRO or CMO navigating crowded competitive categories. Four themes for today. Building a people first go to market organization, so powerful. Differentiating in a commoditized market, I guess I would say so, so painful sometimes. Balancing residential business and MDUgo to market motions, and how to leverage AI community engagement for growth as well. This episode is packed with practical insights for revenue leaders looking to drive loyalty, accelerate adoption, and differentiate in highly competitive markets or less highly competitive markets if there are any of those still out there. Let's dive in. Welcome, Steve. We're so happy to have you here on Selling the Cloud.Steve Smith (02:07)Thanks, Mark. Thanks, KK. It's great to be here. I'm excited to have this conversation. I'm always excited to talk about Live Oak.Mark Petruzzi (02:09)Excellent.Yeah, for sure. And we've had some nice little discussions as well before this. So we think we've got a good one for you. Topic one, building a people first go to market organization. So Steve, you have said your biggest early advantage was hiring people outside of telecom. And tell us a little bit, that was also at some of your other telecom companies that you've worked for or if that's been a new approach at Live Oak.Steve Smith (02:19)Yeah.Mark Petruzzi (02:38)And why was that decision so important?Steve Smith (02:42)I've always looked for people that bring fresh perspectives. think industries that are older, it's easy to get into a rut. I think over past 20 years, I've hired people that ran, for instance, there's a gentleman in Chattanooga, I worked for a company down there, and one of our first hires was the gentleman that ran the rec soccer league program. He was in charge of scheduling all the fields, recruiting referees, and needed someoneHighly organized and local, and his name's Billy Tendal, if he's listening, and we got Billy, we were excited to have him, and now he's probably 20 years in a career in telecom, but Billy was highly organized. He understood people, and he understood what made people tick, and how to navigate all that. People can get a little testy on their soccer field scheduling, so that's how we got Billy. But that was just one example, and at Live Oak,definitely intentionally got people outside of telecom because they bring a fresh perspective. They bring creativity. I look for people that have a customer first mindset and when you have kind of an older industry you need these fresh ideas. You need energy and you need people that are really kind of bought into your mission and what you're doing and if they have the will you know you can teach them the skill but you can't teach that customer first centric thing.We have a lot of people that have sold paddleboards. I've had some top salespeople that have rented beach chairs. The first sales manager we hired who's now a director, she ran sales for Louis Vuitton here in Denver and Aspen. Louis Vuitton and Lululemon are two brands that she worked for. if you're listening, if you're familiar with those brands, like my daughters and wife would knock me down to get into a Lululemon store and...If one customer's upset, they're all upset. And if you have that mindset and you bring that to telecom, it's disruptive in a great way. So yeah, it's always worked out. Always worked out, though.Mark Petruzzi (04:22)Yeah, andSteve, you've already proven that you're bolder than me because I've done that and I have accomplished some of that throughout my career and I've done it in a different way. Forget about just legacy industries, but even new industries or kind of middle of the road industries, that fresh idea is so, powerful.Steve Smith (04:35)Okay.Mark Petruzzi (04:44)But as you were describing what you've gone through, it reminded me of some times that I've lost that battle. And for example, like where I've had to go to a board and get approval for that type of hire or that individual or working, I've worked a lot with private equity companies and private equity company and operating partners coming back and being like, you're crazy. This other person we're talking about is just.Steve Smith (04:49)Yeah.Mark Petruzzi (05:09)12 years and exactly what we're doing here and you're telling me you want to bring somebody from the telecom industry into this SaaS software company. maybe I should have been a little bit more bold and little more, just persevered a little more. And I'd have some more stories that mirror your stories as well, but very impressive.Steve Smith (05:27)Well,don't all work out, but for the most part they do. If you're betting on people, they do. And I like to bet on people. And you get athletes. When you look at teams when they're drafting players, they always have, okay, I need to fill this position. But if they get to the point in the draft where there's an athlete on the board, maybe doesn't fit what they're looking for, but can play, they get that person. They get that person becauseThey're adaptable. They can wear many hats. They can deal with adversity. And then you can figure out where they fit. I think that book, Good to Great, talks about get the right people on the bus first. And then you can figure out where they sit. But get them on the bus. mean, entrepreneurs, a lot of times, and you interview people and they'll say, we want an entrepreneur. And they really don't because it's kind of messy.Mark Petruzzi (06:05)I love it.Steve Smith (06:14)So you have to have, I think in the case of Live Oak, I think we got lucky and blessed that we had some investors that were okay with messy. wanted, entrepreneurs starting something new is messy. For some people that are crazy like me and some of the first 20, 30 people we hired, that's fun. For others, that is absolute chaos and they're gonna get upset quick. So it just takes time, but having those fresh perspectives. The other kind of example I look at is thatThe movie Ford versus Ferrari is a great example of an entrepreneur working with an old company and they took a bet on Carroll Shelby and they crushed it. They beat a brand that had won that Le Mans race hands down for, I don't know, 20 years. And they got so good, they were good at building machines and he was good at managing people that were eccentric but were athletes. But they could build a machine that could go incredibly fast, they could work together to do it. Didn't fit into the Ford mode.Mark Petruzzi (07:03)No way.Steve Smith (07:03)of course, but thatwasn't what they wanted. They wanted to win Le Mans and I think when they won it, the year they won it, they won it first, second, third. They were so far ahead that they had to ask the lead driver to slow down so they could have a photo finish, one, two, and three. So that is a great way to kind of look at it. It doesn't always work out, but sometimes you win, sometimes you learn. I've learned a lot. I've learned a lot, Mark, so you know.Mark Petruzzi (07:16)hahaKK Anderson (07:18)Wow.Well, and.Steve Smith (07:28)It happens.KK Anderson (07:29)in thinking about, especially kind of our theme today with selling in a commoditized market. And, when it's a commodity, it's the same as everybody else, right? These are items that are utility, if you will. And when you were starting Live Oak Fiber, in a telecom industry where there's a lot of competition and everyone in their mind has their sort ofmindset and perspective or perception, if you will, of what a telecom company does, what might differentiate them. when you're hiring outside of telecom and you're bringing in kind of those passionate customer-focused sellers, I think by default you're breaking the mold because they're not just going to go sell a commodity because they don't know anything about it.Steve Smith (08:03)Ahem.Well, and them not knowing about it is a huge advantage too. When we brought people on, it's literally like you get a focus group of people that will tell you how to sell the product because we get in a rut. We use acronyms. Telecom is notorious. We have a lot of acronyms and we get so used to saying and we forget. We think we're selling technology, but it's really a solution. And when you bring someone in that's not from the industry, they'll tell you how you should sell it because it speaksSo you have this own group and I tell them this constantly I'm like always go back to when we first talked like that's the perspective I need don't get wrapped up in the doodads and the Connectors and the acronyms think about how we positioned the product in the beginning and how we spoke about it a good example for us was in the beginning talking about packages for residential customers we Decided that most people most people really believe the internet is the Wi-Fi in their houseAnd most people know how big their house is, how many rooms they have and devices. So we've designed the packages around square footage in homes. And if your home is about this big, most people know, then you probably should have this package. And that made sense. It was easy to talk to people about that. It was a lot easier than trying to tell them about speeds, which nobody understands. The quality of a speed, like a fiber versus a wireless connection or whatever, theyKK Anderson (09:25)I still don't understand that.Steve Smith (09:28)Yeah, nobody does. They just want it to work. They will not say the internet doesn't work, they'll say the Wi-Fi is out. Well, what's the Wi-Fi isn't working. So that's how they relate to it, and that's how we started positioning the products in the beginning. But to get out of that commodity mode is difficult, and it is a race to the zero. And what we decided initially was we would be fiercely local.we don't have, a lot of companies have a mission statement. We decided to have a, why. Why do you come into work every day? And we followed this, Sinek is the one that invented this. He wrote a book, you know, Find Your Why. And if you find your why, then people do more. And our why is to improve the quality of lives of the communities that we serve through technology. And that's it. So if you take your why and apply it to problems as you go through the day,KK Anderson (09:58)Mm-hmm.Steve Smith (10:12)It's really easy to get to a customer focused mindset. We're there to serve. So we talk about the communities we serve and our customers live in these communities and we want to be their local internet company. And we have customers online say, that's, I have, you know, I love my Live Oak. And that when they say that I'm like, okay, we're, we're on message. on, we've, we've, it's the best feeling and it's more than internet. You know, it's we want them to be aKK Anderson (10:30)That's gotta be the best feeling.Steve Smith (10:36)partner they value, not a bill that they tolerate. I think if you rate different types of things that people spend money on, the things that they really hate to spend money on or hate to interact with is the dentist. Sorry for all the dentists out there, but you already know that. But then it's the cable company and probably a close second is your mobile company. And you don't really care to hear from them. You get a bill, you pay it, my gosh, is it really this much this month? And you don't get any interaction from them or any great ideas.We look at as we try to change that paradigm and make it a better experience if they do interact with our people. So, hey, let me help you get your streaming hooked up. Some companies will outsource their technicians. We have full-time technicians. Full-time technicians with Career Path, because that's really the face of our company. Yeah, they're gonna see me, unfortunately. I have a face for radio. Maybe they'll hear me, but they're gonna see those technicians, or they're gonna remember them by name. And sometimes they take their cell number, because they're gonna stay and make sure, hey, I'm gonna...I want this to be almost a white glove experience. When I leave the customers home, everything is going to work. The gaming is going to work, the streaming, they're going to know who to call if there's an issue. And I think that's the mindset we have. And that's how you separate it from the commodity. It's hard. You get a lot of noise toKK Anderson (11:42)I love that.Fiercely local. I absolutely love that. That's incredible. And do you have a commercial organization as well where you're selling to businesses?Steve Smith (11:51)We do. have our sales teams are organized around the customer types. So we have a group that works mainly with residential customers. We have a group that works with business customers. And then we have a group that works with multi-dwelling units. So you have town homes or condos or resort campus locations and homeowners associations. And those are specific sales teams, professional sales teams that understand those customers and what they're looking for. Now everybody knows what everybody does.So there's handoffs. if a business customer, if you sell a business in town and you join a chamber, they probably have a home in the town. So you pass that lead off to the residential team. Or if you're a residential user, you probably know someone that has a small business and you can start to get this cross pollination on referrals and things like that. So that's how we delineated at Live Oak.Mark Petruzzi (12:36)I love it. So Steve, you've compared your approach to the Savannah bananas ticket pricing. I have, and I guess that's kind of simple, transparent, no hidden fees. Make a comment of Savannah bananas there, just a sidebar. When that came out, when I first saw that was out there, my initial reaction was no, never.these guys flipping around and doing that and throwing the ball. But it keeps kind of showing up on some of my sports feeds and surely but surely I'm starting to say like, know, wow, maybe we do see this. Now I don't have any, eight year olds, 10 year olds that would, you know, in my family at this point. So it'd be a little harder to go to Savannah Benton Bananas. Maybe I would have been a little more inclined. ButSteve Smith (13:00)Yeah.Mark Petruzzi (13:23)But I have to say that level of connection they have to their customers, to their target market, it's incredible. So for you, how does that translate into loyalty? How does that transfer into the customer experience?Steve Smith (13:33)It is.Well, to be fair, I didn't know about the Savannah Bananas either when we started Live Oak about three years ago. And I heard about them and a friend said, if you ran a baseball team, this is probably what it would end up as, you know, all these shenanigans going on. And so of course I was interested in it and, but we were already kind of down the path. So we were trying to do the opposite of what the large cable companies did. a lot of times you have fees or whatever you buy online.Mark Petruzzi (13:51)Hmm.Steve Smith (14:05)Every other thing that you buy online, you say it's $12.87. It's literally $12.87. It's not $12.87 plus some strange fee, some strange fee. It is what it is, except for, unfortunately, a lot of these subscription telecom services. It starts to get a little wonky. So we just eliminated that and we don't have those fees. And we had to overcome a lot of kind of market confusion around that. We even offered aThe first promotion we did, which we still offer, is Price for Life. Because people literally feel like, okay, I get it, you're gonna give me this rate for a year and then you're gonna come back to me and jack it up at 20 bucks and I'm gonna have to wrangle my way back. So anyway, that's what we did. But as we got going, I ended up finding out about the Savannah Bananas, which is a great story. The guy that owns it is Jesse Cole. And I started listening to how he did it and he was a startup. There was a nearly abandoned baseball stadiumSavannah and he said I've got this idea about baseball. He went through the startup Savannah incubator there and they helped him. I mean of course they were like absolutely we'll help you do something with that abandoned baseball stadium that's a kind of an eyesore and he created a brand out of it and he was like he goes through a lot of the so if you order a ticket from the Savannah bananas and it's $20 it's $20.Mark Petruzzi (14:57)Wow.Steve Smith (15:20)It also includes, if you do it at the home stadium, you get a coke and you get a meal. So it's a two hour show, kind of like the Harlem Globetrotters, but with baseball. And it's hard to create that in baseball, but he's done it. And they have meetings all the time. Now he's got spinoffs because there's the party animals and I think there's now there's new teams like the tailgaters and the firefighters. And now he's like running all these groups that are, banana ball. They have like rules about banana ball, butMark Petruzzi (15:26)Yeah.He did it.Steve Smith (15:45)if you watch him, talks about the customer experience and that's everything. he's super successful and we just happen to be in the same area at the same time and I haven't met him yet. But I love everything that he's doing and if I can incorporate more of what Jesse's doing into us, absolutely, because it works. Customers are really connected with him.Mark Petruzzi (16:02)Maybe you shouldsign them up as your corporate sponsorship.Steve Smith (16:08)We're in discussions. a sponsor yet.Mark Petruzzi (16:10)There you go.KK Anderson (16:11)that'sWhat's so funny is I actually remember where I was sitting at Los Tios restaurant on Westheimer in Houston the first time I saw the Savannah bananas. And I was like, what is this? what? Because we're like, why are the Astros not on? And we ended up watching it and we were laughing so hard and we had so much fun that night. I, my customer experience wasSteve Smith (16:22)Yes.Right.outstanding.KK Anderson (16:33)Like, wow, this is so cool. I was immediately on their website. Like, how do I go see them? Yeah, it was really cool. Okay.Steve Smith (16:36)Right, right. Yeah, they get great,great connections.KK Anderson (16:41)Steve, one thing I know you're super proud of is your Net Promoter Score rivals Apple's, which is awesome. And most broadband providers, their NPS scores are in the toilet, or far lower. So I don't know, tell how you achieve that and tell me the numbers. Like what's yours, what's kind of somebody else's? I think it's super important to differentiate.Steve Smith (16:53)their love.We measured quarterlynow. We're going to go to a transactional measurement. For those listening that don't know, a net promoter score is how likely is someone to purchase a service to recommend it to other people. And they rate that number on a zero to 100. most cable companies are very, and you can be negative. So most cable companies, if they're lucky, zero to 10. Most are negative.Mark Petruzzi (17:23)Wow.Wow.Steve Smith (17:24)Well, right, for all those reasons. And then if you get a good, a decent broadband provider, a new broadband provider, you're probably in the 40s or 50s. Google as a company, separate company, probably runs in the 60s. Apple runs in the 70s. We're 76, which we're super proud of. And we measure it every quarter, so thank you, it's a lot. And the best thing about it though is if...KK Anderson (17:41)Congratulations.Steve Smith (17:46)Rich Shea is our COO and he said, we pulled the numbers and he's like, is this true? If people interact with our customer service team, that number actually goes up by 68 points. So that's true, six to eight. It'll go up to 82 84 because we have people that they're bought into the why and they want to solve the problem. So we're very excited about that. We're moving to a transactional model.KK Anderson (17:58)By how many?Wow!Steve Smith (18:11)So you're probably familiar after you have an install or you eat at a restaurant, they say how good was our service? And you rate them, that translates in that five questionnaire thing will translate into a score. And so we use that and we look at that, we try to figure out who's upset and how we can work with them and to bring it up. We're happy with the ones that are happy obviously, but that's just part of, that's just one of the.I call it the money ball statistics that we focus on. We don't focus on all of them. We try to find the important ones. And that's definitely a key one. That's a differentiator.KK Anderson (18:44)so you do like real time customer feedback. Like when, when your technician's walking out the door, they're getting a text message with five questions.Steve Smith (18:50)We'reyoung, that's our next phase. That's what I would call transactional NPS. And that's what we're gonna do next. And I'm excited to see how that looks. And yes, it's gonna rate people down to the resource level, how good you do, but our folks are competitive and they don't, this will be good for all of us. So today we just do it, we do an email and we have a very high participation rate for that.You've got to get a certain amount. I wish I knew the numbers off the top of my head, but it can't just be like five people. can't call your mom and your grandma and have them skew the survey. You've got to have a certain amount to fill it out to get that number. We do it through a third party, it's legit number. We're excited about that.Mark Petruzzi (19:27)Cool.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud episode, Jamie Wilkinson, CEO of Smart4Cloud.ai, continues his insightful conversation with Mark Petruzzi and KK Anderson on how today’s revenue teams must evolve beyond job specs and tech stacks.From building integrated, cross-functional orgs to navigating partner ecosystems, Jamie breaks down how human-centered leadership and honest business assessment unlock true scalability. He also shares the key attributes that define top sales leaders and how to spot high-impact talent in any market.What You’ll Learn:Cross-Functional Alignment is a Growth Lever: Why modern revenue teams can’t operate in silos and how top-performing orgs build “fluidity” between sales, finance, tech, and marketing.Humanizing the Hiring Process: How Jamie’s commitment model goes beyond résumés to find high-performing candidates who align with the company’s story—not just the bullet points.AI Isn’t the Enemy or the Answer: Jamie shares a grounded take on AI: it’s not about fear or hype, but about how humans apply it to improve real lives and sales performance.Build or Buy? Market Expansion Strategy: Jamie discusses when to build internally vs. leverage partner ecosystems, and why brutal honesty is the real unlock for scale.Agility, Honesty, and Culture: The traits Jamie believes will define successful GTM teams over the next 12–18 months.Key Topics:Aligning technical, sales, and product leadershipHow to recruit talent that thrives in integrated orgsGetting past fear-based narratives around AIInternal vs. external capability buildingLeadership traits that matter in “normal” marketsHow to spot people with “G.A.S.” (Givers who actually… care)Guest Spotlight: Jamie WilkinsonJamie Wilkinson is the Founder and CEO of Smart4Cloud.ai, a human-first revenue talent partner for modern B2B teams. With deep experience in building technical + sales hybrid teams, Jamie brings practical wisdom and a no-BS approach to growing revenue orgs that work.Resources & Mentions:Part 1 of Jamie Wilkinson’s episodeGuest Mention: Napoleon Baligan, founder of 1-800-MattressReference Book: To Sell is Human (by implication)Podcast: Selling the Cloud🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders who’ve done the work. Subscribe wherever you get your podcasts.Mark Petruzzi (00:31)KK, can you take us into topic three?KK Anderson (00:33)Yeah,the third topic is what we're calling the integration effect. So it's how technical excellence amplifies sales performance. And I just would like to piggyback on what you were just saying about the destination, right? destination. And so when we think about the strategy around how to get to that destination and the alignment between thetechnical leaders, product leaders of an organization, the revenue leaders, the marketing leaders, like all of the different kinds of cross-functional like that's, how do the best revenue leaders orchestrate these various functions so that everybody is going to the same destination?Jamie (01:13)I think there has to be a fluidity and an alignment there. I think if you look at kind of years past when I first came into the industry or even was just working right, I think everything was very. Segmented And that was too many hits from American football.Everything was very segmented finance was finance compliance was compliance tech was tech sales was sales Marketing was marketing. But if you look at a really successful business now, there's a fluidity and there's an alignment where it may not Completely gel together but the best Finance guys are the people that are understanding what's happening in sales understanding what's happening in marketingunderstanding what's happening in compliance and how that's relevant to what they're doing in finance. The best salespeople are understanding what's happening in finance and how they can utilize that or what's happening in tech. So I think that if you look at any amazing business, particularly SMEs, right? Who are massively profitable and charging forward a dramatic rate, those businesses will be very in twine. They won't be segmented.everybody will have some kind of touch point on everything. And I think the difference between 20 years ago and now is that alignment and that kind of fluidity between the different parts of the business.Mark Petruzzi (02:40)Yeah, and you know what? I was putting together some of these questions and what I wanted to get to is how much better you are and your company is at recruiting sales leadership and sales reps because of the fact that you also recruit those technical skills as well. Or for example, in Salesforce, you recruit, you know,technical architect, solution architects, all of that. And maybe I even restricted us a little bit with some of that thinking as you've already brought us into some other areas. So what I'm taking away here is the importance of, as you're describing, the integration between all these functions. We're talking about technical mostly, but whether it's coordinating with marketing or product management or...All of that stuff, the more you can bring to the equation, especially in today's age, the more valuable you are as a recruiter to your clients. the clients, so the companies now, I mean, in general, you've seen deals won and lost time and time again because of this whole coordination between sales and these other functions. When you recommendI guess maybe the biggest part of this question is when you go out and you find the talent for your clients, how do you make sure, how do you figure out who's gonna be world-class at the collaboration or who's gonna be average or worse?Jamie (04:10)wow, question. For us, you know, we go through a process of, call it a commitment model, but it basically is the undressing of a, of an opportunity. you like, there was nothing locked out. Everything is visible. And again, you're looking at ultimately the conclusion of what somebody needs to do and what needs to happen. I think the play out with, with candidates is, is always the context thatrather than taking them through a stage process, you take them through a story or you take them through a journey. So this, you know, this is where we're starting and this is where we need to get to. This is your, your place in the process. This is your role in the process and understanding that they've got the ability to tell that story. Sounds a bit cheesy, but it's true. You know, it's kind of like, right. Okay. Rather than just reading the book, can you actually be in the book?And from candidates, I think it's really important to candidates as well, because we, so much of the industry sells jobs in bullet points and job specs, which are about as interesting as me. Right. ⁓ and, and we try and move away from that. We try and understand what people are actually needing, why they're needing it and what's going to happen if that, ⁓ that solution is fulfilled.So we can break it down into a much more real scenario. think we need to get away from, you know, boring ads with, you know, X, Y, and Z required, da, da, da, da, da, you know, the importance of talent solution providers like ourselves is the fact that we can take something that looks.pretty dull and bring it to life. Because when you bring it to life, it becomes real. And then you can understand who's going to do well and who's not. Clearly to a point that we can't control human beings, but what we can do is to really try and understand people and understand the role itself and how that's going to pan out. And I guess my overarching answer to that is try and humanize a job spec. There you go.Mark Petruzzi (06:31)Excellent. So KK, can you help us kind of pull this all together?KK Anderson (06:32)There's a, there's a.Yeah, I was just going to say there's ⁓ a big element of, in our conversation today and gosh, in the conversations I've been having all day around, you know, to sell is still human, to lead is still human. And yes, we have AI and we have some incredible robust ways to accelerate being human and to become superhuman, right? But it's human, right?Jamie (07:06)We are always gonna need people, but you know, I'm not in the side of the room where I'm concerned that iRobot is gonna take over the world and we're gonna have to run for the hills and we're gonna live in tents whilst the robots run the cities.The reality of it is, that right now where we are in life, there's some incredible technology that's allowing some wonderful things in the health industry, you know, probably more so than anything else. I think it's unbelievable what they're doing. But the reality is that all of these things are being built by humans, right? And all of these, all of these technologies are being created by people. People are always going to be here, right? People are always going to be pushing the narrative andI just think we need to get away from this kind of scaremonger scenario where people have, we're never going to, know, nurses aren't going to have jobs. Yeah, they are. They are right. Teachers. There's going to be no more teachers. Everybody's going to get taught by a laptop. No, that's not the case. Certainly not at the moment. And why don't we just stop kind of going one way or the other? Because I think there's a, there's a naturalnegative reaction to tech from certain people, know, my mother, for example, right, you know, the elderly, a lot of the time where they see it as a concern, it shouldn't be a concern. And it shouldn't be the answer. It should be, we have an opportunity to use some incredible technology to better people's lives, to help people's health.to help people learn, help people sell, help people make more money, so and have a better life and provide for their families. Like stop freaking out. It's not one way or the other. Like they're together.KK Anderson (09:02)ImagineMark Petruzzi (09:02)Jamie, I love that.KK Anderson (09:03)what we will be able to do.Jamie (09:06)I mean like, you're just stupid.Mark Petruzzi (09:09)And Jamie, that quote, think, it's profound. mean, it shouldn't be a concern. AI shouldn't be a concern, and it shouldn't be the answer, because it's not the full answer. so there's that happy medium. KK, you'll bring us to this final topic we had here that I look at it asJamie (09:23)Yeah.Mark Petruzzi (09:36)You know, what Jamie does as a recruiter, what good recruiters do, what good leaders do is, you know, the ability to bring this all together to increase sales effectiveness, to allow market expansions to happen quicker, more efficiently. So let's, if you have a question, jump in. If not, I have one too.KK Anderson (10:02)I do. it's hard, like going back to this last topic after such a profound statement that you just made there, I think, I can't wait to see the clips from this. But yeah, let's talk about market, market expansion strategy. So you work with direct customers through, you also work through systems integrators, right? ⁓ How should revenue leaders think about buildingJamie (10:13)God.KK Anderson (10:30)internal capabilities versus like leveraging partner ecosystems when they're when they're going to be expanding into new markets. Like do you have a philosophy or best practice? ⁓Jamie (10:42)no, I think my answer would be the same. think, you know, businesses have an opportunity right now to better themselves through technology, but technology isn't the answer because if we don't have the right people, then the technology becomes irrelevant. And I think, I think at the moment there is, you know, the market is pretty risk adverse, right? With regards to, you know, the economy's up and down like a yo-yo.And I think that people are concerned about cost and outlay, which I get, and they're not incorrect for having that. But I think.I think there needs to be like a truth pill. And I think people need to kind of take the truth pill and look at their business and be honest with themselves. And, you know, whether it's staffing or, you know, more heads, whether it's technology, whether it's, you know, the fact that what they have isn't great and probably needs rectifying in order for them to allow themselves to progress at a quicker rate.think people just need to be honest. think I do think there's a lot of the market at the moment, just, you know, they are like to call it the ostrich. You just find a bit of mud outside and whack your head into it and stand there for a while and pretend that everything's okay. Don't be an ostrich. Just be honest. You know, the only way that you can make things better is if you actually know what you've really got.KK Anderson (12:10)And I guess that determines whether you build an internal team or you use a, know, outsource it, yeah.Mark Petruzzi (12:11)Very interesting.Jamie (12:18)100%. Yeah. Or you do both. Or, you know, you, I think we, we had the, we had the steamroller of, of kind of post COVID where everybody was going bonkers and doing extremely well. And the economy was amazing. And there was a lot of over hiring and you know, we came out the other side and it was, it was pretty torrid. Um, and it was tough for everybody. It's, know, especially the recruitment industry and,You know, people ask me about the market now and quite frankly, you know, is it still bad or it's not good. it's terrible. It's kind of like, no, it's not. It's probably just normal. But we were spoiled and in a place where we thought that it became normality and it wasn't. We were, we were in, you know, we were on the, we were on a hot streak. were riding the wave all the way. And then all of a sudden the wave stopped and we fell off. And I think now the ocean is just kind ofbobbing along right normally but I do think that there's an opportunity out there for every business owner for every sales leader for every salesperson be agile be fluid understand the opportunities and the people that you're working with be thorough be honest and you'll be fineMark Petruzzi (13:38)All right, so we need a little bit of Jamie prognostication here and some forecasting. So looking ahead 12 to 18 months, what capabilities, you know, across the board here, let's keep it more around sales leadership and other leadership within a company. What will separate the leaders who can scale their businesses successfully in this market?that you're describing this normal market rather than the abnormal market we had for four or five years. And what should these leaders be investing in now? And I know one thing you're gonna say is people, and that should always be a core part of it. And they should. ⁓ But what else? Like how do they put it all together?Jamie (14:32)I agility is really important right now. I think any business that allows themselves to be agile and move accordingly is gonna grow at a better pace than others. I think being stagnated and just doing what you do isn't the market anymore. It's not a transactional market. That's not what we're in.We're in an opportunistic market. think understanding your product, understanding what you're doing and understanding what's working is important. And I think it sounds kind of crazy that I'm saying that, but I do think that there is a real problem with that right now in the industry, in certain, in certain businesses. think ⁓ understanding your people, understanding who's in and who's not.I have a term that I use all the time and I say, you know, the most important thing to me and my business is people that have gas. ⁓ The third word is a naughty word, which I won't say, but the first two words are giver.So I think you can probably guess what that means if people have gas then people care if people care people will do something if people do something You've got a chance of winning So look around you and work out those people have gas and if they have gas we're in a pretty good place and then you can start to figure out your business but there has to be a cumulative want and desire for any business to work because You're only as good as your weakest your weakest link, right? ⁓And I do think that, you know, when I look at, there's one particular business that I look at that's unbelievably over a four year period. And it's somebody that you know, Mark. AndIt's just desire. Everybody they've brought into that business is just on it. They want it. And it's not whether they're in sales or in finance or in marketing. And again, it comes back to what I talked about earlier on, culture.KK Anderson (16:47)I'm sorry.Mark Petruzzi (16:47)Isn't it incredible how simple it can be if we really can parse it down? All right, we're going to move you into the last step of this whole journey with us and one we love the most, our rapid fire questions. And the first question I'm going to ask you, and I'm going to make a comment first. So Jamie is still ripped. He's still in great shape.Jamie (16:54)massively.Mark Petruzzi (17:15)But I bet you there was a time when you were early in your career and you were, you know, knowing you probably eight to 10 % body fat going on. When you were young and starting all that, tell us about the first revenue critical hire you helped the company make and how you did that then versus how you would do it again with all the experience you have now.Jamie (17:17)Thanks, Mark.Where? Plus, I'm going deep into the history there. ⁓Mark Petruzzi (17:45)Well, tell usKK Anderson (17:46)First lane.Mark Petruzzi (17:46)first,have you ever been sub 10 % body fat? That's, yeah, I figured you'd have that. No, yeah, you still look great.Jamie (17:50)Yeah, yeah, yeah. Not at the moment, but yeah, many moons. ⁓so my first...KK Anderson (18:01)First, revenue critical hire.Jamie (18:03)Yeah. Okay. Yeah. So I think I remember it. I was working for Hayes at the time. ⁓ And Superguy. ⁓ And I went very much on personality. ⁓ You know, I talk about buying personalities, amiable, pragmatic, analytical, extrovert.And irrelevant of how I come across, I'm massively amiable. I like working with people that I like, whether that's a good or bad thing. And I really liked the guy and he was kind of purely based upon that. And luckily it worked out because he was quite good. However, if he'd been terrible, then I wouldn't have known because it was kind of like, oh, he's a cool dude. You know, we'd like the same things. You've got a job. I mean, it was just...It was terrible really, ⁓ luck was on my side because he did turn out to be a guy.KK Anderson (19:02)That's awesome. Who, Jamie, who is your favorite CRO or sales leader to follow? And I think I already know how you're going to answer this, but as it relates to building world-class, I do!Mark Petruzzi (19:03)Excellent.Jamie (19:13)You think I'm going to say Branson, don't you?Mark Petruzzi (19:16)Yeah.Jamie (19:16)Well, Richard Branson's up there, but there's a, do you know, do you guys know Napoleon Baligan? Yeah. I think his story is so cool. And he completely took a punt on something that he had no idea if it was going to work. And it did. So I love his story. The whole 1-800 sofa was it? And 1-800 mattress was him. Yeah.Mark Petruzzi (19:39)Yeah, yep,very cool. Yeah.Jamie (19:41)Which was such a cool thing,Just plug the numbers in and spell whatever you're selling. It's kind of very random, but very cool. So he's up there.Mark Petruzzi (19:51)and perfect idea and thought for the times. Like it was just built for where we were. Everything was phone-based.Jamie (19:56)Yeah, well he completely, heSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Jamie Wilkinson, CEO of Smart4Cloud.ai, joins Mark Petruzzi and KK Anderson to explore how the best revenue organizations combine technical talent and sales leadership to create scalable, high-impact GTM engines.With 25 years of experience in both technical talent strategy and revenue organization design, Jamie breaks down how CROs and CEOs can avoid siloed growth models by integrating sales and technical infrastructure, especially in today’s AI-powered ecosystem.What You’ll Learn:Tech Talent as Revenue Infrastructure: Why roles like solution architects, SEs, and customer-facing engineers are now critical for sales success, not just delivery.Overcoming Tool Sprawl: How to focus less on “more tools” and more on extracting real value from your existing stack.Culture > Tech: Why a strong leadership culture still outperforms even the best tech when it comes to execution.The Visibility Gap: How AI platforms like Collective[i] help sales orgs see what’s really happening so they can coach, forecast, and prioritize smarter.How to Hire for AI-Era Sales: What today’s technical-hybrid sales roles look like, and how to recruit for adaptability, not just hard skills.Key Topics:Sales leadership architectureCustomer-facing technical roles in modern GTMStrategic use of AI tools in sales orgsAligning technical capabilities with deal velocityWhy forecasting is broken—and how to fix itThe difference between productivity KPIs vs. outcome KPIsRevenue visibility and operational clarityLeadership lessons from elite team sportsGuest Spotlight: Jamie WilkinsonJamie Wilkinson is the founder and CEO of Smart4Cloud.ai, where he helps revenue leaders architect both technical and sales teams to drive market advantage. With a background in elite sales recruiting, technical hiring, and growth strategy, Jamie brings a unique lens to what it takes to scale high-performance organizations in the AI era.