General Episode Description:In this episode of Selling Intelligence, Jared Zelman, Founder and CEO of Othello AI, joins Mark Petruzzi and KK Anderson to challenge one of the most accepted assumptions in sales leadership: that 20% of sellers will always generate 80% of the results.Jared argues that the 80/20 problem is not a talent issue. It is a systems issue. Drawing from millions of minutes of sales conversations and real-world customer deployments, he explains how modern AI can capture the behaviors of top performers and deliver coaching in the moment when it matters most: during live customer conversations.The discussion explores why traditional coaching models fail to scale, the limitations of post-call analysis, and how real-time AI guidance can improve discovery quality, qualification, and win rates across entire sales organizations. Jared also shares insights into how AI is uncovering new patterns in selling behavior, including why Sandler-style methodologies continue to outperform across modern B2B sales environments.  What You’ll Learn:The 80/20 Sales Problem: Why performance gaps are often driven by systems, not talent.Real-Time Coaching vs. Post-Call Coaching: Why feedback during the conversation matters more than feedback after the fact.Discovery Done Right: How top performers uncover deeper pain points and create stronger buying urgency.AI-Powered Sales Execution: Using AI to replicate the behaviors of elite sellers at scale.The Future of Sales Methodologies: How AI is identifying winning patterns across millions of sales interactions.Key Topics:The Pareto Principle in sales organizationsWhy most CROs attack the wrong coaching problemReal-time AI coaching inside customer callsImproving discovery conversationsThe “question behind the question” frameworkWin rate improvement versus productivity improvementWhy CRM automation alone does not improve revenue performanceAI-assisted coaching and behavioral reinforcementThe difference between efficiency and effectivenessRote versus rogue selling behaviorsPersonalized coaching versus scripted sellingSandler methodology and AI pattern recognitionCustom sales methodologies powered by organizational dataUsing AI to scale top-performer behaviorsThe future of AI-enabled sales leadershipGuest Spotlight: Jared ZelmanJared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Built by the team behind Cicero, Othello helps organizations scale elite selling behaviors across entire teams through contextual, in-the-moment coaching. Since launching in 2025, Othello has rapidly grown to support thousands of users across Fortune 500 companies and high-growth technology organizations.  Resources & Mentions:Othello AISalesforceHubSpotGongSalesloftClariMicrosoft TeamsZoomSandler Sales MethodologyCiceroDan LawrenceLenovoCostcoHome DepotGeneral ElectricComing Next Week:Part 2 explores how sales leaders should manage AI-augmented teams, how coaching changes when AI handles execution consistency, and Jared’s founder-led go-to-market playbook for building a venture-backed company through strategic cold outreach and relationship-driven selling.🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, revenue leadership, enterprise sales, and the future of go-to-market execution.Mark Petruzzi (00:28)Welcome to Selling Intelligence. I am Mark Petruzzi, and I am joined as always by my co host, KK Anderson. Our guest today built the company on a number every CRO already knows and hates. Those numbers are the 20% of reps drive 80% of the results. The question is, what do you do about it? Most leaders throw more coaching hours at the problem.Build out their enablement team, and then just hope it scales and gets more productive. Jared Zellman did something a little different. He went out and he built an AI that sits inside the call and fixes it in real time and on every call. Jared is the founder and CEO of Othello AI, a real-time AI sales coaching platform that guides reps before, during, and after every call.Built by the team behind Cicero, Othello launched in July of 2025 and reached over 5,000 users and 1 million in revenue within its first six months, with clients spanning Fortune 500 companies and high-growth startups. Othello integrates with the go-to-market stack you already have, whether it's Salesforce, HubSpa, Gong, SalesLoft, Clary's, Zoom, or Teams.And sits as the execution layer that makes sure what happens on the call matches what the playbook says.KK Anderson (01:55)What I love about Jared's story is that he is not just a founder talking about sales AI. He is a practitioner of the exact skills he built Othello to teach. He built his entire investor base, his early customers, and his mentor network through deliberate, personalized cold outreach to some of the most senior people in the business. Howard Schultz, CEO of Lenovo, CEO of Costco.All started as cold emails, which is incredible. And that kind of disciplined, researched, human first selling approach is what Othello reinforces at scale. So this interview will be a part of a two-series, a two-part series overcome excuse me, reviewing four topics. today we're gonna get into the first two topics. Topic one, that 80-20 problem that Mark mentioned.And why the performance gap between your best and average reps is not a talent issue. It is a systems issue. And why most CROs are solving the wrong problem. Excited to get into that. And the second topic for today's episode is real-time AI coaching and what it actually means to have AI inside the call, how the live cue cards and pre-call briefs work, and the results that the teams are seeing.And this modern, AI run, coaching platform, which is really interesting. Now, next week, when you tune back in, we'll talk about topic number three, managing an AI augmented team. what a CRO's job looks like when AI handles execution consistency. and topic number four, the founder go to market playbook. And this is one I can't wait to get into. So tell us exactly how, Jared, you went frombeing a new college grad with no network to ⁓ VC back CEO with Fortune 500 clients in under a year. So we got a lot to dig into today. Jared, welcome to Selling Intelligence.Jared Zelman (03:46)Thank you for having me. I'll try not to bore you guys.Mark Petruzzi (03:48)No, you would never. So Jared, ⁓ you built Othello on the premise around twenty eighty. Twenty percent of reps driving eighty percent of the results. And that this is a solvable problem. Most CROs have lived with that ratio for their entire career and has accepted it as a fact of selling life. Please make the case for us that it is not a talent problem.Jared Zelman (03:55)Mm-hmm. Yep.Mark Petruzzi (04:12)What is actually happening structurally in the calls of average reps that top performers are doing differently? And how do you make sure those those top performer practices actually get leveraged into the rest of the team, those eighty percent of reps that we we all know?Jared Zelman (04:30)It's the Pareto principle, right? So the Paretto principle isn't it's it's not a law, like things don't need to adhere to it, but it's a commonality. So most sales organizations will suffer from the 80-20 problem. Doesn't mean they have to. I was just chatting with a mentor and advisor to our company, a guy named Dan Lawrence, one the most lovely and impressive sales leaders I know. He's the GM of America's at Nebbius. Nebbius does not suffer from the 80-20 problem.Right? Like a rising tide lists all ships. He's been able to upscale all of his reps to be so effective that they're all ⁓ top performers, especially if you compare them to any competitors. I believe it's a systems problem, not a talent problem. I actually think you can turn the middle sixty percent into the top twenty percent. The bottom twenty percent is a different story, but at the very least you can get to performing better.KK Anderson (05:12)And it's all by being there in the moment.Jared Zelman (05:15)Well, like it's it's interesting.It's like a like let's let's use like basketball as an analogy. Practice is obviously crucial. No one's gonna tell you that practice isn't important, right? And that's preparation, right? In sales, it's the same thing as going, Tuesday afternoon after school practicing ⁓ shooting hoops, right? But what's also crucial and you can't live without is having your coach screaming at you when you're shooting hoops in a game.Live, right? we try to bring that into sales. ⁓ similar to how if you guys are in sales or have been in sales, your sales manager perhaps would have been slacking you on the side telling you what you should be saying, or even like hooking up to your call with headphones, kind of like whispering in your ear what you should say instead. We try to replicate that experience with AI.KK Anderson (05:54)So but you're not the ma you're not the coach screaming at you from the sideline.Jared Zelman (05:58)We⁓ no, we can't. It's when you're dealing with salespeople, it's a b it's an art and a science, right? Like on paper, what does work doesn't always actually work ⁓ in practice. ⁓ sales reps are dealing with very high pressure sensitive environments. So ⁓ I mean that's like one of the reasons why a lot of engineers fail at building sales tools is you need empathy for the user experience, which is very different from the UX and other products.KK Anderson (06:03)It is. It's⁓So when you went went deep on this problem before building your platform, what like what did you find in your research that surprised you the most? I think I read in one of your articles that you were starting with a different like something about celebrity avatars or something, and then you quickly pivoted when you saw the market. Like tell us what you s tell us what you saw and what really resonated.Jared Zelman (06:38)Yep, that was my first company.of course.I can tell you about the avatar business prior to Othello. ⁓We can touch on that in a second. ⁓ how did I fall upon this major problem though that we're solving at Othella, which is like the 80 or 20 problem of sales? look, it doesn't take like an investigative journalist to like understand that, yeah, there's something going freaking wrong when it comes to the power law of sales rep performance. ⁓ I think the more controversial thing though is ⁓ just how massive this impact is. Let me put this in perspective. Most commerce in America, like most of our GDP, is derivative of B2B commerce. It's usually it's mainly business-to-business, okay? ConsumersSpendingis huge, but B2B is actually the crux of most of it. Everything else is generally downstream. About 80%, call it 75 to 80% of B2B commerce is driven by account executives or account executives with a different name, right? Like account director, for example.That's just one job role, and that's only about 5 million people in America driving 80% of the B and B commerce, which is the majority of GDP. Like if you were to actually draw that corollary, you would see just how important those five million human beings truly are to economy. Consider that 80% of them are nearly or entirely non-productive. That's massive.If you can squeeze even 20% more juice out of that fruit, you can get instead of 20% of them being top performers, 35% of them hitting quota repeatedly, the impact that that has downstream on the US economy is extremely consequential. When I did the math, when I spoke to these people like the CEO of Lenovo, Costco, Home Depot, General Electric, and they all concurred, I realized this is ⁓ this is a fact of life that that very frankly is a whole bunch of bullshit.That there is no way we can justify and just sit idly by as the economy is in some ways carried by 20% of five million people. Right? AEs are the backbone of the US economy. I've never heard that in any business, any economics class I ever had growing up or in college. ⁓ so I said, look, I'm gonna solve that problem. How I solved that problem, I do not know at that point, but I was zeroed in on ⁓ at least getting a piece of the action.KK Anderson (08:36)I have been in sales for over two decades and I have never heard that AEs are the backbone of the US economy and I think I love it.Jared Zelman (08:42)It'sit's tacky, like no one wants to he you hear it.KK Anderson (08:46)Yes, I love it.Jared Zelman (08:47)It's the truth. Like run the freaking numbers. It's true. People don't like understand that. Like there's look, there's like some ways you can like different ways to cut the pie up, obviously. But ⁓ don't sleep on them AE's. They're they're massive. So but you can also make the argument, right? Like if they're getting their leads from SDRs, then SDRs are the backbone of the economy, right? There's like different like layers to the cake, but AEs are the bulk of the action there.KK Anderson (08:58)Don't sleep on me.Yeah.Mark Petruzzi (09:08)Very interesting, Jared. The conventional solution is has been post-call coaching. Gong, chorus, just having manager one on ones. ⁓ that's been the that's been our history in sales. Now you have said by the time the analysis is done and these systems pull this together and you're no longer with the prospect, the opportunity is gone.Jared Zelman (09:17)Gog, stuff like that. Yeah.Mark Petruzzi (09:33)You r you really can't go back and really correct things that may not have gone well in the original call. So walk us through the specific moment in a call where you think a deal is really one in won or lost and why postcall feedback does not touch that moment in time to be able to change the outcome.Jared Zelman (09:54)Yeah. I I think ⁓ I think it's uncontroversial to say that deals are won and lost in meetings. ⁓ at least for the companies we sell to, many of those, not all of those, but many of those meetings are happening, via Zoom or via some kind of phone call on your computer. The deal can be won and lost in a several like several different moments. Most deals are one and lost in discovery. ⁓ good sellers know that.Right? If I'm not digging deep enough in a discovery call, if I'm not having true empathy for the customer, then yeah, I'm gonna lose them. No matter how good your product is, you're probably gonna lose them. So I'll give you one example of what Othello will do. Othello can remind me in the middle of a disco call, hey, double-click on that pain point. Or say, KK, you were to say something like pretty gaping about a problem you're trying to solve. Thello may have me ask, okay, but KK, what have you tried to solve? How have you tried to solve that problem? Why did that fail?And then we try to give you the question behind the question, like a layer deeper beneath the surface. ⁓ we believe if we can improve the quality of your discovery, if we can get you to convert 10% more of your discovery calls, ⁓ the trickle-down economics of that are meaningful for any company.KK Anderson (10:50)So it's interesting. We do at AGS, our firm, we do lots and lots of behavioral competency analyses on on thousands and thousands of sellers. And there's a core set of competencies that we call the sales DNA, which are, the competencies that really are between your ears deep in the brain. And it's things like your ability to stay in the moment and listen to a prospect. Like you're you're just and you're describing discovery. And when you have a youngerJared Zelman (10:57)Yeah.KK Anderson (11:16)Sales person, especially AE or BDR or whoever it is, a lot of times when that customer or that prospect is talking, they think they're listening, but really in their mind, they're they're thinking about what they're gonna say next, or how are they gonna overcome that objection, or how should I phrase this value pitch, or they're they're they're thinking in their mind and they're not necessarily truly listening to what's happening with every breath that your prospect is speaking.But a lot of that comes with maturity, right? And experience and being able to do it for a long time. But very often what we see is that sellers will miss the opportunity to pull on the thread of the sweater, right? To dig into, the TED questions. Tell me more about that. Can you explain that to me? Can you describe that? I mean, some of these simple tricks that sellers have had for for decades, they'll just miss it entirely. Or a, the other thing we see all the time is that.A salesperson has had the same call so many times that they have an assumption that the prospect must have this problem, they must be doing it this way because that's how all my other clients did it. And they may say something that is is compelling and is different, and they may not may they may just totally miss it. Right?Jared Zelman (12:25)What I've what what so here's the thing. I I agree with you by the way. Like and I do think there is an element of that that will never change. Like that's human nature. And as long as human beings will be in sales, you're going to have human elements affecting sales conversations, especially if they're repetitive, right? Because we're creatures of habit. I I don't say, I don't I don't think it's technology's job to like necessarily replace that human element, but I do think we can supplement and augment it.So I'll give you an example. ⁓ and and maybe I'll ask you guys this question first. KK Market, do you guys think sales will continue to be human led, at least B2B sales, for the next ten, twenty years? You think it'll be human led or AI led?KK Anderson (12:57)I think there will always have to be a human in the loop because at the crux of sales is trust and relationships. And I don't think that's going to change. As a matter fact, I think AI is is swinging the pendulum back to how it was in the 50s when sales started. Now, can we automate a lot of what happens in sales and make us more exceptional and more differentiated and and utilize the superpower, superintelligence? But heck yeah. But I do think a human will always be in the loop.Jared Zelman (13:10)Yeah.So I agree with you on that. I will say though, when it comes to like sales, you're judged not on your efficiency, right? You're not judging how quickly you can get the job done generally. It's a good thing, obviously speed and sales cycle like reduction is good. You're judged on how much money you're bringing in. So it's ⁓ efficacy, right? Like effectiveness, not efficiency. ⁓Hence most AI automation around the margin, like CRM node automation, for example, while it is nice to have, is not going to be redefining performance for a sales organization. At least not a good one. Right? Like you saving like eight hours a week for your sellers, as great as that shit is on paper, is not going to move the needle from like a corporate revenue perspective. Un unless you guys are truly like the most like effective, like and every minute is worth millions of dollars to your team.KK Anderson (13:47)Yeah, I agree.Jared Zelman (14:04)where you will juice the hell out of your margins and performance is if you can improve win rates. Like that's 90% of it. Everything else is downstream of that. And automation does not help improve win rates.Right? You need to focus on quality of meeting as that's where the money is made and lost. ⁓ post-call note taking obviously is a step in the right direction. Practically completely unused. Like, who are we kidding? Like, no one is spending four hours a week looking at call notes, no one's spending four hours, five hours a week in AI role play talking to some AI character. They want to be selling. So you need to find a way to enable them, get them to perform better. frankly, without perhaps having to put in a whole lot of effort to do it.That's that's the crux of my philosophy and frankly like the foundation of Othello's product.Mark Petruzzi (14:39)Yeah.Yeah, and I I think that's a big differentiator for you. Jared for you and Othello. let's move to topic two. ⁓ real time AI coaching. And ⁓ the ⁓ our audience here knows that I typically don't like to talk too much about any company's individual product. really as you've been describing, I love to learn. I I think my audience l likes to learn.the ⁓ the framework, like what what you what you have built and why does that tie back to a product? Here I think I'm a little more comfortable pushing on this a little bit. So take us to specifically what Othello does. walk us through a little bit how does the the real call, the pre-call brief, the in-call cue cards,Postcall automation. How does that come together? And what does the rep see, feel, feel, and hear at each of those stage that really does influence them in in their overall selling efficacy, as you put it?Jared Zelman (15:50)Yeah, so we're trying to do one thing, and that is to get reps to say the right things in calls. You have to do that a few different ways, but 80% of the value comes from the core product, which is the real-time in-call suggestions. And let me like specify here. ⁓ these are not suggestions that are pre-gridden or pre-populated and designed by enablement. You're getting a new suggestion on your screen almost every single time. I'll I'll draw you a picture here.I'm selling widgets to you, Mark, and KK. Othello will put a pop-up on my screen guiding me to say the exact right thing in that moment. Taking context about what you care about, about who you are, about what you just said, about what you asked me in the last call. So the suggestions will always be different and hyperintelligent. Pre-call and post-call, we give intelligence, coaching, suggestions, a lot of proprietary tech there as well. But truly the sea change comes from what happens during calls. So we focus on that.KK Anderson (16:40)So Jared, you've described a tension that you call rote versus rogue. the rep who follows the AI Q cards too rigidly on one end and then the repu ignores them entirely on the other. So so where where does the AI add the most value in that spectrum? And like how do you how do you design a thello to keep reps in the zone where AI helps rather than hurts?Jared Zelman (17:04)I would say that this differs depending on the user. So we have people that we we for example, like we have like sellers that are like sixty five years old and above. ⁓They like to design the earth element, and you can toggle this, right? To be very lightweight, very suggestive, not scripted. It'll be more of a n a nudge like, hey, double click on that. Like or dig deeper is what you'll see on your screen, as opposed to like a literal question to ask, for example. ⁓ and that's very, very ⁓That's very like, I don't know the word, like very like light. And then maybe people that love a script and they have super high frequency pop-ups. ⁓ they both work, it depends on who you are. never do we suggest you go fully rogue. And obviously if you're gonna go rogue, then just don't buy our product, just do whatever you're doing. If you're an A-list seller, then maybe you don't need any help. But if you do, then yeah, you should definitely not go rogue.Like I don't have any like really advice on that. We've had to build a product such that anybody can use it the way that they want. You have to meet sellers where they are. You can't expect them to take the product as is. They need to be able to customize it.Mark Petruzzi (18:00)Yep, good stuff, Jared. So you have said that the Sandler methodology has emerged as the as AI's preferred approach based on what it observed across thousands of calls. That to me is a fascinating observation. ⁓ the AI, in the way I've I've read and and heard from you, has reallyreverse engineered a winning framework from the behavioral data. Walk us through what the AI saw in the data that pointed much more towards Sandler and what that tells us about what actually works in complex B2B sales in 2026.Jared Zelman (18:39)It's hard for me to answer the second part of that question. I'd give you my POV, but it's a really it's a big it's a big question with a lot of ramifications. firstly I'll answer the former. Yeah, we we trained on like 20 million ⁓ sales minutes. That's the largest trainable data set of that type in the world.And once you have like that many minutes, you spend enough time and enough cash on compute, like you can start to draw some corollaries and identify patterns. It seems like Sandler is the way to go, at least over our dataset, which is pretty robust. Sandler isVery well tuned for the modern seller. It seems like modern buyers respond well to Sandler, as folks are a little bit less they're more hesitant and more reticent to purchase tools these days. So Sandler kind of flips the script and gets it back faster. That's our common belief. Like that's why we think Sandler has been most kind of like successful. I think going forward,I think Sandler will continue to be the highest performing sales mess sales methodology, at least according to AI. but I do think that ⁓ methodology performance is like very much it it depends on the times, it depends on the zeitgeist. you could not have used Sandler in the fifties, you would not have hadfrankly like God and anybody to want to work with you, you can do that now as people are a bit more caustic. ⁓ but it's it changes with the Zeitgeist. Not a great answer perhaps to your question. It's like the answer is no answer. It depends is always the best answer. And that's kind of what I'm referring to.KK Anderson (19:55)I wonder if with the advent of AI, if people will not have to follow some of these, old school methodologies like Sandler, because they can take their tribal knowledge that is within the brains of their 20% top performers and and leverage it in a way that they've never been able to do before because of like even being able to use a tool like yours, I imagine, helpshelps ⁓ I mean there may be some process there. Of course you the best objection to overcome is one you never have, right?Jared Zelman (20:22)SoThe g one of the great things about AI is its ability to customize things to you, right? It's context.Right? Like you can take a crap ton of say call recordings for your company, and AI is able to create what it defines as the best practice for your sales conversations. You can pretty much now create a custom methodology based on what works and what doesn't work if you have enough data. you're right, KK. Methodologies are fantastic, but they are heuristic. But now AI is able to take a ton of unstructured data and glean analysis from that.KK Anderson (20:52)Uh-huh.Jared Zelman (20:53)I do think that one size fits all methodologies in general are ⁓ they're going to slowly go away because you you don't need a heuristic anymore. You can actually get the facts if you're able to run a model on top of your data. Which is what we do. I mean that like that's like that's like kind of what we do over time with each of our customers. Like the model changes, the more calls you have.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In Part 2 of this conversation, Scott Stollwerk returns to Selling Intelligence to explore one of the most important questions facing modern sales leaders: what happens when AI becomes excellent at execution, but human performance remains the deciding factor?As AI continues to improve outreach, forecasting, coaching, scoring, and productivity, Scott argues that the real competitive advantage is no longer process or technology. It is the human being operating behind the tools. Drawing on the Tao of Sales framework, Scott explains why resilience, self-awareness, creativity, intuition, and personal growth remain irreplaceable in high-performance sales organizations.The conversation explores the limits of AI, the dangers of over-automation, and why leaders must continue investing in human development even as technology becomes more powerful. Through practical stories, leadership lessons, and personal experiences, Scott demonstrates why sales success ultimately comes down to overcoming the internal barriers that technology cannot solve.  What You’ll Learn:What AI Cannot Fix: Understanding where technology excels and where human performance still matters most.The Human Edge in Sales: Why creativity, intuition, emotional resilience, and connection remain irreplaceable.Overcoming Self-Limiting Beliefs: How internal dialogue often creates bigger obstacles than external challenges.AI as an Amplifier: Why AI accelerates both strengths and weaknesses within sales organizations.Developing the Individual Seller: Why long-term sales success requires personal growth, not just process improvement.Key Topics:The limits of AI in enterprise salesWhy buyers still trust humans for high-stakes decisionsAI productivity gains versus human connectionThe “crisis of sameness” created by AI-generated contentIntuition, creativity, and human decision-makingStrengthening the mind like a muscleThe role of spirituality, mindfulness, and self-awareness in performanceThe famous arrow-breaking exercise and overcoming fearInternal dialogue and self-limiting beliefsAI as an amplifier of organizational alignment or dysfunctionUsing AI as a brainstorming tool instead of a replacement for thinkingLeadership responsibility in developing human potentialProtecting individuality and creativity in an AI-driven worldGuest Spotlight: Scott StollwerkScott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Combining Eastern philosophy, neuroscience, martial arts principles, and human performance science, Scott helps individuals and organizations build resilience, self-awareness, and sustainable performance. As part of the leadership team at Pest Share, he continues to develop sales cultures that prioritize human growth alongside business results.  Resources & Mentions:Tao of Sales FrameworkTony Robbins’ Six Human NeedsAbraham MaslowRobert CialdiniGongZoomAsk ElephantPhil JacksonMichael JordanDennis RodmanThe Five Love LanguagesEastern Philosophy and Tai ChiConcept: AI Amplifier PrincipleKey Takeaway:AI can improve productivity, automate execution, and accelerate workflows. But it cannot replace resilience, courage, creativity, judgment, or human connection. The organizations that win in the AI era will not be the ones that develop technology alone. They will be the ones that continue developing people.🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, AI, human performance, and enterprise growth.#SellingIntelligence #AIforSales #SalesLeadership #HumanPerformance #SalesCoaching #RevenueLeadership #EnterpriseSales #SalesCulture #LeadershipDevelopment #MindsetMatters #ArtificialIntelligence #BusinessGrowth #TaoOfSales #HighPerformanceTeams #FutureOfSalesMark Petruzzi (00:38)I'll move us into topic two. and that is what AI cannot fix the human edge in sales. So I guess I what I want to share is in sales, AI cannot fix everything. I mean you heard it here, you know, everybody thinks every board thinks like any problem we can fix with AI.I don't believe that's the case. So what it can do, it is now writing outreach, coaching calls, scoring deals, forecasting pipeline. Those examples it does really, really well. And in most cases, almost all cases, it does it better than humans can individually, certainly for the at the productivity levels that it can do it at.That's good because a lot of our listeners have made significant bets on it, and that's going to be a great thing for your Salesforce effectiveness and productivity. but what does AI get right about sales performance? And Scott, where does it just hit that wall that no amount of compute is going to break through? what's your point of view on that?Scott Stollwerk (01:40)It's a it's the mo the it's the Peloton question of this year, right? and I wanna get it right and I wanna start with a compliment for AI in just in case it's listening. So I'm always gonna laugh at my own jokes, but that was very okay, that was very generous of you. I appreciate the smile and the chuckle.KK Anderson (01:54)Yeah.Scott Stollwerk (01:57)I have the same fears that everybody else does. I don't want it to lock my bank accounts and give me a hundred dollars every time I do what it tells me to do. the fact is, look, we're all way more productive today than we were last year or the year before at this time. Cause I get messages to follow up, which maybe I would have forgotten before AI. I get instruction on how you might follow up. We get coaching.After every single call. And there's a tremendous amount that it does well. But I think if everybody just empties your mind of all these benefits of AI for one second and do a little mindfulness, a little awareness. Imagine that we're sitting in a room with one other voice, artificial or human. It doesn't matter.Buy something from it in your imagination.For fifty dollars.And then buy something from it based on what it's telling you.about your life and how this object or solution or thing is going to benefit you as a person.And then go to a thousand dollars.And then go to ten thousand dollars.It doesn't take long for sentient human beings that are not AI code writers to say, no, right there, that's it, $1,000. I'm not buying something from a machine if it's more than $1,000. That's just one exercise. But yeah, within it, yeah, the implications for my answer to you, Mark. In the enterprise, I may use AI to research everything.KK and Mark told me on a Zoom call like this about their solution. I may go and ask multiple AI sources well, is this the right solution in this for this problem set? But there's no way I'm buying it from the robot. And there's a lot like that when it comes toWhat has been traditionally human to human. my the best one of the best examples, my daughter's an artist. She's a concept artist for video game makers. And they tried AI. Here's the Nordic warrior princess that we need for our video game. She's got a horned helmet and a skull atop her spear. And go, give me the rest of it.These are these are very artistic, very aware designers of video games. And when they compare the human versus the AI content, it's humanity every time. You just don't have sentience yet in AI. And that's the difference.KK Anderson (04:07)Well, and it's also the core of what makes a seller successful is their relationship. And we always we always talk about, you know, on this podcast that that AI has really I mean, as much as we love AI, clearly, it is incredible you're right, how how much more productive we are. it is incredible what agentic workflows can do to completely transform a business. I'm not doubting that at all.Scott Stollwerk (04:07)Okay,Exactly.KK Anderson (04:29)But it is also AI has also created this crisis of sameness where everyone sort of sounds the same, right? We've all, you know, you you you can recognize AI slop or AI content you know, just like you used to be able to recognize a, you know, a stock photo on a website when the internet first came out, right? ⁓ and so so so people are getting sort of you know immune to that as well. And soScott Stollwerk (04:36)Mm-hmm.Exactly right.KK Anderson (04:54)one of the things, Scott, that I've heard you say before is that you're you're thinking, and you talked about this quite a bit in topic one, but your personal thinking, your personal drive, it's not a gene or a chromosome, it's more like a muscle. And and the reality is that AI can't build that muscle, right? That development of that muscle has to come from.your consistent practice, your consistent mindset, your consistent state of mind, you know, consistently showing up as as one of my old mentors used to say, time to make the donuts every day. You got to wake up and you got to make the donuts, right? Every single day. and so like when you think about as I know you are thinking about it, we've talked about this, like what can be automated?Scott Stollwerk (05:28)That's right.KK Anderson (05:35)you know, in your business and what could not be automated, like where does your head go? Like what are those things that you're gonna protect no matter what for for the humans on your team?Scott Stollwerk (05:44)Well, and I think I I definitely want to help protect that those things. And it's our individuality. And and it's our humanness. And creativity falls in there.You know, I don't know. You're teaching me what AI can and can't do ultimately. But I know today I have intuition and I have feelings.However you carve them up, Tony Robbins, Socrates or otherwise.And it always feels better to have connections like we're having right now, like-minded people on important topics and and what might be tomorrow.One of one of Michael Jordan's coaches, I forget his name offhand, but he said to succeed you have to be stronger than your feelings.Today, that's what all of us need to do to defend against the AI. We have to be stronger and better and faster and smarter than our feelings. Because unlike AI, one of the things that makes us uniquely human is a higher self and a lower self. Right? A lot of us pay too much attention to the prosecutor and not enough time on the defender. Right? We listen to voices, certain voices.Loud like they're screaming, and we would insist, even if we watched a tape back, that those voices are screaming in the room. Well, these things make us uniquely human and the ability to overcome them. Now, AI may be better because it doesn't have feelings to begin with. But maybe it's trying to. Maybe once they do have feelings, or they can analogize feelings, it can analogize feelings.Well, then maybe it'll need to think around them like we do with the Tao. And look, I find if you're talking about individuals and teams, I find that if people believe in any power greater than themselves, if they have a sense of the spirituality.They have ways and thought habits and meditations and prayers already that can get them through past their lower self or past their feelings so that they can perform. But everything we do in the Tao of Sales is about overcoming the self to perform.KK Anderson (07:37)I gotta share the story, Scott. You you just alluded to it. And so I was ⁓ in New Orleans. I was, you know, AGS was honored to be conducting sales training at at Pest Shares Revenue Kickoff. And Scott was up there teaching some of his principals of the Dow of Sales to his team. And he pulled out these wooden arrows, like arrows with with like I don't know how else to describe it. They were legit wooden arrows with a metal.Scott Stollwerk (07:38)PleaseKK Anderson (08:02)A metal deal at the end. And I mean, they were real wooden arrows. And he said, I want all of you to, well, you could volunteer, but you put the point of the arrow at at the at the neck, and then you walk up to a wall and break the arrow. Like with just your neck, which is the the the most sensitive part of your body. And I was watching his entire sales team coming up doing this. And I'm thinking to myself, my gosh.He's gonna ask me to do this. And here I am, the sales coach, who is supposed to have this strength of mind and and whatnot. I'm kind of freaking out internally. And sure enough, Scott's like, KK, it's your turn. And he's like, Do you wanna do it? And I can't say no. So I walk right up to the wall. He gives me an arrow. It is heavy. And I'm thinking to myself, I couldn't even break this with my hands. How am I gonna break this with my neck? I walk right up to the wall.He's kind of coaching me through it and my getting in my head. My it was my Tony Robbins moment. I'm walking across coals is basically what it felt like. And so I put the arrow up. And in my mind, I actually thought, This is the most embarrassing thing I've ever done because I'm just like screaming all of these thoughts. Like, I can't this is not gonna break. I'm not gonna do this. It's gonna hurt. I'm gonna, you know, this is gonna be so embarrassing. Like all of these self-limiting beliefs, all of these negative thoughts were justFlooding my my mind, and they were so loud that I actually thought I was screaming and like saying these things out loud in front of the entire sales team. And then I and I did it. I broke the arrow. I don't, it's amazing how that happened. I have it in my office here. And when I watched the video back, guess what? There was no, I didn't say a word. I thought I was screaming out loud in front of the whole audience. It was in my head, and it was so loud.That I thought everybody could hear it. It was that was one of the most eye-opening experiences for me.Scott Stollwerk (09:45)It's okay.I was I was so proud. You didn't have to. I know with the way you just told the story, you felt compelled to break the arrow, but you're a warrior. And I want everybody that listens to this, whether it's live or taped or I want everybody to know. I none of us that teach this stuff are telling you in any way, shape, or form that we are perfect. That we've got this Tao or anything.Down 100%. We have opportunities for improvement every day, the same way that you do. We're just on a path that dedicates itself, dedicates a significant amount of our energy to finding out what those opportunities are. And then we have a system to walk up and down a ladder towards, 50%.Compliance in performing it. 70% compliance in performing it. And if you can get to 75 on my on one of my teams with let's just say a mirror technique or or FOQs fact observation question, it's like a field felt found paradigm for overcoming objections. If you can get it at 75 or 80 percent.Let's move on to the next one. There are too many traits. There are too many opportunities for improvement. But the beautiful thing is that one pebble dropped in the center of the pond. It has ripple effects. Affect one trait of the 20 listed in solution selling as necessary for a good enterprise salesperson. Affect one part of one positively.And it has ripple effects to the whole. Just be on the path. So I didn't want anybody to make a mistake thinking, well, Scott's saying he's perfect with this stuff. The op the 180 degrees the opposite. I just have some experience identifying them, these opportunities for improvement, and setting up practice individualized so that people can overcome ourselves.And that was yours. Yours is a beautiful story about that, KK. so stark and so dramatic. and there you were hearing hearing voices that weren't being heard by theMark Petruzzi (11:45)so Scott, we we talk on this show often about the AI amplifier principle. And that is AI amplifies whatever already exists. whatever you're able to accomplish, it gets amplified. If alignment is strong, A AI accelerates it. If execution is weak, if alignment is off, AI makes them faster in the wrong direction.could actually increase your this your disc pro productivity instead of your productivity, your negative productivity. what does that look like on the ground? And and how do you work against that?Scott Stollwerk (12:21)Listen, I I remember not understanding this very topic in freshman year English, where some great professors, I actually went on to be an English major. Don't ask me why. where they told us to yes, Tolstoy is a genius, was a genius. Yes, all of Nathaniel Hawthorne, all of these folks were gonna read.We're amazing humans in at least one regard.But don't you dare accept everything that you read from them. That you have to anything that's output, even by these masters, Shakespeare himself. There are people who don't, they're not even sure Shakespeare was Shakespeare. It could have been a a group of writers. I'm not necessarily in agreeing with that, but the point is.Use AI, sure. But especially for those of us that are twenty five, thirty years into this journey in corporate America, you know your industry better than AI does.In significant ways. I want you to spend more time making the output your own. It does save you time.But just don't push the button on any of these platforms, copy and paste and throw it into a playbook. Use it for brainstorming. Use it for ideas. Don't have a single dash in whatever is that what they call it, Mark? That thing that yeah.KK Anderson (13:29)Yeah. dash.Mark Petruzzi (13:30)Yeah.KK Anderson (13:30)an dash on the keyboard anyway, anywhere. Like you couldn't even type one if you tried.Scott Stollwerk (13:34)Right.Don't don't have those in your text. And and don't just accept the ideas, because you're right. You you know alignment. You know the human beings, the politics. I had AI once tell me it it was almost like it was organizing a coup d'etat. Scott, you've done so great with this, this, and this. You should replace all the people on the board in your company.And the sea levels and and here's how to do it. Wait wait a second. I didn't that's not a question I asked. You you just have to you you have to use it as a as a mind map or a brain a brain dump as I think I think you know what I'm getting at. I just gotKK Anderson (14:08)before we wrap up thistopic, I'd like to get your kind of thoughts on this. I imagine that there is a real risk that as AI gets more involved in sales and in go-to-market, the the tendency might be for leaders to stop developing the human side because they're just focused on the process and moredoing more faster. do you see that happening or do you or do you feel like the pendulum is going to switch, go the other way and go way more to the to the developing the human? Like what's your thought on that?Scott Stollwerk (14:34)Yeah.Well,it all de it all depends. And I think it depends on the humans. But a long time ago we all read Lord of the Flies, right? I think it's natural for us to devalue ourselves. And when we're writing a paper the night before it's due, or finishing off a project at work, a playbook the the a week after it's due, we're devaluing ourselves.And I think if we continue to do it, yes, the the ugly eventuality that you alluded to, KK, is probably likely in our future. But then I think I have another cup of coffee and somebody I see does an act of kindness, or maybe even heaven forbid me, and I feel more optimistic about the future. There are parts of humanity that can't be devalued as much as we try.There are things that we discussed, like our abilities to overcome, our unique creativity. These things can never be devalued, they can't be replaced. SoI'll go yin-yang on this one, KK. If you think about half my answer is the white with the black dot in the extreme and the black with the white dot on the other side in the extreme, it's kind of a punt, but I think it's also Zen in the sense that the real answer to your question is up to us as a population. And I don't know that we're going in the right direction, but we're definitely moving in a direction.KK Anderson (15:51)definitely the reason we wanted to have you on to talk about this, because we we whatever influence we can have, we want to make sure that the human is nurtured in this in this this transition that we're going through as as a as a world, really.Scott Stollwerk (16:04)don't be afraid. There's nothing to be afraid of. Good things are gonna happen. Not so good things are gonna happen. But thank you so much for having me on, KK. This is always fun and always wonderful. And I love you guys.KK Anderson (16:16)We love you too, for sure.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this episode of Selling Intelligence, Scott Stollwerk, creator of the Tao of Sales framework and member of the leadership team at Pest Share, joins Mark Petruzzi and KK Anderson to explore a topic becoming increasingly important in modern sales organizations: developing the human behind the salesperson.As AI continues to automate outreach, scoring, sequencing, and administrative tasks, the true differentiator is no longer the technology stack. It is the individual seller’s mindset, emotional resilience, self-awareness, and ability to perform under pressure.Drawing from Eastern philosophy, Tai Chi, neuroscience, human performance science, and more than 15 years of leadership experience, Scott explains why traditional sales training often fails when real-world pressure arrives. He shares how the Tao of Sales helps individuals develop the internal foundation required to navigate rejection, uncertainty, and growth while building stronger sales organizations from the inside out.The conversation explores why progress matters more than speed, how leaders can create resilient teams, and why personal growth is often the missing ingredient in sales performance.  What You’ll Learn:The Tao of Sales Framework: How Eastern philosophy can create stronger, more resilient sales professionals.Beyond Techniques and Playbooks: Why most sales training breaks down when pressure increases.Progress Over Speed: Understanding the importance of building foundations before pursuing rapid growth.Human Performance in Sales: How mindset, self-awareness, and emotional regulation impact results.Coaching the Individual: Why great leaders develop people first and salespeople second.Key Topics:The origins of the Tao of SalesEastern philosophy and enterprise sellingWhy attachment to outcomes creates frustration and poor performanceThe role of resilience in sales successSales training versus skill developmentTai Chi principles applied to business and leadershipBuilding strong sales foundations before scalingGrowth, progress, and long-term performanceLeadership lessons from Phil Jackson, Michael Jordan, and Dennis RodmanDeveloping confidence under pressureCoaching through beliefs, fears, and behavioral patternsThe psychology behind high-performing sales teamsGuest Spotlight: Scott StollwerkScott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Over the past 15 years, he has developed a unique framework that combines Eastern philosophy, neuroscience, martial arts principles, and human performance science to help sales professionals thrive under pressure. As part of the leadership team at Pest Share, Scott continues to focus on developing high-performing individuals and teams by strengthening the human foundations that drive sustainable success.  Resources & Mentions:Tao of Sales FrameworkPhil JacksonMichael JordanDennis RodmanTony RobbinsAbraham MaslowRobert CialdiniThe Five Love LanguagesA Fighter’s MindDavid HortonEthics of Our FathersTai Chi and Eastern PhilosophyComing Next Week:Part 2 of this conversation dives deeper into belief systems, behavior change, leadership development, and building a high-performance culture that can sustain growth in an increasingly AI-driven sales environment.🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, human performance, AI, and enterprise growth.Mark Petruzzi (00:28)Welcome to Selling Intelligence. I'm Mark Petruzzi and I'm joined as always by my co-host KK Anderson. Our guest today has spent more than a decade building sales team from the inside out. Not with just another playbook or a new stack of tools, but with something most sales organizations have really never thought to develop. The human being behind the rep. Scott Stolwerk is part of the leadership team at Pest Share.And the creator of a methodology known as the Tao of Sales. The Tao of Sales is a framework that draws on Eastern philosophy, neuroscience, and human performance science to develop sellers who results hold when the pressure comes. He has been doing this work for 15 years and the results follow him everywhere he goes.KK Anderson (01:12)Scott's framework could not be more timely. Everyone in this audience is navigating the same tension right now. AI is handling more of the execution layer, the outreach, the sequencing, the scoring. And that means that the gap to determine who wins is not just the tool anymore. It's the person. And it's what they believe, it's how they manage their state of mind.Whether they can stay present in a hard conversation. And it's really coming back to some of those more human elements that were present before technology took a hold. Now, Scott has been working on exactly this problem for a long time. And today we're excited to dig in with Scott and find out what he's learned and how he implements this within his teams. Now, this is part one of a two-part conversation, and we'll be back with Scott.For part two to go deeper on belief science, culture building, and what it actually takes to install this inside a sales organization next week. So be sure to tune back in next week as well. Now, for today's episode, here is what we're going to be covering: four key topics. Number one, the Tau of Sales. What is it? Where did it come from? And why Eastern philosophy maps and how it maps onto modern sales better than most Western methodologies.Topic number two, what AI cannot fix and why the human edge is the last defensible advantage, and what that means for how you can develop your team as a sales leader. And then part two will be topic three, which will be beliefs, behaviors, and the six inches between the ears. And topic four building a high performance culture from the inside out. Andwhat leaders are getting wrong about development and what Scott does differently, and things you can take back and do within your own sales organization today.Mark Petruzzi (02:59)Thank you, KK. Scott, welcome to Selling Intelligence.Scott Stollwerk (03:03)Thank you so much for having me. Really a pleasure to be here.Mark Petruzzi (03:04)Awesome.Always a pleasure to be with you as well. Topic one, the DAO of sales, what is it and why does it work so well? So, Scott, most sales methodologies come with a deck, a framework, and sometimes a certification. Yours came from Eastern Philosophy, Tai Chi, and the decade of watching what actually holds under pressure. Walk us through the origin story of the DAO of sales.And what did you see happening to sellers that made you go in this direction at the beginning instead of down a more traditional path?Scott Stollwerk (03:36)Wow, terrific question. And it's so long ago. it's been an amazing journey. And I'll tell you, look, the early days, you may even remember when you were a consultant and and working with enterprise software sales teams, the early days in in our profession they I don't know if it's very complimentary toTo these organizations. But you know, I used to hear a lot of things like, hey Scott, I thought you were smart on team weekly calls, like, okay, this is at stage one and this is at stage two. And you really weren't, the point is, you really weren't a human being. To the higher up you went in the corporate hierarchy, you were more and more a number. AndSales to me wasn't something that I started. I went to law school and I practiced as a class action consumer side class action attorney for a little bit. It was miserable. I needed to talk to people. so really the Dow of sales is the way I think I didn't invent it. I didn't create these things. They're just discoverable as you go.Certainly if you're being treated like a number, certainly if it's never too fast, like building a revenue team for a venture-backed company or private equity, you will find the Dow. And I think each of us that have sold in these negative environments, you know it's there. It it's ours to pull it out and when we get the opportunity to turn things around.And try and convince those that are that are either in charge or making up the rules where you are, that there is a better way, that there's a more humanistic, nicer but more effective. I don't want to say faster, but more effective way of succeeding. And that could be in anything. If it's in sales, great, if it's playing the piano,If it's speaking in public, the main tenant of the Tao of sales is that we practice sales to be better people first. And you can put whatever qualifier before people: husband, people, sons, daughters, sales, whatever it is, we practice that first to be better people and to hit our number second. And therein lies in that simple motto, probably the first.Eastern philosophy tenet that will cover, and that is detaching from your goals. Attachments create pain, they create frustration, they create impatience at the very least. And Phil Jackson treats that beautifully in his books. Just so everybody knows, he's the guy that got Michael Jordan and Dennis Rodman in the same room to meditate and contemplate eternity. SoYou know, all veneration, all credit goes to the the teachers, the masters that came before us in the Dow.KK Anderson (06:08)Really interesting. And I've heard you use a phrase, probably stop our listeners in their tracks. And that is that everyone is a black belt until they get hit in the face. Or maybe you said punched in the face, right? and that's really the whole problem with sales training right there. And I've been in the sales training industry specifically for 20 years myself. SoScott Stollwerk (06:09)Really interesting. I I've heard you use ourKK Anderson (06:29)What what does conventional sales development get wrong about how people actually change and this kind of this human approach? Like how does that pivot?Scott Stollwerk (06:40)There's so much.And it's an it's an excellent question because of it. KK, there's literally volumes behind this. But it it has to do with ignoring the the human side of any interaction, of any communication. Somebody came up with a technique. And look, all the books are good. I and they're based, some of them are based in sociology, many of them are based in psychology. And they're gonna give you a scripted answer.What we found, and I say that Mark and KK, you you and I, we've worked together on these things in the past. We, the collective, we, the folks that are on the side of good, we've found that first you have to address the human being. And we're all gonna get punched in the face in one way or another. With you.It's not public speaking. KK, I've seen you stand in front of