🎧 Listen now and follow Selling the Cloud for practical GTM strategies and sharp conversations at the edge of sales, leadership, and growth.Mark Petruzzi (00:00)Welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Jamie Wilkinson, CEO and founder of Smart4Cloud.ai. Jamie brings nearly 25 years of experience helping revenue leaders build both the technical capabilities and sales leadership teams that drive predictable growth. As the founder of Smart4Cloud, he specialized in understanding how technical talent strategyand sales organization design work together to accelerate revenue. How it works across cloud SaaS, cloud pass and AI management platforms. However, what Jamie truly unique is his dual perspective on revenue architecture. He understands both how technical capabilities enable sales success and how sales leadership structure determines market execution.At Smart for Cloud, he's helped revenue organizations across financial services, healthcare, energy, and technology sectors build integrated teams where technical excellence and sales leadership amplify each other. Jamie has seen how the best revenue leaders orchestrate both technical talent and sales leadership to create competitive advantages. Today, Jamie will share how revenue leaders should architect both technical capabilitiesand sales organizations for maximum impact. And also why traditional siloed approaches limit growth and how CROs can build integrated revenue engines within their overall go-to-market strategy. Four themes we'll explore today. Technical as revenue infrastructure, building customer-facing technical capabilities.sales leadership architecture and designing world-class revenue organizations. let's jump in. And first off, Jamie, again, thanks so much for joining us today.Jamie (01:58)No problem. My pleasure.Mark Petruzzi (02:01)Awesome. Okay, topic one, technical talent as revenue infrastructure. How do you build customer facing technical capabilities that help supercharge your selling model and your sales effectiveness? So Jamie, most CROs think of technical hiring as someone else's problem until a deal stalls because they don't have the right technical expertise for customer success.How should revenue leaders think about technical talent as a revenue accelerator?Jamie (02:33)Wow, I think, the first thing that comes to me is the fact that we have to, we're in a changing world right now where the AI's presence, technical presence is becoming larger and larger within any organization, whether it be a manufacturing company, whether it be a financial services business, whether it be a sporting company, a media company.And I think we're getting lost at the moment where we're not understanding how to fuse human beings with technology. And I think that there is almost an air of arrogance and concern around tech and how it can enhance. think too many businesses see it as a cost rather than an aid and assist.another weapon in the armory. I think there's a big problem at the moment where there was millions and billions and trillions of dollars spent on tech without a real understanding of how to use it or utilize it. And no market is something that we've talked about at great lengths. I think there's businesses that have spent a fortune on tech, whether it be a CRM, a HCM, whatever it might be. Andthere really isn't a true understanding of how they can maximize or utilize the technology that they've embedded into their businesses. And I think right now, for me personally, and what I'm seeing in the talent space and what I'm seeing specifically in a lot of partners is that there isn't an understanding of how they can use the tools that they've purchased or brought into the business. And then the partners with the end users,Whilst there can be a focus a lot of the time on new tools or upgrades, I think there needs to be a slowdown in what people are doing and actually to look at what they've got and how they can maximise that and do they need to bring in talent or...additional resources to allow them to actually utilize the products that they have or do they need to bring something in to allow that product to work to its fullest capability because so many products at the moment are fusing together. This isn't a one product market. know, every CRM is linking in with 10, 15, 20 different products.So right now it's, I think it's a question of how can we use, what do we need to use, and then how can we use it to the best of its capabilities? Because I think there's a a huge divide at the moment and lack of understanding.KK Anderson (04:50)You know, what's interesting is that so internally, like you're describing for, for your own texts, your own sales tech stack, it's, everyone will tell you it's bloated. You know, it's fragmented. it's all point, you know, pointing to a specific one problem. All of them say they're AI, different kinds of AI. It's just, there's a, there's a million different directions, like you said, that you, that you can go. But when you're hiring.And when you're staffing for your clients and they're looking for like a sales engineer, right? Or a technical role, even on the customer success side of the go-to-market, someone who will be nurturing that account, working that account from a technical perspective. customers now are demanding more AI capability or different...I don't know, iteration of different tools and programs to the point where those technical roles are more imperative than ever when it comes to being able to retain or expand an account. So how do you hire for that? What technical roles from a staffing perspective are absolutely critical for a sales organization to have on both sides?Jamie (06:03)Well, if you look there's some really good examples at the moment and I won't name companies specifically because I wouldn't be professional, but there's certain GSIs out there that have spent billions of dollars on creating AI platforms that theoretically is taking care of a part of the process, albeit web design and a lot of the administration. But if you look at the upper arcals, the solution architect or a technical architect, this is very muchbased upon a human being and their capability and their enhancement of the technology and the AI that they're using or utilizing in the lower echelons of the program. You can't have one without the other. And at the moment, there's so much reliance upon tech in the context that people think it's gonna solve problems. It will, if the people that are using it know what they're Otherwise it won't, it will create more.So technology, listen, I'm a technophobe, right? It freaks me out every time we get a new piece of software. But the reality of it is if I know how to use it and the people that are teaching me how to use it or implementing it are doing a good job, it's going to enhance my business or me personally. But if I don't know how to use it or I don't know how to utilize it within my business or why it's there, it becomes a problem.So right now I've seen multiple businesses almost they're going overboard on tech. There's too much tech. It's kind of like slow down, understand what you're using and what you're using it for and how it can enhance your business. And you need people in order to do that. You can't install tech and then the tech, a robot walks into the building and sits next to you and has a chat. people for tech.don't get me started on the videos of them playing football and falling over and and then falling out of the ring. I mean, ridiculous.Mark Petruzzi (07:43)that's great.Jamie, you brought me right into an area that I wanted to cover before we go too deep in the rest of ⁓ our analysis here. So I wanted everyone to hear that beautiful British accent that you have for the people who don't know you. ⁓ I also should share ⁓ I'm friends with Jamie. So, I don't think he'll that?Jamie (08:05)supposed friends.Mark Petruzzi (08:06)Exactly. Some days. Exactly. So a couple of things I want to share about Jamie so you see the perspective of kind of how we've been able to build these businesses. Not only is he a brilliant individual, he's got that British accent now, although I guess he's officially American because he was born in the US. He spent a lot of time in the UK, which probably stopped him from getting that NFL contract.It was a little harder to pull off an NFL contract when you're in the UK for most of your life, but he's played American football. He's really, really good at it. I don't know if you could see it all. ⁓ Well, better than me. So we talk about how he tried and failed at a couple of the opportunities to go in and get in front of NFL teams. And the beauty is he's tried and failed.I've failed and failed because I've never been in front of an NFL team, although I did play a little college ball. So I share that because, but it comes down to, you know, a lot of us really good sales leaders, recruiting company leaders like you are. We leverage our athletic perspective and idea as well into how we build teams and how we build productivity within our teams.Let's jump into an example and maybe you can give us an example of when you've had the right technical hire that you help bring, it helped get into an organization and it immediately enabled the sales team to close bigger deals or accelerate their sales cycle as a whole. Talk about the revenue multiplier effect and how important that is. And the last thing I'll say on this before I hand it over to you, Jamie, is the fact that when it comes down to it,this happens in the services companies we work with over the years. Certainly it happens in the SAS market, the general technology sales side. But man, it's happening in manufacturing companies and med device companies like that technical side of the equation, no matter what your industry and almost all companies other than commoditized organizations. And that's what I really feel like you have.Such a perspective on that that most of us have never really been able to think about and pull together. So share an example or two there.Jamie (10:15)Sure, I'm actually going to share an analogy from football. By the way, I was never good enough to play. I just tried and failed. So thank you. Definitely. I was nowhere near where I needed to be, but it was fun. But a football analogy, when you think about technology and you think about business and how you can utilize that technology for the best for the business to increase revenues and culture capability output.It's no dissimilar to a football head coach with a playbook. So if you think the playbook is the technology and the people are the players, the playbook only works if the players are correct. And if the playbook is fantastic and the players are terrible, they're still going to be terrible. And if they don't understand the playbook, the plays aren't going to work.So that's my first analogy. You know, love an analogy. And second of all, the most important thing for me, and I've seen it in multiple businesses, in multiple strains, whether it be a lead generation tool, CRM, a really amazing automation system, they all come back to the same thing in the context that the best products or the best technologyallows you to see your business and what's happening. Whether it be a CRM, Mark, whether it be, the product that we talk about a lot and KK, right? It's about, it's like a greenhouse. The best technology basically just uncovers everything.So from a sales leader perspective, you can see exactly what's happening. You know, what are people doing? What's the forecast? What's working? What's not working? What's good? What's bad? What's indifferent? How can we push further on this? How can we pull back on that? People should be using technology to understand their businesses first and foremost, before they do anything. Because unless you understand what you're dealing with, everything else is irrelevant because it's like boxing in the dark. I mean,You're going to swing punches and you're not going to hit anything. So the first thing I would say about technology is allow yourself to have tech that absolutely strips away any blinds, curtains, nets, any darkness. So you can see everything good, bad, ugly, indifferent is irrelevant. Unless you can see what's in front of you, you cannot enhance it. That's my biggest lever with regards to tech.KK Anderson (12:17)That's really fascinating. You're describing collective iron, aren't you? though. You have the visibility, the transparency to just be able to see. And a of times, it's what people aren't doing. There are so many hanger-ons. I feel terrible saying that, but I see it all the time. Sellers who are in roles, they're not hitting their quota. They haven't been hitting their quota.Jamie (12:25)for sure.KK Anderson (12:37)And what do you know? They're not even in, I actually had a coaching call today and the guy I was coaching was like, this guy's ghosting me. He's not calling me back. I'm like, well, how many times have you called him? Once. it's gotta have been more than once. We go look in the CRM. It's been like twice over a three week span. It's like, you know what I mean? And technology just shows you that kind of thing right away.Jamie (12:58)mean, it's like it's like having an automation system, right? Which is, which is fantastic and allows you to, you know, keep in contact with people and jogging memory or send an email, all this kind of stuff. And I'm not going to go into it too much, but I have an avid hate for people that don't write their own emails. and I quite like grump grammatical errors because it means that it's been written by somebody butI have a huge issue with the context that we're looking for so many answers and how we can push our businesses forward, how we can create more revenue, how we can save on cost, how we can get rid of some human beings and replace them with some kind of AI technology. But we don't even know what's happening. We have no idea. We're pushing people and driving people's KPIs within sales environments.When we don't even know if those KPIs are the important KPIs or the KPIs that are actually going along that journey that result in a sale. We don't know. ⁓ we need to do more of this. Do we? Do you really know that? Have you actually had some kind of transparent view of specifically that KPI? No, you just think you just guess, which, you know, kind of takes me back to the point that I made earlier. How many people are guessing?Is this a guessing game? Or is this a game where we actually want to know what we're doing? With some kind of outcome. It's crazy. And it'sMark Petruzzi (14:12)and then we start guessing with AI and guessing with data as well in some cases.Jamie (14:18)look, we look for answers inside of tech, but we don't even know what tech we need. given us this great cell, right? We're on shark tank or whatever it's called. And we're getting blasted with this incredible tool, which could be incredible.Mark Petruzzi (14:23)Yeah.Jamie (14:32)but we don't even know what's going on inside our business. So why are we going to buy this all? That's weird. That's like, that's like taking your car into a garage and it doesn't work. And somebody comes out with this incredible ratchet set and you go, okay, I'll buy it. But you have no idea what's wrong with your car. It be, it might be the tires. Nuts.Mark Petruzzi (14:47)That's incredible. You know what's cool about this and your role, Jamie, as the CEO of Smart for Cloud, as someone who's been and runs some very fast-growing recruiting firms throughout your career, that's where the mindset of what you bring to your clients really adds so much value. You bring that...technical side of this rather than just sales, you know, the technical component in the evolution and the integration of all that, you bring that those perspectives about technology. And I know you do this for your clients all the time. And we need more of that. We need more individuals who are bringing a function like you are recruiting, but everything else with it.the strategy, the ideas, the thoughts, you know, and that stuff all comes for free. That's kind of your added value, and I know you built the team that can do that as well. So before we jump to topic two, I just, if there's anything you want to comment on that, ifJamie (15:48)I just,all I'd say to the public is invest in your people. Your people are going to make your business amazing, not some piece of tech or kit that you have no idea what it is. Allow yourself to develop something where you're infusing a great team and a great business with great technology because not one of them is correct. Both of them are.but you've got to marry them. Otherwise it's going to be a divorce real quick. And you're to be like Henry the eighth with several wives and a lot of deaths. So don't do it.Mark Petruzzi (16:14)Yeah, incredible. Allright. So topic two, sales leadership architecture, world-class revenue organizations. KK, do want to kick off a question or two on that?KK Anderson (16:26)Sure.So let's shift to leadership, sales leadership itself, right? And you work with companies every day and you help them hire everything from account executives to chief revenue officers. What is fundamentally different about building sales organizations for a fast moving...tech, AI company versus like a traditional SaaS or like a legacy model? Is there a differentiator that you're noticing in today's market?Jamie (16:55)Wow, that's a great question. Quite honestly, there shouldn't be. There probably is. But the reality of it is that best sales leaders can sell some spangly new piece of AI technology, or they can sell a shoe at Macy's. It doesn't really matter. The reality of it is that...Sales for me is about presentation. It's the, best set. I've always said this, Mark has heard me say this before. The best sales people don't sell. They present. So they understand the issue that you have through understanding what your business is actually doing, because you understand what your business is doing. And then they will give you the product that you need in order to push your revenue and push your business forward. The best sales teams and the best sales leaders will always do one thing first. And that's create a culture.because everything else pales into insignificance. People work for businesses because of culture. People work for leaders because of culture. People get up in the morning with a smile on their face because of culture. People go home at night and don't mind thinking about having to work the next day because of culture. Create a business around culture, not around anything else. It's irrelevant. anything in the history of the world that's been successful, Richard Branson,KK Anderson (17:51)what you're selling. I love that answer. That was the right answer, Jamie.Jamie (17:58)I know you're going to ask me a question in a bit and I'm sorry to stick this in there, but it's really important. Richard Branson, only a number of years ago, sat inside a board meeting and looked at his CFO and said, what's the difference between turnover and GP? That my friends is the answer. He...is a multi-billionaire made more money than anything because of the culture that he created with Virgin still to this day and he didn't even know the difference between turnover and GP what a legendMark Petruzzi (18:25)Well, the beauty,Jamie, he takes that culture and he's just put it into different industries, into into record production, like one to the next.Jamie (18:30)everything.radio, TV,But he built every single business on two things, on culture and hearts and minds leadership. That was his, yeah, that was his thing.Mark Petruzzi (18:44)Well, it's very similar to how you run your Yeah, the profits aren't as high, but it There you go. Okay, next question here. So when revenue leaders are from 10 million to 100 million ARR, or with a lot of the service companies that you work with,they're not managing around ARR. They're driving their bookings, their delivery. ⁓ But it's all coming together, right? A lot of the GSIs that you work with now is spending a lot of their time trying to create and build products and bring them to market as well. So ⁓ what's your framework on like helping your clients determine the right leadership structure? And how do youhelp them to avoid the pitfalls of over hiring or under investing in their leadership side of the equation?Jamie (19:38)good question, I think there's a couple of things. think first of all, you need to understand where they want, what the destination is, So the destination from an immediacy.six months, 12 months, two years, five years, but where are we trying to get to? And what do we need in order to get there? But I think it's always easier, easier as a leader. And in fact, it's easier as just as a salesperson, right? Start at the end. Don't start at the beginning, but go over here. Cause it's way easier to go backwards than it is forwards. Because if you understand the destination, then you can then work out the periodic steps that are required in order to get there, right?If I'm speaking to a business, it's always a case of okay, right? This is what you're doing You know, there was a particular GSI worked with for a number of years Fantastic people an incredible leader and it was always about okay. This is the number What's the end result how do we how do we need to look here what do we need to look like here?What do we need to do in order to get here? Whether it be candidate experience, whether it be, you know, putting together some software with regards to, you know, giving that to the candidates prior to them going on the journey with the client. was a numerous things, but unless you understand what it is you're trying to achieve, then it's really difficult to sit there and go, okay, I was reading something the other day about somebody saying thatThey wanted to create an environment that was basically within recruitment, within talent solutions, where they wanted to have a business that was producing more revenue than any other business per person or per head.I mean, you might as well go and make your tea in a chocolate teapot because how on earth are you going to... unless you have some sort of software that I have no idea about where you can look at every business on earth, which is impossible. When you look at things like that, I mean, that's just words. That's just smoke, right? It doesn't mean anything.They need to understand what they need, what they want to achieve personally. It's irrelevant what everyone else is doing. It doesn't matter. It's about what they want to achieve. We want to get to X. Okay, cool. What do you need in order to do that? Do you need to get a new CRM? Do you need to bring in, you know, more AI specific technology? Whatever it might be, right? Do you need to spend more money on marketing, the website, whatever it might be, but you need to understand specifically what the goal is.Not, I'd like us to be successful and I want us to be the best and I want us to be the greatest. it's all that stuff. honestly, it's just words. And I think that the more ingrained people can get in their core mission and the end destination and what that end destination is with facts.with numbers, locations, people, whatever, right? Whatever your business is, you have to understand the destination. If you don't know the destination, go and think about it and work out where that destination is. And it doesn't mean that the destination can't change because it can. And it often does when we hit with things like COVID or, you know, political kind of scenarios that were affecting certain economies or certain sectors.Things change, but you have to have something. Have your destination. Understand what that destination is. Otherwise, don't get started.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Stephen Messer, co-founder of Collective[i] and LinkShare, shares a bold and timely vision for the future of sales—one that trades CRM inefficiencies, seller churn, and impersonal cadences for AI-powered intelligence, real buyer relationships, and a return to value-based growth.Stephen unpacks how Collective[i] is building the world’s first economic foundation model for B2B sales—a neural network that learns from billions in live market signals and transforms the way companies forecast, prioritize, and engage. If you’re leading a revenue team, this episode will challenge how you think about data, your CRM, and the very structure of your go-to-market engine.What You’ll Learn:The Real Cost of Today’s Sales Stack: Why CRM-driven workflows have created inefficiency, seller burnout, and buyer distrust.How Collective[i] Works: The power of neural networks that learn from shared, anonymized go-to-market activity—while keeping client data private and secure.Cruelty in Sales (and How to Fix It): A raw and honest take on how modern sales workflows punish reps and buyers—and how AI can fix it.The End of Data Entry: How Collective[i] automates pipeline visibility and eliminates the need for reps to “feed the system.”The Rise of Relationship-Centric Growth: Why trust, storytelling, and insight—not spam—will win in the next generation of GTM.Key Topics:What’s wrong with current sales tech (and why it’s unsustainable)How Collective[i] trains its neural net to understand real buying behaviorThe shift from CRM-driven sales to AI-first revenue intelligence“Lifeguards” and the shadow sellers that make or break dealsWhy buyer relationships have eroded—and how to rebuild themThe moral case for better GTM designReal examples of AI uncovering hidden pipeline riskWhy average sellers will become exceptional (or obsolete) with AIGuest Spotlight: Stephen MesserStephen is the Co-Founder of Collective[i], a next-gen AI platform reinventing how companies forecast, collaborate, and close. He’s also known for co-founding LinkShare, the affiliate marketing pioneer acquired by Rakuten for $425M. A seasoned entrepreneur and thought leader, Stephen now leads Collective[i] in building the world’s first neural network for B2B sales.Resources & Mentions:Collective[i] – WebsiteCI Forecast: Collective[i]’s weekly go-to-market leadership eventBook mentioned: Predictable Revenue (and its long-term impact on sales culture)Topics discussed: AI-powered forecasting, seller efficiency, CRM alternatives, cadence fatigue, relationship rebuilding, data trust modelsListen now and follow Selling the Cloud for more unfiltered GTM insights from the leaders shaping the future of sales.Mark Petruzzi (00:00)Welcome everyone to Selling the Cloud, the podcast where we decode the art and science of B2B selling in the ever-bombing world of SaaS. I'm your co-host, Mark Petruzzi. And I'm KK Anderson, excited to join you on this journey where each week we explore the strategies, insights, and experiences of some of the most innovative thought leaders in the world of sales today.Welcome to today's episode of Selling the Cloud podcast. We are beyond excited to have Stephen Messer, co-founder of Collective Eye with us today. For those unfamiliar with Stephen, he co-founded LinkShare, which revolutionized affiliate marketing and 10 years ago, co-founded Collective Eye with his amazing sister, Heidi Messer and brother-in-law, Tad Martin.Together they've created the world's first economic foundation model that studies how the world buys and sells. It's a groundbreaking development that is completely disrupting the sales landscape. Their neural network has roughly 5 % of the world's GDP under advisement today and growing rapidly. So what makes Collectivize so revolutionary? It is its deep learning and natural language processingthat allows predictive insights to come forward to sales teams with amazing precision. It boosts productivity and it delivers clean, powerful data back into CRM systems. This is a true game changer for sales organizations. It enables teams to make smarter data-driven decisions and scale effectively. This episode is packed with valuable insights for sales leaders, so be sure to grab a pen and take notes.You'll probably want to listen more than once as well. Here are three objectives for today's episode. Steven, to learn how you and your amazing team has built the most powerful neural network in sales tech, creating competitive advantages for your clients, what it means to become an AI-charged selling organization, and why that's crucial for sales teams today, and why traditional CRM datais often inaccurate and how it impacts sales effectiveness and how CollectiVie is cleaning up CRM data across your client base. Steven, let's dive in. You've had an incredible career from founding Lynx Air to now leading the charge at CollectiVie. Can you walk us through how you got to where you are today and what has led you up to being a guest here on Selling in the Cloud?Well, thank you for first of all, thanks for having me here and thank you for letting me reach your audience. I know how important your audience is and I'm excited to have the opportunity to talk with them. So going back in time, you know, I've been fortunate enough to work with my sister and now my brother-in-law. I think all of us have one thing in common, which is we grew up in a world where revenue is really important. My father passed away when I was very young. My mother took over the family business.that they had created together, which was a corporate maintenance business. We literally cleaned offices and from a very young age, we would sit around the table talking about what it takes to make sure that we could make it through another week. And for anyone here who's listening, almost all people I know who are involved in sales found their way there in some way, or form, because they were willing to take the risk to grow something and make something more meaningful for their family. So.Whether it LinkShare, which is really just a commission-based selling on the web, which we started in 1996 and sold to Rockington in 2006, or Collective Eye today, which is really to support for collective intelligence to help sales professionals and revenue organizations really upgrade. I think the one commonality was freeing up people from the fear of what it takes to make the number that they need to, to support their family.and also providing a better service for their customers, which all entrepreneurs think about endlessly. Wow. Stephen, can you walk us through, you know, what were some of the, what did it take and what were some of the challenges of building this incredible neural net that you've built here at CollectorEye? You know, it always seems obvious after 10 years of struggle. I think when we started the business 10 years ago, we beganon this concept of first principles, which is, okay, you have a new technology neural nets. Now this is before chat, GBT became popular. ⁓ but we, we would look back and said, okay, this is a powerful technology. It's going to change the landscape, but it operates a lot differently. One of the things that needs the massive data set to learn. And for those who don't know, chat, GBT is great. Anthropics great, but they're for the most part studying language.So they're really good mimics of how the world operates. It's auto fill to the max. Let's put it that way. But they're not able to learn everything. And in many ways, it's a general type of, ⁓ or a very narrow type of intelligence as opposed to general intelligence that humanity has. So we look back and said, okay, could you apply this to Adam Smith's problem of the invisible hand, which is the economy operates in a way that you can't... ⁓follow. But if you could follow, you could optimize it. And we had some early examples. ⁓ If you go back 10 years and you look at Uber, you might have said, okay, let's get this straight. You've got a web app that's going to connect supply and demand around livery, car service. ⁓ How are they going to be able to maximize and operate the entire world of taxis, ⁓ rental cars, ⁓ you name it. ⁓ And here we are 10 years later andNot only have they done that, but they've optimized to make sure cars are in the right place, that they're getting the right fee, that the good drivers are getting the best passengers. They have done this very quickly and they really leverage a lot of neural nets to help figure out everything from pricing to matching. And we looked and said, okay, early on, this is a proof point that if you can aggregate enough of a particular economy in one place, you could really optimize it. Now everyone said, no one's going to share data. Nobody would do that. In fact, II would bet there are people on this call who are watching this video who are saying, yeah, my company would never do that. But we look back at first principles said, do people do this already? And sure enough, if you look at almost every company today, not only do they do it, but they do it in the majority of the way they operate their business. I'll give an example. Would you ever lend or extend credit to a customer based on their payment history to you alone?I mean, if you want to get fired, you would, but almost always you go to a credit bureau. And what do you do a credit bureau? You give this neutral third party a history of how everyone's paid you. They combine it with all their customers and they give you back a credit score back. Now it doesn't give anyone's history away. It keeps everything confidential. Yeah, that works. We do it in Google every day. You do a Google search. Trust me. They see all of your competitors searches, the companies they're looking for, the people they're trying to find. Same thing with LinkedIn.That happens. You do that with advertising. Your advertiser on one hand is being bought through Google and trying to leverage their network to find the right buyers and other places like that. And we do that happily with lead gen. We do that happily in all the places we are at. But then it comes into our company and we say, no, we can't do that. The only revenue groups have done that. And in exchange, they end up being the most expensive portion of the business with the least results.And so we said, that's got to change. And so for 10 years we've gone out and we now work with some of largest companies in the world, regulated around the world. ⁓ And sure enough, when they do their details, they realize not only is this more secure, not only is this better, but it enables us to have better returns. And that's sort of the flywheel effect that has made our business grow so quickly. Yeah. You know what? It's, it's been amazing to, to watch you build this over the years and to see how these large companieswith all their attorneys and everything else have dove in. And it all comes down to the way you keep all this data blinded and private. But what it brings is this amazing data when you can put it together in this kind of way is so much better than just one company's data. And it's also so much more impactful.because as you build this into this amazing neural network, it's really, I guess it's all about the data and not about the data all wrapped up into one. Meaning it's about what this data together in this combined collective way can help you do for your clients and help you really predict what's going to happen next with your clients. So can we go little deeper into that and how does it reallyto give a competitive advantage when you have this kind of data and you have this type of intelligence behind you, AI intelligence behind your go-to-market, what does that do and how do you create these sustainable competitive advantages that you're helping your clients drive every day?Well, let's start with something that I think is important. There's a lot of leaders. You reach probably the best leaders of almost any group of I've ever come encountered. And what I think is hard for them to fathom in this change is the recognition of the amount of cruelty that the current model pushes on employees and customers. Let's cover that. And then I'm going to talk about what it does to change things.Because I would argue there's a lot of your leaders that are listening to this thinking, what do you mean? I'm not cruel at all. You know, this is just how it's done. But there is a huge amount of cruelty. Let's start with the sellers and the revenue organization. Think about the cruelty of asking somebody to go in, log everything they do every day, non-revenue producing their commission based sellers, go in there, log what they do, find the people that they're supposed to talk to, try to hope to turn leads into something meaningful.and basically prospect all day long when we know for a fact that 85 % of revenue comes from references and referrals.Think about the cruelty of asking them to learn how each different group buys as if they're Columbus or Magellan. Now we know about Columbus and Magellan because they survived the risky journey. But there are a lot of explorers that did not, and we do not know their names. And if you think about sales today, the average churn rate in a sales organization is 35%. There is a cruelty to everybody involved.in setting people up for that kind of failure rate. If you think about your customer, it's even worse. And you know this, we have bombarded them. We have machine gunned them to death with communications. To try to get to the 15 % of prospects we don't know, we are willing to destroy our brands and our reputations by bombarding them with these cadence tools and bombardment tools to the point where they now hide from us.And I will tell you, we call it cadence when we send it, but it's spam when we receive it.And you cannot change those terms. Why do I say that's cruel? Think about a customer today. Well, let's go back 20 years when sales was a relationship driven event. I promise you for every leader that's listening to this call today, they remember a time when, when there were events, they were invited by their customers to join dinners. Frankly, in revenue, we were the most fun people. We had connections to everyone.We knew about every job opening and we knew everything that was going on in the companies. And like McKinsey or BCG consultants, we knew what was being successful and our customers appreciated our ability to share insights that we had gleaned from an overall market. They valued the time we spent with them. We built relationships. We took them with us over time. We kept them honored. It was our job to make sure that the rest of the company delivered the results and those buyersWe it because we helped them become more successful and grow their careers. And the more we helped them, the more they helped us back. Here we are today. They hide from us on Slack. They hide from us on groups. They have groups together where they tell us we're not allowed to join. When there are events, they try to hide from us in every way possible. We are no longer invited to them. When we try to invite them to speak, they don't want to speak to us. When we give them advice, they think it's biased.They do not see us as the partner they used to see us as. If that is not cruelty to everybody involved, I do not know how to help you. So AI offers us a chance to change all of this. And I think when we think about the network that Collective Eye has built and the community that we are building, it is to look and say it is our job not to go to the lowest value.And in fact, I think all these cadence tools have driven us to how do we get cheaper? I see the newest thing is AI SDRs. And don't get me wrong, I'm in AI, but trying to drive down the price to bombard people means our results are so bad that the only way to keep that up is bombard in even more ways than possible. And if we haven't driven our customers into hiding, I don't know what else we can do to do it. Rather than go low value.We must embrace providing higher value to our partners. And that's really what AI is all about. And can I give one last example? I going too long? We need for you. No, please do. Keep going. I think the current sales stack of all these technologies are the way we tried to mass produce, you know, a revenue funnel in the last 15, 20 years. I think what that has done.is move us into this role of how many activities can we do? How cheaply to get whatever conversion rate we'll take. And I can tell you coming from e-commerce that never worked there. In fact, it's gone the exact opposite. Whether you look at influencer marketing, et cetera, it is really about how to connect to our customers and offer value. So we think we're about to go through a massive switch with AI where instead of trying to get the mediocre to be average, which is the old sales staff.How do I use MedPic or medic or whatever, all these things to try to force everyone to be exactly the same. I think we're going to go and start moving because AI takes average people and makes them exceptional. And that's the mission we're on. If we fail, mark my words in 10 years, sales will no longer exist. People will do product led growth because if customers don't want to talk to people anymore, that's the only option they have left.And I think that'd a shame. Wow. You know, I think of AI as personally, you know, as someone who's been in this landscape for 20 years, as the great equalizer. Right. It takes some of the mundane processes of doing sales every day and just does it for you. Right. And it's incredible. It's almost like having like alittle Jarvis on your shoulder, right? Like Tony Stark, know he's, you know, we talked about him yesterday on your Collective Eye forecast, but it's just incredible that you're right. takes a good salesperson and makes him extraordinary. Right? Well, think about yourself. Like you guys were early adopters of this. So you may realize something that your market may not, which is today,Part of the reason why the skills of the current group of sellers over the last 15 years has really destroyed relationship building. It's destroyed the ability to actually understand a customer's needs. Like we talk about all these things we use to work hard to train people, but you know, there's a funny thing when, when they did studies this year to look at the, do what they call functional MRIs of the brain, what they realized was our spatial skills shrink. So now we have this GPS.that tells us where we go, all that skill sets disappearing in our brains. We used to need it, right? If you were going from the East to the West on a horseback, you kind of needed to know you were going West, or if you ended up North, it would get cold fast, right? So we had these skills that all humans had, but it was lost. And what it shows you is when you don't use these skills, it goes away. A lot of the sales stack in the way over 15 years, and I frankly blame this book called ⁓ Repetitive Revenue or Predictable Revenue.I forget the name of the book. I read it years ago that everyone got all hooked on, which is like, we're going to mass manufacturing sales. And what it did was it sort of said, just do these things. And if you do these things, you'll win. And all these things work when you're the first one doing them until everybody does the same thing and they all have low value. Then it goes to zero. And that's sort of what's happening. And if you look at your STRs, if you look at your newer sellers, when you say build a relationship with them, they look at you and say, does that mean like click on LinkedIn?No, it does not. For anyone who's been around a long time, you know, relationship building is about trust. How do you add value? And KK, you said it yourself. We do an event at Collective Eye for our community called CI Forecast. You can go to ciforecast.com and see it. And every single week we bring the world's greatest leaders. Yesterday, you came to Michael Useland, the guy who brought us Batman in the movie theaters. Well, all right. He talked about storytelling, a skill that sales professionals have had for years.Now we give them scripts to read. It's a big different from being a storyteller to an actor. And for anyone on the other side, it's easy to spot the difference between someone who can make a complex story simple and someone who's reading a script, but doesn't understand what they're saying. This is an example of some of that skills that I think we've lost that we have to regain because customers want to reach out to people that add value that can make a complex story simple.They definitely don't want to talk to someone who's reading a script anymore.Well, I'm going to go and I'm going to use this time now to lodge a complaint against Steven you and collective I. My complaint is, you know, having, as you mentioned, being become an early adopter and a huge fan of everything you do at Collective I, I have kind of ⁓ I've lost in some ways my ability to speak.with my prospects, not my clients because they're there with me, but new prospects. And here's a little bit of a backdrop on it. Early in my life, I actually was able to take some great courses in college, high school, in Spanish, and then later on Italian as well. And I was looking to learn both the languages for different reasons, travel I wanted to do in the future.And what I learned, traveling to Italy and Spain and other parts of the world that speak those languages, that I no longer spoke Spanish or Italian. I spoke this version of Spatialian, would be the best way I could describe it. Which what it would do, it would allow me to communicate in these countries, but for the most part, there would be individuals, especially if it was like a teenager hearing me, that would giggle.when I would say that, you know, I would say my sentence, which would be this version. So my point back to collective I is I feel like I'm speaking Spatialian a little bit in that I have learned now through you and your team and the great work we've done with our clients together that there's a new way to think about sales. And it's not about the old CRM way. It's about thinking about the future and it's about thinking ofeven data, data that you're gonna be generating today and tomorrow, not data you generated three years ago. And I find myself, like I said, sometimes I move too quickly with my prospects and they're not there yet. So over time, I've learned how to do this. I've learned to communicate a little better along the way.But I've got to blame that all on you because I see the world from a selling perspective very differently than I did two or three years ago. So I guess maybe we can, you know, flush that out a little bit more. Tell us more of your points of view on that. And then you could probably even describe this better than I do. How do you use the new capabilities and products like Collective Eye to really build more effective selling organizations?Look mark, you're 100 % right. There is a CRM paradigm mentality which thinks about things as failstacks And so the first part of this this blog this podcast was really about what's changed Let's get into the details here of the meat of what's going on for the second half of the podcast Which is really the value which is okay What has changed or you it's easy to say there's a CRM paradigm and then there's an AI paradigm And sometimes that sounds like marketing speak. Let's get right into it, right?In the CRM paradigm, what you're doing is you're typically trying to compartmentalize what people are doing into one tool, training them on that tool and having that tool do what it's doing. What that in theory means from a data perspective is you have silos of data where you have partial information. AI's changed that whole paradigm. says the whole stack goes away. What we're looking for is every interaction of everybody who's involved in this revenue endeavor.Whether that be new business, whether it be a renewal business, whether that be upsell or cross sell, or generally relationships across a large organization in different regions. There is a relationship that you and your organization have with the customer. It says to you, how do I figure out what's going on? Well, the first thing is it watches and helps by observing what's going on. You hit the nail on the head. This concept of entering data by people with paid.licenses and I only bring up the paid licenses because it means there's a whole bunch of shadow people that you didn't buy licenses for that you're just not capturing data on and saying, it's okay. That goes away in AI. And in fact, just so your users know, because our, even our revenue model will seem weird to them. There are no paid licenses for individual users. It is completely complimentary. If you come from the SaaS world, you've got to think I've lost my mind.But if you come from the AI world, you don't want to lower the data quality by creating economic incentives to stop good data. So can I give an example? We call the group of sellers that never get to be seen, the shadow group, we call them lifeguards. Now you might ask, what do I mean by lifeguard? Well, I look and say, here's the deal.If all you do is study the most active people in the pool, you get a picture of the pool that is fine, right? Those are in your world, the sellers, but there are a few people that don't get in the pool often, but when they do, they really matter. That's the lifeguard, right? When the lifeguard jumps in the pool, it paints a very different picture of what's happening in that pool than you would have thought before. But if you're not tracking them because you say, ⁓ they're not in the pool often. Why should I buy license that mattered? Well, then I don't really care.But you get a different view of the world in our world, lawyers, finance people, sometimes client success people, sometimes ⁓ a friend who knows this buyer or a board member. These are people that aren't in the pool often, but when they are, ⁓ boy, it matters. And you want to know what's going on and it can change the outcome today. People essentially try to cost manage those licenses down.And so they don't get access to that. In particular, one group that you know well matters. You do deal with a partner. Each one's got their own CRM. No one knows what's going on in the other guy. But what if I can just invite my partner in at no cost and they can join even one opportunity at no cost where the AI then observes their activities and captures it for you to work together on. This kind of way of thinking not onlyimproves data quality, but it also provides a better view into how everybody's working together, where the risks are, how you can work together and help each other out in a way that's never been done before. That's an example very simply of this AI mindset shift. Yeah, I love it. I know you can. let me I guess let's let me just unleash a little more here there from the standpoint of you.you know, our audience knows that we work really hard to not just talk about products or companies that we're presently working at. And I know you always, you bring so much more general information to the podcast that you go on because you are such a forward thinker in all this. But I'm gonna...just take us a little deeper into CollectivEye because I just feel it's so relevant and this is something I would feel remiss if I didn't do. So when you look at what can be done now with a product like ⁓ CollectivEye, there is all of that stuff that you described that sales reps dread doing, that information that they would put into a CRM andthe time that they spend, you all these latest two research studies that I've seen, and both of these have happened in the last 12 to 18 months, both Gardner and also Salesforce did amazing studies where they tried to just document where sales reps were spending their time. And they found, and they both came up with a very similar number, somewhere around 30 %...was all they were selling in any given week or given month. And the rest of the time was inputting data and giving updates to sales leaders and different, you know, five different levels of an organization if they're in a big enough company. So take us a little deeper into, you know, how easy that is to take that and turn that equation around with leveraging a product like Collective Eye.And how excited do these sales reps get when all of this information is done in an automated fashion for them and they then get to jump onto a system like Electabye and use that in a strategic way and forget about what the sales managers and CRO gets to do at their levels. So take us a little deeper. want to kind of take a little bit of our hand cuts off here.So let's go back to that cruelty. mean, the good thing about cruelty is when you remove it, changes the, the, the way you think about the problem. So, so there are two pieces. So for any of the leaders who are listening to this call today, they're going to think, okay, how big of a deal is it? Half my sales team doesn't do it. I we even called it rigor. Like we had terms for these things, but the nice thing about part about AI is that we are able to, remove that work. Instantaneously without retraining a sales team.We do this by connecting to the APIs of all the digital technologies they use today, but we can do it behind the scenes. We can do it in a GDPR compliant way. We can do with high security and what we can do it in a way where it changes the nature of the paradigm. There's two challenges you need to overcome to solve your data quality issues. The first is you need a powerful neural net to understand how to follow the rules around the world of privacy correctly.That's the first one. And you have to find a way where you don't need to train sellers to do things. The second thing is you've got to reward people who use the application to make sure that they're not hiding information deals that they don't want listed out there. So we solve that by making sure that one, the work is done automatically behind the scenes. It's quick. It's easy. It's reliable. It's safe.The second thing is every time a seller opens an opportunity, they immediately get unique insights that we have learned from our network that they can apply to winning a new deal. There's got to be a reward for sharing information for the seller. And that it's not simply about getting data automated. There has to be a reward. I always talk about all to all these privacy people out there who always worried about data.my God, we have to make sure that people don't use cookies. And if you spent time in Europe, you know, if you try to go on a website, you have to go through 16 clicks just to get past the cookie approval. I don't think it's about lack of knowledge. I think it's a lack of value. In America, we will give all of our information to our supermarket in exchange for coupons. We have no problem because we're getting a value in exchange for giving up data for sellers. It's the same thing. We've got to provide value to those sellers.so that when they will have information, they want to update you sooner about it, as opposed to punishing sellers by trying to do things that hurt them. And Collectivy does that by immediately giving insights that they can leverage, that they want to get earlier to win more business.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In Part 2 of this Selling the Cloud conversation, Josh Payne dives deeper into the future of AI-first growth teams, and how CoFrame is helping B2B orgs replace legacy handoffs and static workflows with continuously learning, automated systems.Josh shares how teams are deploying AI to automate experimentation, generate code, and even shape strategy in real time. He outlines what it takes to build with AI in production (not just in prompts), how roles like “growth engineer” are evolving, and why building competitive advantage in 2025 means more than just adding ChatGPT to your stack.What You’ll Learn:How AI Is Reshaping Growth Roles: Why marketers are evolving into orchestrators, engineers, and agents of optimization.Beyond Prompting—Toward Infrastructure: How CoFrame builds stable, repeatable workflows with AI that can learn, adapt, and improve continuously.Real-World Agent Use Cases: From UI code generation to multivariate testing and funnel orchestration, Josh shares how real AI agents are driving results.Why Speed > Strategy (Sometimes): Why fast learning cycles and live tests can outperform static GTM plans.How to Start Now: Advice for teams getting started with AI-based systems—without needing a research lab.Key Topics:AI in modern GTM orgsCode agents vs. code generationAutomating testing, design, and targetingThe rise of “quant growth” as a functionBreaking down silos with intelligent workflowsWhen to trust AI—and when not toCoFrame’s real-world implementation storiesGTM roles of the future: orchestrators vs. operatorsGuest Spotlight: Josh PayneJosh Payne is CEO of CoFrame and a leading voice at the intersection of AI, UX, and growth strategy. A repeat founder and AI researcher, he previously created GPT-Migrate and led growth products at top SaaS and fintech companies. His mission: make the web feel intelligent again.Resources & Mentions:Website: CoFrameConcepts: AI agents, orchestration layers, living interfaces, growth stacksTech Stack Mentions: GPT-4, Claude, OpenAI fine-tuning, VWO, Retool🎧 Listen now and follow Selling the Cloud for more GTM conversations on scaling with AI, orchestrating growth, and building what’s next.Mark Petruzzi (00:02)Welcome to today's episode of Selling the Cloud podcast. We are excited to welcome Josh Payne, founder and CEO of CoFrame. Josh is a serial entrepreneur and AI pioneer who has co-founded multiple successful companies, including Autograph, a 2 billion plus unicorn backed by A16Z and Access Bell, which has been acquired by Tata.He's also the creator of GPT Migrate, one of the first popular coding agents and has authored over 20 papers and patents in AI. At CoFrame, Josh is building the future of digital interfaces, websites and apps that continuously optimize themselves using AI. The company recently raised 9.3 million from Coastal Ventures.and partnered with OpenAI to develop breakthrough UI code generation technology that's driving a 30 % plus improvement in conversion rates for mid-market and enterprise clients alike. Today, Josh will share how AI agents are revolutionizing growth marketing and website optimization, what it means to build living interfaces, and how go-to-market teams should prepare for the autonomousoptimization era that we are in today. So welcome, Josh, welcome.Josh (01:31)Thanks so much for having me, Mark. Good to see you.Mark Petruzzi (01:33)Excellent. Thank you. Okay, four themes we'll focus on today. From static to living, the AI powered interface revolution, the OpenAI partnership building visually grounded AI at scale, autonomous growth, how AI agents are replacing manual optimization, and the future of marketing technology and growth engineering. So first area here, Josh, for us to jump into.You describe CoFrame as creating living interfaces rather than static websites. What's fundamentally broken about how we think about digital experiences today?Josh (02:15)Yeah, so the problem with digital experiences as we know them, it comes on both sides. There's the problem from the business side, which is that it takes a lot of effort to make these digital experiences like websites or apps better for our customers. And people tend to spend a lot of money and time doing so. On the customer side, it's also an issue because you have these experiences that are one size fits all. They're not adaptive. They're not personal, you know?They lack the context of you as a person. And the way that we're approaching this is the problem is, let's think about this from the ground up. If you could redesign the concept of digital interfaces today in a world where AI is possible and as powerful as it is, you know, look at the trend of where things are going in terms of the capabilities that it has. How would you design these customer experiences?And that was really our impetus, which was, let's think about a world in which these digital interfaces were living in a sense, they could be adaptive and personal from the ground up. And so what we're doing essentially is, is enabling that capability for the businesses that we work with and their customer experiences, allowing their, their teams to not have to do all that grunt work and trying to continuously stay on top of.⁓ of making those customer experiences better at great cost and ⁓ great time.KK Anderson (03:51)Like, what would a use case be or an example, just to go a little deeper into living interfaces? I think it sounds amazing.Josh (03:59)Absolutely. The biggest one that we focus on at the moment is website optimization. So you're probably very familiar with the idea of websites being a conduit for which consumers can interact and transact. And the problem with websites today is that, like I was mentioning, it takes a lot of effort to improve the conversion rate ⁓ of these sites. 95 % ofplus of traffic on the internet doesn't convert, right? It's people who go to a website and they check it out and they decided that maybe it's not a fit for them or they don't get the punchline, they don't get the idea. And this is truer in other industries than it is, know, for instance, in e-commerce, this is a huge, huge problem because the website is everything, right? And, you know, consumer finance tends to be a big one as well. And so,What you end up seeing is ⁓ these teams spending a lot of time running experiments on these websites. You'll have a product manager or a marketer come up with a concept or an idea of what to test. They'll pass that on to a designer. They'll come up with designs and concepts. They'll then go and pass that on to an engineering team, which will go and implement the idea to be tested in the website. And that handoff process, that whole process takes weeks, sometimes months.to do. And just an insane amount of time, when you look at the dollar value of time, an insane amount of cost and headcount. ⁓ And so it's a very broken process. It's still very beneficial and valuable, because every win that you get, every better version of that experience, tends to give you significantly more revenue, because you're stacking those conversions over time. You start to see the compounding benefits.It's really, really painful. so the use case here that we're very focused on at CoFrame, at least, is bringing this idea of adaptive, personalized websites where different people can have different experiences that are suited to them to really help to increase that end KPI that the business cares about, usually a conversion KPI.Mark Petruzzi (06:20)So Josh, you have built multiple successful companies in different paradigms. What made you pivot from traditional SaaS to this AI-first approach with CoFrame?Josh (06:35)Yeah, I mean, this is a big question a lot of operators are facing right now, which is, how is the role of software going to evolve in this world of AI? I think we're seeing the commoditization of software. starting to see, on the flip side, we're seeing a lot of incredible new capabilities that AI is enabling. I actually think that one of the biggest opportunities right now in the space overall, in the world, istaking processes that are manual and take a lot of work and then applying ⁓ sort of an AI first mindset to that to figure out how can we automate or optimize different parts of that process and then deliver that outcome with way less effort involved. So an example here of what we're doing, know, conversion optimization, like I was saying, that kind of takes, you know, design and engineering and product management and a bunch of different manual functions that are tedious. And soOur approach was, can we break down that whole long process that is delivering the outcome, which is basically experiments for your website and use AI to significantly accelerate and then automate that ⁓ end to end. Now there's still human involvement for sure. And there's, there's like a gradient of, of involvement, right? But on the level of completely manual to completely automated, we're gradually moving toward that automation piece. And I think that that's.really the biggest opportunity currently in the world of AI is looking at what is currently manual and trying to figure out systematically how can we automate that and ⁓ make it not as painful ultimately.KK Anderson (08:17)So really interesting. where in your professional opinion do most companies go wrong when they're trying to optimize their websites and their digital experiences? And I heard what you said earlier. And by the way, once four to eight weeks have passed and the new website is launched, that content is stale. there you are going back at it again.Talk to me about where they go wrong and how you recommend that they shift.Josh (08:53)Yeah, soI mean, a big thing that I see a lot is people are just not testing enough. know, there's that when you look at the math behind conversion optimization and experimentation, it's pretty astounding. you know, if you like, think about ⁓ a series of tests that you run, you find a couple of wins within those tests. It's not like those wins are going to give you, you know, a boost of revenue for that month and then you're done. No, that win stays with you for good, for the most part.And they also compound over time. So if you find a 2 % conversion left here, a very small left here, you know, and then a 5 % over here, and then a 3 % over there, you suddenly have 10 % in aggregate conversion left. That could be 10 % more revenue, you know, over the course of forever. Right. And so that comp, that's why compounding is so powerful here, because you start to be able to see, you know, this like, this, this, this super linear growth.⁓ of your business value.Mark Petruzzi (09:56)Yeah, what I love about that, Josh, is you're kind of taking us to continuous, instead of periodic testing. it's just, and that's the beauty of AI and it's the beauty of the intelligence that it's building in some of these large language models that, like you said, it compounds, they get better, they get smarter, and that's phenomenal. And, you know, I guess we're putting the A-B test out ofJosh (10:05)Yes, exactly.Mark Petruzzi (10:26)at a commission at this point, because unless you want to look at it as A-B testing 24-7. yeah, so ⁓ what's the first thing a growth leader should understand about moving from this periodic optimization to this continuous AI-driven improvement?Josh (10:32)Yeah, A to Z testing.KK Anderson (10:35)Yeah.Josh (10:46)Yeah, so first thing is just like a mindset shift, right? A-B testing is valuable and it has its place. And you can still compound those wins over time with A-B testing. ⁓ We are now living in a world where the cost of creating new experiments is very low. So what I like to usually think through ⁓ when it comes to opportunities in the AI space is we talked a lot about automation, right?like taking something that is manual and autumny. I think that's the biggest opportunity currently. ⁓ Now, there's another piece of this, which I think is also very valuable, we think of that a lot, which is what wasn't possible before that is now possible. So net new superhuman capabilities. So first is taking a human capability and then just performing that. And then the second bucket istaking something that just wasn't possible before or feasible or reasonable to do and doing that. And so continuous optimization actually falls in that second bucket. The first bucket being here's how people are optimizing today with A-B testing. And we're just going to automate that. The second bucket is what new types of tests are now possible with AI. And I'll give you a simple example of this. ⁓KK Anderson (11:54)The superhuman?Josh (12:11)⁓ Let's see, Booking.com is actually probably one of the closest to this. They're a really, really advanced company when it comes to growth and optimization. They're running a thousand plus experiments at any given time. ⁓ But with their level of traffic, they could be running probably tens of thousands of experiments at any given time. ⁓ That's just not feasible to do ⁓ with ⁓ purely with human labor, right? It would just not make sense from an economic standpoint of time spent.KK Anderson (12:34)humans.Josh (12:40)And so yes, you'd have to cut tests off sooner. You'd probably have to use things like multi-armed bandits, advanced techniques to test lots more variants. ⁓ But in doing so, you're squeezing more value out of all that traffic that they have. And so if you can 10x your testing velocity, ⁓ that's A, not very feasible to do without the assistance of a technology like AI. But also B, it's very valuable if you can do it.And so that's where we see this idea of continuous testing coming into play.KK Anderson (13:16)and that compounds over time. Yeah.Josh (13:19)yeah, that's the beautyabout compounding. It's like every win that you get, you know, builds on itself. And so the faster you compound, the more value your business is going to be receiving. And that's why a lot of our customers have been able to see like really big benefits very quickly with us.KK Anderson (13:25)Mm-hmm.Well, and last question before we move on to the OpenAI partnership, which we're excited to learn about. So how hard is it to go from your periodic optimization or shall we say once a year optimization for some companies to this? Is it a big lift to switch? Do you have to change your whole website? What does that even entail?Josh (13:58)Yeah, it depends on how you're doing it. ⁓ I mean, I could speak to the co-frame piece of this, obviously. And for us, we come in and we're operational on day one with the companies that we work with. So it's no lift, basically, except for approving variations. The approval workflow still exists. And you have to make sure every variation and every experiment is given a sign off by the relevant stakeholders. for listeners at home, thinking about their own websites and how we can incorporate continuous optimization.⁓ There ⁓ are tools out there that support this, testing tools. I think about tools like Optimizely or Adobe Target for the enterprise segment or VWO for the mid-market or lower market segments. ⁓ These are tools that we sometimes, at CoFrame, sit on top of ⁓ and we're the ones creating those tests. Really the important thing to keep in mind here is to enable continuous optimization.It's a hungry engine. It's a very powerful engine, but it's very hungry. It requires a lot of shoveling coal in. In this case, the coal are variations. ⁓ So you have to make a lot of variations, and then those have to be based on what you're learning from the tests. And so the way that you can do this at home is by incorporating these models into how you're testing. So you're using Claude or using OpenAI, know, Chachiputti to create the variations, whether they be copy or.or code or even images sometimes and things like that. It's not easy ⁓ to set all this up, but once you do, it's very beneficial.KK Anderson (15:38)Really cool. So let's go into, sorry, Mark, you go ahead. No, no. Okay. Yeah. I'm anxious to get into the OpenAI partnership. Okay. So you recently partnered with OpenAI. Congratulations. That's exciting. And you're developing what you call a first of its kind UI code, code generation. So break that down for us and tell us what this breakthrough actually means for business leaders.Mark Petruzzi (15:39)That sucks.No, no kick us off. Bring us to topic topic two.Josh (15:44)IYeah, let's jump in.Thank you.Right, so one of the big challenges with models today is that they are very good at coding, but they're not as good at kind of like visually grounded coding. What I mean by that is when you look at a user interface, having the eye of a designer to figure out how is this code going to actually look when it's put into a user interface, especially when it comes to a pre-existing brand. So we're all operating in the world ofexisting websites with existing assets and styles, and you have to stay on style and on brand and adhere to those guidelines. And a big shortcoming of today's models has been ⁓ how do we make sure that the code that we're writing when we create these variations from a layout or a user experience perspective are in adherence with these guidelines. So that was the technical challenge. ⁓ The way that we approached solving itwas we created a large data set of a bunch of different websites out there. And we trained a model to be specifically good at creating new sections of websites that were aligned with the existing brand of the existing websites. And so ⁓ our initial approach was to basically remove one of the sections and then create a textprompt that describes what that section was in as much detail as possible, ⁓ and then use a model to create a new section that was based on that prompt. So you're basically masking out one section of the site, saying to a model, hey, look at this existing site with everything except for that section, and then create me that new section that I'm describing verbally to you. And then that's the task, and it actually creates that new section, and it's basically graded.on how well it adheres to what the original section actually looked like. So that's the task that we use to train it. It's very similar to actually how transformers are trained in predicting the next token. But a little bit more of advanced predicting the next section instead of maybe the next token. And so that was the way that we set up the problem.Mark Petruzzi (18:15)Mm.Josh (18:30)And we were able to achieve state-of-the-art results with visually grounded cogeneration with this. And so what that means for businesses is that now, at least ones that work with CoFrame, but others maybe that would use a similar approach to train their own UI cogeneration models, ⁓ now you can have a model that really knows your brand, your visual identity, and can then create new experiences, new sections, new pages entirely, potentially. ⁓based on what it knows about your brand. It's almost like having a designer and a front-end engineer paired up, but they've been on your team for 10 years and they know your brand really, really well.KK Anderson (19:10)That's really cool.Mark Petruzzi (19:12)So that's very cool. Josh, tell us, I guess the biggest thing that's jumping out on me is a little more of the playbook here. How did you convince OpenAI to work with you on the fine tuning of this GPT-4.0 vision? Knowing how fast they're growing, how distracted they are as an organization. So tell us a little bit about how you made that all work.a little bit of the why. Like why are they so excited with your vision of brand consistent UI generation versus other things that may be popping around out there in the marketplace.Josh (19:53)Yeah, I think it comes down to just it being a really interesting problem. So in one that is interesting from a couple of different angles, one is of course the technical challenge. You know, this is a new domain ⁓ relatively, you know, like visual plus code. And so that's a really interesting combination of those two. But then there's also, it's interesting from a business standpoint, right? Like being able to create visually grounded user interfaces. That's like a really great.⁓ thing to do. It's really core piece of this movement now, which we're seeing in like, you know, consumer products and even enterprise products that are creating, you know, code for new experiences. I think companies like Lovable and Replit and Bolt, like the ones that are just taking off right now, then ⁓ Claude and ⁓ Claude code and cursor, and there's a bunch of others too. And soI think that that's why they were all so interested in this is because it's kind of a key piece of that equation, the front end or the user experience piece of this. How we ended up working with them is another story. had actually, I've been friends with several folks at OpenAI for a long time. ⁓ to school with a bunch of them who had joined early on andI was at the time, I probably should have gone and done an internship there as well. I was off doing my own things usually, but it would have been probably pretty fun to be part of that early team. Anyway, I've been catching up with a bunch of them. And we were actually in the process of creating our own foundation model for UI cogeneration, right? Because this is pretty unique problem. And what we'd started to see was that ⁓Visual ⁓ Vision Language models or VLMs were actually showing a lot of really strong promise in the open source world, ⁓ separate from the closed source models. ⁓ There was a model called Moon Dream that was out that was showing astonishingly powerful results despite it being very small. And so we were thinking, what if we made our own really strong coding LLM and then combine that with a strong vision component ⁓ usingyou know, the technical term here is a clip model. And so that's that was like our initial thinking, which was if these closed source model companies like OpenAI are not going to release something that's really powerful here, ⁓ then why don't we do it ourselves? ⁓ The mistake there was, of course, thinking that they wouldn't release something as powerful. And so when I was catching up with with some of my friends there, ⁓KK Anderson (22:39)Yeah.Josh (22:45)I was mentioning this and they were like, hey, we're going to be doing something. And the moment I heard that, was like, okay, it's over. All this effort that we're putting in is going to be wasted. ⁓ You should not try to compete with these companies on that turf. ⁓ Luckily, they were, I think, impressed about how we were approaching it and asked to partner ⁓ on this. We had the data, they had the model and the team, and we kind of combined forces and did a really big sprint together for...Mark Petruzzi (22:54)All right.Josh (23:14)several weeks and got something out in time for the announcement. And then we announced it together.KK Anderson (23:27)That is really cool. Go ahead Mark.Mark Petruzzi (23:31)So, I think you have the next question, if you'd like.KK Anderson (23:32)So.Okay. So now, so talk to me about kind of your go-to-market as it relates to, know, thinking about how you're going to go to market with this product. And obviously OpenAI Partnership gives you a competitive advantage. Like, you know, how defensible is it? You know, as other companies try to replicate this approach. you, do you have any competitors?Josh (24:02)Yeah, great question. The go-to-market approach has really been interesting because there's actually a number of different channels that we've been able to tap into. ⁓ And I know, Mark, you're actually an expert advisor at BCG, right? So you probably have seen a lot ⁓ of companies, a lot of SaaS companies approach BCG and say, hey, we'd like to work with you. BCG is actually a company that we're starting to work with as well. And that's been really beneficial.Bain as well, we've done a little bit with. so partnerships through consulting firms have been interesting, especially on the enterprise level and looking at ways that we can bring value to these consulting firms, which are usually a little bit more, I would say hands off and sort of like advisory. But showing value quickly and getting outcomes quickly is something that is really beneficial for their model. And so that's how we've been able to partner with large consulting firms.partnering with agencies as well, where maybe they don't have a conversion optimization practice. Maybe they're more in the paid media space or what have you, or SEO. And we can basically provide this as an added service to their offerings. ⁓ But most commonly, we're just going direct, right? We're finding people through conferences, word of mouth, customers will share and give references and stuff. ⁓ We'll have...LinkedIn, know, campaign, not campaigns, but just like announcements of things and people will come in that way. ⁓ It's been, it's been a lot of just kind of like, you know, the momentum, keeping the momentum going and the energy in the space. think a lot of people are indeed excited about the AIs, you know, spin on it. And, the partnership with the OpenAI has actually been really helpful on the go-to-market front in terms of just like, guess, you know, credibility and they have that halo effect. so.That's been awesome. wasn't our intention at all. It was really just let's build something cool with these folks, but ⁓ it's definitely been beneficial.Mark Petruzzi (26:09)that's cool, Josh. Yeah. And I've done some work with Vane over the years as well. And you're in the hands of great companies there. And it so fits into what their mission is versus what you all are doing at CoFrame as well. So let's talk about the technical challenges to orchestrating all this. What have you had to overcome in making AI generate on-brand visually consistent interfaces?Josh (26:25)Mm-hmm.Mark Petruzzi (26:39)mean, that's the key right there.Josh (26:42)Yeah, mean, that in itself is a technical challenge. I the models are, I have found, ⁓ they're very strong in writing code and kind of doing the quote unquote heads down work. They're actually less strong in the visual creativity side of it. They have less of a strong sense of sight than they have a sense of, I guess, logic, if you want to call it that. ⁓That has posed a challenge, right? You know, our world is a lot about taste. It's a lot about making sure something fits in with the rest of the brand. ⁓ Conversion optimization is not simply, does this random experiment do better or not? It's about making sure that every experiment that we run is going to not only, you know, meet, but exceed the expectations of the people reviewing them on the customer side that we work with and making sure that they're actually impressed with the result before we even run the experiment.And so that's a part of, you know, selling ourselves as Co-Frame actually. We'll go into sales calls and we will, before even working with someone, we'll show them some variations of their website. ⁓ That's kind of the beauty of the technology is that you're able to do that. Something that would otherwise take weeks of several people's time. ⁓ It's so easy for us that we can show them in a, just a qualifying call, which is kind of nice. ⁓ It's very helpful for sales.But in order for models to be good at that, they have to be good at visuals. And most times, models off the shelves are just not good at seeing something and understanding how this is going to fit in naturally and natively with their brand. And so that was the core technical challenge here. Another challenge here ⁓ was gathering the data that was required for this. so luckily, ⁓ we were able to scrape the internet.publicly available websites, ⁓ we basically, that's the nice part about this problem, which is that everything is basically out there for everyone to see. There's no concern ⁓ around data issues and stuff like that. But the challenge there was making a data set that actually reflected the problem that we're trying to solve, which was how do we get a model to more accurately create a new section of the site that isaligned with the rest of website. So that was not an easy challenge to solve either. ⁓ but you luckily, when when the infrastructure is in place, you can kind of scale it up as much as you want to. And that becomes really, really powerful.KK Anderson (29:26)So.Mark Petruzzi (29:26)Great, all right, let's move, well,we wanna move on to topic three, but I have, I keep kind of diving into one item that maybe we can do a quick sidebar in, at least in my own brain. So tell us a little more about what type of competitive advantage this creates, you know, and then how defensible is this for the companies, for your clients that jump in with you in this?KK Anderson (29:47)Yeah.Josh (29:52)Yeah, those are both great questions. we actually look at competitive advantage and defensibility a little bit in reverse. It's not what's competitive, what's like a defensible competitive advantage for a co-frame, but rather how are we creating that for our customers?Mark Petruzzi (30:09)Yes, and that's exactly where my question is focused on. Like how do you do that with your, how do you help your clients achieve that?Josh (30:16)Exactly. so that's the key piece. And I think flipping on that on its head creates this insane amount of alignment between us and our customers. ⁓ But basically with each customer, what we're doing is we're building essentially a very embedded, intelligent team member or team overall ⁓ that is working for them 24 seven. It's a team of, know, front end engineers and designers and PMs and marketers.That's what CoFrame basically is. That is, over time as we're running more and more tests, we're learning more and more about what works for their business. And for the most part, what we've seen is, you know, what you learn about a specific business is pretty bespoke to that business. That's not the only reason why we completely silo the business data and so on. We do that also because it's just the right thing to do. you know, businesses would be concerned if we weren't doing that. But...We certainly have found that within a given business, as this quote unquote team, embedded team gets more smart, that business has an increasing competitive advantage against other businesses that aren't 24 seven continuously optimizing and learning. You know, it's, it's, it's, it's one of those advantages. That's the beauty of compounding. We talked about earlier, but the cool part about compounding is that, you know, it might start slow, but then suddenly you have a runaway advantage. There's no way to catch up. And so.That's what we are basically providing for our customers.Mark Petruzzi (31:49)Excellent, KK, will you bring us over to topic three?KK Anderson (31:50)Absolutely.Yep. So let's talk about autonomous growth ⁓ and how AI agents are replacing manual optimization. And so you said that you've demonstrated 352 % improvement in click through rates with enterprise clients, which is incredible. ⁓ How should growth teams think about integratingAI agents into their existing marketing stack.Josh (32:21)that's a fantasticquestion. And that actually comes down to your own business. I actually have ⁓ a lot of thoughts here. marketing agents, agents in general, it's a very general topic, right? And so it's important to of like approach that from the right mindset and not just say like, here's, I'm not going to be prescriptive here because ultimately every business is different. Every workflow is different. First thing to kind of note is thatWe are approaching this new world where basically ⁓ you have to make sure it impacts the bottom line. That's really, really important. ⁓ You have to make sure that it gives you an edge in whatever you're implementing agent technology into. And there is starting to become this organizational mandate as a result. The CEO of Shopify, Tobi Ludke, he recently put out a memo in which he was saying, before asking for resources, people have to demonstratewhy they can't do what they're trying to do ⁓ using AI. And so it's starting to become a mandate. So it's good that you're asking this question. The tactics that I have for evaluating whether or not to incorporate an agent into your workflow, how and when to use agents, ⁓ the first thing is to take a systems thinking mindset ⁓ to the workflow you're trying to automate here. ⁓ This is a little bit fuzzy, butor fluffy, should say. you know, systems thinking is actually really, it's a really relevant thing to have. kind of, it's like, to me, it's