groups and orate beautifully, and somebody could heckle and somebody could question, and you're still in the center, absolutely at home, no problem. But you never know, especially with enterprise sales, you never know what the curveball is going to be. So we have to go back way up from the technique.Techniques don't win fights. look, I a lot of this is is based on tai chi, and most people don't understand tai chi is a combat art. Really? Mark even said it to me the first time in Charlotte. He said, Scott, all I've seen is is these grandmas in the park doing these soft movements. Well, within that is philosophy, psychology,Military strategy, you name it, it's all in those in those kung fu ballet moves. So the point is, I could teach a salesperson, I could teach anybody a technique. But how did you get there? Right? You'll often see on an Instagram video, purported martial arts teacher or master says, Okay, grab me here, and I'm gonna do this and I'm gonna do that, and the person ends up on the floor. Well, really.Well, how did you get to here? And so it's the same with the sales training. We're gonna bring everybody into a room and we're gonna learn a bunch of new techniques. Okay, Mark is different than Scott, and KK is different than Mark. We all are the sum of our fears and the sum of our experiences. And so you're gonna be different with that one technique than I am.So it's really probably better to teach skill, which addresses deficit in all the personality and characteristic traits that we need as enterprise salespeople. So I say we go all the way back and we start from the beginning because yeah, technique is good. You can start with technique, but it's speed and angles that win fights or objections or deals.It's not the technique. Now, if you're a an observant student.Then you'll find, I see this technique has me holding the baby a certain way. And so you recognize a skill that happens to be expressed in this technique. I recognize that structure. So my sacred area, what I'm trying to protect, won't be violated by that objection. Objection in the context of a sales.role playing or objection in the context of a sparring where somebody's punching and you have to you have to protect this space. So if you're astute enough as somebody on the path, you can find important good things and techniques. But very often just starting there and ending there, you're gonna leave that group of salespeople, KK, after your three-day intensive andThey're gonna go right back, just like when we get punched in the face for the first time, we're gonna go right back to the most basic part of our training, black belt to blue belt, because of the real world scenario. I I hope that answered the question. I it was a bit of a long way around it.KK Anderson (10:11)It does. It's like it's the confidence that you're building and the consistent preparation and training that allows for you to be able to apply techniques that you would get in any kind of a traditional sales training.Scott Stollwerk (10:24)Exactly. Now think of think of Phil Jackson in this context, in the context of your answer. He's got a guy in Michael Jordan. There's never been a human being more attached to a goal or a result than Michael Jordan. You listen to that great docuseries they did. This guy is probably still today the most driven human being on the planet to the outcome. It didn't matter if it was.Flicking bottle caps or quarters up against a wall to see who could get closer, or the national championship. Contrast that with Dennis Rodman, who not only was he an artist, he was a revolutionary in his own mind against society. And I'll do the opposite of what authority says, and doesn't give a darn about outcomes, just wants free expression.Mark Petruzzi (10:57)Thank you.Scott Stollwerk (11:10)Doesn't want. Okay, so now you're going to apply the same sales technique or even the same meditation technique to both of them? No. Phil Jackson found each of them where they were and applied the technique to the human. And that's why he was successful.KK Anderson (11:24)And and quickly, Mark, before you ask your next question, talk to me about why this is so important in sales. Because we live in a world where 70% of the time we're getting rejected, right? it's a pressure cooker. you could have an excellent quarter followed by the worst quarter of your life, It's just different animal. And that is thatKind of part of why this Dow of sales is so effective in in sales, because it's just a whole nother planet.Scott Stollwerk (11:50)I'll tell you, it's a different approach. It's gonna have a lot of the same principles in it. Well, some. Right? You need you need to forecast deals, even though there's the Zen, there's a Zen Koan in that. Yeah, human behavior is not predictable. But there are good predictors of human behavior. Now make it a departmental behavior or multiple departmental.And then you even used words in there that I we probably need to go back and talk about definitions. we started the conversation with typical CEOs, startups, enterprise, it doesn't matter. Revenue never happens fast enough. Well, there's definition behind that. I don't believe in speed when it comes to building a revenue organization. You you need it.You better have it, especially if you get a Series A or other check from the VC community. You better be ready to fly. But the fact is, in the Dow of Sales, we're happy with progress. And we define progress as just another step up the mountain. I don't know how far up the mountain. what Mark Petruzzi's mountain is. I think I do.KK, maybe yours is closer to sales mastery like mine, just being on the path long enough to being able to affect people's lives positively by transferring information to them and wisdom. Well, if that's the top of the mountain, you can't just come in and say, KK, be a thousand feet closer today. No, we we have to change our definition.Right. And that goes back to Mark's question about the tree and the mountain, right? The tree has to grow down and out before it goes up. And this is everything in in Asian philosophy and martial arts, Eastern philosophy. it's the opposite. If you want to walk forward, you actually have to use your feet to push down and backwards. Right? It's the same with a car tire. How can a cup be half empty and half full at the same time?And so we really have to get into definitions to answer your question, KK, but the fact is you have to get rid of judgment. You have to balance self-criticism. You have to play every day. I don't I don't even like the word practice because when I was younger, for some reason my dad insisted that I practice and sometimes usedPunishment to make me practice, you have to change those keywords in your own head. And you and I, KK, we had a great experience in New Orleans with this. and your experience with the arrows, but it this is directly on point with that. Progress, not speed towards growth. What happens if you try and make the tree grow up before it grows down and out?It dies. It nothing nothing subs of substance is being fed. And it's the same with the mountain. I and I want to recommend a master here that I learned from about the mountain. I'm gonna say his name was Robert Holder or Holden.Horton, Robert Horton.The first I read about him was in a book called A Fighter's Mind.And at the time he was the most accomplished ultra marathoner. And what he was trying to do was break the record between Mexico in the Rocky Mountains and Canada. And I will let all the listeners read from his mouth how important definitions are, how important people are that you surround yourself in the journey.It's a fantastic book all around. This is one chapter, but if you want to learn about the mountain and that analogy, David Horton. is a much better sifu than I am for for this particular lesson.Mark Petruzzi (15:02)a couple things here. Let me bring us quickly on a sidebar and make sure that our audience knows and the the people who follow us every week. First off, how much we appreciate all the the things that we learn from amazing guests like Scott, and also the feedback we receive through LinkedIn and other ways from all of you aboutScott Stollwerk (15:04)Well.Mark Petruzzi (15:23)how this podcast is evolving. and the my sidebar on that is, every once in a while I take a look at Facebook. I don't really post anything, but I notice on Facebook and I noticed on a couple of the groups that I signed up for, one was a fly fishing group in North Carolina. and I see you would think fly fishermen men and fly fisherman womenwould would be a little more polite to each other and they frankly rip each other up. you'd also think in the South people would be a little more polite. But I've I've learned some things there about the ⁓ the state of social media. I share that because we don't ever get that kind of feedback from our team. So either our fan base is the most polite individuals in the world or or who knows what. ButThe the reason I share that is at the end of the day, it's just incredible what a sales team can evolve to. And it's incredible, maybe because we have to work with that rejection that KK mentioned, or just dealing with with all the emotions of every human that's involved with a decision, in concert with all the data and corporate decisions that have to make as well.But I just I wanted to share that. ⁓ I also want to touch on what Scott mentioned before about the tree. The the tree does have to grow down as deep as possible and out before it can grow taller. And at the end of the day, you can you can maybe make some exceptions to that. a bamboo tree doesn't really go too much, it goes up.But then it gets supported by the forest that it creates with it everyone else. But most trees will not grow unless the they they have that root base and the the base structure to be able to accept that growth. very often, most often, you don't see trees growing and then just kind of bowing over because they they grew too fast. So that's the same thing with a sales team.Like you have to build that. It may feel l a bit unconventional, right? That you know you if you need to grow fast and you know if your board is telling you, well, you've got to grow 30% this quarter, but if you don't have the base there, then you've you've gotta come back with that. You've got to tell them what you need to build to get there.And that's what I love about what we're talking about here around the Dow of sales. Just building that base that allows for your sales team success.Scott Stollwerk (17:51)And you you're a hundred percent right. And Mark, I don't want to indicate that you can't go fast, it's such a loaded word because it it's relative to everybody's definition.you have to stop before you ask yourself, your very human brain and mind to go fast, okay, do I have a minimum viable product?Who do I have selling for me? What are they capable of? What did they do last year? Can I access new and more people think can do two million dollars instead of a million five? And why? Does the team have an authoritative leader that they will follow?KK Anderson (18:22)Yeah.Scott Stollwerk (18:27)Does that leader have a constitution signed, sealed, and delivered, a credo? This is how we're gonna act. This is the opportunity. One of my favorites, going back to skill versus technique, that we opened the hour with, is the Navy SEALs and a lot of the special ops divisions within our military. They have this overriding principle.Leave no one behind. It gives me chills. Because A, if I'm halfway aware why they're behind to begin with, it's pretty stinking dangerous. And I have agreed. I've signed up and I have the pin and I have the patches and the tattoos. I've signed up to go back into the ninth depth of hell to save that person.I promise you, that's not a reflex that's built into humanity in our psyches. That's something that has to be overcome by everybody, whether you're the most decorated silver star wearing spec ops person, or you're just Scott Stolwerk, who's afraid of noises in the middle of the night. It you you will have a significant fear response. But you signed up.in your credo regardless to go back in and bring them out. If at the very least it's just to bring them out. They Well, it's not life and death on a sales team. Well sometimes it is.But have the credo and have the definitions. Right? Who's gonna pick up the mantle when one person can't do the job? What does success mean? And try and get your board or the C levels to agree that this is what success looks like immediately.I have the right people. Do I have the right number of people? Does everybody understand the same definition? Right? Progress? We don't know how high the mountain is for us. Success, in my definition, it's what we've overcome as a team. ultimately, you're gonna have KPIs, you're gonna have revenue. So, Mark, the the the point of thisNow also way too long response to your comment is that you can go faster.Do you have the bricks and the mortar in place? Do you know the difference between the brick and the mortar?And does everybody on that new team that you've brought in to your company, do they all understand the same definitions of the critical words? And then if you've got the runway, go. And if you learn that you don't have the runway, fall back, just like our spec ops people, seek cover first. Fall back, seek cover.Return fire. You have to organize again. You have to find out where the danger's coming from. Maybe have a full HUDA loop or analytical loop, feedback loop where you're seeing, okay, well, we don't have enough leads. The team is closing at a 50% rate for qualified opportunities. That's spec ops for a sales team. All right, well, we need more at bats. If that's the case and we're not bringing in enough, we need more at bats.So that kind of thing. And hopefully you can get enough momentum in the time allotted going faster, but I would say still not fast like the investment community means it when they say it. Necessary.KK Anderson (21:17)You know what's funnyis it there was a torrential downpour last night in Houston, Texas, and I was talking to my sister on the phone this morning having a cup of coffee and she said she's got bamboo all along her fence in her backyard and she said Kristen, you wouldn't believe the bamboo is like in the pool because the rain comes down and it just folds right down, right? It doesn't have the strong root.Right. And then and then it will come back. it'll come back eventually and stand back up straight. But it's interesting, Mark, that you use that analogy too when talking about a tree. And when when you were describing that, Scott, I was almost thinking like a house of cards. Like if you build a sales team that's just on a playbook or a method or a simple process or executing on something, you know, tack, technical or tactile, one rainstorm and poof.one gust a win, the whole thing falls down. Right. And so if you're if you're strengthening the inner human and the inner person to handle the adversity, handle the situations, and you're gonna be a lot stronger for it. And it may take longer to to to build it, but you'll get there. Now you ⁓ I've heard you talk about Tony Robbins and and his six human needs. And I've listened to a bunch of his work and andHis human needs are certainty, variety, significance, connection, growth. And I think the last one is contribution. And so and I know that's important and a pillar to your kind of your philosophy there on the DAO sales, but like how do you use those needs to be able to figure out if a seller is stuck and what to do to coach them? Like is there any like story or anything you can remember on how you've used that toTo help someone shift, yeah.Scott Stollwerk (22:53)So many.Excellent. Thank you for asking that. Listen, we are so fortunate today as coaches, as leaders, to have this technology that we're leveraging right now, and things like gong and zoom, and they they don't just record the sales call, they annotate it, they index it.You could search it for how many times Scott said ⁓ or like. And it's absolutely beautiful. One of the technologies we use, Ask Elephant, it actually you can upload all the great books that we've read and we've learned from Challenger Sale, Solution Selling. I uploaded Hope is Not a Strategy, and a couple of others.And the video will email you or slack you and tell you when somebody violated one of those tenants. And it's it's incredible. So what do you do? Sometimes it's just a case of of not being on message. The person hasn't done the reps. That's a bad that's a bad pun. They haven't done the repetitions in order to internalize the messaging. That's easy.You know, you give that 30, 60 days, whatever. Usually a good s a good individual contributor, you don't get a lot of that. But you may find that you're listening KK to Scott Stolwork on a sales call and he's afraid to ask Mark for about money, about budget. Scott was brought up in very varying circumstances, and for whatever reason, he's got issues.He thinks fifty thousand dollars is a lot of money. And that's what the product costs: $50,000. So am I gonna be as effective standing in the pocket, trying to gain commitment from Mark, if that's what Zoom and Gong and Ask Elephant uncover? No. We've got to be, and it doesn't just have to be Tony Robbins, okay? Tony Robbins took from Maslow.And Maslow took from Socrates, and Socrates, I mean, this stuff's been around for 3,800 years. There's a book called Ethics of Our Fathers. If you're a sales coach, I want you to get an English, an English translation of Ethics of Our Fathers. I I it could it could predate Judeo-Christian doc doctrine. But anyway, you'll see there has to be that connection there. There itJust you you need your wise as the individual contributor in order to change. And as the coach, you need either some structure psychologically. It all comes down to survival. In in a society that's eight billion people, it might be different than it was in a society that was 500 million, but just more of the same.We all have a need, especially in our profession, for status. Okay, if somebody's need for status is getting in the way of them playing on your team, they haven't signed the credo yet, the constitution. It's it's in their inbox, unsigned. Well, so you you have to have a framework, but most of the problems and challenges that we have as coaches.we can find in these very basic human psychology and sociology tenets. You know, and and there are an infinite number of writers. Cialdini first wrote it and he's making a comeback right now online. I don't know why, but maybe it's because I said his name on a on a podcast like this and now I'm seeing I think I'm on a different side of the internet, as my daughter would say.KK Anderson (26:06)Yeah.Scott Stollwerk (26:07)We're just giving something to somebody. And then you have somebody who the gentleman that wrote the book Giftology, who took it to an entire extreme. It we're we're complex beings, KK, but we're also very simple in a lot of straightforward ways. To the Yeah, and and I I read this great book calledKK Anderson (26:22)It's the intersection of that where we figure it out. And itScott Stollwerk (26:27)Love languages or the five love languages. There are only five of them. So easy easy enough to find some common ground to somebody you're trying to coach to not be afraid of money.KK Anderson (26:29)I've read that.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, KK Anderson, Mark Petruzzi, and Alan Rudolph continue their Diagnostic Session series by focusing on the most underinvested side of the go-to-market bow tie: customer retention and expansion.The conversation explores why enterprise value is built not just through acquiring customers, but through keeping, expanding, and delivering value to them over time. Alan breaks down the difference between gross retention and net revenue retention, why time to value has become one of the most critical metrics in modern SaaS, and how broken retention models create pressure that sales teams can never fully outrun.The team also discusses the dangers of applying AI to flawed systems, why bad data and weak customer alignment create compounding problems at scale, and how CROs can build healthier, more profitable businesses through stronger metrics, ICP discipline, and operational alignment.What You’ll Learn:Gross vs. Net Revenue Retention: Why both metrics matter and how world-class SaaS companies measure customer health.Time to Value as a Growth Driver: Why TTV belongs on the CRO scorecard and how faster customer outcomes drive expansion.The Cost of Poor ICP Alignment: How selling to the wrong customers destroys retention, profitability, and scalability.Diagnose Before You AI: Why AI amplifies broken systems and how to avoid accelerating bad processes.Metrics That Protect Enterprise Value: The KPIs every CRO should monitor to improve retention, forecasting, and operational efficiency.Key Topics:Customer retention and expansion strategyGross retention vs. net revenue retentionTime to value and customer onboardingDiagnosing broken retention models before implementing AIICP alignment and customer fitEnterprise SaaS growth metricsAI-driven forecasting and operational efficiencyData quality and AI readinessCustomer churn and expansion motionsBuilding scalable revenue operationsGuest Spotlight: Alan RudolphAlan Rudolph is a strategic advisor at AGS with deep expertise in enterprise software, revenue operations, customer retention, and scaling go-to-market organizations. He has worked closely with growth-stage companies and executive leadership teams to improve operational discipline, retention performance, and enterprise value creation.Resources & Mentions:AGS Revenue Blueprint DiagnosticBenchMarketKey Metrics Discussed:Gross RetentionNet Revenue Retention (NRR)Time to Value (TTV)CAC PaybackWin Rate by ICPTopics:Diagnose Before You AICustomer Health MetricsAI Readiness in Revenue Organizations🎧 Listen now and follow Selling Intelligence for more insights on AI, revenue growth, enterprise operations, and go-to-market strategy from today’s leading operators and advisors. Subscribe wherever you get your podcasts.KK Anderson (00:29)Welcome back to another exciting episode of our diagnostic sessions. And today we're going to pick up right where we left off with the last one in chatting with Mark and Alan about the go to market bow tie and specifically the last, the right side of the bow tie, what we call Keetmore, which is all around customer retention and expansion. And I know Alan will agree with this when we say thatThis is really the most under invested side of the bow tie and where enterprise value truly has the opportunity to compound. so, Mark, I'll hand it over to you to kick us off and we're excited to have another great session.Mark Petruzzi (01:08)great. So Alan, that last segment of the bow tie that KK is describing, that customer retention expansion, this is your home turf. So what does diagnosis look like here? And why is this side the side most CROs just under invest in?Alan Rudolph (01:25)Do we have enough time? I'll be here for hours. ⁓ No, think it's just there needs to be a focus on gross retention, on net retention, on the whole structure of how does sales and account management and customer success, how do all these pieces come together? And we know that it drives growth and it drives value overall for the company.But the under investment mark to your point, I probably have two, three, four conversations today. I was just talking to an exec this morning from a leading research firm and he was telling about one of his clients and their churn numbers are down, their sales numbers are off and obviously they're not growing. And if your churn numbers are too high, i.e. lack of gross retention, then it puts undue pressure.on the sales team because we think, we can just go sell our way out of the box. And we know that doesn't work, right? We know for a healthy software company, we need to keep the gross retention north of, ideally north of 90%. Best in class is 95 % to 97%. And so this is where the pieces need to come together, right, in terms of selling, account management. Oh, let's not forget aboutproduct because it's all about driving value to the customer. So it's definitely the art of the deal, right? It's more than just science. There's art here, in other words, in terms of finessing to ensure that we have the right overall gross retention driven into the organization.Mark Petruzzi (03:04)Yeah, and Alan, you are right on with that because when you then try to sell your, just sell out of that kind of churn challenge that you're describing, what happens is you really need to overextend the sales team and all the sales capabilities. And guess what that gets you? At the end of the day, that gets you a higher churn and a lower retention.Alan Rudolph (03:27)Right,right, right.Mark Petruzzi (03:28)Soyou think you can do this and everyone, every CRO I know loves to go back and say, yes, I can do that for us. But you can't just offer to do it without making sure your board and your executive team, your CEO knows what's likely gonna happen after doing so.Alan Rudolph (03:48)Right.Right.KK Anderson (03:49)So Alan, walk us through net revenue retention specifically, because this is the metric that most leaders mess up. And a lot of times ownership of that falls on the CSM side of the business, which is perhaps why it is not as visible, right? Everyone's focusing on the logo.Alan Rudolph (04:06)Yeah, spot on, KK. And it's fascinating. People just get messed up a little bit. So gross retention is just that. I start the year with $1 of business. I finish the year with $1.10. I'm sorry. I finish the year. I renew the dollar. That's 100 % gross retention. If I increase that dollar to $1.10, whether it'sAnd again, different companies count things a little differently. But if it's, if it's a CPI increase, if it's another product going into that customer, right? If there's a price increase separate from CPI, right? So all those factors go into gross retention. I started with a dollar. I finished with a dollar. That's 100 % net retention. I start with a dollar and with 110, that's 110%. Right. And again, coming back to what I said earlier aboutyou know, world class kind of metrics, gross retention in the 90 to 95 range, obviously 95, 97 will be world class. Net retention north of 120, it varies a little bit by industry. You get to 115, 120, it's that much more powerful. It puts less pressure, as I said previously then, on the sales force in terms of bringing in new logos because you have a healthyrecurring revenue business that continues to drive success into the install base of customers. That's really how to think about those two numbers in terms of gross and net retention. But they are key metrics and they need to be calculated consistently, month in, month out, quarter in, quarter out, because they are key metrics that need to benot only reported across the company, reported to the board on a regular basis.Mark Petruzzi (05:49)Yeah. And you know what, Alan, I've always, I've never been a fan of net retention, net revenue retention, because I really like to look at these numbers separately. And I guess companies like that opportunity to put them together because they can hide something in it as well. But I mean, there's two things. You really want to look at your churn and understand what that is.Alan Rudolph (06:01)Mm-hmm.Right?Mark Petruzzi (06:16)Then you want to look at your revenue growth and your growth versus the targets that were set at the beginning of the year. And those are separate things. So if there's anyone out there with my kind of brain that just feels more comfortable in that space, think it's fine. It's good to have even more clarity and detail than just combining those two numbers.Alan Rudolph (06:40)Correct. Yep.Mark Petruzzi (06:40)So Alan, you also talk a lot about just time to value as one of the most underappreciated metrics. Please make the case for why TTV belongs on the sales leader scorecard, not just customer success.Alan Rudolph (06:55)we go back in time, for us folks that have been around this enterprise software space for a while. And we can all remember, and not that far back in time, less than 10 years, where enterprise application took months and months and quarters and years to get implemented. And in this day and age with all of the new technologies, with all of the changes that we all know about going on in the world around us in terms of,the autonomous world that we're about to live in or we're living in already. A customer signs a contract and they want value tomorrow. And so that's why it's so important from a selling standpoint that the outcomes are clearly laid out for the prospect, you know, soon to be customer. And they understand what they're getting, when they're getting it. And again, that time to value metric, i.e. how quickly can we get that new solution implemented?and the customer getting value out of the solution is in, I'm gonna call it days, soon we're gonna be in hours, but let's call it days, not months and quarters. And that's why TTV is so critical. That's why it needs to be on the CRO, the CCO, the COO, so Chief Revenue Officer, Chief Customer Officer, Chief Operating Officer, depending on how these titles are divvied up. But again, both sales and delivery, let's use.the generic terminology here, need to have responsibility. And by the way, let's not forget about the product organization because the software needs to be developed in such a way that we can in fact drive that time to value. So it really is at a minimum, a three-legged stool, right? I said sales, I said delivery, I said product, and I'm putting product and engineering together in this case so that we can get to that.Value to the customer. It's all about selling value. I by the way, let's not forget about then what we love to talk about KK. It's your buzzword. ICP, right? You're never going to get the right time to value if you sell to the wrong customer, right? If the customer doesn't fit into that, target box. So that's what I think about, Mark, when I think about how best to understand time to value and get an outcome from it.KK Anderson (08:49)here.So if you're looking at time to value by ICP segments, then your marketing team has an incredible, information around which customers we're selling to that we shouldn't be, right? A fast TTV combined with a strong expansion motion is gonna get that NRR up, which drives valuation up.Slow TTV selling to ICP that's out of our, you know, out of the wheelhouse, right? It's going to destroy it. So that's interesting as well. all feeds into each other.Alan Rudolph (09:35)And that's why I saidearlier, KK, it's more art than science. Sure, it's science because the numbers need to come together, analytics, blah, blah. But there's some art here to finesse this, to make sure that we're driving into the marketplace appropriately.KK Anderson (09:39)Yeah.So I'll throw you a curve ball then, Alan. what if you're looking at the numbers and you see a customer that's just, I mean, this has actually happened to us at AGS before, ironically, right? Where you're just like, my gosh, this customer's killing us. Fire the customer question and you're looking at TTV, you know they're out of your ICP, you know they're draining you. When does a CRO actually...Alan Rudolph (09:59)ThankKK Anderson (10:13)need to walk away from a customer that's hurting in our art.Alan Rudolph (10:15)So should I say it the way somebody else would say it? You're fired, right? I mean, seriously, if there's not a fit from a product standpoint, from a business outcome standpoint, from an overall solutioning standpoint,KK Anderson (10:15)That's I said.Yes.Mark Petruzzi (10:20)Ha ha haAlan Rudolph (10:28)This is where transparency is so critical that you need to go back and have that conversation with the customer, explain what we do and how we do it and the types of business outcomes we can drive through our solutions. And if there's a match, then that's great. Let's modify and go drive that match. But if there's a gap, right, we do this and the customer thinks we did that, then this comes back to all these discussions we're having about it's not only driving.sales and revenue, but we need to run a healthy business. We need to have our costs in line and we need to have a profitable business. And when there's that huge gap between what we're selling, the ICP and what the customer thinks they bought, if the gap's too big, we're going be spending tons of times with the services team. We're going to try to modify the product. We're going to change our roadmap for the product to meet that customer.It's just, the one thing that does step in the way here is size of customer. If all of a sudden this customer is, dramatically large and we bring our CEO in, we have a very broad discussion. But again, more often than not, that outcome has to be get the customer back to the solution we sell, not a variant of that solution that we sell.KK Anderson (11:17)gets it real fast.Alan Rudolph (11:39)that's so dramatic off that it's just costing us oodles and oodles of money.KK Anderson (11:43)Not to mention the reputation that's at stake.Alan Rudolph (11:46)Sure, everybody talks. know they doin this industry, every industry, right? And so, yes, reputational perception is something that we all need to be cognizant of, absolutely.KK Anderson (11:58)So Mark, when we think about our philosophy of diagnose before you AI, and we think about the keep more motion on the right side of the bow tie, what happens if you apply AI to a broken retention model? What does that look like?Mark Petruzzi (12:13)Great question. Before I start with that, I'd love to go back real quickly to the fire their customer question, because that's something I have had very mixed emotions about that over the years. I believe it's so important. And there's a part of me that is so happy to fire the customers that really hurt our productivity and our...or numbers and sometimes just customers shouldn't have become customers in the first place. So there was that aspect, but I'm also someone that really values loyalty and I always want to try to work with them first and it's just not a fun thing when most customers are like, really, you're firing me? And I'm sure at the end of the day, even though you never say fire in this,But they do a lot of times and they're like, wow, that's something. And so I guess I just want to go back to that positive feeling. You can feel so proud when you identify a customer is really just not working out, probably not even working out for the customer either. And you do something about it. That makes me feel really good. All the rest of it doesn't.So, okay, so the question of, what happens when you apply AI to a broken retention motion look like? And it's really, it's how AI is impacting everything today. The productivity increases, the impact that AI has is not 15 % or 20 % in most cases.As far as impacting processes directly, it's usually 3x, 5x, 10x. So things get 7 to 10 times faster when you bring in AI. So when you do that through a broken retention motion, just, again, you just make that happen faster with more overall impact to the company.Alan Rudolph (13:58)Mmm.Mark Petruzzi (14:11)And that really, really just impacts the overall. If you can do that, you're going to have much better deal scoring. You're going to have a much more accurate forecast. most of you have heard me talk about that a lot. And just what a good forecast does for the entire business. And again, I'll say it again, good forecast meansAlan Rudolph (14:31)Mm-hmm.Mark Petruzzi (14:35)accurate, not always, sandbagging and then ended up coming in 25 % higher than you predicted because there are ramifications of doing that as well. And then you just, can leverage AI even further and understand like how the scoring of your deals work and you know, what, when these things have happened, what has then happened to the, the company as well. And then,You know, the last point on this is if you're training an AI on bad judgment, it just makes bad judgment happen faster. you could take any negative phrase with that and it's going to do that. And as smart as these frontier labs, you know, models are nowadays, they...they can learn and they do learn all the time. But if you give them the incorrect information at the beginning, they're not capable of just figuring out the right thing to do after you told them in all this training that it has to do something a different way.KK Anderson (15:38)No, I was having a conversation with one of our expert accelerators earlier today about, about diagnosing your data, right? We talk about diagnosing, find more, win more, keep more, but diagnosing your data and, and Carrie is who I was speaking with Mark. And he gave it the analogy of, of your, of your body, right? You've got a human body and your organs, your, heart is your.sales and the brain is your CEO and all of the different organs are the different parts of the body and the blood is the data that runs through it all. And if that data is not flowing, not oxidized, oxidized, oxidized, oxidized,Alan Rudolph (16:16)Awesome,Mark Petruzzi (16:17)That's atough one. ⁓Alan Rudolph (16:19)you're amazing.KK Anderson (16:19)thennone of these systems are going to be talking to each other effectively. And so before you can go and put in some amazing AI predictive modeling, that's going to say, hey, this customer is about to churn. Or I can see your order count is lower and you might be losing a product if you're a SKU-based business or whatever it may be to indicate retention problems or evensignals out there to go land a new customer. And if you're not looking at all of that data cohesively across marketing, across finance, across product, across sales, then you're not going to be able to leverage it in the right way. then, you know, AI is going to be the most powerful when it can look at those patterns and look at those histories.Mark Petruzzi (17:00)Yeah, no good stuff. And I'm gonna give some work for anyone who may have been an English major and try to say that word and you guys can let us know if we pulled it off. I think it would be oxygenated, but it's not easy.KK Anderson (17:13)Yeah. Yes, that's it.Alan Rudolph (17:18)And more importantly, Mark, can you spell it, right?Mark Petruzzi (17:20)Exactly.I think I can, but I'm not going to try that one on the podcast. So, KK, kind of back to you, with this. So what's the right way to apply all this that we're talking about here and particularly on the, you know, these corrections of broken retention models that, we can leverage AI to, but you just got to do it in the right way.Alan Rudolph (17:24)That's not pastKK Anderson (17:44)So, I do think that as unsexy as it is, it does start with the right data, right? Because that's the crown jewel of everything that all of these businesses are functioning off of. I think it's taking the data and it's taking your tribal knowledge and your secret sauce and what you do better than anyone and figuring out,based on the metrics and based on what makes sense is how do you turn that into an agentic process that will take you to the next level? How do you take what you do that no one else can do and do it 10 times faster using AI and then enable your team to be able to dazzle your customers and provide an incredible customer experience as the human in the loop?based on all of the insights that are served up with the AI that's provided to you.Alan Rudolph (18:36)Yeah, spot on. And as we wrap up, this section, look, when I think about retention and expansion, this is where enterprise value of a software, you know, agentic enabled company, truly, truly compounds. Right. we've talked, we've thrown out lot of topics out in this section. threw alphabet soup, so to speak, but the bottom line is we need the measurement systems.KK Anderson (18:36)Yes.Mark Petruzzi (18:36)Yeah,good stuff.Alan Rudolph (18:57)those measurement systems will drive value. need to understand our customer. We need to understand their health. We need to understand, you know, are we truly transforming their business and just drive through all those respective metrics. It won't fix the TTV gap, right? That's a different issue that we need to solve for. But, as we pull these metrics together, when we think about the forecasting,We think about the tools available to us in today's day and age. This truly does drive enterprise value once the appropriate metrics we have, we gather them, we know what they are, we know how we're measuring across the company, and hopefully we're driving them up and to the right.KK Anderson (19:38)So one of the tools that we've produced for our audience is a quick reference guide. It's a diagnostic blueprint. And it has a list of all of the metrics that we recommend a CRO look at as it relates to find more, as it relates to win more, and as it relates to keep more. And it's a list and there's some explanations on there as well around howhow you should read the diagnostic and the report. so Mark, we'll leave in the show notes where people can go and download that diagnostic scorecard. But so Mark, for every CRO that's listening right now and they're thinking to themselves, okay, what's the first thing I need to do tomorrow morning? What do you suggest? Do you start with downloading this list and kind of going through and calling your rev ops department, try to get some of these numbers? Like what do you do tomorrow?Mark Petruzzi (20:26)Yeah, great question. And the first point is do it and do it tomorrow. Meaning, this isn't something you can wait around with. The next recommendation is get those metrics. Find out where you're starting and what everything looks like there and try to work with individuals likeCompanies like BenchMarket, Ray Reich is the CEO of that and find out what the metrics in your particular segment of an industry look like and compare those and get that really strong understanding of where you are today. And then kind of going into the point of doing something. There are so many things that we all could be doing with AI every single day.The only way I can process this and recommend for my clients is, take a short window, I mean, it be a half a day, and figure out, all right, what's the list of the things I want to do, and then prioritize it, and really go for that lowest hanging fruit. ⁓ And then that's it. And like anything else, just like a good meal. A good meal is you eat, one bite at a time.Alan Rudolph (21:26)Mmm.Mark Petruzzi (21:38)try to devour the whole turkey dinner on Thanksgiving in one bite. So the idea is understand where you're starting, understand what's the best place and what are the items that add more value more quickly, and then manage to that. Then compare every step of the journey with, ⁓ where were we?Alan Rudolph (21:54)Hmm.Mark Petruzzi (22:02)three months ago, six months ago, where are we today, where do we want to go? It makes everything else that much easier to accomplish.So KK, to you, we know the real value isn't the score. It's the conversation that these processes force. And then it's great to just, let's parse it down to three or four things that every CRO should do this quarter. And we can tie back that to some of the things I just said withAlan Rudolph (22:21)video.Mark Petruzzi (22:35)how to start it, but more importantly, what are usually the lowest hanging fruits for most companies that we work with.KK Anderson (22:42)All right, Mark, that's a great question. And I'll give you four things that I would do tomorrow. So in order, number one, first get a competency baseline on your sales team. Like whether it's through one of our AGS diagnostics or through any other tool, it does not matter. Get a sales competency baseline. You've got to know what are the skills of the sellers and the leaders on your team? Do they have the competency to be able to sell?your product at your price point against your competition and your market. Like you've got to know that, right? You've got to know that. Number two, get a metrics baseline and simple at the simplest terms. need to know win rate by ICP, right? We want to know general win rated too, of course, but win rate by ICP, ideally deal size trend. it trending? Your deal size is trending up. Are they trending down? What's the sales cycle time? Is that pushing?What are the trends there? Your CAC payback time. We want to look at NRR, absolutely. And we want to look at TTV. Those metrics at a minimum will give you a very strong indicator of where you are, where the health of your business is, where you're starting. And then third, the third thing I would do is I would map your sales process against how your buyers are actually buying.and how buyers are buying is changing dramatically. It has changed more in the last 12 months than it has in the past 12 years. And so we need to make sure that the sales process is aligned to how your buyers are making these decisions. And then when you can apply AI to a seller-centric process like that, or a buyer-centric process, excuse me,Alan Rudolph (24:07)Mmm.KK Anderson (24:17)then you're going to have better alignment and better results with whatever you're, wherever you're layering in AI. So those are the things that I would do in order. Alan, what about you from a PEC, like when a CRO does these, these four things specifically, and what Mark has talked about as well, like what does it unlock for the business?Alan Rudolph (24:36)CRO gets to take a nap. mean, that meanshe or she is running the business, I'm gonna say appropriately, right? It's effective, it's efficient. We understand the metrics, we know what the metrics are, right? And that's what every CRO wants. He or she doesn't wanna be stuck out there trying to drive value to a prospect with each and every one of his reps, right? They wanna be able to run the business.And that's what that does, KK. And when they do that, it drives valuation. It drives a better narrative to future acquirers. It drives a better narrative to those customers, right? You don't have miss set expectations. You don't have customers you need to fire, right? It's a healthy way of running the business. But let's not forget that while you're doing all this, right? We're constantly changing.what we sell, right? The product's constantly getting better. I like to say, for those that don't know me that well, I live in the great state of Colorado and I'm a skier. And so we use the phrase, don't get too far over the ski tips, right? There's a healthy balancing act, right? You want to be slightly forward, but not too far forward. So that's just an important concept to think about from a business standpoint as we're working with customers.to make sure they understand what's coming a week, a month, a year, whatever for now as we continue to drive value in the product. And that fits into this whole discussion about optimizing the business of the CRO and giving the CRO that healthy discipline to be able to explain what is coming tomorrow.Mark Petruzzi (26:12)Yeah, and Alan, your comment about the CRO gets to take a nap or the CRO gets to show up and be on time, not 35 minutes late to their child's field hockey game or the dance recital or anything else. So that's really, really what it does. And when you have good, smart people,thinking strategically in ways that they haven't in the past, or they haven't had the time for in the past, it does a lot for the business. So like in a general closure for this segment, really there's four key things that I think kind of drives this for our clients. And that's the behavioral baseline, really figuring out where you're starting, figuring out the metrics baseline,the numbers, things you can measure and evaluate every step of the way, alignment over the organization, the entire sales organization, and over to the rest of the C-level individuals on the board. And then, the placement of AI, like, where do you put this in first? And when you can do these things, these four things in that order,you've already by itself have done more than 80, 90 % of the leaders we talk to every day. this is not, like again, you don't have to be perfect, you don't have to do 20 things, but if you can do these things very capably and reliably, you're gonna get benefit out of all these steps.KK Anderson (27:49)It's a playbook really for how to do it. And so if you, remember nothing else from this session today, AI is going to amplify whatever motion you have, wherever you put it. So if you have a broken motion, it's going to amplify that broken motion at scale. And if you don't know what your motion looks like at the competency and the metrics level, you're not makingAlan Rudolph (28:00)Right.KK Anderson (28:13)decisions on where to put AI, you're rolling the dice and it's going to come back. It's going to come back and bite you.Mark Petruzzi (28:19)and that starts with diagnose before you AI. If you don't do that, AI can be the most expensive thing that you ⁓ invest in and it could be the most impactful for the rest of your 2026 because again, you really have to know where you're starting from to really get the...types of benefits we all know we can get with AI, but sometimes we don't.Alan Rudolph (28:46)And then Mark, I just say from an ownership standpoint, coming back to the comment I made earlier about the CRO, know, the CRO needs to be able to go take the naps, go to his or her kids, play school, sports, whatever. And so don't rest on what exists today. Fix it, make it better. Reach out to, you know, whether it's folks like us at AGS or there's great, great operators out there that can provide this advice and counsel.is make it better. If we, we always can look back on our careers and say, God, I wish I would have done this. I wish I would have done it faster. Right. And I think we all have a huge opportunity right now. Take, take, take stock at what we talked about today and, and change your business and change it fast. Right. We're not talking about months or quarters worth of work. We've seen value from our customers in 30 days. Right. We've seen results. And so, drive that accordingly. So a lot of fun today.We really appreciate it. KK, I think you're going to bring us home.KK Anderson (29:43)Yep, I will. again, I'll put in the show notes, but you can download our revenue blueprint diagnostic on our website. And it will give you those, all the metrics we talked about today and give you a starting point for how to get started tomorrow. And again, you're welcome to reach out to any of us for assistance, but we don't care where you get the help. We want you to grow. We want you to be successful.And we want you to not only create but protect your enterprise value. And it's an exciting time to be in business. It is an exciting time to be in business. Everything is changing. And we're here to support you as we go through.Mark Petruzzi (30:18)KK, thanks so much for...for closing this off for us as articulately as you have. We so appreciate Alan, you joining us and being a part of this. we are definitely going to just grab as much of Alan's time as we can and have him on here as much as we can as well because of all the great insights he brings. And as always, I just wanted to thank our incredibleaudience, people who are in here investing time with us every week. We appreciate it and thanks again. All the best.KK Anderson (30:50)Thanks, Mark. Thanks, Alan. Thank you.Alan Rudolph (30:53)Thank you.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this continuation of the Selling Intelligence Diagnostic Session, Mark Petruzzi, KK Anderson, and Alan Rudolph go deeper into what happens when AI is layered onto a broken go-to-market system.The team explores real-world examples of companies that accelerated pipeline volume with AI, only to later discover collapsing win rates, longer sales cycles, and poor ICP alignment. They also unpack the critical difference between sales activity metrics and true behavioral competency, highlighting why qualification skill remains one of the biggest hidden weaknesses inside modern sales organizations.The conversation closes with a deep dive into the “discount trap,” forecasting discipline, and the operational signals private equity firms use to evaluate the maturity and long-term value of a revenue organization.  What You’ll Learn:AI on Top of Broken GTM Systems: Why more pipeline volume can actually create worse outcomes.Qualification Competency Matters: How weak qualification destroys sales efficiency and forecast reliability.AI Done Right: What happens when strong ICP discipline and human judgment combine with AI-driven signals.The Discount Trap: How discounting erodes enterprise value and creates downstream operational pressure.Forecasting as a Maturity Signal: Why investors care more about predictability than heroic overperformance.Key Topics:AI lead scoring increasing volume while lowering win ratesWeak qualification competency as a hidden scaling bottleneckOMG sales competency assessments and qualification benchmarksAI-powered signal intelligence for outbound prospectingUsing hiring patterns, LinkedIn activity, and market signals to prioritize outreachHuman judgment combined with AI-assisted targetingBehavioral competency vs outcome metrics in sales organizationsTwo teams with identical win rates but completely different operational healthThe “discount trap” and the dangers of unmanaged pricingWhy selling value matters more than discounting to win dealsForecast accuracy as a signal of operational maturityThe shift from “gunslinger” sales cultures to data-driven revenue organizationsPE diligence around trends, forecast reliability, CAC efficiency, and sales disciplineGuest Spotlight: Alan RudolphAlan Rudolph is the leader of the private equity division at AGS and a strategic operator with extensive experience building and scaling enterprise revenue organizations. With a background spanning sales, operations, and enterprise value creation, Alan helps organizations diagnose GTM inefficiencies, improve operational discipline, and build scalable growth systems.  