this combination of AI ⁓ knowledge and knowing what the capabilities of these models are and these agents are. And then your domain knowledge, which in this case is marketing knowledge. And then finally, a general growth mindset. I know that's a fluffy term, but like having kind of that impetus to think about new ways of applying this stuff.And so the systems thinking that comes into this is the combination of those three things. More tactically for marketing, there are several areas where this is applicable. Paid media is a big one. Looking at how ads can be, you can create different variations of ads and then optimize them over time. And there are companies that are doing this and providing ⁓ tooling for this. Coframe is going to be doing this at some point soon. ⁓ There's companies like Icon and ⁓There's a bunch of them. Google and Meta are going to be doing themselves. There's conversion optimization for a website. That's of course what Coframe is doing. There's lifecycle marketing, emails, email campaign optimization. There's SEO, there's content operations, a bunch of stuff. The next tactic I have here is getting to know the capabilities of your AI colleagues. Trying to figure out where do we use certain models in what situations? For instance,Claude is really great at general coding. So is now the 03 in the sort of like GPT series from OpenAI. Gemini from Google is great at long context. And so you can put a bunch of different collateral into it and have it analyze it. So my call to action for the listeners here would be get to know the different models out there and try to figure outwhere are their limitations, where are their strengths. This is going to be evolving over time. So this is going to be really important to stay on top of. The next tactic I would have here is to prototype and see what's possible. You want to try to get your hands dirty and figure out what's going to show promise. ⁓ then just basically what you learn from prototyping, you should be able to have a sense for, OK, how do we apply this to my workflow and the agents that I'm trying to build?At that point, it's really important to make sure that you're building things with what are called evals, making sure things are, you ⁓ you're actually measuring quantitatively the outcomes that you want your agent to be able to deliver. ⁓ And at the point where you do that, you know, you're in a really good place. You have a closed loop and you're ⁓ able to, with some level of reliability, automate a workflow, which is an amazing thing. And that's, think, like I was saying earlier,the most promising part of the new AI world we're entering into.Mark Petruzzi (36:48)Excellent. All right, let's move us to the final topic here, and that's the future of marketing technology and growth engineering and how does this all come together for us? And the biggest question is, and this is gonna seem like I'm asking you to predict something that's 50 years in the future, because in this space, looking ahead even just 18 or 24 months is so difficult and the changes are happening daily, minute,minute by minute. But let's say we look at 18, 24 months, how do you see the convergence of AI and growth marketing evolving? And what should marketing leaders be one, for, and secondly, driving within their companies to allow that information and those new capabilities to be executed on as quickly as possible for them?Josh (37:42)That's a fantastic area. You know, it's a, it's a really great question. I have this, this article, um, which I think would be a good one to check out. If you're looking to dig deeper into this topic for the listeners at home, it's on this newsletter called every by Dan shipper. Uh, it's called the new science of growth marketing. And in it, what I try to talk through is this correlation between growth marketing and finance. Interestingly enough.So in finance, what we saw was previously, before the advent of computers and so on, people traded manually, traded stocks, bonds, other assets. And it was a very manual, very tedious process. It still is manual to an extent. People are certainly doing discretionary trading on their own. But what transformed finance in the 1980s and 90s and 2000s⁓ was the emergence of quant finance. So quant trading and using quantitative methods, computers, ⁓ to do algorithmic trading of these assets. And what made that possible for finance was that the problem that you're trying to solve, it wasn't a simple problem, but it had a simpler output. It was either, you know, predict a price orMark Petruzzi (38:46)Yeah.Josh (39:10)even simply a buy or sell indicator of a stock. Now the output for marketing is not something as simple as a price or a buy or sell. It is copy, is code, it is assets. ⁓ And until recently, that wasn't really possible to do with the models that we had at our disposal. But with the advent of generative AI, that is the native modality that AI is operating in.And so what we're starting to see, and we will, I think, increasingly see, at least what I say in the article, is that just as quant finance ⁓ revolutionized the financial industry, we are going to start to see this idea of quant experimentation and quant quantitative growth methods revolutionize growth and marketing, where you'll have these strategies that are autonomous to an extent, ⁓ executed by machines.being able to work 24 seven on your behalf and test things autonomously and make changes and personalize at a way deeper level than that was previously possible. And that's a really powerful thing because, know, to date it's been extremely tedious and time consuming to run these experiments. You require, you know, like an engineer and a designer and marketer and so on, just to get a single AB test out the door, can take weeks. What if it take minutes or hours?you know, or less, you know, so ⁓ we're starting to enter a world where continuous optimization is then possible, all the new superhuman capabilities that we talked about earlier. ⁓ And that is what I like to think of as quant growth or quant experimentation. And I go into a bit more detail into specific strategies ⁓ in the article, very high level strategies, know, nothing super profound, but ⁓ I think it's gonna be very, veryimpactful for the growth industry and for companies that use it.KK Anderson (41:14)So last question before we move on to our rapid fire ⁓ section. So what's going to be the highest value work for humans? Right?Josh (41:27)Yeah, so it's a great question.the answer to this one, at least I kind of just borrow from this similarly borrow from what we've seen in the quant industry, right? Where instead of actually performing the trades, humans are responsible for coming up with the strategies, you know, ⁓ we have now more professionals in the financial industry than we ever have. ⁓KK Anderson (41:46)Okay.Josh (41:53)despite a lot of those manual tasks being taken by machines. ⁓ Similarly with the invention of the steam engine and electricity. ⁓ Well, the steam engine took a lot of the manual effort out of ⁓ transportation. ⁓ But we have now seen an entire new industry built up that has given a lot of jobs in performing higher level work that involves steam engines or is involved in the creation of steam engines.There are a lot of such examples. So I think what we're going to end up seeing as applied to this industry is growth people, marketers, engineers alike, are going to have to focus less on the tedious work of writing the code, coming up with the specific assets, coming up with the specific analysis of the data and the results, and rather guiding the strategy for their businesses.I also think we're going to see an explosion of businesses overall. We're going to, people are going to be way more empowered to be solopreneurs and, you know, small businesses and entrepreneurs and do more and offer more with less. And so we're going to start to see just like more opportunities where growth can be applied. I do think that growth teams at large, large companies might shrink because a lot of the grunt work is going to be taken on by AI. But ⁓KK Anderson (43:00)Yeah.Josh (43:20)there's going to be a lot more opportunity for many, many more types of businesses out there to use these advanced growth tactics as well.Mark Petruzzi (43:28)And I just want to point out that that last question that KK presented was submitted by a bot, by a robot, because they want to know how they can leverage us now into working for them instead of the other way around. it's already happening. That was not from a human. OK, we're going to go rapid fire over the last three minutes or so here. This has been great, Josh. So thank you.KK Anderson (43:42)Hahaha! ⁓Josh (43:43)already happening. wow. That's amazing.Mark Petruzzi (43:57)So Josh, what was the first product or service you were ever responsible for selling?Josh (44:05)wow. That's a great question. It has nothing to do with my current industry, but it has all to do with who I am, which is music. I had a little jazz group back in high school and we made some albums and reinvested the proceeds back into the band and made recordings, more recordings and did little touring. So yeah, that was my first exposure to business.KK Anderson (44:14)That's right.Mark Petruzzi (44:28)So everything you touch is successful, right? Is that how it works, Justin?Josh (44:31)Definitely not, butI appreciate that.KK Anderson (44:37)Okay,who's your favorite CEO to follow?Josh (44:41)man,that's a, it's a great question. I'd have to say Eric Schmidt, ⁓ he's like next level, maybe the best operator in the whole world, ⁓ just insane story. And, ⁓ I've had the opportunity to learn some things from him directly and work with him through a couple of different things. And so, but I think he's awesome.Mark Petruzzi (45:02)Very cool. Okay, a tool other than CoFrame that every growth leader should be using.Josh (45:11)man. Well, I think it's really, really important to have a really solid sense of your data for sure. So some type of, some type of analytics platform, Amplitude's a really great one. know, Adobe analytics, ⁓ post-hoc, et cetera. I think that, you know, the more you have a sense of what's happening in your business, the more you're going to be able to improve it and measure, measure those outcomes.KK Anderson (45:39)Question, do you have to have one of those to be able to use CoFrame?Josh (45:42)No, no, we actually come with full data, you know, analytics included, but we do plug into these, these systems.KK Anderson (45:49)Okay, now for my favorite question. Advice that you would give your 21 year old self.Josh (45:55)that's a goodone. man. ⁓ Okay. So I think that what I would probably say is like, like basically hype is not the same as substance. You know, I've, I've, I've seen a lot of, a lot of hype in my career so far. ⁓ And, you know, easy come easy go. Like things will just like, there'll be bubbles, they'll collapse and there'll be things thatthat what you want to be doing is basically subtracting the noise to try to find the true signal and keep this level of groundedness to try to figure out what is truly valuable here and think from first principles what is going to be durable and sustain over time. And so I'd really urge myself, I guess, to really focus on the substance.Mark Petruzzi (46:45)Oh, I love that, Josh. And as a, know, as a reoccurring, you know, individual who's launched different companies, been CEO of multiple companies at this point, I love to have you, I love to hear you thinking about that in those terms. Because, you know, I have a lot of friends who have done the same from, you know, different company to the next and...they start doing it a few times at the CEO level and they start to think that's their job is to always drive that hype through the market. And even sometimes within their own organization, they think they need to have credibly positive energy in their business at all times. And that's not life as we know it. And ⁓ having that realistic approach is really impressive.Josh, thank you so much for taking the time with us. This was great and we're excited as we go along to learn more about Code Frame and see how we can leverage that into some of the work we do with clients.Josh (47:54)It's been a pleasure, Mark. Thanks so much for having me, Mark and KK. Really good to see you both.KK Anderson (47:54)Yeah, absolutely.Thank you, Josh.Mark Petruzzi (48:01)Perfect, all right. Thanks, all. Thanks, Josh. Thanks, KK. Cheers.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Josh Payne—Founder & CEO of CoFrame and creator of GPT-Migrate—joins Mark Petruzzi and KK Anderson to explore how AI agents and continuously optimizing websites are changing the future of digital growth.Josh shares how CoFrame is helping mid-market and enterprise companies drive 30%+ increases in conversion by building adaptive, AI-powered interfaces that test, learn, and optimize in real time. He also unpacks how his team partnered with OpenAI to create a state-of-the-art UI code generation model—and what this signals about the future of growth marketing.Whether you’re a CMO, growth lead, or founder looking to build durable competitive advantage through AI, this episode will shift your mindset and your roadmap.What You’ll Learn:From Static to Living Interfaces: Why websites are broken—and how AI agents can continuously optimize them based on real-time data and buyer behavior.The End of Manual A/B Testing: How Josh’s team automates experimentation at scale to unlock compound conversion lifts without traditional resource bottlenecks.Inside the OpenAI Partnership: How CoFrame trained a UI-specific code generation model that understands brand, layout, and style—then deployed it at scale.Building Competitive Advantage with AI: Why businesses that embrace continuous optimization today will outpace those stuck in manual, quarterly workflows.Designing the Future Growth Stack: How AI agents, data orchestration, and strategy automation will transform marketing roles and unlock new GTM velocity.Key Topics:Living interfaces vs. static websitesAI code generation for brand-consistent designScaling experimentation with AI agentsThe future of CRO: conversion rate optimizationAI in paid media, lifecycle marketing, and SEOStrategy design vs. manual executionHow to evaluate AI models like Claude, Gemini, GPT-4Building “quant growth” systems for marketingWhy the next big AI use case is growth engineeringGuest Spotlight: Josh PayneJosh is the CEO of CoFrame and a repeat founder with deep roots in AI. He previously co-founded Autograph (a $2B+ unicorn), created GPT-Migrate, and authored over 20 patents and AI research papers. At CoFrame, he’s pioneering AI-first digital experiences that adapt to users in real time.Resources & Mentions:CoFrame: https://coframe.comArticle: The New Science of Growth Marketing – EveryTech: GPT-4 Vision, Claude, MoonDream, OpenAI fine-tuningTools Mentioned: Optimizely, Adobe Target, VWO, AmplitudeTopic: Quant growth, UI code generation, AI agents🎧 Listen now and follow Selling the Cloud for cutting-edge conversations with the builders, strategists, and GTM leaders shaping the future of sales, growth, and AI.Mark Petruzzi (00:02)Welcome to today's episode of Selling the Cloud podcast. We are excited to welcome Josh Payne, founder and CEO of CoFrame. Josh is a serial entrepreneur and AI pioneer who has co-founded multiple successful companies, including Autograph, a 2 billion plus unicorn backed by A16Z and Access Bell, which has been acquired by Tata.He's also the creator of GPT Migrate, one of the first popular coding agents and has authored over 20 papers and patents in AI. At CoFrame, Josh is building the future of digital interfaces, websites and apps that continuously optimize themselves using AI. The company recently raised 9.3 million from Coastal Ventures.and partnered with OpenAI to develop breakthrough UI code generation technology that's driving a 30 % plus improvement in conversion rates for mid-market and enterprise clients alike. Today, Josh will share how AI agents are revolutionizing growth marketing and website optimization, what it means to build living interfaces, and how go-to-market teams should prepare for the autonomousoptimization era that we are in today. So welcome, Josh, welcome.Josh (01:31)Thanks so much for having me, Mark. Good to see you.Mark Petruzzi (01:33)Excellent. Thank you. Okay, four themes we'll focus on today. From static to living, the AI powered interface revolution, the OpenAI partnership building visually grounded AI at scale, autonomous growth, how AI agents are replacing manual optimization, and the future of marketing technology and growth engineering. So first area here, Josh, for us to jump into.You describe CoFrame as creating living interfaces rather than static websites. What's fundamentally broken about how we think about digital experiences today?Josh (02:15)Yeah, so the problem with digital experiences as we know them, it comes on both sides. There's the problem from the business side, which is that it takes a lot of effort to make these digital experiences like websites or apps better for our customers. And people tend to spend a lot of money and time doing so. On the customer side, it's also an issue because you have these experiences that are one size fits all. They're not adaptive. They're not personal, you know?They lack the context of you as a person. And the way that we're approaching this is the problem is, let's think about this from the ground up. If you could redesign the concept of digital interfaces today in a world where AI is possible and as powerful as it is, you know, look at the trend of where things are going in terms of the capabilities that it has. How would you design these customer experiences?And that was really our impetus, which was, let's think about a world in which these digital interfaces were living in a sense, they could be adaptive and personal from the ground up. And so what we're doing essentially is, is enabling that capability for the businesses that we work with and their customer experiences, allowing their, their teams to not have to do all that grunt work and trying to continuously stay on top of.⁓ of making those customer experiences better at great cost and ⁓ great time.KK Anderson (03:51)Like, what would a use case be or an example, just to go a little deeper into living interfaces? I think it sounds amazing.Josh (03:59)Absolutely. The biggest one that we focus on at the moment is website optimization. So you're probably very familiar with the idea of websites being a conduit for which consumers can interact and transact. And the problem with websites today is that, like I was mentioning, it takes a lot of effort to improve the conversion rate ⁓ of these sites. 95 % ofplus of traffic on the internet doesn't convert, right? It's people who go to a website and they check it out and they decided that maybe it's not a fit for them or they don't get the punchline, they don't get the idea. And this is truer in other industries than it is, know, for instance, in e-commerce, this is a huge, huge problem because the website is everything, right? And, you know, consumer finance tends to be a big one as well. And so,What you end up seeing is ⁓ these teams spending a lot of time running experiments on these websites. You'll have a product manager or a marketer come up with a concept or an idea of what to test. They'll pass that on to a designer. They'll come up with designs and concepts. They'll then go and pass that on to an engineering team, which will go and implement the idea to be tested in the website. And that handoff process, that whole process takes weeks, sometimes months.to do. And just an insane amount of time, when you look at the dollar value of time, an insane amount of cost and headcount. ⁓ And so it's a very broken process. It's still very beneficial and valuable, because every win that you get, every better version of that experience, tends to give you significantly more revenue, because you're stacking those conversions over time. You start to see the compounding benefits.It's really, really painful. so the use case here that we're very focused on at CoFrame, at least, is bringing this idea of adaptive, personalized websites where different people can have different experiences that are suited to them to really help to increase that end KPI that the business cares about, usually a conversion KPI.Mark Petruzzi (06:20)So Josh, you have built multiple successful companies in different paradigms. What made you pivot from traditional SaaS to this AI-first approach with CoFrame?Josh (06:35)Yeah, I mean, this is a big question a lot of operators are facing right now, which is, how is the role of software going to evolve in this world of AI? I think we're seeing the commoditization of software. starting to see, on the flip side, we're seeing a lot of incredible new capabilities that AI is enabling. I actually think that one of the biggest opportunities right now in the space overall, in the world, istaking processes that are manual and take a lot of work and then applying ⁓ sort of an AI first mindset to that to figure out how can we automate or optimize different parts of that process and then deliver that outcome with way less effort involved. So an example here of what we're doing, know, conversion optimization, like I was saying, that kind of takes, you know, design and engineering and product management and a bunch of different manual functions that are tedious. And soOur approach was, can we break down that whole long process that is delivering the outcome, which is basically experiments for your website and use AI to significantly accelerate and then automate that ⁓ end to end. Now there's still human involvement for sure. And there's, there's like a gradient of, of involvement, right? But on the level of completely manual to completely automated, we're gradually moving toward that automation piece. And I think that that's.really the biggest opportunity currently in the world of AI is looking at what is currently manual and trying to figure out systematically how can we automate that and ⁓ make it not as painful ultimately.KK Anderson (08:17)So really interesting. where in your professional opinion do most companies go wrong when they're trying to optimize their websites and their digital experiences? And I heard what you said earlier. And by the way, once four to eight weeks have passed and the new website is launched, that content is stale. there you are going back at it again.Talk to me about where they go wrong and how you recommend that they shift.Josh (08:53)Yeah, soI mean, a big thing that I see a lot is people are just not testing enough. know, there's that when you look at the math behind conversion optimization and experimentation, it's pretty astounding. you know, if you like, think about ⁓ a series of tests that you run, you find a couple of wins within those tests. It's not like those wins are going to give you, you know, a boost of revenue for that month and then you're done. No, that win stays with you for good, for the most part.And they also compound over time. So if you find a 2 % conversion left here, a very small left here, you know, and then a 5 % over here, and then a 3 % over there, you suddenly have 10 % in aggregate conversion left. That could be 10 % more revenue, you know, over the course of forever. Right. And so that comp, that's why compounding is so powerful here, because you start to be able to see, you know, this like, this, this, this super linear growth.⁓ of your business value.Mark Petruzzi (09:56)Yeah, what I love about that, Josh, is you're kind of taking us to continuous, instead of periodic testing. it's just, and that's the beauty of AI and it's the beauty of the intelligence that it's building in some of these large language models that, like you said, it compounds, they get better, they get smarter, and that's phenomenal. And, you know, I guess we're putting the A-B test out ofJosh (10:05)Yes, exactly.Mark Petruzzi (10:26)at a commission at this point, because unless you want to look at it as A-B testing 24-7. yeah, so ⁓ what's the first thing a growth leader should understand about moving from this periodic optimization to this continuous AI-driven improvement?Josh (10:32)Yeah, A to Z testing.KK Anderson (10:35)Yeah.Josh (10:46)Yeah, so first thing is just like a mindset shift, right? A-B testing is valuable and it has its place. And you can still compound those wins over time with A-B testing. ⁓ We are now living in a world where the cost of creating new experiments is very low. So what I like to usually think through ⁓ when it comes to opportunities in the AI space is we talked a lot about automation, right?like taking something that is manual and autumny. I think that's the biggest opportunity currently. ⁓ Now, there's another piece of this, which I think is also very valuable, we think of that a lot, which is what wasn't possible before that is now possible. So net new superhuman capabilities. So first is taking a human capability and then just performing that. And then the second bucket istaking something that just wasn't possible before or feasible or reasonable to do and doing that. And so continuous optimization actually falls in that second bucket. The first bucket being here's how people are optimizing today with A-B testing. And we're just going to automate that. The second bucket is what new types of tests are now possible with AI. And I'll give you a simple example of this. ⁓KK Anderson (11:54)The superhuman?Josh (12:11)⁓ Let's see, Booking.com is actually probably one of the closest to this. They're a really, really advanced company when it comes to growth and optimization. They're running a thousand plus experiments at any given time. ⁓ But with their level of traffic, they could be running probably tens of thousands of experiments at any given time. ⁓ That's just not feasible to do ⁓ with ⁓ purely with human labor, right? It would just not make sense from an economic standpoint of time spent.KK Anderson (12:34)humans.Josh (12:40)And so yes, you'd have to cut tests off sooner. You'd probably have to use things like multi-armed bandits, advanced techniques to test lots more variants. ⁓ But in doing so, you're squeezing more value out of all that traffic that they have. And so if you can 10x your testing velocity, ⁓ that's A, not very feasible to do without the assistance of a technology like AI. But also B, it's very valuable if you can do it.And so that's where we see this idea of continuous testing coming into play.KK Anderson (13:16)and that compounds over time. Yeah.Josh (13:19)yeah, that's the beautyabout compounding. It's like every win that you get, you know, builds on itself. And so the faster you compound, the more value your business is going to be receiving. And that's why a lot of our customers have been able to see like really big benefits very quickly with us.KK Anderson (13:25)Mm-hmm.Well, and last question before we move on to the OpenAI partnership, which we're excited to learn about. So how hard is it to go from your periodic optimization or shall we say once a year optimization for some companies to this? Is it a big lift to switch? Do you have to change your whole website? What does that even entail?Josh (13:58)Yeah, it depends on how you're doing it. ⁓ I mean, I could speak to the co-frame piece of this, obviously. And for us, we come in and we're operational on day one with the companies that we work with. So it's no lift, basically, except for approving variations. The approval workflow still exists. And you have to make sure every variation and every experiment is given a sign off by the relevant stakeholders. for listeners at home, thinking about their own websites and how we can incorporate continuous optimization.⁓ There ⁓ are tools out there that support this, testing tools. I think about tools like Optimizely or Adobe Target for the enterprise segment or VWO for the mid-market or lower market segments. ⁓ These are tools that we sometimes, at CoFrame, sit on top of ⁓ and we're the ones creating those tests. Really the important thing to keep in mind here is to enable continuous optimization.It's a hungry engine. It's a very powerful engine, but it's very hungry. It requires a lot of shoveling coal in. In this case, the coal are variations. ⁓ So you have to make a lot of variations, and then those have to be based on what you're learning from the tests. And so the way that you can do this at home is by incorporating these models into how you're testing. So you're using Claude or using OpenAI, know, Chachiputti to create the variations, whether they be copy or.or code or even images sometimes and things like that. It's not easy ⁓ to set all this up, but once you do, it's very beneficial.KK Anderson (15:38)Really cool. So let's go into, sorry, Mark, you go ahead. No, no. Okay. Yeah. I'm anxious to get into the OpenAI partnership. Okay. So you recently partnered with OpenAI. Congratulations. That's exciting. And you're developing what you call a first of its kind UI code, code generation. So break that down for us and tell us what this breakthrough actually means for business leaders.Mark Petruzzi (15:39)That sucks.No, no kick us off. Bring us to topic topic two.Josh (15:44)IYeah, let's jump in.Thank you.Right, so one of the big challenges with models today is that they are very good at coding, but they're not as good at kind of like visually grounded coding. What I mean by that is when you look at a user interface, having the eye of a designer to figure out how is this code going to actually look when it's put into a user interface, especially when it comes to a pre-existing brand. So we're all operating in the world ofexisting websites with existing assets and styles, and you have to stay on style and on brand and adhere to those guidelines. And a big shortcoming of today's models has been ⁓ how do we make sure that the code that we're writing when we create these variations from a layout or a user experience perspective are in adherence with these guidelines. So that was the technical challenge. ⁓ The way that we approached solving itwas we created a large data set of a bunch of different websites out there. And we trained a model to be specifically good at creating new sections of websites that were aligned with the existing brand of the existing websites. And so ⁓ our initial approach was to basically remove one of the sections and then create a textprompt that describes what that section was in as much detail as possible, ⁓ and then use a model to create a new section that was based on that prompt. So you're basically masking out one section of the site, saying to a model, hey, look at this existing site with everything except for that section, and then create me that new section that I'm describing verbally to you. And then that's the task, and it actually creates that new section, and it's basically graded.on how well it adheres to what the original section actually looked like. So that's the task that we use to train it. It's very similar to actually how transformers are trained in predicting the next token. But a little bit more of advanced predicting the next section instead of maybe the next token. And so that was the way that we set up the problem.Mark Petruzzi (18:15)Mm.Josh (18:30)And we were able to achieve state-of-the-art results with visually grounded cogeneration with this. And so what that means for businesses is that now, at least ones that work with CoFrame, but others maybe that would use a similar approach to train their own UI cogeneration models, ⁓ now you can have a model that really knows your brand, your visual identity, and can then create new experiences, new sections, new pages entirely, potentially. ⁓based on what it knows about your brand. It's almost like having a designer and a front-end engineer paired up, but they've been on your team for 10 years and they know your brand really, really well.KK Anderson (19:10)That's really cool.Mark Petruzzi (19:12)So that's very cool. Josh, tell us, I guess the biggest thing that's jumping out on me is a little more of the playbook here. How did you convince OpenAI to work with you on the fine tuning of this GPT-4.0 vision? Knowing how fast they're growing, how distracted they are as an organization. So tell us a little bit about how you made that all work.a little bit of the why. Like why are they so excited with your vision of brand consistent UI generation versus other things that may be popping around out there in the marketplace.Josh (19:53)Yeah, I think it comes down to just it being a really interesting problem. So in one that is interesting from a couple of different angles, one is of course the technical challenge. You know, this is a new domain ⁓ relatively, you know, like visual plus code. And so that's a really interesting combination of those two. But then there's also, it's interesting from a business standpoint, right? Like being able to create visually grounded user interfaces. That's like a really great.⁓ thing to do. It's really core piece of this movement now, which we're seeing in like, you know, consumer products and even enterprise products that are creating, you know, code for new experiences. I think companies like Lovable and Replit and Bolt, like the ones that are just taking off right now, then ⁓ Claude and ⁓ Claude code and cursor, and there's a bunch of others too. And soI think that that's why they were all so interested in this is because it's kind of a key piece of that equation, the front end or the user experience piece of this. How we ended up working with them is another story. had actually, I've been friends with several folks at OpenAI for a long time. ⁓ to school with a bunch of them who had joined early on andI was at the time, I probably should have gone and done an internship there as well. I was off doing my own things usually, but it would have been probably pretty fun to be part of that early team. Anyway, I've been catching up with a bunch of them. And we were actually in the process of creating our own foundation model for UI cogeneration, right? Because this is pretty unique problem. And what we'd started to see was that ⁓Visual ⁓ Vision Language models or VLMs were actually showing a lot of really strong promise in the open source world, ⁓ separate from the closed source models. ⁓ There was a model called Moon Dream that was out that was showing astonishingly powerful results despite it being very small. And so we were thinking, what if we made our own really strong coding LLM and then combine that with a strong vision component ⁓ usingyou know, the technical term here is a clip model. And so that's that was like our initial thinking, which was if these closed source model companies like OpenAI are not going to release something that's really powerful here, ⁓ then why don't we do it ourselves? ⁓ The mistake there was, of course, thinking that they wouldn't release something as powerful. And so when I was catching up with with some of my friends there, ⁓KK Anderson (22:39)Yeah.Josh (22:45)I was mentioning this and they were like, hey, we're going to be doing something. And the moment I heard that, was like, okay, it's over. All this effort that we're putting in is going to be wasted. ⁓ You should not try to compete with these companies on that turf. ⁓ Luckily, they were, I think, impressed about how we were approaching it and asked to partner ⁓ on this. We had the data, they had the model and the team, and we kind of combined forces and did a really big sprint together for...Mark Petruzzi (22:54)All right.Josh (23:14)several weeks and got something out in time for the announcement. And then we announced it together.KK Anderson (23:27)That is really cool. Go ahead Mark.Mark Petruzzi (23:31)So, I think you have the next question, if you'd like.KK Anderson (23:32)So.Okay. So now, so talk to me about kind of your go-to-market as it relates to, know, thinking about how you're going to go to market with this product. And obviously OpenAI Partnership gives you a competitive advantage. Like, you know, how defensible is it? You know, as other companies try to replicate this approach. you, do you have any competitors?Josh (24:02)Yeah, great question. The go-to-market approach has really been interesting because there's actually a number of different channels that we've been able to tap into. ⁓ And I know, Mark, you're actually an expert advisor at BCG, right? So you probably have seen a lot ⁓ of companies, a lot of SaaS companies approach BCG and say, hey, we'd like to work with you. BCG is actually a company that we're starting to work with as well. And that's been really beneficial.Bain as well, we've done a little bit with. so partnerships through consulting firms have been interesting, especially on the enterprise level and looking at ways that we can bring value to these consulting firms, which are usually a little bit more, I would say hands off and sort of like advisory. But showing value quickly and getting outcomes quickly is something that is really beneficial for their model. And so that's how we've been able to partner with large consulting firms.partnering with agencies as well, where maybe they don't have a conversion optimization practice. Maybe they're more in the paid media space or what have you, or SEO. And we can basically provide this as an added service to their offerings. ⁓ But most commonly, we're just going direct, right? We're finding people through conferences, word of mouth, customers will share and give references and stuff. ⁓ We'll have...LinkedIn, know, campaign, not campaigns, but just like announcements of things and people will come in that way. ⁓ It's been, it's been a lot of just kind of like, you know, the momentum, keeping the momentum going and the energy in the space. think a lot of people are indeed excited about the AIs, you know, spin on it. And, the partnership with the OpenAI has actually been really helpful on the go-to-market front in terms of just like, guess, you know, credibility and they have that halo effect. so.That's been awesome. wasn't our intention at all. It was really just let's build something cool with these folks, but ⁓ it's definitely been beneficial.Mark Petruzzi (26:09)that's cool, Josh. Yeah. And I've done some work with Vane over the years as well. And you're in the hands of great companies there. And it so fits into what their mission is versus what you all are doing at CoFrame as well. So let's talk about the technical challenges to orchestrating all this. What have you had to overcome in making AI generate on-brand visually consistent interfaces?Josh (26:25)Mm-hmm.Mark Petruzzi (26:39)mean, that's the key right there.Josh (26:42)Yeah, mean, that in itself is a technical challenge. I the models are, I have found, ⁓ they're very strong in writing code and kind of doing the quote unquote heads down work. They're actually less strong in the visual creativity side of it. They have less of a strong sense of sight than they have a sense of, I guess, logic, if you want to call it that. ⁓That has posed a challenge, right? You know, our world is a lot about taste. It's a lot about making sure something fits in with the rest of the brand. ⁓ Conversion optimization is not simply, does this random experiment do better or not? It's about making sure that every experiment that we run is going to not only, you know, meet, but exceed the expectations of the people reviewing them on the customer side that we work with and making sure that they're actually impressed with the result before we even run the experiment.And so that's a part of, you know, selling ourselves as Co-Frame actually. We'll go into sales calls and we will, before even working with someone, we'll show them some variations of their website. ⁓ That's kind of the beauty of the technology is that you're able to do that. Something that would otherwise take weeks of several people's time. ⁓ It's so easy for us that we can show them in a, just a qualifying call, which is kind of nice. ⁓ It's very helpful for sales.But in order for models to be good at that, they have to be good at visuals. And most times, models off the shelves are just not good at seeing something and understanding how this is going to fit in naturally and natively with their brand. And so that was the core technical challenge here. Another challenge here ⁓ was gathering the data that was required for this. so luckily, ⁓ we were able to scrape the internet.publicly available websites, ⁓ we basically, that's the nice part about this problem, which is that everything is basically out there for everyone to see. There's no concern ⁓ around data issues and stuff like that. But the challenge there was making a data set that actually reflected the problem that we're trying to solve, which was how do we get a model to more accurately create a new section of the site that isaligned with the rest of website. So that was not an easy challenge to solve either. ⁓ but you luckily, when when the infrastructure is in place, you can kind of scale it up as much as you want to. And that becomes really, really powerful.KK Anderson (29:26)So.Mark Petruzzi (29:26)Great, all right, let's move, well,we wanna move on to topic three, but I have, I keep kind of diving into one item that maybe we can do a quick sidebar in, at least in my own brain. So tell us a little more about what type of competitive advantage this creates, you know, and then how defensible is this for the companies, for your clients that jump in with you in this?KK Anderson (29:47)Yeah.Josh (29:52)Yeah, those are both great questions. we actually look at competitive advantage and defensibility a little bit in reverse. It's not what's competitive, what's like a defensible competitive advantage for a co-frame, but rather how are we creating that for our customers?Mark Petruzzi (30:09)Yes, and that's exactly where my question is focused on. Like how do you do that with your, how do you help your clients achieve that?Josh (30:16)Exactly. so that's the key piece. And I think flipping on that on its head creates this insane amount of alignment between us and our customers. ⁓ But basically with each customer, what we're doing is we're building essentially a very embedded, intelligent team member or team overall ⁓ that is working for them 24 seven. It's a team of, know, front end engineers and designers and PMs and marketers.That's what CoFrame basically is. That is, over time as we're running more and more tests, we're learning more and more about what works for their business. And for the most part, what we've seen is, you know, what you learn about a specific business is pretty bespoke to that business. That's not the only reason why we completely silo the business data and so on. We do that also because it's just the right thing to do. you know, businesses would be concerned if we weren't doing that. But...We certainly have found that within a given business, as this quote unquote team, embedded team gets more smart, that business has an increasing competitive advantage against other businesses that aren't 24 seven continuously optimizing and learning. You know, it's, it's, it's, it's one of those advantages. That's the beauty of compounding. We talked about earlier, but the