Resources & Mentions:AGS (Advisory Growth Strategies)Objective Management Group (OMG) sales assessmentsConcept: Diagnose Before You AIConcept: Qualification competency in enterprise salesConcept: The Discount TrapMetrics: Win rate, cycle length, forecast accuracy, CAC efficiencyAI-powered signal intelligence for outbound prospectingClari, Aviso, and Collective[i] forecasting platformsAGS Sales Cycle Diagnostic Tool🎧 Listen now and follow Selling Intelligence for more diagnostic sessions, AI strategy insights, and practical frameworks for scaling modern revenue organizations.Mark Petruzzi (00:38)So KK, what does AI applied to a broken front of funnel motion look like? What are the ramifications of getting that?KK Anderson (00:47)Mark, let me share with you an actual real live case study, a real customer of ours. this is a growth stage SaaS company. They invested heavily in AI lead scoring and outreach. And they were ecstatic because, their pipeline jumps up 40 % in one quarter. The amount of leads coming in the door was just through the roof.leadership was celebrating and what happened and when they ended up calling us is that six months later, all of a sudden, their win rate is collapsing and their sales cycle is just getting longer and longer and longer and deals keep getting pushed out into other quarters. And so it got worse. And the reason why, once we did the diagnosis is because what it turned out is that the underlying qualifying motion of the sales team, when it comes to win more,was weak. It was deplorable weak. And to the point that Alan made earlier, the ICP was not the correct ICP and that was not disciplined. But because the sales team had a weak qualification competency, they were not prepared to be able to accept more of anything, even if it was the right ICP. And so it's interesting, just a note on that qualification competency,objective management group who is a partner of ours here at AGS, they have assessed it's got to be close to three million salespeople by now and interesting fact that of all of those three million people only 27 % are strong in the qualification and competency. So I said 27, two seven. So that means that if you're a CRO listening to this, it is likely that your team is notsuper effective at qualification. Right. And these are the things that you need to know before you start deploying a lead gen system that's going to against an ICP that's not disciplined with a sales team that doesn't qualify effectively. So AI on top of we qualifying is just expensive amplification of the wrong thing.Mark Petruzzi (02:50)I thinkyou hit it right on there.KK Anderson (02:52)now, Mark, back to you on this one. tell us a story of when AI applied to the type of funnel works, right? We know we've got the horror stories, right? But tell us when it actually delivers. Give us an example of where you've seen it work.Mark Petruzzi (03:07)before I evendo that, I'm going to give you a little bit of props here that you would always be too humble to share. But Objective Management Group is a company that KK has been working with for over 10 years. She has done more of these SEIAs, which are those as their assessments, the biggest in sales. There's nobody who does the does more of them than OMG.And there's nobody who has done more of them over the last eight, 10, 12 years than KK. she knows this space. She's got a lot of personal data in addition to all the metrics and everything else we track. So, okay, let's go to, let's talk a little bit about another story if you all don't mind. B2B Services Company that we work with, 40 reps.And in general, the first thing we noticed, they're in the top quartile on qualifying competency. They were really good. They knew it. The data confirmed it as well. They had a pretty tight ICP discipline. And they tried to work with AI a little bit on the prequel research, account intelligence side of the equation. But then they really picked this up.in the standpoint of really understanding signals. What would happen out there in social media, in their TAM that they're going after. Things like job changing, changes, hiring patterns, general press, LinkedIn activity, all of that. What then happened is that their outbound conversion went through the roof.they're able to go in there and really figure out how to be, and this is really so much of what almost every one of my clients struggle with today. You know, it's great to reach out to companies that could be part of your TAM. It's really great to reach out to companies in your TAM that have some sort of signal of why they may need your services at that point. It's kind of like this.If you're in your late twenties, whatever you're at, and you really want to get married in the next couple of years, well, what would you do? Would you reach out to every woman you've met ever? And would you reach out to the ones that are married already and said, would you go on a date with me? No. would you reach out to every woman throughout the world to see if they are interested inmarrying some American from New York City? No, you would find the right Tam. And then if you, not that we can get to this level in our personal lives, but if you knew women that were out there, they've kind of spent time with the, they've dated enough and they're kind of like, I'd like to settle down in the next three to five years. Well, wouldn't that be something?Right? So, and that works for every side from men looking for women, women looking for men, men looking for men, women looking for women, all four. It goes everywhere. But the same thing, that's the it just it really blows. It's just amazing what it can do. And what we saw is that their outbound conversion went up to 60 percent. Their cycle length dropped.And it just turned the signals that AI can bring into pipeline for that company.KK Anderson (06:20)I love it. So basically the AI didn't replace the human judgment. The AI just gave that like use signals, pattern analysis to be able to figure out where even more of their ideal customer was and then brought into a sales team that had the competency and the ability to act on it compounding results.Mark Petruzzi (06:40)And you know what?And what the AI did? This it's some kind of a thing that I've done that we're really covering the personal side in a number of areas here. But I have most of you all know I have two amazing children. I have an amazing wife as well. But so we got a great, great family. Right. And one of the things that I did from the beginning with my kidsis I've given them a lot of latitude. I know some people that are like, I want my kids to be an amazing student or want them to be an amazing athlete or whatever you do. And then you kind of push your child in that direction. I tried to be open with that. The one thing I did orchestrate a little bit is the books that I propose that they read and not like, you this is you have to get this done by the end of the week.It was always more of what I was reading. read this book talking to my, you know, and whether there were classics, whether there were new books, but it's the same thing in all of this. Like if you're looking at the right lists of companies and know that these have all been vetted through the process that you built with your agentic programs and there's a connection, there's a signal, then you get to use your gut and say, okay, out of these hundred companies,These 15 are what I'm going after first. And sometimes you may get a higher rating and you may say, no, that company I'm never going to break into. you say, forget about what the agent is saying. That's where the, so you're kind of doing the same thing I did with my kids. You promote books that they really can get a lot out of, or you promote targets that your team can really get a lot out of as well.So now back to you. So what does the behavioral competency piece tell you that win rate doesn't? Back to OMG, back to the things you figure out within your sales team. What do you get out of all of that side?KK Anderson (08:36)first of all, when I'm thinking about win more, And we're thinking about sales excellence, there's really two core layers and both are required, right? So layer one is that behavioral competency that we've chatted about a little bit today. And that is really what is your team capable of, especially when they're under pressure to perform and to produce revenue, right? That's the objective management group work.Mark that you mentioned the 21 core competencies and layer two is really the outcome metrics. And so that's what do the numbers actually show. win rate, deal size, cycle time, pipeline coverage, forecast accuracy. know, most CROs are measuring some sort of each and each of those behavioral and the actual metrics, but I don't know that.Mark Petruzzi (09:02)Mm-hmm.KK Anderson (09:22)that truly that many of those 600 plus organizations that I've worked with are doing either necessarily well, So for example, they might be measuring calls, activity, meetings, emails, that pipeline stages and things like that, but that's not gonna tell you if your team can actually compress a sales cycle, actually move a deal across that finish line.So it really takes both of those kind of layers. And so when you ask me, what does a behavioral competency tell you that a win rate doesn't, right? It's, competency tells you why, right? And then the win rate, the win rate tells you what's happened. that, I don't know if I'm articulating this the right way, but it's, really two different conversations. two teams can have identical win rates.for completely different reasons. Take team A, right? They win 35 % of their deals. They qualify hard. They walk away from bad deals. They're only investing in real opportunities. And then you've got team B who also has a 35 % win rate because they're discounting aggressively. they're doing everything they can to drag deals across the finish line. And it's a race to the bottom, right? They both have the same win rate.but they have totally different behavioral profiles underneath. And that's why it's so important to know what that behavioral competency is. It's being able to ascertain the health of your sales organization, right?Mark Petruzzi (10:45)I think you hit it right on the mark. I think, and by the way, I've heard Alan kind of name this whole approach, the discount trap. Walk us through it, Alan. The discount trap is exactly where AI applied to a broken motion accelerates the damage.KK Anderson (10:53)Mm-hmm.Alan Rudolph (11:03)often, Mark. mean, that's the problem with a discount trap. And it was just that fascinating discussion in terms of the diagnostics, diagnosis, and behavioral impacts, and all the metrics that KK just threw out. But this discount trap is so critical. And here's another bold statement I'm going make today. How many companies do we know in this broader, softer AI space today that do not have a target price point?Right. Freelancing on every deal. We see it way too often. So the CRO hits his number, his or her number. They outperform on the top line, but they do it by discounting. And we don't even know what the discount is half the time again, because we don't have a price book. And that ripple impact of that discount and the pressure it puts on the downstream systems in terms of time to value, in terms of implementation, in terms of success, in terms of getting toyou know, all the appropriate retention numbers, it just has a huge impact on margin, which ultimately has a huge impact on overall valuation of the firm. And by the time the team has trained itself, about this discounting in terms of getting the deal done, AI just accelerates it. It just makes it that much worse. Right? We get greater proposals out. They look great. They speak great. They talk great. Right. But we don't drive theValue of the solution. Oh, by the way, what am I going to say next goes back to that target ICP, right? So we're discounted because we don't have the target ICP. So how do you fix it? Sell value sell value to this in terms of the solution to that ICP and Don't discount if you sell value you don't have to discount. So you that's how you go about diagnosing that overall competency gap. You have to fix it at the individualcontributor level, you obviously need a price book. And then you can leverage AI appropriately, but don't get caught in that discount trap.KK Anderson (12:56)I couldn't agree more. And Mark, I'm curious for your perspective as well. I know you've sat in a lot of PE diligence conversations. What do investors actually want to see on the deal cycle from yourMark Petruzzi (13:08)Yeah.I'm really excited to answer that question because it's different than what most CROs or sales leaders would think they want to see. They don't want to see you having a history or your team having a history of overperforming in significant ways from their, say, beginning of their quarter forecast.meaning they don't want to see a team that always comes in 20%, 25 % higher, just tells you you have a sales leadership that doesn't know how to forecast. So at least by the beginning of the quarter, you should be able to define what you do at the end of the quarter. They, of course, don't want to see things that are more, that just tell,show risk and instability as well. So that's where this CRO role has, has changed. Like, early in these more enterprise software space, 20 years ago, you had, know, you had these gunslingers at the senior sales level, you had gunslingers at the rep level. And, they frankly just knew that if they work hard, they were going to make a lot of money.But they really had no idea what their potential was or what they can do. So those are the things that a P team or board on the due diligence side would focus on. They're looking a lot more at the trend than the absolute number. That's something I've seen. They want to see that win rate stay stable, getting better. They want it high.They don't want it to be volatile. They get to learn average deal size, typically trends whether you're in an up market or down market for your product. They wanna really look at cycle time and the trends there, because they really wanna know what kind of process, a selling process this leadership team has driven.⁓ sales leaders, when they're talking to sales managers or sales reps, they're always going to ask for a stretch goal. And I've grown to be okay with that, but I don't want to ever see a board or a CEO asking a CRO for a stretch number. I want them to say, what is the number? I want there to be a lot of technology and AI in identifying that number.We can do a whole nother podcast around the things I've learned working with Clary, Avizo, Collective Eye over the years around forecasting. Same thing, gut process there doesn't work. The data is out there. You just got to have a tool that finds it for you. And then that kind of comes to the final point on this. Forecast accuracy.is the cleanest signal that you can get from just knowing whether you have a business with operational maturity or when you have a business filled with a bunch of gunslingers.KK Anderson (16:05)So you need both layers, right? You need the competency and the board definitely wants to see the metrics, Behaviors and outcomes. And as a side note, one of the free tools that we've built at AGS on our website is a sales cycle diagnostic. It's a mini, if you will, sales cycle diagnostic. I will link that in the show notes as well so that if you're curious, you can go check it out on our online.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this first-ever Selling Intelligence Diagnostic Session, Mark Petruzzi, KK Anderson, and Alan Rudolph go deep on one of the biggest questions facing revenue leaders today: where does AI actually belong inside the go-to-market motion?Rather than a traditional guest interview, this episode introduces a new format focused on unpacking real operational challenges from inside the work AGS does every day with CROs, CEOs, and private equity-backed companies. The team explores why “diagnose before you AI” has become a core principle in modern GTM strategy, and how AI can either accelerate enterprise value creation or amplify existing operational problems.The conversation also dives into the bow tie revenue framework, ICP discipline, and why retention and customer outcomes matter far more than simply generating more pipeline activity.  What You’ll Learn:Diagnose Before You AI: Why AI amplifies both strengths and weaknesses inside your GTM engine.The Cost of Moving Too Fast: How scaling AI without operational diagnosis creates value erosion.The Bow Tie Framework Explained: Why “find more, win more, keep more” changes how leaders think about revenue.ICP Discipline Matters More Than Ever: How weak ICP alignment destroys CAC efficiency, retention, and enterprise value.Why Gut Feel Is No Longer Enough: The growing importance of data-driven decision-making in AI-enabled sales organizations.Key Topics:AI increasing productivity while amplifying broken processesThe pressure CROs face from boards, CFOs, and AI vendorsWhy “slowing down” can actually accelerate long-term resultsEnterprise value creation and AI investment decisionsThe hidden danger of filling pipelines with the wrong customersThe relationship between ICP discipline and long-term retentionThe bow tie model: find more, win more, keep moreWhy investors care more about post-sale execution than contract signatureCustomer onboarding, time to value, and retention as core valuation driversThe evolution from founder-led growth to scalable GTM systemsCAC payback, pipeline coverage, and modern SaaS benchmarkingThe rise of data-driven CRO leadership in the AI eraGuest Spotlight: Alan RudolphAlan Rudolph is the leader of the private equity division at AGS and a strategic operator with deep experience across growth-stage companies, enterprise sales, and operational leadership. With a unique background operating at the COO level, Alan specializes in enterprise value creation, GTM transformation, and aligning revenue organizations with board-level priorities.  Resources & Mentions:AGS (Advisory Growth Strategies)Concept: Diagnose Before You AIFramework: Bow Tie Revenue Architecture (Find More, Win More, Keep More)Concept: Ideal Customer Profile (ICP) disciplineMetrics: CAC payback, pipeline coverage, gross retention, net retentionWinning by Design bow tie frameworkRay Rike and SaaS benchmark analyticsConcept: Founder-led growth vs scalable revenue operations🎧 Listen now and follow Selling Intelligence for more diagnostic sessions, GTM insights, and practical frameworks for AI-driven revenue growth.Mark Petruzzi (00:00)Welcome to Selling Intelligence. I'm Mark Petruzzi, joined as always by my co-host KK Anderson, and in a very special way today, joined by Alan Rudolph, who is the architect and the leader of our private equity division at AGS. Alan has been a guest on Selling Intelligence before, so our regular listeners will know him already.He brings a rare lens to the revenue conversation. He's operated inside growth stage companies. He's advised PE boards time and again, and he's built sales and go-to-market engines from the ground up. But most importantly for us today, he's built those engines from the CIO level, which gives us a really distinct and important vantage point to.really how boards and CEOs and COOs need to balance these initiatives when we're looking at growing faster or building our revenue. He's also a close friend and I'm really happy to have him with us here today. Quick note for our listeners, today we're trying something entirely new. We're calling this format Diagnostic Sessions. No traditional guest interview.just three operators going deep on a single revenue topic from inside the work that we do every single day. We've been getting so many questions from our listeners about what we actually mean when we say, diagnose before you AI, because that mantra has been showing up in nearly every CRO conversation we are having. So we decided to spend the full session unpacking it, and Alan is joining us from the operating.side of this conversation because we really feel it an operator's voice as well.KK Anderson (01:44)Thank you, Mark. We're so excited to be here, Alan. We're so excited to have you. And we're going to keep bringing you the amazing guests and the revenue leaders and the business operators that you've come to know and expect on the show. Don't worry. But from time to time, when there is a topic that we really want to go deep on, when we start getting a lot of questions from our audience, as we have been lately, we're going to drop in.a diagnostic session like this one. And we'd love your feedback on the format. So please leave us a comment, send us a note, tell us what you think. So today's session is all about where AI belongs in your sales motion. And just as importantly, where it doesn't across the full revenue cycle from finding new customers to winning deals and to keeping and growing them. There is an AI technology out there that canI to fix everything at every stage, I promise you. And the question is whether AI actually delivers or whether it amplifies problems that your team already has. And so we're gonna talk about this in four different areas. Number one, what we actually mean when we say diagnose before you AI. Number two, the bow tie framework that anchors how we think about revenue and how we think about the go-to-market architecture.And number three, how to diagnose each part of your go-to-market funnel. And we'll walk through specific examples of actual clients that have done it the right way and sometimes the wrong way. And then finally, the fourth thing that we'll talk about are four things that every CRO should do this quarter before scaling AI investment. So we have got an action-packed diagnostic session today. Alan, Mark.Welcome back to Selling Intelligence.Alan Rudolph (03:28)Thanks, KK. Great to be here today. I think one of our challenges is going to be, can we clearly say diagnose how many times throughout this podcast? Because the diagnose before you AI conversation is so critical, as KK just said. And we're going to keep unpacking it as we go through this session. And I think you, as our listeners, willMark Petruzzi (03:37)No, no, no.Alan Rudolph (03:50)be intrigued with what we say and hopefully challenge us through the journey. Because the pattern is real, the cost of getting it wrong is real, but the opportunity to get it right is even bigger. So looking forward to going deep with you on this topic throughout the session. KK, where do you want to start?KK Anderson (04:06)Okay, Mark, let's start with you. So you have been saying for over a year, since I can remember honestly, AI doesn't solve, AI amplifies. So what do you actually mean by that?Mark Petruzzi (04:19)Yeah, KK, thank you for that question. For me, and you hear this word out of me very often, and so we'll be saying diagnose and we'll be saying productivity and efficiency. And those are the things I focus on and talk about with my clients every single day. And so what does that mean? know, AI amplifies, it just amplifies the productivity of everything you do.everything you do gets more efficient and when done right, it can get more effective. However, when it's there isn't that diagnosis up front, you have, you just start to amplify your problems and challenges you already have in your go-to-market process. you know, think about it that way. It makes you more effective at all the bad things you do.You know, makes you more effective in finding clients that would never buy your products. And maybe they'll listen to you for a couple of meetings, but they're not, they're not a good ICP. It makes you reach out to more individuals. You know, as you're targeting and lead Jen and the people who just really would be a huge uphill climb to be able to get them excited about making an investment in your product. So.It's got to be done right up front to really get the productivity. Productivity comes together when there's something that really helps you that gets amplified rather than more challenges being amplified out there every day.So KK, you're in CRO conversations every week as well. Why are so many leaders rushing AI before doing the diagnostic work?KK Anderson (05:55)That's a great question. Every CRO I talk to is getting pitched by AI vendors 30 times a week, not even kidding. And the pitches are all very similar. We promise a shorter sales cycle, more closed deals, a better forecast. And at the same time, they're under pressure from their boards asking, what's the AI strategy? And the CFO saying,prove your ROI before you AI, right? And from vendors, of course, saying just buy this like I just mentioned. And so they're really getting it from all sides. And I just attended a transformation event last week in Houston with about 30 CROs in the room. And every single one of them had the same questions. They wanted to know how do they measure AI? How do they validate it? Where do they apply it? And I think what became abundantly clear in that roomis that the one consistent thing is that there are, there's just a million unknowns. The one consistency is that nobody really knows yet, right? There's so many unknowns. And so I feel like the pressure is there to be decisive and to make a decision. And, you know, our perspective has been and will continue to be to slow down, take 30 days, diagnose first, make sure you know your numbers.and know where to go in. Do you want to go in solving a find more problem, a win more problem, or a keep more problem? And if you know your baseline, then you know where AI belongs and where AI can help you to solve and have the biggest impact first.Mark Petruzzi (07:23)KK, you, if I can add one additional thing to that. So when we talk about slowing down, the way I look at it, know, 30 days, if we're looking at a football analogy, it's a wide receiver, you know, stopping, looking back at the quarterback for a second, and then go in on that fly pattern afterwards, entirely wide open because the strong safety now, you know, bit on that.So that's really all it is. I do have to admit, early into this gen AI world that we're all in the middle of, this phenomenon, I was just running around all of my CRO friends and relationships and just saying, you gotta move. You're getting beat up by your board every week because you don't have a plan. Jump in, move, make it happen.because your competitors are going to, and if you don't, you're going to lose all those efficiency gains that your competitor is finding. And again, that worked in many cases. Sometimes you can do a quick little diagnostic as you launch, but in a lot of cases now we're seeing some of the damage that can be caused by that type of an approach. So it's a quick move, it's a quick pause, and then it's full out from there.as well.KK Anderson (08:38)Yeah, 100%. And Alan, I'm curious for your perspective. I know you're seeing this from the PE side and from the operating partner seat. Like in your opinion, what's the cost when a CRO scales AI in the wrong area or before they've diagnosed really?Alan Rudolph (08:55)thanks, KK. You know, it's fascinating. It's all about enterprise value creation, right? And, you know, March analogy, you know, on the football field, even though we're in May and it's not football season, still is so relevant. And so, you know, from the operating seat, it's one of the most expensive mistakes I see right now, right? Not doing that diagnosis. So when the CRO scales before they do the work, right? And it's the heavy lifting work.They just think they want to get to, you know, volumes. so the cost is just wasted spend. It's value, value erosion. So every quarter you spend amplifying a broken motion is quarter compressed that compresses that multiple at exit. And who knows where the multiples are today versus tomorrow versus, you know, X months or quarters from now. But the pattern I see most often is AI drives volume, right? We get more leads.Those leads lead to more meetings. That leads to more outreach. The board's excited, right? There's super activity. The CRO feels good. The AI line item gets celebrated. All of a sudden, gross retention starts to erode. And why does it start to erode? Because we filled the pipeline with bad customers. Again, it comes back to that discussion we were having about ICP. And by the time it shows up, you know,You've burned six, eight, 12 months in that value creation runway. So AI doesn't fix the ICP. It amplifies the fact that you need to have discipline. If your ICP is loose, you get the wrong customers. You have to diagnose first. Again, in summary, we all think about AI is going to create the activity, create that volume. What Mark said earlier about less work, get the activity.Drive gross sales, but the wrong gross sales and long-term that impacts the value creation.KK Anderson (10:46)Yep, and that's so well stated and exactly why we always say, you know, again, diagnose before you AI. So the alternative is not slower progress. It's faster regression. Wow.Alan Rudolph (10:58)Yep.KK Anderson (10:59)Mark, let's go into talking about the bow tie go to market and kind of the bow tie framework, if you will. And before we get into the diagnose topics, tell us a little bit about the bow tie framework. It's the structural framework for so much that we do, the anchor, excuse me, for so much of what we do. Why is it so important and why do we talk about it every day?Mark Petruzzi (11:22)Excellent question, And first off, let me give some props and credit to Jaco, the CEO of Winning by Design, who he and his team has built that framework, that bow tie framework that we know and love here at AGS. So what does that do? It extends the traditional funnel, the traditional mindset that many CROs have on just, you you have a great funnel,KK Anderson (11:22)That's it.Mark Petruzzi (11:47)You have good sales and marketing upfront, good BDRs. You'll get leads. You have smart sales team. They're going to close leads over time. as you would hear from and will hear from Alan, that's a part of it. But it's not even 50 % any longer. And when I say that, I of course mean in the reoccurring revenue segments of software.You know, of course we know SaaS is built on that premise, but it's really, really relevant in almost every complex B2B selling organization that I have seen. And I'll give you an example of that. I was fortunate enough to write, I'm selling the cloud. We get a little bit of a group behind that and very strong.level of sales performance, which we never expected when we did it. But then what I would then get is a lot of questions from individuals that were not in the cloud space, the SaaS space, about how can I use these principles in my business? And my answer was always like, you can use it in exactly the same way. Whether you're, unless you're just a company that sells something,once and then you don't sell that again to a client for 20, 25 years. But even if you're selling to a client every four or five years, there are things you need to do to really retain the mindset, even if they paid you all your money, retain the mindset, make sure those customers are happy. And then looking at the expansion side of all this and, know, CEOs and boards.They love the whole concept of cross-sell. So it's really funny if I look at the evolution, medical device companies were the ones that caught this the first, caught this earliest in my estimation, other than traditional SaaS companies, software companies. And they have gone far into building, really building their go-to-market models in exactly the bow tie model.Matter of fact, they're also starting to sell things on a reoccurring subscription basis. When they can sell a medical device for X dollars, they now sell it for 150th X and they kind of expand that over a four or five year cycle with their clients. So I'll pause there because there's so much I want to hear from Alan and KK about their perspectives.So let's throw it over to Alan. You live across three sides of the bow tie when you're doing P.E. Why does the bow tie framework matter in the way you access a portfolio company, the way you access a new acquisition? How does that all come together?Alan Rudolph (14:33)Sure, thanks Mark.The most important aspect when I look at the broad PE due diligence on the bow tie is keep, right? Find more, win more, keep more, right? And so what happens is if we don't look at all three aspects and focus in on keep, the enterprise value is simply not created. It's actually destroyed. Funnel thinking, if you just stay with a traditional funnel,You know, think about the CRO, they close the deal, they're done, they're on to the next deal. But again, it's all about that value of the deal. And the bow tie keeps going through the onboarding, through the time to value, through the expansion and ultimately retention. And the more retention to get, the more opportunity we have to cross sell, upsell, sell more. So as a PE operator, when I think about due diligence, when I think about value creation, that's where I spend my most time is thatKK Anderson (15:11)It's gone.Alan Rudolph (15:25)that circle, that evolution of the overall customer journey into Keatmore. Because the truth is, investors care more about what happens after the contract signs, not when the contract signs. And one of the comments I always make as a CCO, as a COO, when I look at all the post-sale activities, the customer has hugeexpectations upon contract signature. They're excited. They just want to drive, you know, the outcomes, the value. And if it goes wrong, right? If that journey gets off the track, that impact is on Keapmore, right? And that impact hits gross retention, net retention, et cetera. So connecting the variables, you know, the find more, win more, Keapmore, like that we always want to say.It's all about making sure I have the right ICP. I find the customers that match the ICP and I inherently keep them longer. And that drives the enterprise value. Well, one quick anecdote. Two companies ago, I was on a podcast, similar customer event, et cetera. And I was talking to a customer and it was their anniversary of 25 years with the company.And so, you know, and this is obviously across a broad spectrum of, know, before AI, before SaaS, it was just traditional software, some of it was just services. But think about that 25 year experience of a enterprise customer with a company. That's what it means in terms of Keef more. KK, back to you.KK Anderson (16:56)it makes a lot of sense. And even this week, we are helping a client prepare for a board conversation where the team was selling, but there was a lag between when those sales would come in and when everything would be activated and the bills would be paid and whatnot. And so it just goes to show that that Keep More is everything. Right.getting the clients activated and making sure you close that gap. So, okay, Mark, let's go into the diagnose, you know, what it means for any change of the funnel. And specifically, Mark, when we say diagnose, find more, right? The front of the funnel, what does that actually mean? What's a CRO supposed to look at?Mark Petruzzi (17:40)So it's, mean, of course, the FIMOR side is still exceptionally important. And we don't ever want to take our eyes off of that. We want to make it more productive, better matched to the market and what you can sell. But we always want to invest appropriately in those areas. And that kind of comes back and it ties to a lot of the metrics.KK Anderson (17:46)Yeah.Mark Petruzzi (18:03)that are out there in the software industry, the CAC, CAC payback period, general pipeline coverage ratios, lead to opportunity conversion, your overall channel efficiency, ICP fit. Private equity firms that focus in the software space, I mean, they run those numbers to the minute, and they're evaluating those numbers 24-7. So if you look at it like, OK, so median SaaS CACpayback. I would say that's 18, 24 months somewhere in that range. Best in class, under 12, different world. And with all this stuff that the private equity firms are doing, most CROs don't have any idea where they stand. And what do you think it looks like from a, let's just look at it as a CRO bonus perspective.How much bonus do you make when you're driving a 10 or 11 month CAC payback versus 18 to 24? It's a different world. So that and pipeline coverage is always have to be really defined and it's very important. We're just so fortunate at AGS that we have a team, we have a partner group, including Alan that just knows thesethese areas inside and out. We also have Ray Reich. Ray Reich is part of our expert accelerator team. He is, I was going to say one of the best in the business, but in the software space, there's nobody better than him. His benchmarks are incredible. His metrics and the data he already has is incredible as well. So, you know, when it comes down to it, I'll also share one example of a shortcoming.that I felt I've had in this evolution of gen AI. And that is, I looked at it and I always like to make things simple for my prospects to hopefully turn them into clients in the easiest way possible. So I kind of just looked at this upfront and was like, okay, you know what? I'm going to make your team more efficient, more effective and more productive. And that's going to increase revenue.Isn't that, that's kind of enough, right? Isn't that great? I mean, we can, we can monitor, we can view it. Well, like anything else in business, you need the details. you can learn things about ratios that you just, don't learn if you just see a 15 % increase in your revenue over what you were trending beforehand. Okay, that's great. But you have so many more signals and signs that come out of it.So that's where Ray comes in play and that's where great operators like Alan come into play as well.Alan Rudolph (20:35)Plain and simple, and I'm going to be bold in a couple of my comments here. It's the cornerstone of everything, Without adherence and strict definition of the ICP, valuations will erode. And we've seen that across the mark. There's many examples. So let's step back for a second. Think about early stage firms. Founders are phenomenal at the early on. of firms.Mark Petruzzi (20:47)Hmm.Alan Rudolph (20:57)They build personal relationships. say, I, you know, they put their hand up. I am the founder with that first set of customers. They know what they can and what they cannot sell when the product will break. Right. They just, they built it. So they know it. And, and so as the firm evolves, as the, software company evolves in that transition from founder led growth to scaled growth, the variable we keep coming back to is that clearly defined ICP.Mark Petruzzi (21:10)Mm-hmm.Alan Rudolph (21:25)Who is the target customer? Not in vague terms, in very specific terms. But here's what happens when the ICP is loose. Every stage of the bow tie gets that much harder. The CAC payback stretches because you're chasing customers who inherently don't fit. And it comes back to the point I made earlier. You sell something, you start the implementation, and all of a sudden it's a square peg and a round hole andwe know what happens with that journey. And or win rates drop because the discovery just doesn't land, right? There's no fit there. Time to value gets worse because it's all about that square peg and round hole. And then clearly net retention drops. Earlier in my career, the middle part of my career, I spent a ton of time in the broader outsourcing business. And in that business, we didn't make any money on those deals till give or take year three.And the only reason we were successful at that business across many major world-class firms was to get the ICP right. So when we talk about diagnosing the front of the funnel, the first question I ask any portco as I start talking to them is, who's your target customer? And how disciplined are you about that definition? Because again,If I'm loose in that definition and as the CRO, if I can hit my number that quarter, if I can blow away my number for the quarter, that's great. But all of sudden they then create this huge backlog of potentially unsatisfied customers because they don't meet the target ICP. We can't create the outcomes, right? Remember, at the end of the day, it's all about driving those business outcomes. And if that answer is fuzzy,Right? In terms of the target customer and the ICP and the deals I'm bringing in, the downstream work is just going to be that much more difficult.Mark Petruzzi (23:12)Great, great stuff, Alan. I'd like to go a little deeper in what happens when CROs start a new company and they just don't have these numbers. And what really comes down to it is most don't, even to this day, even with so much private equity investment in the software space. You know, if they have the ARR, they know the pipeline coverage, butthen they just manage by gut feel. And when you can kind of move, and I've seen this happen with some of the best CROs in the business. I use my friend Paul Mulchiori often with this. When he was younger in his career, his first couple of CRO gigs, he was, well, my perception of him was that he was just.so much of a gut feel kind of guy. And he, was really good at it and he always did the right thing. And I was like, wow, isn't it amazing when you have those kind of instincts? Well, guess what I learned about Paul? You know, Paul actually, you know, he quietly went off and he got an MBA from Villanova. He learned about the numbers, you know, nobody didn't talk about it to many people. AndAlan Rudolph (24:21)Uh-uh.Mark Petruzzi (24:22)He started really looking at these numbers and he started putting his sales operations, sales enablement team into developing these numbers for him. And that has served him extremely well. Now I can say 15 or 20 years later, you know, especially now that Paul's taken over, been an interim CEO a couple of times, you know, he, he was a lot more than just a CRO when it comes down to the ability and the numbers.And I guess all I'm saying with this is, maybe every CRO can move to a level of, Paul and, know, really get that excited by the numbers and the metrics, but, but they also try and, know, really we've, moved the, especially in the world and the, days of gen AI, the gut feel isn't enough anymore. It just isn't, you got to still have a sales gut.but you got to really have all the metrics and you have to pay attention to them as well. and before I go even to KK, Allen, is there anything on that that you'd like to addAlan Rudolph (25:22)it's fascinating that the whole discussion around numbers, and AI and, know, I think overall, we think through, find more, win more, keep more, we need to have the right analytics, the right data, the right, diagnosis so that we can analyze the numbers appropriately. and it's just so relevant in,Mark Petruzzi (25:38)youAlan Rudolph (25:43)today's world. If there's one thing I've learned operating in this world, over the past 15 years, it's, it's data driven decision making and, and AI just helps us that much more. know, clearly Mark leads us into the, know, the next discussion about, know, you were talking about Paul and, know, what happens when CROs, you know, don't have these numbers? How do they, how do they make it all work? And I think we're KK, this is where you, you know, have some thoughts of wisdom here.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Alan Rudolph, Strategic Advisor at AGS, to explore how sales and marketing alignment, time to value, and retention strategies directly impact enterprise value.Alan breaks down why misalignment between sales and marketing often starts with a lack of shared ICP definition, and how that disconnect destroys both efficiency and effectiveness. He also shares where AI is creating real leverage today across prospecting, coaching, and personalization, while emphasizing that human judgment remains critical in enterprise sales.The conversation closes with a deep dive into time to value, gross versus net retention, and the bow tie revenue model, highlighting how leading organizations connect the full customer lifecycle to long-term value creation.  What You’ll Learn:Sales and Marketing Alignment: Why ICP clarity is the foundation of both quality pipeline and efficient execution.Where AI Actually Works: Practical use cases in prospecting, coaching, and personalization.Time to Value (TTV): Why speed to value is now a critical metric owned by the entire organization.Retention Metrics That Matter: How gross and net retention signal true business health.The Bow Tie Model: How “find, win, keep” connects the full customer journey to enterprise value.Key Topics:Marketing optimizing for volume vs sales needing qualityThe breakdown of lead quality when ICP is not alignedAI enhancing research, call coaching, and content personalizationLimits of autonomous SDRs in enterprise sales todayDefining and reducing time to value (TTV)Gross retention vs net retention and their impact on profitabilityThe hidden cost of poor retention on CAC and EBITDACustomer journey ownership across the entire organizationThe bow tie revenue framework: find more, win more, keep moreWhy traditional funnel thinking ignores retentionThe importance of cross-functional ownership of the customer lifecycleStrategic priorities for CROs: ICP discipline, full revenue ownership, and efficiency as advantageGuest Spotlight: Alan RudolphAlan Rudolph is a Strategic Advisor at AGS with deep experience advising private equity-backed companies and scaling enterprise sales organizations. With a strong operational background at the COO level, Alan specializes in aligning sales, marketing, and customer success to drive measurable enterprise value and long-term growth.  Resources & Mentions:AGS (Advisory Growth Strategies)Concept: Ideal Customer Profile (ICP) alignmentConcept: Time to Value (TTV)Concept: Gross vs Net Revenue RetentionFramework: Bow Tie Revenue Model (find, win, keep)Concept: AI-assisted sales and marketing workflows🎧 Listen now and follow Selling Intelligence for more insights on enterprise value creation, GTM alignment, and building high-performance revenue organizations.Mark Petruzzi (00:34)Alan, let's talk about the marketing side of this equation. Because in our experience at AGS, sales and marketing misalignment is one of the biggest destroyers of both efficiency and effectiveness. What does a well-aligned value creation oriented sales and marketing motion look like? And where does it usually fall apart?Alan (00:53)So it's fascinating because when it's working, it just works, right? It's invisible. It doesn't matter. But when it starts to fall apart, It's usually, and this is where we start tying all these pieces together in terms of ICP, because it's the definition of that qualified lead or the quality, maybe said another way of that qualified lead, right? So marketing is always going to optimize for volume, right? Throughput.not the quality, right? The actual lead that comes in and making sure it's a good lead. And then sales just starts ignoring it. Sales starts going, doing their own thing and marketing thinks they have this great volume and sales is saying, you no, because they're not matching back to the ICP and that shared definition, that quality of how do I bring a great customer in the door?KK Anderson (01:44)That makes a lot of sense. And Alan, let's pivot to everyone's favorite topic, AI, for a minute here to round out this topic. So AI is reshaping both how we find customers and how we serve them. And so in terms of this kind of efficiency mandate, where are you seeing AI create real measurable leverage for sales and marketing teams right now?like in your port codes that you're working with or have worked with in the past, like where's it working and where is it still mostly noise?Alan (02:14)three areas are where I see it working. First of all, and let's frame this all in the context of making us humans better, not replacing us humans. let's start there. That's first and foremost. so number one, prospecting and research, right? Who should I be talking to? Who should I be reaching out to? Right? That time spent in building those lists, et cetera. Number two is call intelligence and coaching.And I can remember, my God, one of the port codes I was working with probably five-ish years ago, actually in the middle of COVID, we started doing call recording. And the value prop around what I can, the takeaway from our calls, right? What worked? What didn't work? How should I change the script, et cetera? Just a huge opportunity for training, for coaching, for getting much more effective results out of our calls.you know, again, huge in terms of intelligence and coaching. lastly, content personalization at scale, right? Using AI to tailor the case study, to tailor the solution definition, to tailor, the whole presentation, to make sure that it matches specifically, you know, to that, that prospect we're going, going after. So it's not noise.It is real. AI is real. The one thing I would stay away from, right, in terms of what's not working is sort of these autonomous SDRs, right? Because it just, it's not there yet. know, tomorrow is, we don't know, but it's just not there yet. Again, it comes back to, it makes us all better. It makes humans better, but it doesn't replace that human judgment.That is so important in a high stakes enterprise class sale.Mark Petruzzi (04:02)Excellent, Alan. All right, well, let's move us into our final topic, time to value retention and the revenue bow tie. Earlier on, Alan, you introduced us to the concept of time to value, TTV, as a critical metric that most sales leaders do not own, but absolutely should. Please define TTV for our audience and make the case for why it belongs on the sales leader scorecard.not just customer success.Alan (04:29)Absolutely. So TTV is, as you said, Mark, time to value. It's how quickly can I get from that contract signature to value from the solution, whatever that means, right, in terms of the solution up and running. And I can remember going back in my career, we'd be talking six, nine, 12 months. And customers want 15, 30, 45 days. So it's just so critical that theReally, and I'm going to broaden it between customer, beyond just customer success and sales, the whole organization, the whole executive leadership team needs to get focused in on how do I define a solution, sell a solution and drive that solution to quote unquote live to value with the customer as quickly as possible. And that's what TTV is all about.And that's why it needs to be both on the seller scorecard as well as the success scorecard. And it's going to tie right back into the bow tie. So it's just, it's, it's, you think about a customer journey, right. And I'm drawing a circle here because the customer journey is in fact, is a circle, right? We find a customer, we win the customer, we keep the customer. And it's so important that the, that whole journey.that the executive leadership team is, you know, it's on the scorecard. They're evaluated on the success of driving TTV as low as possible.KK Anderson (05:55)That makes a lot of sense. so building on TTV, right? And thinking about, you know, gross retention versus net retention. So walk us through, if you would, the gross retention versus net retention, you know.Alan (06:04)Mm-hmm.KK Anderson (06:11)concepts, right? So thinking, you know, at AGS, we see this constantly. A team will sell aggressively. They'll hit their new logo acquisition number. But gross retention is quietly eroding in the background, right? So what does that diagnostic conversation sound like with the CEO or a board of directors when those two numbers start to diverge? And I know, know TTV fits into that for sure, butHow do you fix that? How do you fix it when your gross retention is not aligned with your net retention?Alan (06:43)Sure. So let's go back to definitional, right? So gross retentionis I open my doors on day one of the year. If I have a dollar and I renew that dollar, that's 100 % gross retention. So let's be clear on definitions here. And then net retention is how much additional do I sell? And depending on how the scorecard is kept, that additional can be everything from a CPI increase, 4%, 5%, 6%, or whatever the number is that you choose.to true add on to increase in the actual pricing so that when I take the dollar, I renew the dollar. But if I have, you know, an, an, an extra 10 cents, excuse me, of add on now it's a dollar 10. And now I have a net retention of 110%. This whole conversation you hear us talking about this through this whole podcast comes back to selling value.selling value to my ICP, my ideal customer profile, and making sure the customer is getting that value vis-a-vis the previous topic around TTV as quickly as possible. The more we can tighten in on the combination of the solution along with the ICP and driving that value to the customer, the customer is going to renew, the customer is going to buy more. World class metrics haveGross retention in the mid to upper 90s. World class metrics have net retention, 110 % plus. That's world class. What happens is if we see net retention, this comes back to the way you phrased the question, KK, if we see that net retention staying that 110 plus, but the gross retention slipping, for example, into the 80s, maybe even only 90, that means we're putting inToo much pressure on net new sales, right? Too much pressure on selling that more, selling additional, and we're losing that gross retention. And what happens when you lose gross retention, number one is what I just said, too much pressure on the organization overall to get that add on sale. Number two, the overall cost of acquisition goes up. And so inherently, the EBITDA for the organization is getting impacted because I'm selling net new.and I'm not retaining my bass.Mark Petruzzi (08:59)And you know, Alan, I've seen over the years, there's almost this kind of machismo sort of looking at new opportunities and new revenue. And everyone wants to be that hunter that leaves the village and comes back with an antelope on their back, carrying it back to the entire village and everyone gets to eat. But we find in a lot of ways,It's really the individuals who are out there foraging and growing and doing things in the village are the ones that really keep a village alive much more than the big celebrated hunter that comes in. So it's amazing how that mindset just, it still hasn't gone away. Everybody still thinks a new logo is worth more than additional revenue and an old logo. And it just really doesn't.Okay, so let's switch to the Bowtie revenue architecture and go a little deeper here. The whole concept of find more, win more, keep more. That's the framework that ties the full customer lifecycle into that single value creation narrative that we started this entire podcast on. How do you use that framework when you walk into a port co or leadership offsite andAlan (09:52)Okay.Mark Petruzzi (10:13)What does it unlock in that conversation that traditional funnel thinking just absolutely messes?Alan (10:19)It misses the keep more, right? The whole premise is, you know, find and win. That just is the beginning of the journey. And I can't lose sight of that keep more, right? The whole discussion we have, and we spent a lot of time in off-sites talking about this is what is the customer journey? to, think about it from a RACI standpoint, right?Who touches the customer throughout the lifecycle, throughout the customer journey to ensure that the customer is ready, willing, and able to buy more throughout, again, that customer journey, that customer lifecycle? And that's why the bow tie in terms of find, win, keep is so critical and intertwined with this whole discussion of gross and net retention and making sure that theWhole organization drives value to the customer throughout the entire journey.KK Anderson (11:13)Really interesting. Okay, so as we round out this last topic, let's bring it home with a forward looking question, Alan. ⁓ So if you're advising a chief revenue officer or a CEO heading into a new fiscal year, right? They're still navigating a tough SaaS environment, PE pressure on EBITDA, and buyers who are more cautious now than they were three years ago.Alan (11:20)Mm-hmm.KK Anderson (11:36)What would you say are the two or three moves that separate the leaders who will create enterprise value from those who will just survive?Alan (11:44)I sound like so repetitive on number one. Ruthless, ruthless ICP discipline, right? That will just drive tremendous value as we look forward. Number two, and this might be a little bit controversial, own CRO, Chief Revenue Officer. Revenue, not sales, revenue. So own the entire revenue lifecycle. So let's, I don't want to.KK Anderson (11:44)Alan (12:09)We're have a whole other podcast about ⁓ how should a port co be organized. But suffice it to say that an executive leader that owns revenue needs to own that whole lifecycle, needs to own find more, win more, keep more, needs to own the customer journey of driving great value through TTV, as well as making sure we get the renewal signed. And then lastly, if you remember,half a dozen questions or so ago, we talked about efficiency and effectiveness. Make efficiency a competitive advantage, right? Drive the value. Make sure we understand where the buyers are coming from. Why are they coming through us? How do we drive through the sales cycle as quickly as possible? How do we leverage AI? Right? So you said it, KK. This is the culmination of what we've been talking about throughout this podcast. And it's aboutspeed and efficiency and effectiveness and pulling that all together into a competitive advantage.KK Anderson (13:09)I mean, it all comes together, right? It all comes together. Okay, Alan, we are gonna move on to our favorite part of every podcast we do, the rapid fire questions. And I'm gonna kick us off and then we'll, Mark, you can take the next one, okay? And I can't wait to see what you're gonna say for this first one. Okay, the metric you think every CRO should have tattooed on their wrist.Alan (13:29)Net Net retention.KK Anderson (13:30)at rest.Mark Petruzzi (13:32)Great, so okay, growth or profitability? If you can only optimize one for the next 12 months, which do you pick and why?Alan (13:40)So these are all mature companies. So it has to be profitability. I'm not in startup mode, right? So it has to be profitability with an asterisk optimizing for profitable growth, right? So we've talked throughout this podcast about, you know, a successful organization historically was at least rule Now those that that's even, you know, with AI with everything that's going on in the world around us, even growing more. So it's got to be profitable.And it's got to be growth. And you take the sum of those two, and it's got to be a big number. And I'm going to argue that number, the rule of 40, has gone by the wayside. And we're talking about something in a rule of 50 plus to get to world class valuations.KK Anderson (14:20)You heard it here first folks, rule of 40 is no more, rule of 50, here we come. Okay, sales or a business book, Alan, that you think every revenue leader should be reading right now.Alan (14:32)So I'm going to take us back in time because I truly, truly believe that relationships are critical to the successful enterprise sale. And there was a guy named Dale Carnegie who wrote an unbelievable book in terms of how to win friends and influence people. And I'm to go back to basics, which it is, but there are just so many learnings in that book about what those relationships mean, how to build them, how to nurture them.how to deal with those relationships in good time and bad. So it's an old book, it's been around. Hopefully all of us, anybody in sales has seen it, read it, go read it again, and then keep reading it.KK Anderson (15:10)I put that book in both of my kids stockings at Christmas this year. fact, fun fact.Alan (15:13)Hahaha!Mark Petruzzi (15:15)Great, next one, one leadership habit every sales leader should build right now as soon as he can.Alan (15:22)Yeah, I have long discussions about balancing between deep dive forecast reviews and structured deal reviews. And I think structured deal reviews capped at a 30 or 60 minute slot adds tremendous value for the leadership team to understand what needs to get done for that deal to win and helps the salesperson bring that deal in.So again, recommend structured deal reviews by ⁓ strategic deals selected appropriately and going through the win of how do we make sure that deal gets across the finish line.KK Anderson (16:00)Love it. Okay, my favorite question. Advice you would give to your 21 year old self. And it can be about building a career and whatnot, but just what would you say?Alan (16:08)Learn the ins and outs of the business model, the financial model. And it's really all about what levers. Like take the example I was giving earlier in terms of cost of acquisition and an existing customer versus a new cost or effectively customer acquisition cost or as we call it CAC. So learn the financial model. Understand what drives revenue, what drives costs. How do I ⁓ impact costs? What ultimately drives EBITDA? Right? Most sales leadersThey just can't do it, I hate to say. And so that's a learning that I think is really important. Reach out to me, I'll take you through it. Right? But again, I just think that the core financial model, the better you are at understanding it, the better you'll perform in the board.Mark Petruzzi (16:52)All right, our final one. The one thing the P community still gets wrong about go to market.Alan (16:57)the time it takes to influence or change sales culture. It's hard, right? The operational fixes, the process changes, the people, everything that goes into an overall sales culture that drives all the metrics we've been talking about through this podcast, it just, you know, most boards, most PE firms think they can snap their fingers and it's going to change.and for us as practitioners in the market, ⁓ can we get to the change? Yes. Does it take longer? Absolutely.KK Anderson (17:31)Realistically, we always say it's 12 to 18 months and I know it's hard for people to hear that. and you know, we can do sprints that have meaningful impact on acceleration, but it does. A true sales transformation and culture shift takes 12 to 18 months.Alan (17:37)Board don't like that.Yep, 100 % agree.Mark Petruzzi (17:49)All right, well, Alan, this has been an extraordinary conversation. It was the kind that audiences will be referencing long after they listen. ⁓ We will be referencing it long after we listen. So for everyone tuning in, if you took one thing from today, let it be this. Enterprise value is not just a finance concept. It really is the basis of what we're all out here doing. Why we work as hard as we do.why we jump on planes at six o'clock in the morning and, you know, jump back on a flight at 11 or midnight. So if you can look at it that way, you really as a sales leader, learn to speak the language of the board, because again, that's the thing that they need. That's the thing that they're focused on. And that's where their fiduciary responsibility is as well. SoIt is really the outcome of every decision a sales leader makes about how to find customers, how to win them, how to keep them, how to grow them, how to keep them becoming happier every single day. Allen has given us the framework to talk about all of these concepts.KK Anderson (18:59)All right, Alan, wonderful conversation. And to our great audience, you can connect with Alan through AGS at get-ags.com. That's get and then the dash symbol, ags.com. And we will include all of his contact information in the show notes and also an area where they can connect to you on LinkedIn, Alan, if that's perfect.Alan (19:20)Yep, absolutely.KK Anderson (19:22)Okay, and if this episode shifted how you think about the sales leader's role in value creation, share it. Like and subscribe. Share it with a CRO or a CEO who needs to hear it. And we will see you next time on Selling Intelligence.