cool part about compounding is that, you know, it might start slow, but then suddenly you have a runaway advantage. There's no way to catch up. And so.That's what we are basically providing for our customers.Mark Petruzzi (31:49)Excellent, KK, will you bring us over to topic three?KK Anderson (31:50)Absolutely.Yep. So let's talk about autonomous growth ⁓ and how AI agents are replacing manual optimization. And so you said that you've demonstrated 352 % improvement in click through rates with enterprise clients, which is incredible. ⁓ How should growth teams think about integratingAI agents into their existing marketing stack.Josh (32:21)that's a fantasticquestion. And that actually comes down to your own business. I actually have ⁓ a lot of thoughts here. marketing agents, agents in general, it's a very general topic, right? And so it's important to of like approach that from the right mindset and not just say like, here's, I'm not going to be prescriptive here because ultimately every business is different. Every workflow is different. First thing to kind of note is thatWe are approaching this new world where basically ⁓ you have to make sure it impacts the bottom line. That's really, really important. ⁓ You have to make sure that it gives you an edge in whatever you're implementing agent technology into. And there is starting to become this organizational mandate as a result. The CEO of Shopify, Tobi Ludke, he recently put out a memo in which he was saying, before asking for resources, people have to demonstratewhy they can't do what they're trying to do ⁓ using AI. And so it's starting to become a mandate. So it's good that you're asking this question. The tactics that I have for evaluating whether or not to incorporate an agent into your workflow, how and when to use agents, ⁓ the first thing is to take a systems thinking mindset ⁓ to the workflow you're trying to automate here. ⁓ This is a little bit fuzzy, butor fluffy, should say. you know, systems thinking is actually really, it's a really relevant thing to have. kind of, it's like, to me, it's this combination of AI ⁓ knowledge and knowing what the capabilities of these models are and these agents are. And then your domain knowledge, which in this case is marketing knowledge. And then finally, a general growth mindset. I know that's a fluffy term, but like having kind of that impetus to think about new ways of applying this stuff.And so the systems thinking that comes into this is the combination of those three things. More tactically for marketing, there are several areas where this is applicable. Paid media is a big one. Looking at how ads can be, you can create different variations of ads and then optimize them over time. And there are companies that are doing this and providing ⁓ tooling for this. Coframe is going to be doing this at some point soon. ⁓ There's companies like Icon and ⁓There's a bunch of them. Google and Meta are going to be doing themselves. There's conversion optimization for a website. That's of course what Coframe is doing. There's lifecycle marketing, emails, email campaign optimization. There's SEO, there's content operations, a bunch of stuff. The next tactic I have here is getting to know the capabilities of your AI colleagues. Trying to figure out where do we use certain models in what situations? For instance,Claude is really great at general coding. So is now the 03 in the sort of like GPT series from OpenAI. Gemini from Google is great at long context. And so you can put a bunch of different collateral into it and have it analyze it. So my call to action for the listeners here would be get to know the different models out there and try to figure outwhere are their limitations, where are their strengths. This is going to be evolving over time. So this is going to be really important to stay on top of. The next tactic I would have here is to prototype and see what's possible. You want to try to get your hands dirty and figure out what's going to show promise. ⁓ then just basically what you learn from prototyping, you should be able to have a sense for, OK, how do we apply this to my workflow and the agents that I'm trying to build?At that point, it's really important to make sure that you're building things with what are called evals, making sure things are, you ⁓ you're actually measuring quantitatively the outcomes that you want your agent to be able to deliver. ⁓ And at the point where you do that, you know, you're in a really good place. You have a closed loop and you're ⁓ able to, with some level of reliability, automate a workflow, which is an amazing thing. And that's, think, like I was saying earlier,the most promising part of the new AI world we're entering into.Mark Petruzzi (36:48)Excellent. All right, let's move us to the final topic here, and that's the future of marketing technology and growth engineering and how does this all come together for us? And the biggest question is, and this is gonna seem like I'm asking you to predict something that's 50 years in the future, because in this space, looking ahead even just 18 or 24 months is so difficult and the changes are happening daily, minute,minute by minute. But let's say we look at 18, 24 months, how do you see the convergence of AI and growth marketing evolving? And what should marketing leaders be one, for, and secondly, driving within their companies to allow that information and those new capabilities to be executed on as quickly as possible for them?Josh (37:42)That's a fantastic area. You know, it's a, it's a really great question. I have this, this article, um, which I think would be a good one to check out. If you're looking to dig deeper into this topic for the listeners at home, it's on this newsletter called every by Dan shipper. Uh, it's called the new science of growth marketing. And in it, what I try to talk through is this correlation between growth marketing and finance. Interestingly enough.So in finance, what we saw was previously, before the advent of computers and so on, people traded manually, traded stocks, bonds, other assets. And it was a very manual, very tedious process. It still is manual to an extent. People are certainly doing discretionary trading on their own. But what transformed finance in the 1980s and 90s and 2000s⁓ was the emergence of quant finance. So quant trading and using quantitative methods, computers, ⁓ to do algorithmic trading of these assets. And what made that possible for finance was that the problem that you're trying to solve, it wasn't a simple problem, but it had a simpler output. It was either, you know, predict a price orMark Petruzzi (38:46)Yeah.Josh (39:10)even simply a buy or sell indicator of a stock. Now the output for marketing is not something as simple as a price or a buy or sell. It is copy, is code, it is assets. ⁓ And until recently, that wasn't really possible to do with the models that we had at our disposal. But with the advent of generative AI, that is the native modality that AI is operating in.And so what we're starting to see, and we will, I think, increasingly see, at least what I say in the article, is that just as quant finance ⁓ revolutionized the financial industry, we are going to start to see this idea of quant experimentation and quant quantitative growth methods revolutionize growth and marketing, where you'll have these strategies that are autonomous to an extent, ⁓ executed by machines.being able to work 24 seven on your behalf and test things autonomously and make changes and personalize at a way deeper level than that was previously possible. And that's a really powerful thing because, know, to date it's been extremely tedious and time consuming to run these experiments. You require, you know, like an engineer and a designer and marketer and so on, just to get a single AB test out the door, can take weeks. What if it take minutes or hours?you know, or less, you know, so ⁓ we're starting to enter a world where continuous optimization is then possible, all the new superhuman capabilities that we talked about earlier. ⁓ And that is what I like to think of as quant growth or quant experimentation. And I go into a bit more detail into specific strategies ⁓ in the article, very high level strategies, know, nothing super profound, but ⁓ I think it's gonna be very, veryimpactful for the growth industry and for companies that use it.KK Anderson (41:14)So last question before we move on to our rapid fire ⁓ section. So what's going to be the highest value work for humans? Right?Josh (41:27)Yeah, so it's a great question.the answer to this one, at least I kind of just borrow from this similarly borrow from what we've seen in the quant industry, right? Where instead of actually performing the trades, humans are responsible for coming up with the strategies, you know, ⁓ we have now more professionals in the financial industry than we ever have. ⁓KK Anderson (41:46)Okay.Josh (41:53)despite a lot of those manual tasks being taken by machines. ⁓ Similarly with the invention of the steam engine and electricity. ⁓ Well, the steam engine took a lot of the manual effort out of ⁓ transportation. ⁓ But we have now seen an entire new industry built up that has given a lot of jobs in performing higher level work that involves steam engines or is involved in the creation of steam engines.There are a lot of such examples. So I think what we're going to end up seeing as applied to this industry is growth people, marketers, engineers alike, are going to have to focus less on the tedious work of writing the code, coming up with the specific assets, coming up with the specific analysis of the data and the results, and rather guiding the strategy for their businesses.I also think we're going to see an explosion of businesses overall. We're going to, people are going to be way more empowered to be solopreneurs and, you know, small businesses and entrepreneurs and do more and offer more with less. And so we're going to start to see just like more opportunities where growth can be applied. I do think that growth teams at large, large companies might shrink because a lot of the grunt work is going to be taken on by AI. But ⁓KK Anderson (43:00)Yeah.Josh (43:20)there's going to be a lot more opportunity for many, many more types of businesses out there to use these advanced growth tactics as well.Mark Petruzzi (43:28)And I just want to point out that that last question that KK presented was submitted by a bot, by a robot, because they want to know how they can leverage us now into working for them instead of the other way around. it's already happening. That was not from a human. OK, we're going to go rapid fire over the last three minutes or so here. This has been great, Josh. So thank you.KK Anderson (43:42)Hahaha! ⁓Josh (43:43)already happening. wow. That's amazing.Mark Petruzzi (43:57)So Josh, what was the first product or service you were ever responsible for selling?Josh (44:05)wow. That's a great question. It has nothing to do with my current industry, but it has all to do with who I am, which is music. I had a little jazz group back in high school and we made some albums and reinvested the proceeds back into the band and made recordings, more recordings and did little touring. So yeah, that was my first exposure to business.KK Anderson (44:14)That's right.Mark Petruzzi (44:28)So everything you touch is successful, right? Is that how it works, Justin?Josh (44:31)Definitely not, butI appreciate that.KK Anderson (44:37)Okay,who's your favorite CEO to follow?Josh (44:41)man,that's a, it's a great question. I'd have to say Eric Schmidt, ⁓ he's like next level, maybe the best operator in the whole world, ⁓ just insane story. And, ⁓ I've had the opportunity to learn some things from him directly and work with him through a couple of different things. And so, but I think he's awesome.Mark Petruzzi (45:02)Very cool. Okay, a tool other than CoFrame that every growth leader should be using.Josh (45:11)man. Well, I think it's really, really important to have a really solid sense of your data for sure. So some type of, some type of analytics platform, Amplitude's a really great one. know, Adobe analytics, ⁓ post-hoc, et cetera. I think that, you know, the more you have a sense of what's happening in your business, the more you're going to be able to improve it and measure, measure those outcomes.KK Anderson (45:39)Question, do you have to have one of those to be able to use CoFrame?Josh (45:42)No, no, we actually come with full data, you know, analytics included, but we do plug into these, these systems.KK Anderson (45:49)Okay, now for my favorite question. Advice that you would give your 21 year old self.Josh (45:55)that's a goodone. man. ⁓ Okay. So I think that what I would probably say is like, like basically hype is not the same as substance. You know, I've, I've, I've seen a lot of, a lot of hype in my career so far. ⁓ And, you know, easy come easy go. Like things will just like, there'll be bubbles, they'll collapse and there'll be things thatthat what you want to be doing is basically subtracting the noise to try to find the true signal and keep this level of groundedness to try to figure out what is truly valuable here and think from first principles what is going to be durable and sustain over time. And so I'd really urge myself, I guess, to really focus on the substance.Mark Petruzzi (46:45)Oh, I love that, Josh. And as a, know, as a reoccurring, you know, individual who's launched different companies, been CEO of multiple companies at this point, I love to have you, I love to hear you thinking about that in those terms. Because, you know, I have a lot of friends who have done the same from, you know, different company to the next and...they start doing it a few times at the CEO level and they start to think that's their job is to always drive that hype through the market. And even sometimes within their own organization, they think they need to have credibly positive energy in their business at all times. And that's not life as we know it. And ⁓ having that realistic approach is really impressive.Josh, thank you so much for taking the time with us. This was great and we're excited as we go along to learn more about Code Frame and see how we can leverage that into some of the work we do with clients.Josh (47:54)It's been a pleasure, Mark. Thanks so much for having me, Mark and KK. Really good to see you both.KK Anderson (47:54)Yeah, absolutely.Thank you, Josh.Mark Petruzzi (48:01)Perfect, all right. Thanks, all. Thanks, Josh. Thanks, KK. Cheers.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mike Milburn—former Chief Customer Officer at Salesforce and founding team member of Service Cloud—joins Mark Petruzzi and KK Anderson for a masterclass in aligning product and sales teams around a shared go-to-market mission.Drawing from his 15+ years at Salesforce, Mike shares hard-won frameworks for building product roadmaps that sales can actually sell, developing trust between CROs and CPOs, and scaling alignment across growth stages. This is a blueprint for leaders who want revenue-generating product strategy—not just internal harmony.What You’ll Learn:The Product–Sales Friction Point: How most teams mismanage this relationship and how to turn it into a revenue advantage.Revenue-Calorie Framework: Why Salesforce prioritized roadmap decisions by “calories” and how to balance innovation vs. renewals.V2MOM as a GTM Operating System: What the V2MOM framework taught Mike about prioritization, transparency, and shared accountability.From Anecdotes to Data: How to structure sales feedback into decision-ready inputs for product teams.Product + Sales = One Team: What world-class collaboration looks like—when sales leaders evangelize the roadmap and product leaders join customer conversations.Key Topics:CRO and CPO relationship-building strategiesTranslating sales objections into roadmap investmentThe role of customer success in roadmap prioritizationQuantifying “deal blockers” to influence productRunning effective board conversations around productHow “True to the Core” made Salesforce a customer-led companyScaling product-sales collaboration from startup to enterpriseGuest Spotlight: Mike MilburnMike Milburn is the former Chief Customer Officer at Salesforce and was part of the founding team of Service Cloud. Today, he serves as an advisor to multiple SaaS companies. His career centers on building GTM systems where product, sales, and customer success function as one growth engine.Resources & Mentions:Framework: V2MOM – Vision, Values, Methods, Obstacles, MetricsSalesforce Event: “True to the Core” session at DreamforceRecommended Book: Behind the Cloud by Marc BenioffOther Concepts: Revenue-calorie model, sales telemetry, deal blocker mapping🎧 Listen now and follow Selling the Cloud for more insights from GTM leaders building high-growth, cross-functional teams. Subscribe wherever you get your podcasts.Mark Petruzzi (00:03.044)Welcome to today's episode of Selling the Cloud podcast. We're thrilled today to welcome Mike Milburn, former chief customer officer and many other things at Salesforce for I believe 17 years and current advisor to some incredible technology companies as well, many of which are connected to the Salesforce ecosystem. So 15 years at Salesforce.during a very key time for the evolution of the firm. The transformation from true startup to enterprise giant that we all know and love today. When it comes down to it, what we'd like to cover today is a number of the frameworks that Mike has used to align product and sales team throughout his career and particularly through the Salesforce journey.Four themes we'll explore today. The product sales friction point, why most companies get this wrong, building revenue driven product roadmaps, something Salesforce always did a really good job with, probably mostly led by Mike. Go to market execution, when product and sales team need to move as one, and scaling product sales alignment.All right, let's jump on to topic one, the product sales friction point. Mike, you mentioned that product sales relationship is one of the most critical friction points for CROs, CEOs, and boards as well. What are the fundamental misunderstandings that typically create this tension?Mike Milburn (01:47.64)Thanks, Mark and KK. It's great to be here. I'm really glad that you guys are having this. I can't tell you how many times I've had this conversation in private. so having this conversation in public is just, it's a really neat thing and it's an honor to here. So congrats to that. So I guess I would just kind of like imagine the audience and I would imagine in any company that you're in.And that kind of water cooler, or maybe you're in a car or an airplane and you're having a conversation. And if you're on the sales team, you're talking about, man, I wish I had different products or better products or some sort of anxiety around the product side. And then if you go to the other side of the aisle, imagine that same conversation, the door shuts in the product meeting and you're wondering why you can't sell it. And if you sort of put yourself into that.mode of listening and that mode of parenting those organizations, that's a pretty frequent conversation. So I think that's the place to start, is like an acknowledgement from this virtual audience, how many of you guys have been in that position of hearing friction or anxiety from both the sales side to the product side or the product scene to the sales side.KK Anderson (03:07.463)So that's an excellent point. So when you arrive, let's say you arrive to a new company as a CRO and you discover, let's say that the product is difficult to sell. How do you approach that conversation with the product leadership team and with your board without just saying, hey guys, this product sucks, we can't sell it.Mike Milburn (03:32.034)Yeah. So I think first of all, let's start with the relationships between the CPO and the CRO. And let's start with if you're the CRO identifying the CPO as one of your critical stakeholders to your success. Obviously you're reporting into probably the COO or the CEO of the company, depending on the size and the maturity, but have you properly identified the product leader as one of the key stakeholders kind of colloquial?Locally, I would say are they on your Christmas card list? Have you earned the right to build a relationship that allows you to send a Christmas card to the chief product officer? And so where I start that relationship is really If I'm the CRO, I want to meet the head of product. I want to understand their tenure at the company I want to understand their motivations and I want to understand the successes and failures that I've had with with my predecessorsif you're a new CRO, then there was probably somebody before you. And so what were the things that they did right? And what were the things that they did wrong? Typically where that goes is again, relationships take time to build. So we're sort of jumping into how do you build a trusted relationship with them? You're to have to deliver, but ultimately you want to give the chief product officer the, the trust that you're going to bring them.real-time feedback from the field, you're gonna sell the products that are available, and you're gonna help bring them key insights from customers and partners on what are the things that they should be building. And we're gonna touch on that in a second, but those are really the key things, being able to sell what's available, being able to bring them trusted information about what's going on in the field, and help bring them guidance about where the market is going.Mark Petruzzi (05:30.637)So Mike, tell us about how you built a methodology for navigating this relationship at Salesforce. And how do you make this process kind of board ready and productive and collaborative rather than adversarial?Mike Milburn (05:51.33)Yeah, great question, Mark. So as a, first of all, as a backdrop, you know, I had the immense honor of being one of the guys that started Service Cloud on the founding team for Service Cloud at Salesforce. And of course, Service Cloud is now over $10 billion business inside of Salesforce. And I was there on day one when we booked the first, you know, 30 or 40K order way back in the early 2000s. So that's the framework that I'm going to use. Second is,I think all the credit really goes to Mark and Parker, Mark Benioff and Parker Harris. They created a framework that we inherited, we modified and we enhanced. And that's what I'm going to talk about today. So the way that I think about it, Mark, is what we did in the early days of Salesforce is let's say that you had unit, I don't know, let's say you had 10 calories to burn on product.And let's just for a moment say that all calories are equal, right? We would look at those and we would say, how many those calories are you gonna spend on new or innovation things? And how many products are you, or how many calories are you gonna spend on customer success? And so for argument's sake, let's just take 10 calories. And those calories really translate to resources or funding. But if I had 10 calories,And I devote them all towards the front of the house or all towards sales. And that meant that I was going to create some debt on the renewal side or on the customer success side. And conversely, if I spent all 10 calories and I didn't create any new innovation, I might suffer on sales, but I would really be strong in customer success or renewals. So once you go away from the teeter totter,And you go, well, the natural instinct is to peanut butter and to do five on each, let's say in this, in this hypothetical example. And I think what Parker really did was challenge that idea of peanut buttering and say, let's be really, really thoughtful, deliberate and challenging. And maybe you spent seven calories on sales and only three on customer success or vice versa.Mike Milburn (08:10.134)And let's really think about the trade-offs and let's make those data driven revenue generating success oriented decisions. And so where we took that team was we would take the product roadmap that was based off of that framework. And we would go to the sales leadership and we'd say, can you sell this? And the sales leadership would sign up to sell that. And I think, you know, that, conversation that we started with was.can the product team create a roadmap that the sales team stands behind? And if you imagine that conversation, that's a very delicate conversation. The sales team has to take accountability for, if you're gonna go build something, then the sales team needs to be the one to stand up and say, if you build that, I'm gonna go sell it. There's always problems that come up with pricing or packaging or competition or any one of the various things that happen in the real life world, but.The head of products job is to create a roadmap that is innovative and can support both sales and customer success, which I'm directly calling renewals, usage and adoption. So I think that was the really neat part is once we made a data driven decision, we could then look at our roadmap and say, if I remove one calories from sales, what are the sales impacts?And what are the renewal impacts? And once you have that, the leaders of sales, success and product can all come together and they make the right decisions for the KPIs of the team. And of course that's where the CEO and the ELT come into play. But that becomes a really fun conversation when you have it, you know, when you have it laid out like that, like for this quarter or these two quarters, let's over rotate to sales. And yeah, we might create some customer success issues.If everyone's on the same page and there's no blame game come when the, when the customers incur issues or problems, there's no finger pointing. It's we all made this decision together. And conversely, if you make a decision to go renew all your customers, then that's going to have a lot of benefits and then you might have some, some, sales friction. So it's really creating that alignment and transparency that I was really lucky to be a part of and, mature that process.Mark Petruzzi (10:29.315)So Mike, before we go into our next question, I'm going to open this up a little more strategically. How much did the approach that Mark drove right from the beginning of beat a mom? How much did that get into some of this? Is the methodology that you're talking about building, is it tied to beat a mom or to just kind of work in and integrate on its own along the way?Mike Milburn (10:58.828)Yeah, great question, Mark. So I think of the V2Mom is really a corporate operating plan. And, you know, I've got to be candid and say, think when I first joined and I was baptized in the V2Mom process, I think I wasn't quite on board with how important it was to a company. After a couple of years, I guess I would go back and restate that and say the V2Mom was one of the most important things that Salesforce has as an asset.And it's one of the most important things that I learned. And it's one piece of advice that I've given and driven to any company that I've been lucky enough to work with is the essence of the V2Mom is a corporate operating plan that the exec team creates and they vote on together. And it decides the company's vision, values, methods, obstacles, and metrics. Essentially, what is the operating plan? And if you do it every year, then you're allowed to pivot and change at the speed of business, no matter what size company you are.So think it's incredibly modern. The relationship between the V2Mom and the product roadmap is really simple. If the number one V2Mom is growth, and let's say growth means sales and sales is over customer success, then you should be allowed to spend more of your product calories making products that the sales team wants you to sell. If the V2Mom is customer success is number one, thenyou know, voted on that by the exec team, then you might change the priorities and saying, let's spend more calories together, making products, goods and services that help renewability. So the relationship between the V2 mom, the product roadmap, the sales leadership, the success leadership is the success leadership is it's all part of the exact same formula that drives the corporate operating plan.KK Anderson (12:56.199)And so where like what role do you see the CEO playing out all of this kind of? Facilitating it all you know running them running the balanceMike Milburn (13:06.606)Yeah. So, you we were pretty lucky. We had, you know, we had the legendary Mark Benioff running on that show. And what Mark enabled us to do was he empowered us to create a forum where you're allowed to have a healthy conversation about the VT mom. And I vividly remember, I mean, so many of these meetings all kind of blur together because they were 15, 20 years ago, but I remember somebody in the company standing up and saying, I don't agree with this.KK Anderson (13:11.558)Yeah.Mike Milburn (13:33.13)Maybe the person was an individual contributor, maybe they were an influencer, but when they challenged it, was somebody in the Roman Senate saying, hey, you guys built this, I don't agree with it. And that transparency and accountability was really important. Mark drove that culture. Everyone owned the V2 Mom. Number two was you were allowed to deputize other people for your V2 Mom.So let me make up a little hypothetical situation here. Let's say that Mark is, let's pretend that I'm the CEO, Mark's the head of sales and KK, you're the head of products. And I would say, know, is a number one priority that we sell more and everyone goes, yeah. Well, if Mark's job is the head of sales and your job is the head of product, then you inherit those priorities. And so that's where you can't be parochial or you can't be political. You've got to do the right thing.on the V2Mom for everyone else. And it was more than a faux pas to stand up in a V2Mom meeting and be self-serving. You had to use the V2Mom as the doctrine on how you were going to operate your organization. And you were allowed to deputize other folks. Again, part of the V2Mom conversation that I didn't say earlier was it drives success in a matrix organization.KK Anderson (15:00.006)youMike Milburn (15:00.066)There's some organizations that are more top-down, more command and control, maybe more military or more organizations. And a lot of modern organizations, you know, the CPO and the CRO might not ever report into the same person. They might be dotted lines into the CEO or they might, their peers, right? And so the V2 mom became almost navigate the V2 mom without having to go to the CEO.KK Anderson (15:06.311)youMike Milburn (15:30.124)And when you're empowered as as a, an executive in a company to navigate that without having to go and ask permission or to have somebody navigate those rules. you tend to, you tend to come to the right decision.KK Anderson (15:44.423)You know, it's ironic. Mark and I are sitting here nodding our heads thinking, this is exactly what AGS needed to hear right now. Right? You know, me, every company is no matter the size, is they're navigating growth and navigating our, you know, everything. It's so important. And for the audience who's probably like Googling what is V2Mom right now, can you give an explanation of Salesforce's framework that they've made famous?Mark Petruzzi (15:51.939)I that guy.Mike Milburn (15:52.11)ThanksMike Milburn (15:55.841)Really?Mike Milburn (16:11.586)Yep, absolutely. Okay. So it's called the V2 mom and it stands for vision values, methods, obstacles, and metrics. And so the way that I think about it is, is the vision and values or things that the exec team created and they would socialize for approval and stakeholder value with the company. So that's the first, the V2 part. The mom part is where the work gets done. The methods, obstacles, and metrics.And so you can YouTube V2Mom. You see a lot of companies have borrowed it, but essentially there's about 10 V2Mom methods. And those could be things like say which product has a higher priority. It could mean revenue. It could mean culture. remember when, when one year when we were really going against Siebel and there was a fear that we would turn into Siebel. I think the number one method on the V2Mom was culture.And so that trumped growth. So the M, the first M is methods. That's the kind of how, then the obstacles are what are the things that are going get in the way. And there's a one-to-one ratio between obstacles and methods. And then the measurements are how are you going to get measured on whatever method you wanted? And the, what the execs team's job was to create all the methods and then prioritize those.And one of the really neat moments that I saw happen over and over again was a public discussion on which method is more important. And it sounds like so innocuous. It sounds so easy. But if you were to say, what's more important sales or success? That's a hard one. Cause the more you sell, the more you have to renew, the more you renew, the easier sales get and the more references you get. Which is more important, partnership growth versuscreating a brand. Geez, Salesforce has created an amazing brand. It took time to do that, which is more important. Employee success or creating a great dream force, which is more important, having a great dream force or having 10 events locally or throughout the geos. And so once you sort of create that framework to have healthy discussion, thenMike Milburn (18:35.478)then you kind of get everybody on the same page. So it's a corporate operating plan for the modern SaaS company.Mark Petruzzi (18:42.711)Yeah, and what I love about all of that, is you kind of ties me back to what you said at the beginning and that this calorie breakdown perspective that when you look at it that way, and very few companies do, right? Very few CEOs do. Most CEOs kind of come in to these QBR meetings or wherever they're addressing a team and they're like, know, sales, sales, sales, we need to grow, we need to grow.And then they turn around and they're like, then they start talking about customer success. And they're like, well, customer success has to be perfect in this way and have to do that. But it's not. It is a zero sum game, even in a fast growing company. the process of being mature and analyzing, hey, if we want to grow a little faster,we're going to have to do some things that are going to be a trade off on customer success. Or if we really, really need to make sure that customer success for the next couple quarters is, you know, that our retention is off the charts, then we have to slow down and accept a couple percentage points less on our growth. That doesn't happen often in companies. And I love the way you're positioning it thus far. Let's kick into topic two.Building revenue driven product roadmaps. KK, why don't you lead us the first question there.KK Anderson (20:11.239)So I'm always going to start with sales because that's my passion. And so when we think about SaaS organizations and our clients, how do you ensure that sales feedback actually influences the product roadmap? That's where I think one of the greatest breakdowns is. And honestly,It's that frontline seller who's having a lot of these conversations and the solution architects. That's the feedback that we need to go up. Right. So how do you do that?Mike Milburn (20:45.858)Yep.So this is the, I'd like everybody on the podcast to kind of close your eyes and imagine this meeting. You're in a QBR, you're in your exec meeting and it's your reporting on your results for the quarter. You're getting ready for your next board meeting of any size and scope. And you're looking at, you're the CRO and you're looking at your results.You're looking at your feature pipeline. You're looking at amount of head count and you're painting a vision for the company on where you're going to go. And what if you had a slide that, that, that said for every opportunity, here's the quantifiable problems that we're facing in the field. In other words, you know, you just kind of invoke this frontline sales and then there's,There's RVPs and they go AVPs and by the time it gets up to the CRO, how do you get feedback? And the image that I'm trying to conjure up is, and this might sound low level, but let's start here to get to the high level. What if on every opportunity there was a way to capture objections? And it wasn't a free text field. It was a data driven format. Is it pricing? it, is it competitive? Is it a feature or function?KK Anderson (21:48.027)Uh-huh.Mike Milburn (22:13.654)And that opportunity has a dollar sign value associated to it. So if all the reps in the field were responsible for adding in all of their objections at the, at the infantry level, at the deal level, and the CRO could run a report and say, here's the number of opportunities that I'm facing where I have pricing as a problem. And here's the accumulated dollar sign that is impacted.Or I'm facing a feature and function gap, or I'm facing a critical piece of functionality that will require &A. Whatever it is, if you can associate deal friction with the number of deals and the amount of ARR or the amount of revenue that's associated, now you're having an exact conversation. It's not emotional. You're saying I've got X number of dollars. I'm going to choose 50 million or 5 million or 5KK Anderson (23:05.991)Mm-hmm.Mike Milburn (23:11.074)beans, whatever vector you want. And here is the data behind it that is causing me friction. Then the product organization or the partner organization or any other organization, they can ask you questions about it. They can second guess the quality of the data or what some of it means, but it's really hard to have. It's really easy to have a great conversation. If you come to that meeting with, Hey guys, our second half pipeline.or X amount of revenue. And here are the three biggest blockers we're having to make the second half of the year. We need a flex capacitor. We need more aggressive POC pricing. And we'd really like exec sponsorship on the following 10 deals because we're having a lot of competitive pressure. Now it becomes a fulfillment opportunity for the rest of exec team to rally behind you instead of that familiar pattern ofwhat's happening with the deals and could have, should have, would have kind of that soft squishy. If the CRO can bring concrete examples of what they need to that meeting, then you're getting this CPO on board with you to build the right things to deliver more revenue.Mark Petruzzi (24:30.253)really good points there, Mike. So, okay, so how do you do, know, companies are getting customer requests, customer feedback every minute of every day. How do you determine, just how do you accept that into the process? How do you get that data into your system first? And then...What are the criteria that should help you really drive and make it affect product decisions that will move revenue versus what may make one client feel good or even what may make the company feel good? Like we may look at this and say, yeah, this is an important one. This is important. But at end of the day, if it's not going to move revenue, it's got to be in a different place in that product roadmap.How have you done such a great job with that throughout your entire career?Mike Milburn (25:28.664)You try and make the process easy, Mark. You try and make it transparent and you try to remove some of the black box. First of all, you know, the, the axiom of feedback as a gift is, is not just true if you're not getting feedback, like you're doing something very, very wrong. So let's just start with the sales side. Do you have a system that can quantify from the SEs and the sales team, the blockers that are getting in the way to sell the deal?Do you have that? That is a binary yes or no question. And then can you summarize that by segment or geo? So part of what you implied by that question is if I have a sales team that's selling an SMB in North America and an enterprise team that is selling in Europe and they're asking for things, how do you distill those two things into a criteria?that creates action? And the simple answer is revenue. So let's just make up some, let's just make up something to talk about. Let's say your SMB team has 20 deals, each valued at $1. Right? And that's in North America, that's $20. But your EMEA team, it wants something that is $100, but there's only one deal.And you look at everyone and let's assume that to build those two products is the same amount of calories. Cause when you get different calories, then all of a sudden you're invoking a different vector. But first of all, can you have that conversation? This is no different than having a conversation with your family about where to go on vacation. Do you go on two little vacations and for a couple of days, you'd be on one big vacation. The world's navigated that for a long time, but now all of a sudden the sales conversation is difficult with your product team.As a CRO, can you articulate the number of deals by segment and exactly what the blockers are? Yes or no. If you do not have that mechanism in place, then I would encourage you to use a CRM like Salesforce to create those objects. And you simply, it's part of your sales operations criteria. Every deal gets a blockers or pathways and it's not a free text.Mike Milburn (27:49.12)It is the top lockers and you're able to, sales ops can help you navigate, and, and run those reports. So that's the first side of it. Then, then the second side of it is as an exec team, do you have the framework to be able to decide and have that conversation? I think this is where a lot of these conversations stall is the fear that you have been building the wrong things or, or are you listening in the right way? Maybe.You know, I just said it in a very blunt way, but if you're going to get to transparency, you've got to be able to listen and then you've got to be able to make roadmap decisions based off it. So, you know, I would say, regardless of what's happened in the past from the product and sales organizations, this is your opportunity to reset. Listen to what the sales team is telling you and then build a roadmap that addresses those. And if you're not going to address it, then just like, just like we talked about earlier, say.we're gonna make these other decisions. And if you keep seeing this deal friction, we're sympathizing with you and we're not ignoring it. On the reverse side, on the customer success side, it's anyone that's a customer needs to be able to submit the feedback into your organization to tell you what is causing them to stop or renewal. And part of the unspoken hard part here is time.A product roadmap usually takes a year to effect, which ironically is why Salesforce's roadmap is three RR was three RR three releases a year. So if you're going to get something into the roadmap, it might take you three releases to get that through the system. So you've got to have your radar out both on the sales and server sales and success side long enough to listen and impact that roadmap. The, so that's the time vector then.That's all systematic and programmatic. And again, you should be able to report that to the CEO. You should be able to report that to the board. Then