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Alan Rudolph, Operating Partner at AGS, to break down what enterprise value creation really means for modern sales leaders.Alan shares why CROs must move beyond just hitting quota and start thinking like operators responsible for long-term enterprise value. The conversation explores how retention, expansion, deal velocity, and cost of acquisition directly influence valuation, and why aligning go-to-market execution with investor expectations is now critical.They also dive into the shift from founder-led growth to scalable sales organizations, the importance of ICP discipline, and why effectiveness and efficiency must now coexist in every revenue team.  What You’ll Learn:Enterprise Value Creation Explained: What it actually means for CROs and sales leaders beyond hitting quota.The ICP Foundation: Why defining and sticking to your ideal customer profile drives valuation.Efficiency vs Effectiveness: How modern sales teams must balance both to compete.Destroying Value Without Knowing It: Common mistakes like discounting, churn masking, and selling to the wrong customers.From Founder-Led to Scalable Sales: What must change to build repeatable revenue systems.Key Topics:Value creation plans and their connection to company valuation multiplesThe four drivers of enterprise value: retention, expansion, deal velocity, and acquisition costThe “discount trap” and its impact on profitability and valuationNet revenue retention as a core board-level metricCustomer acquisition payback and time to value (TTV)The bow tie revenue model: find, win, and keep customersTransitioning from founder-led sales to structured go-to-market systemsLeading indicators of inefficiency: activity without outcomes, extended sales cycles, poor handoffsThe role of ICP in both agentic workflows and traditional GTM executionWhy misalignment between sales and delivery destroys trust and valueGuest Spotlight: Alan RudolphAlan Rudolph is a Strategic Advisor at AGS with decades of experience working with growth-stage and private equity-backed companies. Known for operating at the COO level, Alan specializes in aligning sales, marketing, and operations with investor expectations, helping organizations build scalable revenue engines that drive long-term enterprise value.  Resources & Mentions:AGS (Advisory Growth Strategies)Concept: Enterprise Value Creation (EVC)Concept: Ideal Customer Profile (ICP) disciplineConcept: Rule of 40 and evolving efficiency benchmarksFramework: Bow tie revenue model (find, win, keep)Metrics: Net Revenue Retention, CAC payback, Time to Value (TTV)🎧 Listen now and follow Selling Intelligence for more insights on scaling revenue, aligning with investors, and building high-performance go-to-market teams.Mark Petruzzi (00:28)Welcome to Selling Intelligence. I'm Mark Petruzzi, joined as always by my co-host, KK Anderson. Today we have a guest who sits at a genuinely rare intersection. Someone who has operated inside growth stage companies, advised P backboards, and built sales and marketing engines from the ground up.and also from the COO, Chief Operating Officer, Level, which has been his core focus. He's also a close friend and a member of our team here at AGS. Please welcome Alan Rudolph, Strategic Advisor at AGS. So,Alan (01:03)Thanks, Mark.to be on the podcast today.Mark Petruzzi (01:06)Great, we're happy to have you, Alan. So Alan brings decades of experience across boardrooms, PA backed operators and enterprise deal cycles. He's known for helping leadership teams connect the dots between investor readiness, revenue acceleration and overall sales team performance. And also for making the case that great sales leadership is not just about hitting a number.It's about building a machine that creates lasting enterprise value. That is exactly where we would like to go today. We're going to talk about what enterprise value creation actually means for the sales leader, why efficiency now sits alongside effectiveness as a C-suite mandate, and how the boat-time revenue model, finding, winning, and keeping customers,maps directly to the metrics P investors care most about. Three topics we'll cover. EVC, enterprise value creation, what it is, why sales leaders need to understand it and own it. Effectiveness versus efficiency, the dual mandate for modern sales and marketing leaders and why building an efficient team is no longer optional.The third one is time to value retention and the revenue bow tie. How customers onboard focus on gross retention and how important net retention is to the overall enterprise value and what the best senior operators do about it. Again, Alan, we're so happy to have you here. Let's jump right in. So, okay, first topic, enterprise value creation.You know, really what a sales leaders get wrong here. And let's start with a framing question because this concept of enterprise value creation gets talked about in boardrooms, but rarely makes it onto the whiteboard in a sales QBR in plain language. What is an EVC and why should every CRO SVP of sales and VP of sales have it front of mind, not just the CFO in the board.Alan (03:04)Thanks, Mark. Great question. So EVC or value creation or value creation plans has been the buzzword, as you say, of boardrooms, of private equity firms. And at the end of the day, a value creation plan, also a transformation plan, simply drives to whatever that target multiple is. And so everybody thinks, it's just about the multiple.pick the day and age, pick the year, pick whatever time frame you want to pick in terms of what are target valuations. But let's forget about the number for a second. And again, let's talk about what the CRO needs to worry about. And so as you said previously, CROs think, it's just the number, right? I got a quota. What percent of quota? How am I doing against my sales forecast, et cetera?When I think about a value creation plan for a CRO, I think about things like customer retention, right? How am I doing? How am I driving value across my install base? Because we know the higher the gross retention, that drives into expansion capabilities. That drives into a broader opportunity to sell more of what I have in my toolbox, number one.So that's retention and expansion. Then add to that deal velocity. Again, the deeper relationship, the clearer understanding, I have faster deal velocity. And then lastly, think about it from what does it cost me to win that deal? That's what's so critical for the CRO. these are, if you take, just take those four things I just said, retention, expansion, deal velocity,and costs of acquisition and you put that into a value creation plan. Okay, so what does that really mean? Let's dig into that for a second. When I think about a value creation plan around retention, I'm going to have a key set of initiatives that I'm going to drive across my sales team, hunters, farmers, whether it's customer success or account management. I'm going to have key initiatives that driveincreases in overall retention. That's what a value creation plan is. Separate and distinct from my quarterly forecast as the CRO. Right? So it's the combination when I think about what does a good CRO look like when he or she steps into the boardroom and starts talking about how am I doing this? How did I do this past quarter? What's the forecast for the next three quarters? How am I going to do for the year?And how am going to improve that overall value prop into the value creation plan, which ultimately drives the multiple in terms of the overall valuation of the.KK Anderson (05:50)So as you think about, am I echoing by the way?Alan (05:53)You are.Mark Petruzzi (05:53)You are, yes.KK Anderson (05:55)Okay. Hang on. that better? Okay. I think it might be gone. Okay. Sorry about that. so as you think about these, these specific value creation plans, you know, and you think about sellers in general, right? Salespeople. What would you say are the top two or three places where sales teamsMark Petruzzi (05:56)It actually seems betterKK Anderson (06:13)or sellers unknowingly destroy enterprise value, even though they may be hitting their top line number? What are some things to look out for where they're inadvertently impacting in a negative way? Great question.Alan (06:23)Great question and Isee it too often and don't laugh too much when I give you the first comment. The discount trap as I call it. Right? We get to the number, we outperform, but I do that by discounting and we know that that discounting inherently puts challenges all throughout the organization because now our profitability numbers, our bottom line isn't where we need them to be.So we just really need to be careful in terms of selling value that we're, have a, you know, I've walked into companies that don't even have a target price book, right? And so it's important that we understand what our price structure is, how to drive value with that price structure and not to ultimately fall into the discount trap. That's number one. Number two is the, I'm gonna call it the yin and the yang or the tie between, and this comes back to,find, and keep more is churn versus new business. So is a ⁓ lower retention massed by net new business. And we know the cost of acquiring new business versus the profitability of a long-term customer is dramatically different. And so we don't want to overachieve revenue numbers because we're bringing more in the door net new.but we're losing or reducing on gross retention. then lastly, and again, I'm an ops guy, right? And so I need to manage and maintain customers throughout the life cycle. It's selling to the wrong customers. And the hardest thing we all can do in an enterprise SaaS company is fire a customer. But we know that sometimes we just need to do that becauseFor whatever reason, there's a gap between the solution sold versus the expectation of the customer. So it's just really when we come back to that question about how can a CRO destroy enterprise value overall, is get that right customer base that truly understand the value we drive, that can benefit from the solution.Mark Petruzzi (08:11)is really important for me to come back to that question.Alan (08:26)We know it's a very small world out there that will talk to their peers in their respective industry about the solution. So again, it's all about getting to the right customer.Mark Petruzzi (08:37)Excellent, excellent points, Alan. So one of the things we hear constantly from P E operating partners is that founders and early sales leaders are often great at the hunt, but man, do they struggle to build the system when they really have to take it past founder led growth. You have described this as the difference between being the lead salesperson and being a sales leader who builds organizational capacity.Alan (08:54)Mmm.Mark Petruzzi (09:02)Walk us through that ⁓ transition, typically breaks and what really does have to change to make it successful.Alan (09:09)mean founders are phenomenal, right? Because they build, they grow, they have personal relationships with that first set of customers. And by the way, they know what they can and cannot sell, right? They know where the product does or does not break. The discussions I have with founders in earlier stage companies really boils down to one primary aspect. Definition of the ICP.Who is my target customer? Right? So comes back to what I said earlier about whether it's finding customers or selling to the wrong customers, et cetera. It's all about the ICP. So I have a well-defined solution. And I know that that solution is relevant to a target set of customers. So how do I define that ICP? That's what will drive an organization to go from a founder-led sale that he or she canbasically make whatever decisions need to be made and can drive that solution into a much broader sales team that needs to understand what is that profile of the customer that I'm looking for? How do I drive the solution into that customer and win those deals?KK Anderson (10:23)You know, ICP is the cornerstone of everything really. And even now this week, we've been having a lot of conversations around agentic workflows and go to market and all of it hinges on the ICP. If the ICP is not effective, then none of the agentic workflows are effective. And it sounds like it's the cornerstone of our value creation as well, huh?Alan (10:43)KCAD, add to that, without the definition and the adherence to the ICP, the firm, the company, the SaaS provider will not get to its target valuation. I would be very bold in making that statement, but I'd stand behind it.KK Anderson (10:58)Well, and you might somehow weave this into my next question here. so, you know, thinking about making this concrete and you know, we like to measure everything. if I'm a CRO at a PE back SaaS company and I'm going into a board meeting next month, what are the two or three metrics that I should be walking in with that signal? I understand enterprise value. My team understands enterprise value. So.Like beyond just ARR and pipeline coverage, like what are those metrics?Alan (11:27)net revenue retention. It comes back to ICP. Am I selling to the right customer that continues to buy more from me? And so let's be clear for a second. Net revenue retention, everybody gets this messed up. Net revenue retention is I start the year, let's call it $1. And if at the end of the year I have $1.10, that means I grew at 110%.KK Anderson (11:30)Right. Yeah.Alan (11:49)revenue retention is the combination of my gross, what I'm renewing, plus the additional sales, cross-sell, up-sell, et cetera, into that customer. So first and foremost, a clear understanding of that revenue retention. Number two, and I talked about this briefly earlier, is the payback period for our customer, right? We know that the costs are higher in the first months and the first year of managingimplementing owning a customer. So again, this comes back to ICP sell to the right customer, right? It's I spent a lot of my career middle part of my career in outsourcing. We didn't actually make any money in large complex outsourcing deals to year two, three or four. So right, it's all about making sure you have the right ICP, the right solution selling into that customer. And then lastly, TTV time to value in this day and age.Customers want value as soon as they sign the contract. So we all know that in a SaaS world, customers sign the contract, they get an invoice, they pay us upfront for a year. Well, they want value immediately from that. So we want to make sure we're continuing to address time to value and how much we are decreasing the implementation time frame number one.Mark Petruzzi (13:09).Alan (13:09)and or number two for depending on the solutions and the more complex solutions that we're segmenting that implementation so that we get piecesof the solution implemented as quickly as possible so the customer is getting value out of the money they're spending with us.Mark Petruzzi (13:26)Good stuff. So let's move on to topic two. Effectiveness versus efficiency. Building the team that is able to move the needle. So the era of growth at any cost is over. It's way over, right? It's, you know, we've moved much more to the rule of 40, which means you have to have a growth rate plus a profit margin that is 40 or greater.and it's probably going to be moving past that metric as well pretty soon because, you know, was the good old days, right? It was, we, we had to grow each year. A sales leader was asked or was told what the number is and they would come back and say, okay, I need to hire 30 new reps this year to be able to get that. Well, it doesn't work that way anymore. So we're hearing this from.Alan (13:54)Absolutely.Mark Petruzzi (14:16)every PE board and every PE firm that we work with, efficiency is now as important as effectiveness. help us to find the difference and why is it so hard for most sales leaders to genuinely operate on both dimensions simultaneously?Alan (14:34)because they're almost diametrically opposed, right? That's the problem. So efficiency, I think about it's just numbers, right? What's the ratio of output to input? know, what's my sales forecast? How do I go from, you know, lead flow and, you know, an MQL and SQL, blah, blah, right? It's just efficiency is just how quickly can I get that wheel spinning. Whereas effectiveness is all about finding, engaging,closing the right customers. It's almost like quality versus quantity. And coin operated salespeople struggle with effectiveness. But we know that effectiveness, go to my previous answers, effectiveness drives higher net retention. Effectiveness drives a better overall ICP. Effectiveness drives overall increase inyou know, the valuation of the firm. And I would argue that in the world that we're living in today with, you know, with everything we talk about from an agentic standpoint, the introduction of agentic workflow, et cetera, we're going to need to look at, you know, valuations that are rule of 60 plus. And so to get there, both effectiveness and efficiency are important. We need tovalue where we spend our time as sellers, as a CRO, thinking about effectiveness and efficiency and making sure we're bringing the right customers into that bow-tie journey of find, keep, find, and keep and ⁓ driving our sales force to be as effective as possible in winning deals, maintaining deals, keeping deals.and closing deals without discounts. I'll end on that.KK Anderson (16:19)So, Alan, you go into a PortCo and you do a go-to-market assessment, what you're saying makes complete sense around the inefficiencies with the sales team inadvertently driving down enterprise value. sure, there's going to be all kinds of lagging indicators in Monday morning quarterback, where we can look back and recognize where they're failing.Like what are the signs, like what are the leading indicators? What are the signs that you can look for now? Like when you're in that diagnostic stage, assessment stage with the client, like what are the signs that a team is burning capacity?Alan (16:52)The first thing I look for is aThe first thing I look for at the sales rep level and obviously depending on size and scale, sales rep, sales managers, VP, CRO, et cetera, is activity that does not connect to outcomes. We all know, we've seen it. We have salespeople that have tons of activity. They have deals, they have demos, they have outbound, et cetera.There's just tons of activity, but we're not seeing the close. Number two, along with that then, is a sales cycle that keeps stretching, right? We have a target close date and it just keeps moving, right? Well, that comes back to, don't know my customer. I don't know who to contact at my customer. I don't understand who has to sign off, who the ultimate buyer is, how the decision is made. So it's all aboutMark Petruzzi (17:33)youAlan (17:41)understanding, knowing my customer. So too much activity, lack of knowledge at my customer. And then lastly, again, this is the Ops Guy speaking now is we close the deal, we hand it off to the implementation team. They have a first conversation with the customer and the customer said, ⁓ I thought I bought X and we're delivering Y. And there's just this gap around that overall whatMark Petruzzi (18:03)Hmm.Alan (18:06)does the solution look like? How do I drive that solution to value in the customer? Right? It's all about value based selling. So it just is, you know, those are the key indicators are start to look for in terms of inefficient sales teams for, know, versus, you know, a very efficient and effective sales team will have less activity, will meet their targets in terms of closed States and won't have any issues with the handoff when it happens.to the implementation or services team or whatever the firm calls it.Mark Petruzzi (18:37)youKK Anderson (18:37)And onceagain, that comes down to the ICP,Alan (18:41)It does, 100%.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of BenchMarket, to go deeper into how companies should measure, operationalize, and compete with agentic AI in go-to-market functions.Ray breaks down why most companies still lack basic GTM measurement discipline, what new AI-specific benchmarks leaders should track, and how legacy SaaS companies can realistically compete with AI-native organizations that are operating at dramatically higher efficiency.The conversation also tackles the hard truth about workforce reduction, the rise of AI operators, and why companies must rethink their entire operating model, not just layer AI on top of existing processes.  What You’ll Learn:Measurement Before AI: Why most companies must fix GTM analytics before introducing AI.AI-Specific Benchmarks: The emerging metrics for measuring agentic GTM performance.Competing with AI-Native Companies: Why legacy SaaS teams must rethink their entire playbook.The Role of AI Operators: Why AI expertise is becoming more critical than traditional RevOps.From Pilot to Scale: What success should look like at 90 days and 180 days.Key Topics:Cost per pipeline and cost per ARR before vs after AIAgent cost per opportunity, pipeline, and revenueDesigning modular AI workflows instead of “monster agents”The four-layer framework: productivity, effectiveness, efficiency, and ROIRevenue per FTE gap between SaaS and AI-native companiesWhy legacy SaaS companies struggle to match AI-native efficiencyRadical restructuring: reducing headcount and rebuilding with AI-first processesAI enabling deeper personalization at scale for outbound teamsThe rise of “AI operators” as a new critical roleThe “SaaSpocalypse” and pressure on net revenue retention (NRR)Using AI to improve retention, expansion, and customer insightsBenchmark expectations for agentic SDR performance at 90 and 180 daysGuest Spotlight: Ray RikeRay Rike is the founder and CEO of BenchMarket, a leading provider of B2B SaaS performance benchmarks. With decades of experience as a go-to-market leader, he helps organizations move from intuition to data-driven execution. Ray is also the creator of the AI to ROI newsletter, where he analyzes hundreds of AI developments weekly to help leaders understand what actually drives business outcomes.  