you have the live functions. And so this is actually a really neat story, but if you were to go on YouTube and you go true to the core, one of the most profound sessions that occurred, that occurs every dream force is usually it's Parker led, but somebody on the product team gets up.Mike Milburn (30:14.578)And the audience can range from five to 10,000 people. And they lead a conversation of, we being authentic with our roadmap? And this is a really neat conversation because there is no sales team. There's no success team. It's just the customer and Salesforce on stage. And what Parker does a great job of it is navigating. Every customer is going to have wants and needs. Everyone's got their individual requirements, et cetera.And those fit either in, no, we're not going to do that. It's the wrong thing for us to build. We're thinking about it or here's where it's going to be built. And over time, what I think is really neat about true to the core is it shows Salesforce commitment to listening. It shows the customer's commitment towards giving that feedback. And I don't have any data or stats on it, but I would guess that, you know,The reason why, the reason why that's so effective is the customers feel that their voice matters. And so if you combine both those things and you have sales radar and sales intelligence telling you what is necessary to drive a sale. And then you have customer intelligence coming through and saying, what do you intend to build?And then you have something like true to the core, it could be exec round tables, or it could be dinners or whatever mechanism the company feels comfortable. Dreamforce is a very unique opportunity. What you see there is sort of like checks and balances, sort of like the foundation of the United States, right? We've got three different, bodies that help govern the United States. You have the sales team giving you feedback, the success team giving you feedback, and then you have actual customers. You take all three of those pieces of feedback and you look at the roadmap and you should be able to say.KK Anderson (31:51.495)with customers.Mike Milburn (31:56.096)Am I building the right things together?KK Anderson (31:59.463)And I wonder how often what the customer says is different in fact than the othersMike Milburn (32:06.338)You know, it happens. mean, I remember some very contentious, true to the core sessions and you kind of have to be candid and say, is this the right thing for the company to build? mean, the more customers you get, the more the need, do the needs of the many outweigh the needs of the few or the needs of the individual. Also here is the difference between like core product and customizable. So it's one thing for customer to say, I want this turnkey.KK Anderson (32:28.977)Mm-hmm.Mike Milburn (32:32.918)It's another thing to say you could do this and here's how you would do that. My opinion is that customers want transparency. And just because a customer wants something doesn't mean they should build it, but they deserve to be, they deserve to be heard.KK Anderson (32:47.894)I have a question. Just real quick, Mark, if I could, you talk about the three releases a year and that's... It feels like nowadays, that's just... Everyone wants something in the moment. They want real time. They want changes faster. want... I mean, I know it's not really a part of this topic per se, but I guess it kind of is. It's product roadmap and it's more...Mark Petruzzi (32:48.724)You know what's in...KK Anderson (33:15.215)in a real time, faster environment? Like how is the speed of business changing how SaaS companies are releasing and updating?Mike Milburn (33:27.234)Yeah. So this is a great topic. mean, I think we pioneered three releases a day, you know, almost 20 years ago. I guess the way I think about what Salesforce did with 3RR was it gave you some ability to have certainty to what is coming next, what you believe is coming, and then what you believe is coming a little bit longer out. So you sort of know directionally what's happening and it was transparent.The, I felt that same anxiety many times of customers like, want this today and I want it today. I think that's tempered or weathered with building in the right way, building trust, building safety, building security. Some things take more than a day or a week or a month to build. The important thing is that does the company know where, does the customer know where you stand as an organization? Are you being heard?And are you delivering on it? So, you know, we, I personally felt after, after being so many, after being so many, ABCs, executive briefing sessions or customer sessions or dream forces that the customer's desire to have it today is that was less important than Salesforce being able to listen and being able to build the right data driven machinery.It also worked where if a customer said, I want X and nobody had ever heard it, you could tell the customer, you know what? You're the only customer that we've ever heard that's asked for this. And that worked in our favor a lot of times too. So if you speed that up today and people want, know, just in time releases or they want a release every two days, I don't think it changes the equation too much. Can you quantify what is being necessary in order to sell more products?Can you quantify what is being used to renew more products? And if you can deliver it on a frequency of three times a year, five times a year, once a month, once a day, that's great. But I don't think it changes the overall calculus of, you listening to your sales team? Are you listening to your success team? Are you listening to your renewals team? are you, Ergo, you listening to your customers?Mark Petruzzi (35:49.348)Excellent. All right, let's go to our third topic here and go to market execution and when product and sales teams move as one. Tell us a little bit about what world class looks like around product, sales, execution. And when we use that term move as one, I've heard you use that term and that's why I'm asking it.What does it mean for product and sales to move as one?Mike Milburn (36:19.788)Yeah. So.Mike Milburn (36:24.5)One of the great parts that I remember about our internal QBRs at Salesforce was having the sales team kick off or the sales team wrap up one of my product conversations. And imagine your CRO standing up and saying, I'm not the chief product officer.Or I'm not heading up product, but I'm excited about the roadmap and here's why I'm excited. I'm going to go sell this because I believe in it. Now, all of a sudden you're showing alignment with your, with your critical sales component. And I think a lot of the internal meetings turn into sales is the sales job. Product is the product job and everyone just kind of goes off into their silos. So it starts with that message. Does the head of sales.Can they deliver the product roadmap? Can the head of sales demo the product? And this is something that I just find really, really unique and interesting, but I mean, I think it's still the case today that almost every executive at Salesforce is responsible for demoing their product. And there's products that it doesn't make sense and there's really technical and I'm sure we can find corner cases, but it's pretty powerful when the head of sales is able to...KK Anderson (37:18.897)Alright.Mike Milburn (37:43.064)demo in some capacity, even if it's not the world's greatest demo. So I think those two things are one and two. Three is almost no airspace between the roadmap and the sales team. We've touched on it all throughout this conversation, Mark, but you should never ever hear from any sales team. man, I wish our roadmap was different. And I think you hear a lot of that kind of in the background or hallway conversations or exit interviews or.Maybe I'm linked in. Sometimes you hear a lot of that. And conversely, from the product team, selling is hard. And so when you involve the product team in selling and you start to see the art of selling and the science of selling, you're going to see a lot of of sympathies and a lot of energies, know, timely today. Just today, I saw.a CRO for one of the companies I led, he left one company and went to a new company. And when you see the product team respond to that and saying, you're going to do great, John, keep going, we loved working with you. I think that's the job of a CRO is to build those relationships that maybe said a different way. If a CRO is interviewing for their next job,Why wouldn't the chief product officer be one of their key endorse ease or endorsements? That would be a true testimony.KK Anderson (39:12.455)Yeah, it really would. And, you know, take the CMO, the CPO and everybody. what's your, we have recently recorded a podcast with Kathy Minter and she talked a lot about the concept of the unified CRO and having sort of one leader that is overseeing marketing, overseeing product, overseeing customer success and in that way, rather than.know, silent. What are your thoughts around that? Some of what you just said had me thinking.Mike Milburn (39:48.364)Yeah, I think there's some really exciting, I think there's been some, I think there's really exciting new roles that have been created both from CEOs and CROs, you know, and I think the CRO that is just revenue generating or just sales generating, think, I mean, first of all, it's an incredible job with a lot of responsibility and a lot of accountability.But the inputs for that are things like marketing and branding, top of the funnel, the creation of pipeline. So if we're able to understand and navigate brand and marketing, then that's almost a next generation CRO leader. Same thing with system engineering. I've seen customer success fall in there. So it really depends on kind of the company and the investors and kind of the...Also the candidate and the kind of role behind it. mean, at Salesforce, if you look at the current organization, it would be really bad form if you were a sales leader and you couldn't articulate the product or you couldn't articulate the message. Salesforce is lucky. 25 years later, everyone's on brand, everyone's on message. They have the enablement departments to go through that. So I think part of what you're asking, KK, is like you haveYou have smaller companies, medium companies, bigger companies. You have all these different sizes of companies. Then you have private equity investors. And I think this is also an important point that, you know, in the in kind of the previous model, when companies were publicly traded or that was your goal is to IPO and be publicly traded company. Who was your accountable? Who is your accountable stakeholder? Wall Street, the stock price, right?Now with private equity, they have a different set of goals, a different set of goals and a different timeframe for that. So what is the organizational structure that's going to drive value creation? And so I think you're seeing some consolidation in some of those roles, which is really exciting.Mark Petruzzi (41:59.556)And Mike, think you just set up our next podcast together and I don't think we've ever brought you by me back super fast, even though we've had amazing guests along the way. But I think we have to have a discussion after this about getting you back in in the next few weeks and talking and going more deeply into that private equity, private equity and sales, private equity and how that affects strategy within.All these companies that you work with and and we do KK myself as well Yes, we're running lower on time here, but I'd like to get into topic for scaling product sales alignment frameworks for high growth organizations and I think the the core item here is when you when you scale from early stage startup to enterpriseHow does this product sales relationship need to evolve? And how do you make that work? Because we all know these early stage companies of today are going to be the sales force of 2030. So, or at least a couple of them are. Not many, but a couple. And how do you navigate in each environment to get to that full scalability?Mike Milburn (43:24.096)Yeah, great question, Mark. you know, with all the turnover, all the growth and all the pace and speed that the tech ecosystem is in, here's a couple pieces of guidance. if you're the CRO and there was an impromptu board meeting, could you articulate the product roadmap and give your editorial and a data-driven decision on why it's good or conversely why it's bad?Not subjective, not your opinion, but can you give a data-driven, supportable articulation of the product roadmap that, you know, that can you articulate that? That's thing one. Thing two is, are you listening to the customers in your, again, your sales teams are spending all of their time with customers. Are you bringing the product organizationcritical information about the customers buying decisions, their needs, their wants, and are you giving, are you helping another organization build the right roadmap? Number three is, have you done, here's a litmus test one. Have you done a product tour with your top customers and your CPO? Nothing will flush out a correct alignment.or an incorrect alignment better than a dinner or lunch or breakfast with 10 customers, head of sales and the head of product. There's nowhere to go. The door shuts. They start asking questions. What about this? How does this work? Can you have you done that before? And so I think those are three things. If I had to invoke a fourth one, it would be imagine your board meeting and reverse it.Imagine presenting to either your private equity investors or the public counsel and imagine talking about the product roadmap and your alignment with your CPO. That's, think, what your job is as CRO is to build that alignment and build that trust.KK Anderson (45:30.449)So when you were in the beginnings of Service Cloud and you were there with a front row seat, what, any stories come to mind around how that scale and what that experience was like?Mike Milburn (45:40.268)Yeah. I think I shared this earlier. The first meeting I had when I was the GM, was terrified. I thought I was responsible for innovation and I had to figure out all this stuff. I was very, very intimidated by that opportunity. Parker leaned over and he made it just real normal. goes, just listen to what they say. Just listen.And I listened to the sales team talk about, you know, here's the size of the opportunities. Here's the data coming. Here's the telemetry coming out of sales. And then I listened to the telemetry coming out of success. And the picture that came out of that was maybe it was 80%. Right. It was let's build this to drive more sales. Let's build this to build, to help do success. And I didn't have enough calories to, to, to do everything. So then I asked for help and it was, peer group.How would you slice this? Would you do 80, 20, 20, 80, 50, 50, 70, 30? And I navigated that success together. And eventually it was the head of sales who became incredibly supportive of my roadmap in service cloud, which led to growth. And so the head of sales became one of our biggest advocates. so I think that story, KK, kind of, you know, while it was...very, very intimidating and I had a of anxiety going to that meeting. It's sort of, reflect on that and Parker was exactly right. If you listen to what the sales team is providing in data driven organization, then the roadmap becomes almost a fulfillment exercise of how are you going to deliver that in the shortest amount of time? And the innovation is going to come from your product and engineering organizations on how you're going to fulfill the most amount of those things in the shortest amount of time.Mark Petruzzi (47:35.232)Excellent. All right, let's jump into our rapid fire segment here because I can't wait to hear some of these here from your perspective. So, you you're not a CRO. know, that's not kind of not your core, even though you've done so many amazing things over your career. So I guess this question becomes, you know, when in your career have you been asked to sell and what what product or servicewas the first one you've ever really got your hands around.Mike Milburn (48:09.506)Yeah. So I've carried a bag. Actually, Mark, I've been responsible. I've never carried a bag from an AE perspective, but I've been responsible for revenue four or five times in my career. And believe it or not, the first is going back to Salesforce. At a matrix organization, I had no salespeople reporting to me and I had all the accountability of revenue. So I had to stand up in front of Mark and team and the board and, and, and, and announce that. So.That was really the first one. And then every company since then, I've had some relationship, either direct or indirect, with the ownership of revenue.KK Anderson (48:50.983)Okay, who is your favorite, let's say CEO or C-level business mentor to follow?Mike Milburn (48:59.34)Yeah. So I think, so first of all, I keep an internal board of directors. And for me, what my internal board and my internal mentor do is, is they allow me to be accountable to people that I value. And one of the sales leaders that was at Salesforce, that was running one third of the company for a large majority of that time was a gentleman named Dan Del Degan, affectionately known as Triple D.And, Dan came out of Oracle and then was it hugely influential in the growth of Salesforce. Dan later on, joined Greg Buchholz, the founder and CEO of Spring CM and Dan became the president and they sold Spring to DocuSign. Dan is probably the, gentleman that I count as my chairman of my board to, to hold myself accountable, butI think the way that he operates in his value systems, a sales oriented to the topic of this conversation, a sales oriented CEO, I count Dan the top of that list.Mark Petruzzi (50:03.203)Excellent. So yeah, what about a tool that every product leader, well, let's do two of them here. Since you've managed these in a dotted line way, you're responsible for this revenue, you get to see the good, bad, and the ugly, and you get to see it from a slightly different vantage point than if you were.a CRO managing that team day to day, which I think is going to give you even better insights to these questions. So what tool would you recommend every sales leader use to ensure they are aligned with the organization? And then is it any different for a product leader, any different recommendations there as well?Mike Milburn (50:48.578)Yeah. So I had the, I had the opportunity to build these tools. actually the first company I left after Salesforce was Salsify and we built both of these tools natively mark. chose Salesforce for those things. as a, as a platform, on the, on the sales side, think building the data model to be able to support what is sales need. I think it makes sense to build natively on Salesforce. It's close to the opportunity. It's close to.leads opportunities, close one, time in sales stage, all of that makes it very, very simple. On the reverse side, it's really about usage and adoption. So, you know, there's a number of enterprise tools. I don't think I'm wedded. don't have a favorite, but what I want to know as CPO is who's using the products and what does usage and adoption look like?from a telemetry standpoint on a good customer and what does it look like on a bad customer? So I almost think about like, I want the customer's name redacted and I wanna see usage and adoption and I wanna see those trends and I wanna see what's working and what's not working. Then I wanna start asking questions. So every product has got their own internal telemetry tools.I'm not wedded to any of them, but I really believe in usage and adoption to drive the customer success product roadmap.KK Anderson (52:23.079)Nice. Okay Mike, what advice would you give your 21 year old self?Mike Milburn (52:30.95)I would give the advice that if I could imagine the number one relationship to build, would be the relationship between sales and products and never ever have a conversation that sounded or looked parochial about. wish sales did something different. I wish services did something different. I think there's a wonderful skill of empathy. And if you're a product person and empathize how hard it is to carry a bag and you'refamily's livelihood is dependent on you selling something in some frequency, and you reverse that from a sales position, understand how hard it is to ship and QA and deliver products. I think it's the empathy between sales and service, sales and product, I think is just something I wish I'd spent more time on earlier in my career.Mark Petruzzi (53:19.649)I mean, Mike, isn't it just the kind of the secrets of life, you know, having that that empathy in every situation and anybody you work with or coordinate with from a business or personal perspective. So I love the way you just described that. All right, let's close up on.Let's just say this from a product manager, a product manager perspective, somebody who is the CPO taking that role for the first time. Are there any books that can give a little bit of the tricks in the trade that you've read or do you just need to get the work and write that so we all have that insight?Mike Milburn (54:01.41)You know, it's a great question. The one that comes to mind is actually Mark's first book. I think it was Behind the Cloud. And it just boils it down into such, from what I remember, it's been a couple of years since I read it, Mark, but it just boils it down into the raw distilling of what it takes to create a product and get people to sell it, use it, and adopt it. And, you know, in those early days, in the first five to 10 years of Salesforce,We did so much evangelizing, so much listening, but there was so much passion behind it. And so I think that's probably a pretty good place to start.Mark Petruzzi (54:39.615)Excellent. Well, we have kept you a minute more than we asked so we want to keep you on schedule for your day But Mike, this is such an honor. It was so great to to dive deep into some of these subjects with you So great that I feel like we should do it again, but we'll figure that one out from hereKK Anderson (54:56.423)ThankMike Milburn (54:58.36)Sounds good, guys. We'll talk to you soon. Great to be here. Cheers. Bye-bye.KK Anderson (55:00.313)Thanks Mike.Mark Petruzzi (55:00.727)All the best.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mike Milburn—former Chief Customer Officer at Salesforce and founding team member of Service Cloud—joins Mark Petruzzi and KK Anderson for a masterclass in aligning product and sales teams around a shared go-to-market mission.Drawing from his 15+ years at Salesforce, Mike shares hard-won frameworks for building product roadmaps that sales can actually sell, developing trust between CROs and CPOs, and scaling alignment across growth stages. This is a blueprint for leaders who want revenue-generating product strategy—not just internal harmony.What You’ll Learn:The Product–Sales Friction Point: How most teams mismanage this relationship and how to turn it into a revenue advantage.Revenue-Calorie Framework: Why Salesforce prioritized roadmap decisions by “calories” and how to balance innovation vs. renewals.V2MOM as a GTM Operating System: What the V2MOM framework taught Mike about prioritization, transparency, and shared accountability.From Anecdotes to Data: How to structure sales feedback into decision-ready inputs for product teams.Product + Sales = One Team: What world-class collaboration looks like—when sales leaders evangelize the roadmap and product leaders join customer conversations.Key Topics:CRO and CPO relationship-building strategiesTranslating sales objections into roadmap investmentThe role of customer success in roadmap prioritizationQuantifying “deal blockers” to influence productRunning effective board conversations around productHow “True to the Core” made Salesforce a customer-led companyScaling product-sales collaboration from startup to enterpriseGuest Spotlight: Mike MilburnMike Milburn is the former Chief Customer Officer at Salesforce and was part of the founding team of Service Cloud. Today, he serves as an advisor to multiple SaaS companies. His career centers on building GTM systems where product, sales, and customer success function as one growth engine.Resources & Mentions:Framework: V2MOM – Vision, Values, Methods, Obstacles, MetricsSalesforce Event: “True to the Core” session at DreamforceRecommended Book: Behind the Cloud by Marc BenioffOther Concepts: Revenue-calorie model, sales telemetry, deal blocker mapping🎧 Listen now and follow Selling the Cloud for more insights from GTM leaders building high-growth, cross-functional teams. Subscribe wherever you get your podcasts.Mark Petruzzi (00:03.044)Welcome to today's episode of Selling the Cloud podcast. We're thrilled today to welcome Mike Milburn, former chief customer officer and many other things at Salesforce for I believe 17 years and current advisor to some incredible technology companies as well, many of which are connected to the Salesforce ecosystem. So 15 years at Salesforce.during a very key time for the evolution of the firm. The transformation from true startup to enterprise giant that we all know and love today. When it comes down to it, what we'd like to cover today is a number of the frameworks that Mike has used to align product and sales team throughout his career and particularly through the Salesforce journey.Four themes we'll explore today. The product sales friction point, why most companies get this wrong, building revenue driven product roadmaps, something Salesforce always did a really good job with, probably mostly led by Mike. Go to market execution, when product and sales team need to move as one, and scaling product sales alignment.All right, let's jump on to topic one, the product sales friction point. Mike, you mentioned that product sales relationship is one of the most critical friction points for CROs, CEOs, and boards as well. What are the fundamental misunderstandings that typically create this tension?Mike Milburn (01:47.64)Thanks, Mark and KK. It's great to be here. I'm really glad that you guys are having this. I can't tell you how many times I've had this conversation in private. so having this conversation in public is just, it's a really neat thing and it's an honor to here. So congrats to that. So I guess I would just kind of like imagine the audience and I would imagine in any company that you're in.And that kind of water cooler, or maybe you're in a car or an airplane and you're having a conversation. And if you're on the sales team, you're talking about, man, I wish I had different products or better products or some sort of anxiety around the product side. And then if you go to the other side of the aisle, imagine that same conversation, the door shuts in the product meeting and you're wondering why you can't sell it. And if you sort of put yourself into that.mode of listening and that mode of parenting those organizations, that's a pretty frequent conversation. So I think that's the place to start, is like an acknowledgement from this virtual audience, how many of you guys have been in that position of hearing friction or anxiety from both the sales side to the product side or the product scene to the sales side.KK Anderson (03:07.463)So that's an excellent point. So when you arrive, let's say you arrive to a new company as a CRO and you discover, let's say that the product is difficult to sell. How do you approach that conversation with the product leadership team and with your board without just saying, hey guys, this product sucks, we can't sell it.Mike Milburn (03:32.034)Yeah. So I think first of all, let's start with the relationships between the CPO and the CRO. And let's start with if you're the CRO identifying the CPO as one of your critical stakeholders to your success. Obviously you're reporting into probably the COO or the CEO of the company, depending on the size and the maturity, but have you properly identified the product leader as one of the key stakeholders kind of colloquial?Locally, I would say are they on your Christmas card list? Have you earned the right to build a relationship that allows you to send a Christmas card to the chief product officer? And so where I start that relationship is really If I'm the CRO, I want to meet the head of product. I want to understand their tenure at the company I want to understand their motivations and I want to understand the successes and failures that I've had with with my predecessorsif you're a new CRO, then there was probably somebody before you. And so what were the things that they did right? And what were the things that they did wrong? Typically where that goes is again, relationships take time to build. So we're sort of jumping into how do you build a trusted relationship with them? You're to have to deliver, but ultimately you want to give the chief product officer the, the trust that you're going to bring them.real-time feedback from the field, you're gonna sell the products that are available, and you're gonna help bring them key insights from customers and partners on what are the things that they should be building. And we're gonna touch on that in a second, but those are really the key things, being able to sell what's available, being able to bring them trusted information about what's going on in the field, and help bring them guidance about where the market is going.Mark Petruzzi (05:30.637)So Mike, tell us about how you built a methodology for navigating this relationship at Salesforce. And how do you make this process kind of board ready and productive and collaborative rather than adversarial?Mike Milburn (05:51.33)Yeah, great question, Mark. So as a, first of all, as a backdrop, you know, I had the immense honor of being one of the guys that started Service Cloud on the founding team for Service Cloud at Salesforce. And of course, Service Cloud is now over $10 billion business inside of Salesforce. And I was there on day one when we booked the first, you know, 30 or 40K order way back in the early 2000s. So that's the framework that I'm going to use. Second is,I think all the credit really goes to Mark and Parker, Mark Benioff and Parker Harris. They created a framework that we inherited, we modified and we enhanced. And that's what I'm going to talk about today. So the way that I think about it, Mark, is what we did in the early days of Salesforce is let's say that you had unit, I don't know, let's say you had 10 calories to burn on product.And let's just for a moment say that all calories are equal, right? We would look at those and we would say, how many those calories are you gonna spend on new or innovation things? And how many products are you, or how many calories are you gonna spend on customer success? And so for argument's sake, let's just take 10 calories. And those calories really translate to resources or funding. But if I had 10 calories,And I devote them all towards the front of the house or all towards sales. And that meant that I was going to create some debt on the renewal side or on the customer success side. And conversely, if I spent all 10 calories and I didn't create any new innovation, I might suffer on sales, but I would really be strong in customer success or renewals. So once you go away from the teeter totter,And you go, well, the natural instinct is to peanut butter and to do five on each, let's say in this, in this hypothetical example. And I think what Parker really did was challenge that idea of peanut buttering and say, let's be really, really thoughtful, deliberate and challenging. And maybe you spent seven calories on sales and only three on customer success or vice versa.Mike Milburn (08:10.134)And let's really think about the trade-offs and let's make those data driven revenue generating success oriented decisions. And so where we took that team was we would take the product roadmap that was based off of that framework. And we would go to the sales leadership and we'd say, can you sell this? And the sales leadership would sign up to sell that. And I think, you know, that, conversation that we started with was.can the product team create a roadmap that the sales team stands behind? And if you imagine that conversation, that's a very delicate conversation. The sales team has to take accountability for, if you're gonna go build something, then the sales team needs to be the one to stand up and say, if you build that, I'm gonna go sell it. There's always problems that come up with pricing or packaging or competition or any one of the various things that happen in the real life world, but.The head of products job is to create a roadmap that is innovative and can support both sales and customer success, which I'm directly calling renewals, usage and adoption. So I think that was the really neat part is once we made a data driven decision, we could then look at our roadmap and say, if I remove one calories from sales, what are the sales impacts?And what are the renewal impacts? And once you have that, the leaders of sales, success and product can all come together and they make the right decisions for the KPIs of the team. And of course that's where the CEO and the ELT come into play. But that becomes a really fun conversation when you have it, you know, when you have it laid out like that, like for this quarter or these two quarters, let's over rotate to sales. And yeah, we might create some customer success issues.If everyone's on the same page and there's no blame game come when the, when the customers incur issues or problems, there's no finger pointing. It's we all made this decision together. And conversely, if you make a decision to go renew all your customers, then that's going to have a lot of benefits and then you might have some, some, sales friction. So it's really creating that alignment and transparency that I was really lucky to be a part of and, mature that process.Mark Petruzzi (10:29.315)So Mike, before we go into our next question, I'm going to open this up a little more strategically. How much did the approach that Mark drove right from the beginning of beat a mom? How much did that get into some of this? Is the methodology that you're talking about building, is it tied to beat a mom or to just kind of work in and integrate on its own along the way?Mike Milburn (10:58.828)Yeah, great question, Mark. So I think of the V2Mom is really a corporate operating plan. And, you know, I've got to be candid and say, think when I first joined and I was baptized in the V2Mom process, I think I wasn't quite on board with how important it was to a company. After a couple of years, I guess I would go back and restate that and say the V2Mom was one of the most important things that Salesforce has as an asset.And it's one of the most important things that I learned. And it's one piece of advice that I've given and driven to any company that I've been lucky enough to work with is the essence of the V2Mom is a corporate operating plan that the exec team creates and they vote on together. And it decides the company's vision, values, methods, obstacles, and metrics. Essentially, what is the operating plan? And if you do it every year, then you're allowed to pivot and change at the speed of business, no matter what size company you are.So think it's incredibly modern. The relationship between the V2Mom and the product roadmap is really simple. If the number one V2Mom is growth, and let's say growth means sales and sales is over customer success, then you should be allowed to spend more of your product calories making products that the sales team wants you to sell. If the V2Mom is customer success is number one, thenyou know, voted on that by the exec team, then you might change the priorities and saying, let's spend more calories together, making products, goods and services that help renewability. So the relationship between the V2 mom, the product roadmap, the sales leadership, the success leadership is the success leadership is it's all part of the exact same formula that drives the corporate operating plan.KK Anderson (12:56.199)And so where like what role do you see the CEO playing out all of this kind of? Facilitating it all you know running them running the balanceMike Milburn (13:06.606)Yeah. So, you we were pretty lucky. We had, you know, we had the legendary Mark Benioff running on that show. And what Mark enabled us to do was he empowered us to create a forum where you're allowed to have a healthy conversation about the VT mom. And I vividly remember, I mean, so many of these meetings all kind of blur together because they were 15, 20 years ago, but I remember somebody in the company standing up and saying, I don't agree with this.KK Anderson (13:11.558)Yeah.Mike Milburn (13:33.13)Maybe the person was an individual contributor, maybe they were an influencer, but when they challenged it, was somebody in the Roman Senate saying, hey, you guys built this, I don't agree with it. And that transparency and accountability was really important. Mark drove that culture. Everyone owned the V2 Mom. Number two was you were allowed to deputize other people for your V2 Mom.So let me make up a little hypothetical situation here. Let's say that Mark is, let's pretend that I'm the CEO, Mark's the head of sales and KK, you're the head of products. And I would say, know, is a number one priority that we sell more and everyone goes, yeah. Well, if Mark's job is the head of sales and your job is the head of product, then you inherit those priorities. And so that's where you can't be parochial or you can't be political. You've got to do the right thing.on the V2Mom for everyone else. And it was more than a faux pas to stand up in a V2Mom meeting and be self-serving. You had to use the V2Mom as the doctrine on how you were going to operate your organization. And you were allowed to deputize other folks. Again, part of the V2Mom conversation that I didn't say earlier was it drives success in a matrix organization.KK Anderson (15:00.006)youMike Milburn (15:00.066)There's some organizations that are more top-down, more command and control, maybe more military or more organizations. And a lot of modern organizations, you know, the CPO and the CRO might not ever report into the same person. They might be dotted lines into the CEO or they might, their peers, right? And so the V2 mom became almost navigate the V2 mom without having to go to the CEO.KK Anderson (15:06.311)youMike Milburn (15:30.124)And when you're empowered as as a, an executive in a company to navigate that without having to go and ask permission or to have somebody navigate those rules. you tend to, you tend to come to the right decision.KK Anderson (15:44.423)You know, it's ironic. Mark and I are sitting here nodding our heads thinking, this is exactly what AGS needed to hear right now. Right? You know, me, every company is no matter the size, is they're navigating growth and navigating our, you know, everything. It's so important. And for the audience who's probably like Googling what is V2Mom right now, can you give an explanation of Salesforce's framework that they've made famous?Mark Petruzzi (15:51.939)I that guy.Mike Milburn (15:52.11)ThanksMike Milburn (15:55.841)Really?Mike Milburn (16:11.586)Yep, absolutely. Okay. So it's called the V2 mom and it stands for vision values, methods, obstacles, and metrics. And so the way that I think about it is, is the vision and values or things that the exec team created and they would socialize for approval and stakeholder value with the company. So that's the first, the V2 part. The mom part is where the work gets done. The methods, obstacles, and metrics.And so you can YouTube V2Mom. You see a lot of companies have borrowed it, but essentially there's about 10 V2Mom methods. And those could be things like say which product has a higher priority. It could mean revenue. It could mean culture. remember when, when one year when we were really going against Siebel and there was a fear that we would turn into Siebel. I think the number one method on the V2Mom was culture.And so that trumped growth. So the M, the first M is methods. That's the kind of how, then the obstacles are what are the things that are going get in the way. And there's a one-to-one ratio between obstacles and methods. And then the measurements are how are you going to get measured on whatever method you wanted? And the, what the execs team's job was to create all the methods and then prioritize those.And one of the really neat moments that I saw happen over and over again was a public discussion on which method is more important. And it sounds like so innocuous. It sounds so easy. But if you were to say, what's more important sales or success? That's a hard one. Cause the more you sell, the more you have to renew, the more you renew, the easier sales get and the more references you get. Which is more important, partnership growth versuscreating a brand. Geez, Salesforce has created an amazing brand. It took time to do that, which is more important. Employee success or creating a great dream force, which is more important, having a great dream force or having 10 events locally or throughout the geos. And so once you sort of create that framework to have healthy discussion, thenMike Milburn (18:35.478)then you kind of get everybody on the same page. So it's a corporate operating plan for the modern SaaS company.Mark Petruzzi (18:42.711)Yeah, and what I love about all of that, is you kind of ties me back to what you said at the beginning and that this calorie breakdown perspective that when you look at it that way, and very few companies do, right? Very few CEOs do. Most CEOs kind of come in to these QBR meetings or wherever they're addressing a team and they're like, know, sales, sales, sales, we need to grow, we need to grow.And then they turn around and they're like, then they start talking about customer success. And they're like, well, customer success has to be perfect in this way and have to do that. But it's not. It is a zero sum game, even in a fast growing company. the process of being mature and analyzing, hey, if we want to grow a little faster,we're going to have to do some things that are going to be a trade off on customer success. Or if we really, really need to make sure that customer success for the next couple quarters is, you know, that our retention is off the charts, then we have to slow down and accept a couple percentage points less on our growth. That doesn't happen often in companies. And I love the way you're positioning it thus far. Let's kick into topic two.Building revenue driven product roadmaps. KK, why don't you lead us the first question there.KK Anderson (20:11.239)So I'm always going to start with sales because that's my passion. And so when we think about SaaS organizations and our clients, how do you ensure that sales feedback actually influences the product roadmap? That's where I think one of the greatest breakdowns is. And honestly,It's that frontline seller who's having a lot of these conversations and the solution architects. That's the feedback that we need to go up. Right. So how do you do that?Mike Milburn (20:45.858)Yep.So this is the, I'd like everybody on the podcast to kind of close your eyes and imagine this meeting. You're in a QBR, you're in your exec meeting and it's your reporting on your results for the quarter. You're getting ready for your next board meeting of any size and scope. And you're looking at, you're the CRO and you're looking at your results.You're looking at your feature pipeline. You're looking at amount of head count and you're painting a vision for the company on where you're going to go. And what if you had a slide that, that, that said for every opportunity, here's the quantifiable problems that we're facing in the field. In other words, you know, you just kind of invoke this frontline sales and then there's,There's RVPs and they go AVPs and by the time it gets up to the CRO, how do you get feedback? And the image that I'm trying to conjure up is, and this might sound low level, but let's start here to get to the high level. What if on every opportunity there was a way to capture objections? And it wasn't a free text field. It was a data driven format. Is it pricing? it, is it competitive? Is it a feature or function?KK Anderson (21:48.027)Uh-huh.Mike Milburn (22:13.654)And that opportunity has a dollar sign value associated to it. So if all the reps in the field were responsible for adding in all of their objections at the, at the infantry level, at the deal level, and the CRO could run a report and say, here's the number of opportunities that I'm facing where I have pricing as a problem. And here's the accumulated dollar sign that is impacted.Or I'm facing a feature and function gap, or I'm facing a critical piece of functionality that will require &A. Whatever it is, if you can associate deal friction with the number of deals and the amount of ARR or the amount of revenue that's associated, now you're having an exact conversation. It's not emotional. You're saying I've got X number of dollars. I'm going to choose 50 million or 5 million or 5KK Anderson (23:05.991)Mm-hmm.Mike Milburn (23:11.074)beans, whatever vector you want. And here is the data behind it that is causing me friction. Then the product organization or the partner organization or any other organization, they can ask you questions about it. They can second guess the quality of the data or what some of it means, but it's really hard to have. It's really easy to have a great conversation. If you come to that meeting with, Hey guys, our second half pipeline.or X amount of revenue. And here are the three biggest blockers we're having to make the second half of the year. We need a flex capacitor. We need more aggressive POC pricing. And we'd really like exec sponsorship on the following 10 deals because we're having a lot of competitive pressure. Now it becomes a fulfillment opportunity for the rest of exec team to rally behind you instead of that familiar pattern ofwhat's happening with the deals and could have, should have, would have kind of that soft squishy. If the CRO can bring concrete examples of what they need to that meeting, then you're getting this CPO on board with you to build the right things to deliver more revenue.Mark Petruzzi (24:30.253)really good points there, Mike. So, okay, so how do you do, know, companies are getting customer requests, customer feedback every minute of every day. How do you determine, just how do you accept that into the process? How do you get that data into your system first? And then...What are the criteria that should help you really drive and make it affect product decisions that will move revenue versus what may make one client feel good or even what may make the company feel good? Like we may look at this and say, yeah, this is an important one. This is important. But at end of the day, if it's not going to move revenue, it's got to be in a different place in that product roadmap.How have you done such a great job with that throughout your entire career?Mike Milburn (25:28.664)You try and make the process easy, Mark. You try and make it transparent and you try to remove some of the black box. First of all, you know, the, the axiom of feedback as a gift is, is not just true if you're not getting feedback, like you're doing something very, very wrong. So let's just start with the sales side. Do you have a system that can quantify from the SEs and the sales team, the blockers that are getting in the way to sell the deal?Do you have that? That is a binary yes or no question. And then can you summarize that by segment or geo? So part of what you implied by that question is if I have a sales team that's selling an SMB in North America and an enterprise team that is selling in Europe and they're asking for things, how do you distill those two things into a criteria?that creates action? And the simple answer is revenue. So let's just make up some, let's just make up something to talk about. Let's say your SMB team has 20 deals, each valued at $1. Right? And that's in North America, that's $20. But your EMEA team, it wants something that is $100, but there's only one deal.And you look at everyone and let's assume that to build those two products is the same amount of calories. Cause when you get different calories, then all of a sudden you're invoking a different vector. But first of all, can you have that conversation? This is no different than having a conversation with your family about where to go on vacation. Do you go on two little vacations and for a couple of days, you'd be on one big vacation. The world's navigated that for a long time, but now all of a sudden the sales conversation is difficult with your product team.As a CRO, can you articulate the number of deals by segment and exactly what the blockers are? Yes or no. If you do not have that mechanism in place, then I would encourage you to use a CRM like Salesforce to create those objects. And you simply, it's part of your sales operations criteria. Every deal gets a blockers or pathways and it's not a free text.Mike Milburn (27:49.12)It is the top lockers and you're able to, sales ops can help you navigate, and, and run those reports. So that's the first side of it. Then, then the second side of it is as an exec team, do you have the framework to be able to decide and have that conversation? I think this is where a lot of these conversations stall is the fear that you have been building the wrong things or, or are you listening in the right way? Maybe.You know, I just said it in a very blunt way, but if you're going to get to transparency, you've got to be able to listen and then you've got to be able to make roadmap decisions based off it. So, you know, I would say, regardless of what's happened in the past from the product and sales organizations, this is your opportunity to reset. Listen to what the sales team is telling you and then build a roadmap that addresses those. And if you're not going to address it, then just like, just like we talked about earlier, say.we're gonna make these other decisions. And if you keep seeing this deal friction, we're sympathizing with you and we're not ignoring it. On the reverse side, on the customer success side, it's anyone that's a customer needs to be able to submit the feedback into your organization to tell you what is causing them to stop or renewal. And part of the unspoken hard part here is time.A product roadmap usually takes a year to effect, which ironically is why Salesforce's roadmap is three RR was three RR three releases a year. So if you're going to get something into the roadmap, it might take you three releases to get that through the system. So you've got to have your radar out both on the sales and server sales and success side long enough to listen and impact that roadmap. The, so that's the time vector then.That's all systematic and programmatic. And again, you should be able to report that to the CEO. You should be able to report that to the board. Then you have the live functions. And so this is actually a really neat story, but if you were to go on YouTube and you go true to the core, one of the most profound sessions that occurred, that occurs every dream force is usually it's Parker led, but somebody on the product team gets up.Mike Milburn (30:14.578)And the audience can range from five to 10,000 people. And they lead a conversation of, we being authentic with our roadmap? And this is a really neat conversation because there is no sales team. There's no success team. It's just the customer and Salesforce on stage. And what Parker does a great job of it is navigating. Every customer is going to have wants and needs. Everyone's got their individual requirements, et cetera.And those fit either in, no, we're not going to do that. It's the wrong thing for us to build. We're thinking about it or here's where it's going to be built. And over time, what I think is really neat about true to the core is it shows Salesforce commitment to listening. It shows the customer's commitment towards giving that feedback. And I don't have any data or stats on it, but I would guess that, you know,The reason why, the reason why that's so effective is the customers feel that their voice matters. And so if you combine both those things and you have sales radar and sales intelligence telling you what is necessary to drive a sale. And then you have customer intelligence coming through and saying, what do you intend to build?And then you have something like true to the core, it could be exec round tables, or it could be dinners or whatever mechanism the company feels comfortable. Dreamforce is a very unique opportunity. What you see there is sort of like checks and balances, sort of like the foundation of the United States, right? We've got three different, bodies that help govern the United States. You have the sales team giving you feedback, the success team giving you feedback, and then you have actual customers. You take all three of those pieces of feedback and you look at the roadmap and you should be able to say.KK Anderson (31:51.495)with customers.Mike Milburn (31:56.096)Am I building the right things together?KK Anderson (31:59.463)And I wonder how often what the customer says is different in fact than the othersMike Milburn (32:06.338)You know, it happens. mean, I remember some very contentious, true to the core sessions and you kind of have to be candid and say, is this the right thing for the company to build? mean, the more customers you get, the more the need, do the needs of the many outweigh the needs of the few or the needs of the individual. Also here is the difference between like core product and customizable. So it's one thing for customer to say, I want this turnkey.KK Anderson (32:28.977)Mm-hmm.Mike Milburn (32:32.918)It's another thing to say you could do this and here's how you would do that. My opinion is that customers want transparency. And just because a customer wants something doesn't mean they should build it, but they deserve to be, they deserve to be heard.KK Anderson (32:47.894)I have a question. Just real quick, Mark, if I could, you talk about the three releases a year and that's... It feels like nowadays, that's just... Everyone wants something in the moment. They want real time. They want changes faster. want... I mean, I know it's not really a part of this topic per se, but I guess it kind of is. It's product roadmap and it's more...Mark Petruzzi (32:48.724)You know what's in...KK Anderson (33:15.215)in a real time, faster environment? Like how is the speed of business changing how SaaS companies are releasing and updating?Mike Milburn (33:27.234)Yeah. So this is a great topic. mean, I think we pioneered three releases a day, you know, almost 20 years ago. I guess the way I think about what Salesforce did with 3RR was it gave you some ability to have certainty to what is coming next, what you believe is coming, and then what you believe is coming a little bit longer out. So you sort of know directionally what's happening and it was transparent.The, I felt that same anxiety many times of customers like, want this today and I want it today. I think that's tempered or weathered with building in the right way, building trust, building safety, building security. Some things take more than a day or a week or a month to build. The important thing is that does the company know where, does the customer know where you stand as an organization? Are you being heard?And are you delivering on it? So, you know, we, I personally felt after, after being so many, after being so many, ABCs, executive briefing sessions or customer sessions or dream forces that the customer's desire to have it today is that was less important than Salesforce being able to listen and being able to build the right data driven machinery.It also worked where if a customer said, I want X and nobody had ever heard it, you could tell the customer, you know what? You're the only customer that we've ever heard that's asked for this. And that worked in our favor a lot of times too. So if you speed that up today and people want, know, just in time releases or they want a release every two days, I don't think it changes the equation too much. Can you quantify what is being necessary in order to sell more products?Can you quantify what is being used to renew more products? And if you can deliver it on a frequency of three times a year, five times a year, once a month, once a day, that's great. But I don't think it changes the overall calculus of, you listening to your sales team? Are you listening to your success team? Are you listening to your renewals team? are you, Ergo, you listening to your customers?Mark Petruzzi (35:49.348)Excellent. All right, let's go to our third topic here and go to market execution and when product and sales teams move as one. Tell us a little bit about what world class looks like around product, sales, execution. And when we use that term move as one, I've heard you use that term and that's why I'm asking it.What does it mean for product and sales to move as one?Mike Milburn (36:19.788)Yeah. So.Mike Milburn (36:24.5)One of the great parts that I remember about our internal QBRs at Salesforce was having the sales team kick off or the sales team wrap up one of my product conversations. And imagine your CRO standing up and saying, I'm not the chief product officer.Or I'm not heading up product, but I'm excited about the roadmap and here's why I'm excited. I'm going to go sell this because I believe in it. Now, all of a sudden you're showing alignment with your, with your critical sales component. And I think a lot of the internal meetings turn into sales is the sales job. Product is the product job and everyone just kind of goes off into their silos. So it starts with that message. Does the head of sales.Can they deliver the product roadmap? Can the head of sales demo the product? And this is something that I just find really, really unique and interesting, but I mean, I think it's still the case today that almost every executive at Salesforce is responsible for demoing their product. And there's products that it doesn't make sense and there's really technical and I'm sure we can find corner cases, but it's pretty powerful when the head of sales is able to...KK Anderson (37:18.897)Alright.Mike Milburn (37:43.064)demo in some capacity, even if it's not the world's greatest demo. So I think those two things are one and two. Three is almost no airspace between the roadmap and the sales team. We've touched on it all throughout this conversation, Mark, but you should never ever hear from any sales team. man, I wish our roadmap was different. And I think you hear a lot of that kind of in the background or hallway conversations or exit interviews or.Maybe I'm linked in. Sometimes you hear a lot of that. And conversely, from the product team, selling is hard. And so when you involve the product team in selling and you start to see the art of selling and the science of selling, you're going to see a lot of of sympathies and a lot of energies, know, timely today. Just today, I saw.a CRO for one of the companies I led, he left one company and went to a new company. And when you see the product team respond to that and saying, you're going to do great, John, keep going, we loved working with you. I think that's the job of a CRO is to build those relationships that maybe said a different way. If a CRO is interviewing for their next job,Why wouldn't the chief product officer be one of their key endorse ease or endorsements? That would be a true testimony.KK Anderson (39:12.455)Yeah, it really would. And, you know, take the CMO, the CPO and everybody. what's your, we have recently recorded a podcast with Kathy Minter and she talked a lot about the concept of the unified CRO and having sort of one leader that is overseeing marketing, overseeing product, overseeing customer success and in that way, rather than.know, silent. What are your thoughts around that? Some of what you just said had me thinking.Mike Milburn (39:48.364)Yeah, I think there's some really exciting, I think there's been some, I think there's really exciting new roles that have been created both from CEOs and CROs, you know, and I think the CRO that is just revenue generating or just sales generating, think, I mean, first of all, it's an incredible job with a lot of responsibility and a lot of accountability.But the inputs for that are things like marketing and branding, top of the funnel, the creation of pipeline. So if we're able to understand and navigate brand and marketing, then that's almost a next generation CRO leader. Same thing with system engineering. I've seen customer success fall in there. So it really depends on kind of the company and the investors and kind of the...Also the candidate and the kind of role behind it. mean, at Salesforce, if you look at the current organization, it would be really bad form if you were a sales leader and you couldn't articulate the product or you couldn't articulate the message. Salesforce is lucky. 25 years later, everyone's on brand, everyone's on message. They have the enablement departments to go through that. So I think part of what you're asking, KK, is like you haveYou have smaller companies, medium companies, bigger companies. You have all these different sizes of companies. Then you have private equity investors. And I think this is also an important point that, you know, in the in kind of the previous model, when companies were publicly traded or that was your goal is to IPO and be publicly traded company. Who was your accountable? Who is your accountable stakeholder? Wall Street, the stock price, right?Now with private equity, they have a different set of goals, a different set of goals and a different timeframe for that. So what is the organizational structure that's going to drive value creation? And so I think you're seeing some consolidation in some of those roles, which is really exciting.Mark Petruzzi (41:59.556)And Mike, think you just set up our next podcast together and I don't think we've ever brought you by me back super fast, even though we've had amazing guests along the way. But I think we have to have a discussion after this about getting you back in in the next few weeks and talking and going more deeply into that private equity, private equity and sales, private equity and how that affects strategy within.All these companies that you work with and and we do KK myself as well Yes, we're running lower on time here, but I'd like to get into topic for scaling product sales alignment frameworks for high growth organizations and I think the the core item here is when you when you scale from early stage startup to enterpriseHow does this product sales relationship need to evolve? And how do you make that work? Because we all know these early stage companies of today are going to be the sales force of 2030. So, or at least a couple of them are. Not many, but a couple. And how do you navigate in each environment to get to that full scalability?Mike Milburn (43:24.096)Yeah, great question, Mark. you know, with all the turnover, all the growth and all the pace and speed that the tech ecosystem is in, here's a couple pieces of guidance. if you're the CRO and there was an impromptu board meeting, could you articulate the product roadmap and give your editorial and a data-driven decision on why it's good or conversely why it's bad?Not subjective, not your opinion, but can you give a data-driven, supportable articulation of the product roadmap that, you know, that can you articulate that? That's thing one. Thing two is, are you listening to the customers in your, again, your sales teams are spending all of their time with customers. Are you bringing the product organizationcritical information about the customers buying decisions, their needs, their wants, and are you giving, are you helping another organization build the right roadmap? Number three is, have you done, here's a litmus test one. Have you done a product tour with your top customers and your CPO? Nothing will flush out a correct alignment.or an incorrect alignment better than a dinner or lunch or breakfast with 10 customers, head of sales and the head of product. There's nowhere to go. The door shuts. They start asking questions. What about this? How does this work? Can you have you done that before? And so I think those are three things. If I had to invoke a fourth one, it would be imagine your board meeting and reverse it.Imagine presenting to either your private equity investors or the public counsel and imagine talking about the product roadmap and your alignment with your CPO. That's, think, what your job is as CRO is to build that alignment and build that trust.KK Anderson (45:30.449)So when you were in the beginnings of Service Cloud and you were there with a front row seat, what, any stories come to mind around how that scale and what that experience was like?Mike Milburn (45:40.268)Yeah. I think I shared this earlier. The first meeting I had when I was the GM, was terrified. I thought I was responsible for innovation and I had to figure out all this stuff. I was very, very intimidated by that opportunity. Parker leaned over and he made it just real normal. goes, just listen to what they say. Just listen.And I listened to the sales team talk about, you know, here's the size of the opportunities. Here's the data coming. Here's the telemetry coming out of sales. And then I listened to the telemetry coming out of success. And the picture that came out of that was maybe it was 80%. Right. It was let's build this to drive more sales. Let's build this to build, to help do success. And I didn't have enough calories to, to, to do everything. So then I asked for help and it was, peer group.How would you slice this? Would you do 80, 20, 20, 80, 50, 50, 70, 30? And I navigated that success together. And eventually it was the head of sales who became incredibly supportive of my roadmap in service cloud, which led to growth. And so the head of sales became one of our biggest advocates. so I think that story, KK, kind of, you know, while it was...very, very intimidating and I had a of anxiety going to that meeting. It's sort of, reflect on that and Parker was exactly right. If you listen to what the sales team is providing in data driven organization, then the roadmap becomes almost a fulfillment exercise of how are you going to deliver that in the shortest amount of time? And the innovation is going to come from your product and engineering organizations on how you're going to fulfill the most amount of those things in the shortest amount of time.Mark Petruzzi (47:35.232)Excellent. All right, let's jump into our rapid fire segment here because I can't wait to hear some of these here from your perspective. So, you you're not a CRO. know, that's not kind of not your core, even though you've done so many amazing things over your career. So I guess this question becomes, you know, when in your career have you been asked to sell and what what product or servicewas the first one you've ever really got your hands around.Mike Milburn (48:09.506)Yeah. So I've carried a bag. Actually, Mark, I've been responsible. I've never carried a bag from an AE perspective, but I've been responsible for revenue four or five times in my career. And believe it or not, the first is going back to Salesforce. At a matrix organization, I had no salespeople reporting to me and I had all the accountability of revenue. So I had to stand up in front of Mark and team and the board and, and, and, and announce that. So.That was really the first one. And then every company since then, I've had some relationship, either direct or indirect, with the ownership of revenue.KK Anderson (48:50.983)Okay, who is your favorite, let's say CEO or C-level business mentor to follow?Mike Milburn (48:59.34)Yeah. So I think, so first of all, I keep an internal board of directors. And for me, what my internal board and my internal mentor do is, is they allow me to be accountable to people that I value. And one of the sales leaders that was at Salesforce, that was running one third of the company for a large majority of that time was a gentleman named Dan Del Degan, affectionately known as Triple D.And, Dan came out of Oracle and then was it hugely influential in the growth of Salesforce. Dan later on, joined Greg Buchholz, the founder and CEO of Spring CM and Dan became the president and they sold Spring to DocuSign. Dan is probably the, gentleman that I count as my chairman of my board to, to hold myself accountable, butI think the way that he operates in his value systems, a sales oriented to the topic of this conversation, a sales oriented CEO, I count Dan the top of that list.Mark Petruzzi (50:03.203)Excellent. So yeah, what about a tool that every product leader, well, let's do two of them here. Since you've managed these in a dotted line way, you're responsible for this revenue, you get to see the good, bad, and the ugly, and you get to see it from a slightly different vantage point than if you were.a CRO managing that team day to day, which I think is going to give you even better insights to these questions. So what tool would you recommend every sales leader use to ensure they are aligned with the organization? And then is it any different for a product leader, any different recommendations there as well?Mike Milburn (50:48.578)Yeah. So I had the, I had the opportunity to build these tools. actually the first company I left after Salesforce was Salsify and we built both of these tools natively mark. chose Salesforce for those things. as a, as a platform, on the, on the sales side, think building the data model to be able to support what is sales need. I think it makes sense to build natively on Salesforce. It's close to the opportunity. It's close to.leads opportunities, close one, time in sales stage, all of that makes it very, very simple. On the reverse side, it's really about usage and adoption. So, you know, there's a number of enterprise tools. I don't think I'm wedded. don't have a favorite, but what I want to know as CPO is who's using the products and what does usage and adoption look like?from a telemetry standpoint on a good customer and what does it look like on a bad customer? So I almost think about like, I want the customer's name redacted and I wanna see usage and adoption and I wanna see those trends and I wanna see what's working and what's not working. Then I wanna start asking questions. So every product has got their own internal telemetry tools.I'm not wedded to any of them, but I really believe in usage and adoption to drive the customer success product roadmap.KK Anderson (52:23.079)Nice. Okay Mike, what advice would you give your 21 year old self?Mike Milburn (52:30.95)I would give the advice that if I could imagine the number one relationship to build, would be the relationship between sales and products and never ever have a conversation that sounded or looked parochial about. wish sales did something different. I wish services did something different. I think there's a wonderful skill of empathy. And if you're a product person and empathize how hard it is to carry a bag and you'refamily's livelihood is dependent on you selling something in some frequency, and you reverse that from a sales position, understand how hard it is to ship and QA and deliver products. I think it's the empathy between sales and service, sales and product, I think is just something I wish I'd spent more time on earlier in my career.Mark Petruzzi (53:19.649)I mean, Mike, isn't it just the kind of the secrets of life, you know, having that that empathy in every situation and anybody you work with or coordinate with from a business or personal perspective. So I love the way you just described that. All right, let's close up on.Let's just say this from a product manager, a product manager perspective, somebody who is the CPO taking that role for the first time. Are there any books that can give a little bit of the tricks in the trade that you've read or do you just need to get the work and write that so we all have that insight?Mike Milburn (54:01.41)You know, it's a great question. The one that comes to mind is actually Mark's first book. I think it was Behind the Cloud. And it just boils it down into such, from what I remember, it's been a couple of years since I read it, Mark, but it just boils it down into the raw distilling of what it takes to create a product and get people to sell it, use it, and adopt it. And, you know, in those early days, in the first five to 10 years of Salesforce,We did so much evangelizing, so much listening, but there was so much passion behind it. And so I think that's probably a pretty good place to start.Mark Petruzzi (54:39.615)Excellent. Well, we have kept you a minute more than we asked so we want to keep you on schedule for your day But Mike, this is such an honor. It was so great to to dive deep into some of these subjects with you So great that I feel like we should do it again, but we'll figure that one out from hereKK Anderson (54:56.423)ThankMike Milburn (54:58.36)Sounds good, guys. We'll talk to you soon. Great to be here. Cheers. Bye-bye.KK Anderson (55:00.313)Thanks Mike.Mark Petruzzi (55:00.727)All the best.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This special episode kicks off our Mastering Sales with AI series with a candid, high-impact discussion on how revenue leaders can move beyond AI buzzwords and actually apply intelligent selling strategies—especially in volatile markets.Stephen Messer and Paul Melchiorre join Mark Petruzzi to break down the hard truths about what makes AI work in real sales orgs: leadership alignment, data readiness, and daily execution. This is your first step toward modern, adaptive selling—driven by signal, not guesswork.What You’ll Learn:Execution Beats Ambition: Why success with AI doesn’t start with big vision decks—but with specific, high-impact use cases.Your CRM Can’t Keep Up: Why traditional tools break in volatile markets, and how neural net AI models adjust in real time.Forecasting Needs a Reboot: How daily deal signals—red, yellow, green—are replacing “gut feel” and weekly sales meetings.Buyer-Centric Strategy: Why studying sellers won’t help you predict revenue—but studying buyers will.Leading with Insight: How top CROs gain board trust through data, not opinions.Key Topics:Moving from AI theory to operational realityFixing broken forecasting processesLeveraging volatility as a growth advantageRedefining enablement with signal-based coachingWhy AI is a co-pilot, not a replacementHow to scale insights across sellers, teams, and time zonesEvent Recap – Top Takeaways:Start small, win big: Tie AI to real revenue use cases.Clean data wins: No insights without data discipline.AI empowers, not replaces: Give time back to sellers, and sharpen execution.Execution > tools: Adoption follows alignment.🎧 Listen now and follow Selling the Cloud for more episodes in our Mastering Sales with AI series. New sessions coming soon.Mark Petruzzi (00:39)Welcome to this special edition of the Selling the Cloud podcast. Today we're digging in one of the most pressing questions facing revenue teams right now, today. How do you sell and lead when the market gets shaky? We're thrilled to be joined again by our friend and Selling the Cloud regular, Stephen Messer, co-founder of Collective Eye. Stephen is a serial entrepreneur, investor, and one of the most innovative thinkerswhen it comes to applying AI to real world business challenges. With Collective Eye, he's created a platform that brings predictive sales intelligence, once reserved for Fortune 500 companies, into the hand of every seller and sales leader in companies of all sizes. As economic uncertainty rises, many organizations instinctively pull back, but strong sellers and smart leaders lean in. Collective Eye helps them do that with confidence.providing real-time insight into which deals are likely to close, where risk exists, and how to act before it's too late. In today's episode, we're gonna dive deep into three key topics. Why volatility separates strong sellers from the rest, and how leaders can help their team step up. Why traditional forecasting tools break in a shifting market, and how AI gives you the edge.and then how to create urgency when customers are tempted to delay and how to guide them to take action. Okay, let's jump in. Stephen, welcome back to Selling the Cloud.Stephen Messer (02:17)I love being here. Thank you, Mark. Thank you, KK, for having me. You know I love talking to your audience and frankly just talking to you too.Mark Petruzzi (02:24)We love it too.KK (02:24)⁓ that isawesome. We're so happy to have you, Stephen. So let's dive into the first topic, which is how volatility reveals the real sellers. Like, will the real sellers please stand up? And so right now, one of the things that we're seeing across, you know, so many of our clients is hesitation, right? And it's exposing when deals stall and push and delay, it's really exposing sellerswho have relied historically on tailwinds or relied on having a ⁓ well-known logo that they're selling for. And strong sellers, right, they're typically going to thrive in this kind of environment because they're truly meeting the needs and the outcomes of the customer. So what, like in this, just kind of backing up a little bit and thinking about how you sell in volatile times, like what,What do you see or what do you think top performers are doing differently than them?Stephen Messer (03:29)Yeah, well,let's talk about top performers, top organizations, because remember market share is always hard to get in any market. But when there's change, that's usually when markets shift pretty dynamically. And volatility is something that a lot of organizations are sitting today looking around and realizing that they and their architectures are very rigid. They're not very flexible to make change.They're also not getting feedback loops fast enough. And that translates from leadership down to seller. So I say that because, you know, historically we're well, let's put it this way, market volatility, especially when it's external volatility can be very hard to understand. You're asking an individual seller to figure out what's going on or the organization is coming to a group think mentality. And the reason why that's so challenging is because they're using themselves.to try to figure out what's going to change in the world. I think there's nothing harder, right? One, your assumption is it's you. And then the second thing is your assumption is somehow the group think will get us there fast enough. But I think what you've heard me say this before, which is the hardest part about listening to your customer in a high volatility, especially when it's negative market impacts, which is really what we're living through.right now is sort of these shocks to the market that keep coming every other day. And that makes it very hard. What you're hearing from your customer and what their conversations are with you aren't going to help you. They're giving you sort of the Instagram view of the world. And I always joke, the happiest couples look on Instagram in the two months prior to their divorce. They're out there telling you what a great thing is. And I think when market challenges arise,A lot of your customers are afraid to say we're hitting headwinds in our market. That's why we may not be buying and or other things that are going on because they're not sure if it's just them or if it's everyone else and nobody wants to look like they're in trouble because that creates a death spiral and all these other things around it. So what I think I'll highlight is you are talking about the sellers who are able to pick up on those subtle signals or are testing and trying messages almost immediately to test for what's really happening.as opposed to playbook people, or as opposed to people who are just trying to follow the med pic steps. They recognize that as soon as the market changes, I have to start figuring out and sensing what's going on in the market. I think that is one of the more important things to do. But I think I wanted to bring back, because everyone thinks, no, ⁓ it has to do with an individual. So I think it's the whole work fixating on themselves, not trying to understand what the entire market's telling them.and the best people know how to do that.KK (06:24)Really interesting. ⁓ So what if we think about the end-door performers? Like how do, like the ones who aren't pushing and asking the right questions, like how do we, like if I'm a sales leader, is kind of what I'm getting at. If I'm a sales leader and I've got a sales team, I'm gonna have some strong sellers and medium sellers, probably some low sellers. How do I know?How do I know when the times get volatile like this, like who's doing what needs to be done? Like how do I know what's real, what's not, who has happy ears? What do I look for?Stephen Messer (06:51)Yeah.Yeah.Look, Warren Buffett always said it best when the tide goes out is only when you see who's naked. And I think what a lot of the sales organization is going to experience is that a lot of the people that they liked the most in sales were the people who followed their playbooks, were there people who followed the steps exactly. They may, they're probably never the top producers, but they liked it. And what's happening now isthe market has shifted and all those playbooks fail. Always, inevitably. They're doing yesterday's messages, yesterday's sale, yesterday's behavior. And by the way, all their systems are looking at, especially if they're using the older form of AI called machine learning, they're probably looking at the last two years to predict what's going on today. Nothing to do with what today is. So all their systems are falling apart.There's probably a few outliers that are their best sellers and historically been their best sellers, but never listened to anyone, never cared, never paid attention. Those are the players that are best. And I bring that up because those are the players who are just going about doing their job of selling. But the top producers are on their own. All the systems that you're looking at that people have installed.you know, unless they're neural net, they're not adjusting daily to what's going on. So they're all their entire systems are falling apart. Can I, can I give an explanation of what I mean by that? All right. I want you to imagine that if you pick the technology, the older workflow technologies, you know, for forecasting, for deal review, for conversational intelligence, whatever you're looking at, they're all looking at just your company's data.Mark Petruzzi (08:35)Yes, please.Stephen Messer (08:53)for the last two years and using machine learning to look for the average. called, it's a regression model. They're looking at what's the average. So they're trying to figure out whatever worked over the last two years is going to be assigned for what works today. That is a real problem. And I'll give an analogy to try to make it easy. I want you to imagine a plane where all your gauges will work fine so long as the plane is working perfectly.But if an engine catches on fire, something that hasn't happened in the last two years, all your gauges break. Now, I want to be clear. The only time you needed the gauges was when the emergency came up. But they're all designed to break the minute there's something new or unusual that occurs. So if you are using the most common tools that are out there, I'm not going to name their names.Cadence tools, forecasting tools, et cetera. And they're not like Collective Eye where we're using entire networks in a neural net. What's happening is they're not adjusting to the change. Everything just looks like it's broken and you can't figure out what's going on. So you've lost all your tooling to understand daily change. think of this. Most people are still doing weekly forecasting. Or they're figuring out that deals don't work at the end of a quarter.So when you're having volatility, think about what's happened in the last five days, ⁓ Tariffs on, tariffs off, tariffs doubled ⁓ to China. Then it was the Federal Reserve Chief is gonna get fired, then he's getting saved. I mean, I can go through the dailyness. And by the way, this is like the first 120 days. Like, this is like not minor stuff. And everyone's trying to look at their tooling to get a sense of what's happening with their deals.And that tooling is using the last two years that had none of this to decide what's going on. I think that's terrifying. If I'm them, you're flying without gauges in fog. You are literally trying to hope for, does anyone see anything? Does anyone hear anything? I don't know how you do it. And this is a good warning. We're shot over the bow that if you don't have, in our world we call it collective, which is obviously our name.Which is if an AI like a neural net, these newer types of AI aren't learning from everything going on, you are literally trying to ask the people in your org to figure out from a limited amount of data what's actually happening on a macro level. I think that's crazy.Mark Petruzzi (11:31)Yeah. And it's especially crazy, Steven, when we're also in the midst of software and SaaS, software as a service, being entirely different in the world than ⁓ AI. So maybe we can touch a little bit there and maybe tie it back to how the sales leaders leverage the new tools to leverage and figure out who their highest performing reps.Stephen Messer (11:43)displaced. Yeah.Mark Petruzzi (12:01)and highest potential reps are going to be in this new environment and in this new technology space as well.Stephen Messer (12:09)Yeah. Look, ⁓ I think in these times, there's two types of leaders. There's the back to basics leaders. All right. These are the guys where they're like, my God, we're going through this, but I've experienced other problems in the past. So I'm going to follow my old, wait, look, I just really need people to hunker down and do this thing. Now that's kind of like when Walmart started getting hit by Amazon andI could see Walmart executives being like, it has nothing to do with online shopping. What it has to do is we have to get back to better greeters. If we could just do the basics really well, then people come in, people love greeters. You can't do that online. Like you could see this kind of logic. Back to basics, people don't realize that the world is the paradigm has completely shifted. And now again, I wouldn't say this if it wasn't for we're in the midst of this AI revolution where everyone's doing these things. Cause if you had traditional tools and a market collapse, fine.That may be what you do is back to basics. But in the midst of a market change, what happens is people retool everything when they realize there's a better way to handle a downturn like this. This is what happened. If you think about the dot com collapse, everyone shifted over to digital marketing. We came out of the dot com collapse and more companies had web presences, more companies had.Uh, online shopping more companies had shifted their advertising from traditional things like television, radio, and newspapers to online. Like the entire world shifted. switched to Google, like everything moved because there was a better approach. Well, let me tell you, there is another kind of manager that looks and says, okay, everything is changing. How do I now adjust to it and what else, what is going to happen? And if you think about the AI first sales organization, we are not talking about people who are thinking weekly cadences.Right, you've seen this Mark. Daily optimization means you're adjusting to what's happening to your customer, but you're starting with studying your customer. That's what these models do. Like in our model, our customers, we track 5 % of the globe's economy is feeding this model. That's all feeding back everyone a daily view. You know what that's going to happen to your customer before they've told you just cause you're getting feedback loops.Mark Petruzzi (14:17)Yeah.And the old traditional approaches of this, that your competitors, they're just looking at what happened two years ago and what's happening in that company. There is nothing about the buyer and the buyer's journey and what's happening on that side and what the thought process is. And that's where these AI tools that are especially yours being built in a collective fashionYou're getting perspectives and guidance and coaching from your buyers as well. It's not just coming from you or your team because by their actions, your buyers are coaching you on what you should be doing next.Stephen Messer (14:51)Yeah.Look, think about it this way. You are literally, it's April 23rd. For most of the SaaS world, this will be the end of their fiscal year in a few days. And I'm going to bet you that there are a whole bunch of leaders out there who are freaking out because they're going to rely on the last day or the last few days to try to figure out what's actually coming in. And they're relying on quantifying the opinion.of all their reps of what's going to happen as the world is changing. I, as someone who's out there, can't tell you. I can watch all the news in the world. I still don't know what it's going to mean. But my neural net knows exactly what it's going to mean. I can start to see which deals that I thought were good are starting to go red. Because I promise you, if they're a manufacturing org, or they sell to manufacturing orgs, or they're dealing with people who have to import products, their world is changing. But I bet you there's a lot of people you didn't think were going to have downsides that are now.having downsides or reconsidering purchases because they just want to wait and see. And I bet you nobody's paying attention to that because they think I'm going to get this deal over the finish line. I'm going to have to do a little bit more discounting, but I'm going to get it there. And I think they're going to find out discounting is not the problem.KK (16:11)It's not a race to the bottom this time. And so a couple of things that I'm thinking about as I listen. So one, it feels like the last decade, the theme de jour before the AI revolution really was process. Write your sales process, document your process, have everyone doing the same thing. And then we've got all of these systems that allow likevery generic, know, spray and pray is what we call it, know, cadences and, and outreaches and everyone, you know, it was all around activity and process and not really necessarily the right activity or even the right process. Right. And so now with volatility, right, that, that you don't want your sellers like the blind leading the blind, right? You don't want to be like an ostrich with your head in the sand while theyou know, with happy ears, right? That's something that I keep thinking about a lot. so a sales leader needs to be agile and they need to be able to like move on a dime and bag some of the stuff that they've been doing that is actually causing them to go slower. Like what's your thought on that?Stephen Messer (17:31)Look, this is the terrifying thing of what's happening when you have these grounds swells where everything changes, these paradigm shifts that hit. People are really afraid. used to call it in my last company, we used to call it the Tarzan syndrome, where they're afraid to let go of the rope that they're holding onto until they firmly feel they understand the new one. But you never really hold onto the new rope if you're holding onto the old one so tightly, you're just never gonna let go. And what you saw during the dot com change,really when that switched over is you saw changing of the guards. There were some people who just wouldn't let go of the rope. And there are other people who like, this is a time we have to change everything. And I fear that, you you brought it up first. I have heard crazy things like forecasting is a process. Well, if forecasting was a process, Goldman Sachs would have the ultimate process. They don't. They recognize that volatility is the norm. Like this is what neural nets are great for. If you have a large enough data set, we've spent 10 years.tracking the globe's economy, building this model to do this stuff. This stuff can change the way you think about things. I've also heard people tell me how buyer centric they are while only studying their seller. like, there's like, there's a point where you have a realization. Life makes things hard to make it easy for you to change. Not everyone gets that message. Sometimes they think hard is what you have to work through.Mark Petruzzi (18:41)youStephen Messer (18:56)No, I would say if you're sitting there today, if you are watching this and you were wondering, am I going to make my end of fiscal year? Because you are sitting there worried. You have put in place all the wrong systems. You think it works because it worked for 10 years and you are mistaking that what works in the past will work in the future. That is like saying, I'm going to give them all my salespeople quarters to call me from the road because cell phones don't exist.So I'm not going to think about my Salesforce as having a computer in their pocket because now it's a smartphone. Like you change with the times. And if you're using something you bought five years ago, you are using an infrastructure that makes no sense for the modern world. You just haven't gotten there yet. So KK, you are right. I will tell you what the new sales org looks like. And you know it because it's your best sellers are already doing this. One, it is one to one selling. If you are doing mass marketing,Cadence tools, auto dialers, SDRs, I will tell you that is going the way of the Dodo. You can call it a cadence, I promise you your customer's calling it spam. And I know that, and you know that, because when you get it from other people, you think to yourself, my God, I can't believe they sent me this message. I will tell you a few more things that they already know. They're not answering their phones anymore.They're not like these are heads of sales who won't do the stuff that they're telling people to do bombard people. No buyers want you to know them. So why do I bring that up? If you had a daily feedback loop and you guys know this more than anyone else when you see a deal go in the odds change and go down you change your pitch to adjust to what's happening in the market. I'll tell you we sell volatility now. If you are worried about volatility that is why you need daily forecasting with traditional process forecasting as an example.You're going to get a weekly forecast based on people's opinions. I need to know what the world is telling me daily. That, that is the message we didn't sell prior to 90 or 120 days ago. It's a feature of our product. You all have features of your products and services. You're figuring out which features of your products matter more. But if you can't recognize that the old pitch isn't working or not working for this buyer at this company in this region on this day, if you're not getting a daily feedback,You're not going to, you're going to try one, two messages. Yeah, maybe good luck. hope that's enough. Ours we're trying six, seven, eight, nine, 10 different messages with different people. And we all collaborate so we can share which messages worked in which scenarios. And we're sharing that across our whole company. It means we're getting at bats much more frequently. And our message in 90 days, I can tell you has dramatically changed and will continue to change. That is the playbook. Now everybody is unique. Treat them thatKK (21:46)Hmm.Mark Petruzzi (21:47)Yeah, yeah, beautiful. Let's move to ⁓ topic two. And maybe we'll even switch it up a little bit. Topic two is when forecasting breaks, what to trust instead. But I'd even like to take it a step further and just put it out there to your point when everything has changed and will continue to change in ways that we're not used to. We're not used to theknow, speed of change keeps getting faster and faster. And it's, it's kind of been unleashed. It's, know, we, got a real feel for it during the pandemic. You know, I think amazingly, most companies were able to really be nimble and efficient in that. But they're, they're gonna, they're gonna have to get used to that being the, the standard, not the exception. So when you look at that and you look at just general forecasting tools,Stephen Messer (22:16)Yeah.Yeah.Mark Petruzzi (22:45)you know, most forecasting tools or anything that's called the forecasting process is pretty much looking only at historical data. And when the market's changing as quickly as it is today, that data becomes irrelevant very, very quickly. So what are the biggest risks in relying on those outdated forecasting methods? you know, and where does it even go from here? Because...your product is going to keep evolving and changing and daily forecasting is going to turn into hourly forecasting.Stephen Messer (23:19)Yeah. You know, you're a hundred percent right. mean, I will tell you, we could turn on hourly today if you wanted, by the way. We're already set up for that. think, if your forecasting process relies on interviewing your sellers, if your forecasting process relies on using machine learning only on your data, yourself, I think...KK (23:39)your own core force instance, your own, yeah.Stephen Messer (23:43)You are driving a car through your rear view mirror. You are going to crash into something. It is inevitable. It will be deadly. It will be bad. You just don't realize it because you think it's better than it was last year. And there was a period of time when you only had your own data to make predictions on. I look the reason why we look at our whole network, the reason why our customers pull it, the reason why the Wall Street Journal called us the ways for sales.KK (23:46)Eee.Stephen Messer (24:13)was because our assumption was it was easier to study the buyer to predict what the buyer was going to do than studying the seller to predict what the buyer is going to do. That should be obvious. It is crazy. There is an insanity that thinks that by studying my seller, I will predict what the buyer is doing. You are looking at the wrong person. These moments are the moments you realize the logic failure that you have.If you're going daily, you are reacting at the speed your customer is feeling a pain. You will be buyer centric by its nature because you are studying the buyer. If you are doing a forecasting process, you are basically all trying to agree that none of you really know what's going on. It may make you feel good, but it doesn't matter. When we are driving on a distance in a trip that matters, we don't ask our four friendswhat the trip should be, what direction we should take, and how long we will arrive. We go to Google Maps in ways for a reason. It knows about the road ahead. It's learning for more people. These are the moments you realize your systems are broken. They feel familiar. They feel good. But I think we're going to look back in a year, and nobody is going to believe that they used those antiquated systems and antiquated approaches. If you've done it for 30 years, it's antiquated.I think this is a moment where you see a giant transformation. Now, is it that hard to learn? No. It feels like it. When we did COVID, do you remember when everyone was like, how is the country going to survive? And in two weeks, everybody learned to do business on Zoom.KK (25:57)Mm-hmm. It's pretty great actually when you think about that.Stephen Messer (25:59)This is one of those, this is one of thosemoments where like you literally could turn it on. We get our customers live in no time. Literally, you could be live and have it. Yeah, you could literally be there tomorrow seeing how it works. And you could use people like you guys and say, how the hell do I use this thing? It is so easy. It's fear. But you know what? These moments drive people to have to overcome their fear. And that's when they make these big moments of change.KK (26:08)Right. Like, overnight. ⁓Yeah.Well, some of the, you know, historically, when you think back to any recessionary period, some of the some of our greatest companies were founded and took off in a recessionary time. And I'm not saying that that I think we're headed towards a recession, just knowing that things are volatile and people have the same reaction where they tend to sit on their hands. And coupled that with knowing that really and truly there's a massive opportunity.when you have volatility like this, like this is when you can really shine and figure out how your product or service that you're selling can really help your customer solve the problems that they need to solve, like whatever it is, right?Mark Petruzzi (27:11)Yeah.Stephen Messer (27:13)You are 100 % right.Mark Petruzzi (27:13)And KK, just, KK, you just brought us in a great direction here. And I'd like to take the whole conversation up to that point. And I'll start it with a quick story. I've been fortunate enough to have met John Chambers, the former CEO of Cisco a few different times. And the last time I was with him, he told the story to a bunch of us about Cisco and then more generally abouthis view on capturing growth and capturing market share. And his point of view is that there's never any growth that's captured or market share that's captured in high growth situations. Because in his theory, companies just, get on, they catch the wave, they get a little sloppy, which we've seen that over and over again, and they all kind of become more like each other and become more commodities.Stephen Messer (28:04).Mark Petruzzi (28:08)difficult times and he used the example of I believe it was the Kyoto earthquake in Japan when he just instead of like taking his Asia pack unit and just going into protection mode He looked at that and he said this is when we're gonna grab market share and he took a extremely difficult market environment and turned it into ahuge market share grab for Cisco and I mean that really hit home becauseWe're in that situation now globally. What an opportunity to go and really look at this, especially because we have this little word that means so much now and means different things to every different person. But this little word, this little acronym AI, like you can use that and leverage it into that market share grab today.KK (28:40)We are.Steven, one of the things that you always say, and I quote you all the time, is that a seller with super intelligence on their side will outperform a seller without it any day of the week. And it's like, so we've got this volatile time, which is an incredible opportunity, as we've discussed, we've got AI in our corner that we can leverage to be incredibly differentiated. Like, I'm excited. Like, I'm excited about this.Stephen Messer (29:02)Lucky.Yep.Look, if you are a seller or a leader and you're freaking out right now, you are not seeing market opportunity. You have the wrong tooling. If you are there trying to figure out, I going to make my end of quarter? And you've got all these systems that's not working. It is not working for a reason, right? These are the moments where you realize the water has gone out. I am naked. Please help me. And you can make that change and transition very quickly. I think there are companies like us.We are grabbing market share like crazy now because they have installed all these systems. And I'm able to point out, you used forecasting example. We do a lot more than forecasting, but let's just use forecasting because you brought it up. It's taking 20 % of their activity on Friday. You only have so many days left in this quarter and you're going to give up one of them to debate with each other. Your opinions based on what news you read and what you're hearing from customers of what your outcome is going to be. Do you know how many CROs are going to get fired?for missing their number because they had no ability to tell in advance what was going on. And the board who's asking right now, what is this going to mean for our quarter? They are saying things like, I am hearing from my teams, as opposed to, we use a product like Collective Eye, which there's only us, but let's just say, I use Collective Eye and I'm seeing that the AI is telling me.Mark Petruzzi (30:45)Yeah. ⁓Stephen Messer (30:50)this is what's happening with my deals and I know exactly which ones to go into right away and I know exactly which person to talk to and I know exactly how to handle the situation and I'm going to do my best to deal with it but here are strategies that I'm going out there with because I'm trying to do what I can to salvage this crazy market and that is the difference between someone who can show the board that they like.I would argue a lot of these people who are out there, and I'm sorry if they're listening and you're upset, if you're thinking I have put in tooling and I'm trying to manage it, you should be fired. The board should not be relying on you or your company or your team's opinion. That is insane. Can you imagine a banker or a broker saying to you, my personal opinion was this stock was going to do well? No, you better have a quantitative analysis that tells me exactly what's happening so at least I understand what's going on.You are not doing your fiduciary obligation by appalling people's opinion. This is insane. It's insane.Mark Petruzzi (31:45)Yeah. And you know what, Stephen?Stephen, you're taking me into a whole nother point as well. ⁓ And I'll try to make this a little bit of an analogy. But first, I'll start with a premise and a hypothesis. And this is something I truly believe. But sales reps are incredible manipulators. And some of them more than others. But they are really good at delivering their narrative. And what they want to see happenand managing up to their CRO, to their CEO as well. So you're doing this polling as you're describing, and you're getting all these different sales reps to kind of put in their agenda. It almost feels to me like if you were, no matter what your political background is, if you were to say, I want to find out about something that happened, the Ukrainian-Russian peace talks,and you brought on individuals and you brought one commentator from Fox News, one from CNN and one from MSNBC and you found some of the new brands out there. I mean, could you imagine what kind of information you would have at the end of that day and how they would, you would go into one thing and you'd be told one thing and then you go into the other thing and you'd be told an entirely different thing. But that is what happens and we know it.Stephen Messer (32:47)Yeah.Mark Petruzzi (33:10)because we've all been CROs, we've all been sales leaders on this call. And that's what I've never thought of it this way. Maybe it's the political environment we're in today. But that's what some of those days have felt like to me now that I think back at them, because I would be amazed. I would have one sales leader telling me one thing about the economy and another one telling me an entirely different thing. One group that's saying they're gonna hit every one of their commit deals.and one of them coming in and saying, I'm not gonna hit any. And then only to find out that the one that said they weren't gonna hit any hit half. And the one that said they were gonna hit all hit 30%. So it's amazing and your tool does take a lot of that out of the equation. And what it also does is it takes the wasted time because same thing, if you're just gonna listen to political commentary all day long for 12 hours a day, you're kind of wasting your time becauseStephen Messer (33:44)Yep.Mark Petruzzi (34:07)no matter what and no matter how smart you are, you're not gonna get like, you're not gonna get an answer, because there's not one answer.Stephen Messer (34:13)Yeah.KK (34:14)It's impossible toknow without that. And I'll say one thing, and then I want to ask you a question about kind of trusting the data, because I know that there's listeners out there thinking, yeah, this sounds really cool, but how do I know I can trust this data? So I want to go there in a minute. So for us at AGS, where Mark and I are a firm, weStephen Messer (34:28)Yeah.KK (34:37)you know, we use collective eye. And so we, log in every morning and I, and I look at the odds of the different opportunities that, we're, that we're working on. And I always think to myself, you know, red light, yellow light, green light, right? And if a deal has an odds that is like 80 % or higher, I'm like green light, everything's tracking well there. And if we have a team members that have deals that are in the yellow light, which is like, you know, I would say 60 to 75 % or 80%.Stephen Messer (34:50)youKK (35:05)That's where I'm now gonna spend my day. And when I make that phone call to our seller and say, hey, how can I support, how can we create differentiation in XYZ opportunity because it's a yellow light, right? And I know that we really want this and this would be a really great win for us. It's a yellow light. Like, what can we do to really make sure we understand everything at play? And then that's a true coaching conversation, not a...Stephen Messer (35:33)Yeah.KK (35:34)you know, saying the same, you know, stuff to every single salesperson that you talk to on every single call, you feel like you're saying the same thing like a broken record, right? So that red light, yellow light, green light is really cool as far as productivity and being able to coach in the moment, those types of things. But take me back to how do I know I can trust this? Like I know we're going to have some skeptics out there.Stephen Messer (35:43)Yeah.Look, there are, look, my ideal a lot, as you know, with a lot of people say they're snowflake, our business works differently. Our, I would say there's two things to realize. One is everyone thinks that the challenge that they went through to figure out how to sell their product is what an AI has to. And the other thing is they think they're selling a product. Here's what makes all this stuff work so well. One is just understand we're studying the buyer across everyone in our network. It's pooled data.It is like Google Maps. learns from every driver. what part of the challenge that the selling team always is dealing with is trying to figure out how to sell their product, but they don't realize it's a random walk. Their buyer is going through a buying process. They think they're selling it. No, they're going about their process of buying it. Their process is pretty consistent. They're pro. In fact, if you've ever had a customer, you're selling every month.more more stuff to you know their process really well. You know exactly how long it takes. know who needs to sign it off. You know how to pick that one pretty well. It's all the fact that you're selling to new customers all the time that it looks like a random walk. It is things that are feeling similar. It is things that have kind of commonalities, but generally it's a buying process. So when we study that buyer at buying organizations all day long across our network, we're able to make really good predictions.We're taking in your data to learn about you. Yeah, there's some uniqueness. We're going to learn about that. But generally, we're learning that. So the first thing is conceptually recognize that what we're studying is the actual person who can make the decision and their team and their company and everything that's going on all day long. If you understand that, when you start to see the use of the product, because the only way you'll ever believe it is using it. If you use Google Maps or Waze,Mark Petruzzi (37:35)Yeah.Stephen Messer (37:45)And someone told you it could tell you where the police were, you would say, that's BS. Until you see your first example, or where it routes you in a shortcut, or it knows about an accident beforehand, you see an example. If I had told you three years ago about this amazing thing called ChatGBT that could draft and do all these great things, that you would say, Steve, you're crazy. But then you played with it, and you were like, my goodness. And then you played more, and you realized there's better and better ways to write prompts.to get even better results, you start to go down the rabbit hole. There is no way that I, KK, you or Mark will convince people to believe something until they see it for themselves. But here's what I love. What I love are all the people who say, I don't believe it, so I'm not gonna give it a try. I think you need to prove me wrong. That is like me commenting, I don't like Paris, but I've never visited France.Okay, that is not a fair representation. That is an opinion based on nothing. So if you can't take that gamble to try it out, and we give lots of free ways for people to try it out. Intelligence.com is one free way. We give people 14 days to try it and opt out if they don't like it without any cost. We do lots of really cool things to give people the chance to try it. But if you don't try it, you've got a bigger problem. That means you're just trying to reinforce your own bias.that it can't work because you're afraid of something, whether you're afraid it's going to take over your job or whether you're it's not going to work or whether you're afraid you're going to look stupid or you're afraid. Trust me, until you're in it, you just, you don't have the ability to make that decision. Now, can I point out one last thing before I jump off that subject? Cause I think this fear is an important thing. The one group we haven't talked about that will affect every seller that will affect every sales leader and every org right now isThe only natural predator for a CRO is the board. And there are a lot of people out there thinking, I can manage the board. But the statistics of a 15 month tenure on average for CROs say boards don't believe your BS. They have gotten the place where you have spent all this money on tooling that is based on studying the seller, not the buyer.So they do not believe anything you are saying. And if you show up at the end of this quarter or during the quarter when they're asking questions about how is this stuff that's going on affecting our business, and it starts with I think, or my team believes, you have a shark circling around you waiting to feed on you because they are thinking I have a fiduciary obligation to shareholders.whether I'm a PE firm, whether I'm a VC firm, or whether there's gesture investors and they are saying, think, you think the entire business, we have to make decisions on how to do capital allocation, whether we should be staffing up, staffing down, building or retracting. have debt holders and your argument is I've spoken to my team. You don't have a quantitative way to say we use collective eye, it studies the entire.sales world and what it's telling me right now is that we're going to get hit and here's where we're going to get hit or we should be doubling down in this sector because this sector is growing and we can put our money there and we can make up for our numbers because if the answer is I met with my team on Friday and we believe that we're still going to be on track.Mark Petruzzi (41:28)It's trouble.Stephen Messer (41:28)You can hearand you can see the shark circling, thinking, how do we let this guy be in charge of our business?Mark Petruzzi (41:36)Well, especially Steven, you've kind of used the shark analogy, but it is the DNA of those women and men who are typically on boards are entirely different than the typical DNA for a CRO. And they are only, it's black and white. It's what are the reports show? What does the data show? I mean, that's why data as, know, leveraging data science in every function within a companywhy do you think that is such an easy investment for a board to make? They're like, yes, I want more data. And I've been asking you to get more data from your customers for years. And you've got this CRM system. And every time you go and do a presentation, you start the presentation by saying, we don't really have great information on our customers. And we're trying to get better. And we're working on it. So you're 100 %Stephen Messer (42:28)Yeah.We have pipeline cleanup.here's how our pipeline's grown, but we have some cleanup we need to do. Yeah, I sit on boards. I sit on public boards. I sit on private boards. Trust me, here's what they don't see, What they don't see is the CFO comes in, perfect numbers, no opinions. The CMO comes in and shows what's happening in the market.Mark Petruzzi (42:36)It's the same thing.Stephen Messer (42:55)with quantifiable, here's how we got our cact down. Here's where we're spending. We're seeing less conversion right here. The seller comes in, leans back. So let me tell you what's going on. Here's what we're hearing. Here's what we're feeling. Here's what we're saying. Here's how we're changing. We're going to implement methodologies. We're going to change some of our hiring practices. And they're just like, give me something I can rely on. And the numbers they put in the board book come out of systems that they know are fake.like CRM, they come out of things where they're looking at the numbers and nothing adds up because they're like, last quarter, you came and said you had 10 million in ⁓ new pipe, but I'm seeing now 15. Should I read that? And they're like, well, we have cleanup and ⁓ we still have work to do. We're still implementing some things. Our CRM needs to get redone. They're just like, what the hell is going on here? And they're done with it.Mark Petruzzi (43:24)Yep. Yep.Yeah.Stephen Messer (43:53)That's whatyou see happening when you see the high turnover. They're basically saying we have to find someone who can actually manage this business with data. And that is not a process. Let me come back to that. That is a machine spitting out trustworthy, consistently quantified, up-to-date information. I would rather be a CRO walking in saying, look, I'll show you the trend of where the AI was predicting. You can see here.And you know, you could do this in tele. It'll say, you could see here when the tariffs went on, immediately our odds went down and you can see which deals got pushed back out. You could see the impact of that. Now the tariffs came off and you could see exactly how it rippled through. And by the way, when they asked me questions, how great would it be to be able to go on a tele and just say, okay, which parts of our business or which regions or which industries had the biggest impact? And it comes back immediately with an answer. So now you're giving them hard answers with factual information.And then you could bring them to examples and show them. Here's where you can see the customer started saying these things and look how the odds started changing. And now they're like, okay, you have control of your revenue. You have control of your business. That's what people care about.Mark Petruzzi (45:01)Yes.KK (45:01)My heart.Mark Petruzzi (45:04)And Stephen, what they also get, you also get to do as a CRO there is say, okay, this even when you have bad news to report and you could say, well, this is what the numbers with Collective Eye started showing me 30 days ago. And this is what we did. And this is my response. And this is what the team came up with. And guess what? We've seen this response now. We've seen the numbers going up. We're back in a better point.KK (45:24)Yes.Mark Petruzzi (45:34)And like I do that all day long. mean, and when I started using Collective Eye, you know, I, I wanted this to be as amazing of a product. And, and, you know, for me, this started all the way back in, in work that I was doing with BCG where, you know, there was a lot of really smart people that right at the beginning were like, this isn't going to work. Collective Eye isn't going to do what it said. And, and there's all these things and these are people I respect. And so I kind of went in with first like,I didn't believe anything. I was testing all kinds of things. The things you and I have talked about, Stephen, like where, okay, I have three meetings on an account. Well, is that gonna make my account jump up 20 points in the forecast ⁓ odds? And I've done that and I've seen it. And again, yes, do meetings and interaction help your forecast? Usually, but is it the main driver?And right now, like for example, in accounts that me and KK have, that we've had a bunch of great interaction and emails, but the numbers are still going down because there's macroeconomic and geopolitical things happening here that are bigger than our little meetings that I'm having. That's the difference. But I love the concept and I want to just share it one more time for our audience of, you get to do this stuff almost real time.Stephen Messer (46:35)Yeah.Mark Petruzzi (47:00)and see what your actions and your thoughts and those great strategic ideas that you come up with and you get to see how it's really gonna impact your revenue at the end of the day. That's amazing to me.Stephen Messer (47:09)ThankKK (47:14)And if you're going to be like in this case, there's a deal that Mark and IStephen Messer (47:17)you.KK (47:17)are working on right now actually, we, gosh, we feel so good about it, but man, the odds are not good and we're not happy about that. And it's telling us, you know what, don't spend five hours working on that. Go, go bark up another tree, go find something else, go prospect. You know, you, you know, it's, it's, you, you see the immediate impact of the markets on your pipeline, but then that education.Stephen Messer (47:33)Yeah.KK (47:44)just makes you so much smarter. Right? And yeah.Stephen Messer (47:47)So cool.It's so cool. What's so cool about it is what you're both saying is it's hard if you haven't seen this as a someone who's watching this via it's hard to get that like you will see deals where you have tons of activities and the odds keep going down and you'll have deals where you have no activities. The answer shooting up. You're like what's going on? And what it is is that's the market that we're capturing telling you something. And so you all of sudden you're like I mean the first time you'll see it. They're like something's wrong. I didn't do anything on that. I'm like no.KK (48:08)Yeah.Stephen Messer (48:15)Pick up the phone. You pick up the phone, they're like, what great timing. You're like, how did it know? But that's the power of these network models is you start to get this wow factor and you start to realize tons of activity does not indicate that it's working well. Sometimes they're just being really polite. Sometimes even if they wanted to buy, they just don't have the dollars, but they want to learn. There's so many things you learn. And in these moments, I'll give a great example. KK called me up today and she's like, my God, the macro. She's like, I can see in certain deals.Mark Petruzzi (48:30)YeahKK (48:36)Mm-hmm.Stephen Messer (48:44)that are in certain areas exactly what's going on. It's like you can see it on a daily basis. We call it cycle time, which is if I can get down to a daily feedback loop of how did yesterday affect my tomorrow. That doesn't just mean me. That means like everything. How does it, what's happening? I can now quickly react to it because even if it's just putting in a phone call to say, my God, I saw what happened yesterday with Powell. How are you guys holding up? And if they're like, this stuff is whiplash is killing me.Tell me what's going on. Can I give you an introduction to someone? Can I help with this problem in some other way? Like, hey, do you need me to slow down because you're worried about it? You're gonna find out faster and you're gonna not invest the wrong time or good time in bad places. And you also might be able to build a relationship that grows. I will tell you, we are growing faster in the last month and a half than we've ever grown and we've been growing fast. It is because all of a sudden everyone's like, I can't.KK (49:28)I'm not.Stephen Messer (49:41)wait a week to know what's going on. And I definitely don't want to ask people who themselves don't know what's going on. And all of sudden now we're dropping in fast, showing people and they're grateful because they're like, imagine if I had this and it's not too late, right? I have a feeling we're in for a lot more volatility because the world is becoming like.There's a risk of Taiwan going to war. There is a risk that India goes to war with China. There's a risk that the Ukraine problem doesn't get better, that it gets worse. We have Yemen shooting missiles again. We have the threat of Iran war. Like just macro things like that, yet alone what's happening day to day and the disruption that AI is causing in all parts of the business. I don't think we're going through a very volatile period, which is for me, thankfully using collective eye, my own product, because I eat my own dog food. I am excited.KK (50:20)your life.Stephen Messer (50:30)because this is the moment that people realize everything they're doing needs to change. That doesn't happen often. I want to grab it. I want every one of your people listening here to feel excited, not fearful what's going to happen each day.Mark Petruzzi (50:35)Yeah.Yeah, incredible.KK (50:44)Right.One thing I'll also say before we wrap up, this has been such a fun episode. It took me, gosh, what am I now? Almost 49. It took me a lot of years to get to a point where I actually look forward to challenges. Because when I see them, when I find myself in a challenge, my first thought is,cannot wait to grow. I cannot wait to see how I get better and stronger as a result of this. I almost welcome it. I go as far as to say I'm almost looking for them. And so that's sort of the lens and the perspective that we have to have as sales leaders, as sellers going into these times. Don't be afraid to change. Don't be afraid to jump in.That's just my perspective there. And I will say, we're going to put in the show notes here a link to be able to learn more about these great systems as well. So ⁓ head there and make sure you go to learn more.Mark Petruzzi (51:55)Yeah.Stephen Messer (51:56)Look,pair yourself up with the super intelligence. That's my main point. I think you said it best, KK, which is, you ⁓ you can overcome any challenge if you're aware of it. If you're unaware of it, it's just you're living in fear that something is going to drop that's going to blow your quarter. Something's going to drop that's going to blow your pipe. Something's going to drop. That's not going to give you the ability to overcome it because you're going to find out far too late to fix it. Overcoming things is what makes a great seller.KK (51:59)Yep.Stephen Messer (52:24)wake up in the morning and think today is the day I earned my keep. I did something great. And if you get a daily feedback like Collective Eye gives, you will literally wake up saying, this is where I need to be, or it's not worth it. You're not going to get surprises anymore. And I love the point of we can overcome anything. KK, I've seen you do it. I've seen Mark do it. Every one of us who's listening to this has seen great people do it. If given the chance, you can overcome something.not given the chance because you didn't want to listen, which is really what Collective Eye is doing. It's just listening on your behalf and telling you what this means for it's a translator of what the buyer is trying to tell you. If you're not listening, you're not in the game. You think you are, but you're not.Mark Petruzzi (52:54)Yeah, you don't have a chance.KK (53:08)Mm-hmm.Mark Petruzzi (53:09)Yeah.Stephen, I'll close real quickly with a little bit of another story here. it's when I was ⁓ kind of college time, you know, year or two after college. Well, my whole life, I had a friend who actually went into the Green Beret and the special forces and we would always meet up and there would be seven or eight special forces, individuals with two or three of us that wereyou know, the ones who don't have that kind of training and background. And I don't want to make it seem like I'm someone who would ever be looking to get into a fight in a bar or something. But there were bars that we would go to when we knew we had those Green Berets with us, then where we would, you know, we'd never even think about going to without them. And that's kind of the way I feel with Collective Eye. And you just got to use it for good, not...not evil and that's goal.Stephen Messer (54:08)Amen.KK (54:09)YeahStephen Messer (54:09)Amen. Amen. And we will.Mark Petruzzi (54:11)Beautiful.Yep. it's, well, Stephen, first off, it's amazing. We are so grateful for the relationship we have with you and your team. And we're so grateful to have been an early, early adopter and get to leverage it every day. And thank you for taking the time with us today. This was awesome.Stephen Messer (54:33)That's mutual and I hope your community communicates to you because they could get a lot of their questions answered really easily from you guys. You guys are power users. You're amazing. We've loved working with you. We've learned from you and ⁓ so grateful to be on today and hopefully give people some excitement, not fear around this volatile market.Mark Petruzzi (54:52)Yeah, beautiful. Thank you again. All the best.KK (54:53)Absolutely. Thank you, Stephen. We'll seeyou next time, okay?Stephen Messer (54:56)Thankyou guys. Can't wait anytime you want.Mark Petruzzi (55:00)Perfect. And thanks to our amazing audience. Have a great day all. Cheers.KK (55:00)Absolutely.Mark Petruzzi (55:12)It will not let me, there we go, okay.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.