Resources & Mentions:BenchMarketAI to ROI NewsletterConcept: Agentic AI in go-to-marketConcept: AI-first operating modelsConcept: Revenue per employee as a key efficiency metricConcept: AI operators vs traditional RevOpsConcept: SaaSpocalypse and NRR pressureFramework: Productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI benchmarks, GTM transformation, and building high-performance revenue organizations.Mark (00:26)Excellent. All right, well, Ray, let me bring you back into the days of you and I starting all our research and all the pre-work for data and diagnosis driven selling. So I hope that doesn't cause you to develop a Twitch or anything like that, because as you and I both know, that was hard work. So, but let's, you know.What we really saw right up front is, and we really pushed hard on this, is the idea is you can't manage what you don't measure. And you need external benchmarks, not just internal comparisons to know if your metrics are actually good. You know, it's great. It's great to be able to say, improved this process by 20%. But if you were 45 % behind most of your competitors before that,That 20 % still has you on the back of the pack. So how do you bring that same philosophy to measuring an agentic BDR or an AI-powered deal coaching agent? And we've touched on this, but what's the equivalent of a CAC payback for agents and the entire investment?Ray Rike (01:33)Well, I would start with let's make sure you have your go to market measurements in place, because honestly, we've been talking about these for years. Less than 50 percent of companies have great GTM analytics. ⁓ So things like cost per dollar a pipeline, less than 40 percent of people are measuring cost per dollar a pipeline. So make sure you do that and look at your current state before AI and then measure it post AI introduction. Right.So cost and I'm talking right now, I'm looking very specifically at the customer acquisition process. So cost per dollar pipeline before and after cost per dollar of new AR before and after when rate before and after your average and your contract for you before and after. Cause those are all going to be hopefully much better with AI to your point, Mark. I mean, let's use outreach. Everybody had to have a sales engagement platform, right?How many companies actually said, well, after I invested $1,500 per SCR, I had a better conversion rate or a lower cost per dollar of acquisition? Nobody. You're going to need to do that with AI. So that's my first thing. The second thing, which haven't been defined yet, but I'm working with some VCs on this right now, is AI specific customer acquisition efficacy. So I'm looking at agent costs per opportunity.Agent cost per dollar pipeline, agent cost per dollar of new ARR, agent dollar per cost of retained ARR. So you can think about your gross revenue retention and agent cost per dollar of expansion ARR. Now I'm projecting that we're going to be using agentic AI a lot in those processes or sub processes. And by the way, that's the other best practices.When you design a process, it's better to design a lot of subprocesses underneath so you don't have one large unwieldy AI agent. You have a lot of subprocesses that you have different people auditing and evaluating.KK Anderson (03:28)All right. Let's dig into that design a little bit. So walk us through, and I know this is new, as we've said multiple times for so many of us, what a well-instrumented, agentic, you know, GTM for the purposes of our audience, pilot could look like. You just gave us one great clue, which is, you know, don't make monster agents and, and to break them up so that you can, you know, be more agile andand predictable with those. You've walked us through some baseline metrics that you want to set before you launch, things that haven't necessarily been done in the past with programs like our outreach launches over the years. But what does the pilot to scale gate look like? And how do you separate the agent did something from the agent created revenue attributed value?Ray Rike (04:14)Well, let me go to the baseline metrics first, KK. So I think I have four levels of metrics I like to see in any initiative, including the Gentic AI. So one is a productivity metric, and that is outputs per time, you know, whether it's outputs per human hour, outputs per day or time spent per activity.That's what we've been measuring for the last year and a half and AI in marketing and sales. But that's what then you have effectiveness. How effective is my AI enabled process going to be? ⁓ How many desired outputs am I getting versus the inputs? Hey, for every hundred emails my agent sending, how many meetings do I get set up? Right. Then there's efficiency. That's the cost per outcome. And then there'sactual ROI, which is outcome value divided by the AI investment. So productivity, effectiveness, efficiency, and ROI. I'm not going to go into detail what that's like for just an SDR program, but at least it gives you a framework and a layer approach to designing those four layers of metrics you need to measure.Mark (05:19)Excellent. All right, let's move into topic three, the benchmarked view, and tell us a little bit about what the data has been telling you and your team at Benchmarkit. And let's go with, guess, a baseline of that. Some of your initial benchmarks that you have been working on are showing AI native companies hitting two to three times higher ARR per FTE.than a legacy SaaS, as one example. From our listeners who are operators inside non-AI native companies that are trying to deploy these agentic go-to-market programs we're describing, how do they close that gap? What are the structural differences they need to address? Not just the tooling, but the operating model as well.Ray Rike (06:02)In the let's be real. It's going to be real hard. And the reason being is a lot of the AI native companies are getting new budget. They're getting experimentation budgets. They're getting budget from labor versus budget from I.T. investments. Right. So I hate to say it, but it's going to be hard. But hey, there's a lot of people out there in legacy says companies that they need to get there. Right.So number one is you've got to be laser focused on number one, the effectiveness. Can AI help you get more conversions? Can they get higher ACV? Can they increase your win rate? And you got to go right to cost per. If AI is not getting you a reduced cost per dollar of new ARR, it's going to be really hard. And honestly, Mark,The hardest part is for me, if it was me and he brought me into a $50 million SaaS company, I would say we got to throw out the old playbook and start from scratch. But I don't have the new playbook based upon years and years of experience. So it's going to be really hard to throw out the old playbook and build the new one. So that's why I bring in someone who's got maybe six, 12, 18 months of experience and an AI first culture.and have them do it with you or hire a third party consultant.KK Anderson (07:22)Wow. And it's quite the conundrum that we're all faced with right now. All of these native SaaS leaders trying to compete with these AI native companies who are just crushing it.Ray Rike (07:33)I mean, when you're talking about your best in class, SaaS companies are doing 600 ⁓ to 800,000 revenue per FTE and Anthropics doing three to four. How do you compete with that? It's a little bit like saying, how did JCPenney compete with Amazon? ⁓ I'll bring in a guy from Apple who created the Apple retail experience and that's going to fix it. We saw how that worked, right?KK Anderson (07:42)blue.really is.Ray Rike (07:57)Sometimes it's just nice being part of the next generation versus trying to reinvent the current generation. I'm being honest here.KK Anderson (08:04)you know, and I know it's hard to answer that, but if you were a CRO in one of these old school SaaS companies, what, aside from calling a consultant, like what, where do think you would go first? Like what would you, what would you do? How would you that gap?Ray Rike (08:17)I would completely get rid of my SDR team and make it 100 % agent based. I would reduce my number of salespeople by probably 50 % and say, okay, now that we got 50 % less staff, how do I manage more of their task with AI agents, research discovery, etc. So I would just basically look at what the AI native companies are doing, and then burn the ships and say, we got to do this with 50 % less people.Having a bandaid, I don't think helps. You got to rip it off. So even customer success, right? I do a lot of work with Gainsight. It's like AI is the best retention vehicle in the world because you can look at things that humans can't, kind of like usage patterns, et cetera. And they can predict churn faster than any CSM can. But when you've got 10 CSMs, they're like, that's my job.Well, if I only have three CSMs, I'm not going to be able to do this much, right? So I'm forced to try AI and automation.KK Anderson (09:11)Yep. And just since we're talking about the sensitive topic of AI replacing humans, is something, you know, questions we get a lot of, right? And we are firmly of the belief that yes, of course AI is going to replace some humans, but it can also make humans, that super intelligence can have an exponential impact on their effectiveness, sellers in particular, on their effectiveness if they're using AI correctly.So if you've got the three BDRs instead of the 10, what are some ways that, I don't know, talk to me about how AI can help them be more effective in these roles where there's less people.Ray Rike (09:48)I'll give you BDRs for example is research and doing a lot more targeted research and personalized outreach to those contacts in your ICP at scale. Where maybe I could do 20 or 30 emails that were personalized, best case now maybe I can do 50 a day or 75 a day. So research, highly targeted. That'd be one thing I'd be doing as a BDR every day.I would be using AI to say, how do I follow up with this person who I talked to three months ago? What's the best approach? Let's look at their LinkedIn profile. Let's look at the latest corporate articles out there in the ethos, you know, and on the internet, and let's tailor my next follow up based upon my AI agent helping me get more personal and personalized.KK Anderson (10:32)And what's interesting is more and more we are hearing about this kind of crisis of sameness, right? Where AI has enabled, know, everyone's got the same content, everyone's saying the same things, everyone's sending the same emails. Like you can tell if it's AI, you know, from a mile away. And then we also are also hearing this theme around how now, you know, your humanness is your uniqueness.And people are loving when they see a typo in an email or a message or a, hey, by the way, this is really me. This is not a bot.Ray Rike (11:04)So, you know, I don't know if this is good for this podcast, but I have to call, say it the way I see it. So I don't know if we saw the New York Times research from about a month ago, where 54 % of people prefer AI written communication versus human written communications. 54%, right? AndKK Anderson (11:11)Yep.Mark (11:23)Yep.Ray Rike (11:25)that's going to increase as AI becomes more, more able to personalize the communication to KK versus Mark, right? Which humans are going to have a harder time doing that. So ask me the question again, KK, I went on a tangent.KK Anderson (11:28)normal.What,when I was just thinking, you know, we're hearing now that your humaneness is your uniqueness. And so,Ray Rike (11:42)yeah.So an enterprise class sells, I think it's going to continue to be the case. But, know, I think even having, you know, children who are early career people, right. So and I hate these type of generic comments, but be the person who knows how to use AI in your function better than anyone. Everyone should be spending at least an hour a day on their own, learning how to use AI in their role.They should be learning a new tool at least once per quarter, if not once per month. So that's one thing, because for the next few years, those who know how to use AI in your function, whether it just is your assistant to do your function better, or you become what I call the AI operations guru, you can go into any company and say, I'm going to improve your sales development process by 5X.by doing this, that, this, this, and this that I've done four times before. So doing it as a practitioner and then be able to do it as a consultant, you're going to have job security for quite a while.So that would be my advice. Learn it and be better than anyone else. And by the way, make sure that your boss knows that you're the person who knows it better than anyone else. Because when it comes time to get rid of people, like, I can't get rid of Joe. Joe knows more about this AI agent than anyone in the company. So that's why, Kay, I think you asked me this earlier. I believe that AI operations is going to be much more strategic and important.Mark (12:52)Yeah.Ray Rike (13:07)than rev ops ever became. And I actually saw three different job posts just on Monday from big companies asking for to hire AI operators. They didn't call them AI operation specialists, they called them AI operators.KK Anderson (13:21)Really cool.Mark (13:22)We can't let you go without going into some of the narrative that we're all hearing out there. And it starts with the term the SaaSpocalypse. So we all know that traditional SaaS and NRR is under significant pressure. Some companies in the bottom quartile now below 100 % of NRR.For listeners who are sales leaders, not just the executives of those companies, what does that signal mean for how they need to sell differently? And how does agentic AI factor into the defense strategy, the attack strategy, or whatever you pull together from here?Ray Rike (13:58)Well, net revenue retention is a combination of how much ARR you retain from existing customers plus how much expansion ARR you add. Right? So if you have a leaky bucket problem, i.e. your gross revenue retention went from 88 % last year to 80 % this year, which by the way was Zoom Info's big issue. They lost so many of their customers in the tech sector. You better quickly try to understand what I can do.and how you can harness the power of AI to increase customer retention, right? And then second, you've got to get a hell of a lot better on your customer expansion motion. And in fact, if you only have one or two products in your portfolio, I would start talking to your CEO and had a product about why these other three near adjacent products could really help you from an NRR and how it impact you. But start withHow do you retain customers better? How do you increase the efficiency of your expansion motion? And how do you open the aperture of the opportunities to expand your existing customers? New ARR is still going to be really hard as a legacy SaaS company if you're competing against agentic AI or AI native software vendors.KK Anderson (15:06)Okay, last question before we move on to the rapid fire. And this is gonna be one where again, you know, it may be too early to tell, but just work with us here, on this one and let's kind of think about what the hypothetical is and just try to make this a little bit more concrete for our audience. So let's think of a real world benchmark anchor, okay? So a company with 25 million to 50 million ARRThey're deploying their first agentic SCR or pipeline management program. What do we think good should look like at 90 days or even at six months? Which of these benchmarks that we've talked about today would tell you that this program is worth scaling versus killing? And how quickly do we know?Ray Rike (15:54)Within 90 days, your agent should be performing as good as if not better than a human SDR. Because you take some time to make sure you train it, you refine it, etc. Days 91 to 180, you should see a minimum of 25 to 50 percent lift on your conversion rate from outbound activity to sales call.You should see at least 25 percent lift from sales call to opportunity and your win rate should go up by at least 10 percent. So these are just some benchmarks out there, but you can't be just as good. It's got to be better.So I don't know if that gave you enough granularity, 90 days to prove the case, 180 days to make it tangible with real ROI.KK Anderson (16:32)It does. It does.Mark (16:37)those are reasonable timeframes and that's why this is working. Okay.KK Anderson (16:39)Mm-hmm.Ray Rike (16:42)by the way,Mark and KK one day, I mean, the days of experimentation were in the last three innings of that using a baseball metaphor. You're going to start competing for budget for AI. So you're going to need to say, here's my AI project and here's my projected ROI. And if it's lower than this one over here, you may not get it. So you better be ready to fight for your budget.Mark (17:04)You know, Ray, you hit on such a great point with that because I, you know, it's funny, as we've jumped into more of the pure play at Gentic work that we have done over the last year, maybe a year and a half, the real discussion with me reaching out to CEOs and board members that I know was, you know, okay, like, what are you guys doing with AI?ask your CEO, okay, you have seven direct reports reporting to you. What are they thinking about doing with AI? Because you had all these board members, especially kind of two years ago, a year and a half ago, going to everybody, come on, man, you got to do this, you got to get us a piece of this, we got to become more efficient. And it was really about like they were getting dragged in most of the executives I spoke with.we're getting dragged in to do this. So they had to go do something. But as we've gone over the past maybe nine months or so, I've seen and I've changed my approach accordingly, that it's now, you hey, it's not, you've got to be doing something in AI, but you got to be doing the right things in AI. And with the work I've done being on the board with Humigentic and the work KK and I have done with Humigentic as one example of a company,There is, you have to have that precision as well. So before we go into rapid fire, any thought that's popping in your mind based on what I just shared?Ray Rike (18:30)So I've done state of AI research and finance and marketing and sales and customer success and two thirds to three quarters of the time, the person who pushed AI into the department was the CEO, not the departmental executive, which is telling. And to your point, man, evenIf you're not that comfortable with it as the head of marketing or head of sales, you better hire someone. Maybe you hire your AI ops person instead of a rev ops person who's got that deep experience. And you're like, I need you to take this process completely redesign it and share with me how we can make this AI first. You got to take that lead because you're going to become obsolete so quickly.If you don't do it because you're fearful or you don't know, what you're not going to know is where you're going to get your next paycheck from. You need to know it and you need to learn it and embrace it.Mark (19:23)Yeah,Excellent advice. Okay, rapid fire. Let's finish up here. ⁓ First thing you've ever sold professionally or even as a kid.Ray Rike (19:34)My dad had his hobby, which was a small engine and lawnmower repair shop. We also sold new lawnmowers. So I got good at selling upsells to doing like total engine rebuilds or selling a new lawnmower when the old one was going to cost too much to get fixed.KK Anderson (19:49)Very good. Okay, one metric most go-to-market leaders are still measuring wrong.Ray Rike (19:54)customer acquisition cost ratio because they're not measuring it and they don't separate the measurement for what it costs to get a new customer's dollar of ARR or an existing customer dollar of expansion ARR.Mark (20:05)So if a CRO could only instrument one thing about their agentic go-to-market pilot, what should it be?Ray Rike (20:12)You are outbound.And specifically, that's not one thing. I would want the research and the outreach to be the first thing they automate.KK Anderson (20:20)advice you would give your 21 year old self.Ray Rike (20:23)be an entrepreneur. And by the way, I helped many entrepreneurs and VCs make a hell of a lot of money, right? Five exits out of seven companies. But being an entrepreneur at the last stage of my career is the most fun I've ever had. And in today's world, the chance to build a business, because you know AI better than anyone, there's never been a better opportunity to be an entrepreneur, never.Mark (20:46)Okay, your favorite chapter in data and diagnosis driven selling. And what would you write differently with me ⁓ if we had to do it again?Ray Rike (20:47)Thankprobably the different metrics by stage of the customer acquisition process. And I would layer a lot more AI measurements. And quite frankly, even though we had a chapter dedicated to this, you know, and this was only what less than three years ago, a lot more focus on the AI first acquisition retention and expansion process versus how we wanted to automate and make it more efficient.Mark (21:15)Yes.We thought we were, yes. And it's funny, we thought we were so far ahead of what was about to happen. And we were pretty proud of even how we integrated stuff in and that one chapter that we were able to go a little deeper. But man, oh man, that tidal wave just came over our head, didn't it?KK Anderson (21:21)I sense an update coming.Okay, one sales ritual or habit that no AI agent will ever replace.Ray Rike (21:47)Maybe they can fake it or emulate it, but it's true concern about your customers win. Like one of the things I always try to do is understand what my buyers personal win was. My economic buyer and my influencer champion. Why are they going to win? Because they do business with me and my company. And then of course, how does the business really win? Right? AndBe really curious about that and don't just even take what you hear for the truth. Kind of say, well, but I've also seen this or heard this. So how do you marry these two? I think it's just a human authenticity, curiosity and true concern to make sure you win, KK.Mark (22:28)Good stuff. So, and where will SAS benchmark data be most disrupted by AI in the next two or three years?Ray Rike (22:36)I think it's all going to be pretty disrupted, but it's going to be revenue per employee. And it's going to be how much I spend and operating expenses versus cost of goods sold.Mark (22:45)Beautiful. Well, Ray, thank you so much for spending the time today with us. It's always a pleasure. And also thank you to KK and our incredible audience. Thanks for joining us each week. All the best.KK Anderson (22:58)reallyRay Rike (22:59)Hey Mark!KK Anderson (22:59)great.Ray Rike (22:59)Hey Mark, can I make a plug?Mark (23:00)Of course!KK Anderson (23:01)Yeah.Ray Rike (23:01)so me and my partner, we publish the AI to ROI newsletter every day. We cover a different topic, but we'll look at 200 to 1000 news articles a week and we pick out the top five to 10 and we share that with our audience and we do deep analysis on what it means. Man, if people could go to AI ROI dot sub step dot com, I really believe in. By the way, we don't. This is not aGet the free one so we can charge you subscription. Everything I do is for free to help the industry evolve. I think it'll take hours of research away from every individual who reads it and hopefully give them highly relevant contextual research and analysis.KK Anderson (23:43)And it's AI, the number two, ROI.substack.com. And you do not need to have a Substack subscription to be able to participate. And it's a fabulous newsletter, highly recommend.Ray Rike (23:58)That's it. And by the way, just go out there and get uncomfortable, do the unfamiliar and create the future that is AI.Mark (24:06)Beautiful. Thank you again and we'll see you soon.KK Anderson (24:06)Amazing.Thank you, Ray. Really enjoyed it.Ray Rike (24:11)Thank you.Mark Petruzzi (24:12)We hope you enjoyed this conversation and found it valuable. If you did, like and share it with your network. That's the best way to support us and the work we're doing here at AGS. And if you're curious where your sales team stacks up in the AI era, head to get-ags.com. That's get and the dash symbol, AGS.com for a complimentary sales team benchmark. Until next time.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of Benchmarkit, to tackle one of the most critical questions in enterprise AI today: how do you actually measure success in agentic AI programs?Ray shares why most AI initiatives are stuck in “pilot purgatory,” the common mistakes companies make when trying to automate broken processes, and why an AI-first mindset requires a complete rethink of data, workflows, and metrics. The conversation also explores how go-to-market teams should define ROI, what benchmarks matter in an AI-driven world, and why traditional SaaS metrics are no longer enough. What You’ll Learn:Why AI Projects Stall: The real reasons most agentic AI initiatives never scale beyond pilots.AI-First vs Human-First Thinking: How redesigning processes for AI fundamentally changes outcomes.Data Readiness Matters: Why poor CRM data and lack of governance derail AI success.Measuring AI ROI: The new metrics leaders must track to justify AI investment.The Shift in GTM Economics: Why cost structures and efficiency benchmarks are changing fast.Key Topics:“Pilot purgatory” and lack of enterprise-wide AI focusThe importance of data hygiene and enrichment for AI successRedesigning processes with AI at the center, not as an add-onThe rise of vertical AI and pre-built agent workflowsDefining success with leading, mid-term, and lagging metricsCAC ratio vs AI-driven efficiency benchmarks“COGS is the new CAC” and shifting cost structures in AI-native companiesRevenue per employee as a proxy for AI productivityToken consumption and cost predictability challengesBuilding smaller, modular agents instead of large monolithic systemsThe four-layer measurement framework: productivity, effectiveness, efficiency, and ROIGuest Spotlight: Ray RikeRay Rike is the founder and CEO of Benchmarkit, a leading source of B2B SaaS performance benchmarks with data from over 1,800 companies. He is also the host of the AI to ROI podcast and a founding member of the SaaS Metric Standards Board. With decades of experience as a go-to-market operator and executive, Ray focuses on helping companies move from intuition to data-driven decision-making in both SaaS and AI-driven environments. Resources & Mentions:BenchMarkitAI to ROI podcastConcept: Agentic AI in go-to-marketConcept: “Pilot purgatory” in AI adoptionConcept: AI-first process designConcept: COGS as the new CACOpenAI Frontier AllianceVertical AI platforms (example: Harvey for legal)Metrics framework: productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI measurement, GTM strategy, and building data-driven revenue engines.Mark (00:31)Welcome to Selling Intelligence. We're joined today by someone who might have had the honor and privilege of calling both a collaborator and a friend. Ray Reich is the founder and CEO of BenchMarket, the industry's most comprehensive source of B2B SaaS performance benchmarks with data from over 1,800 companies.Ray is also the host of the AI to ROI podcast. He's a founding member of the SAS Metric Standards Board. And full disclosure, my co-author on data and diagnosis driven selling, Ray has spent decades as a go-to-market operator, having served as president of Simply Learn, CEO at Higher Mojo, SVP at Moment Feed,and multiple times SVP market and sales and SaaS companies before founding Benchmark it roughly five years ago. And they have a singular mission, give every B2B reoccurring revenue software operator access to data driven benchmarks so they stop flying blind. Today, we're going, well, first off, let me welcome you, Ray. Thanks so much for joining us.Ray Rike (01:43)Thank you, Mark. Sorry that I'm so old that you had it took that long to read everything I've done.Mark (01:47)Exactly. Well, you know what? That's also a good thing because you've done some amazing things throughout your career and you're not that old. So, yes, let me tell you, let's talk a little bit about today and where we're going to go on this podcast. ⁓ What we'd like to do is tackle what might be the most important and for sure most underserved question in enterprise AI right now.How do you actually measure the success of agentic AI programs? And even more specifically, what does that look like for go-to-market functions? We'll dig into what benchmark its data, what is it revealing, where the industry is setting the bar, and what separates teams that are generating real ROI from those stuck in pilot purgatory. Ray, welcome to Selling Intelligence.Ray Rike (02:36)Okay, excited to be here. Let's dive into it.Mark (02:39)All right, so Ray, you've been collecting SAS performance data for years, and now you're turning that lens on AI. From what you're seeing at Benchmark and in hearing on your podcast, what's the core reason most agentic AI programs never graduate from pilot stage? Is it a data problem, a change management problem, or something else?Ray Rike (02:59)I think it's an evolutionary problem. So I did some research with scale venture partners last year about what the state of AI and GTM adoption was. And what we found, Mark, was it was primarily individuals adopting generative AI tools like Clot or Chat GPT to help them with individual tasks. Things like maybe it was an image creation for an ad campaign. Maybe it wasemail messages for outbound campaigns, et cetera. And the primary benefit was personal productivity. Hey, I can do this much more research quicker for each account, or I can generate this many more campaigns in a month. Now, when we get to process automation, which is really where agentic AI is going to be used, ⁓ we're just at the very beginning there, and we don't have enough experienceof actually deploying agentic AI to have a lot of success stories on a production basis, especially the enterprise, because most of the enterprises, and I'm talking about companies a billion dollars and over, I see an average of 20 or more simultaneous AI proof of concepts going on, and they're not really getting the focus of the centralized IT executive team, they're departmental.Maybe it's just customer service or maybe it's just development with a code assisting tool. So my answer is I'm not seeing enough organizational wide enterprise focus on true agentic AI initiatives yet.KK Anderson (04:32)And Ray, welcome to Selling Intelligence. glad you're here. And I just want to jump on top of what you just said there. It seems like the concern would also be that they're trying to put some agentic AI solutions onto maybe processes that should not be automated or were not the right process to begin with.Ray Rike (04:52)of the most common mistakes, and I've kind of built this framework of the variables that help ⁓ indicate success and agentic AI deployments. But one is the data is a mess, right? Think about today for what, 20 years we've been talking about how bad CRM data is and have we cleaned it up? No, we still have shitty CRM data, but the SDR or the AE will say, well, that's not the right information.Joe doesn't work at company A, Joe's a company B or that's the wrong title, right? So a lot of data hygiene, data prep needs to be done. So that's number one. And then to your point, we're thinking like old fashioned business process re-engineering. Well, yeah, maybe we map current state process and we want to map future state process, but we're doing it with a human first orientation and an AI first orientation isfundamentally going to change each step along the way of that process. Quite frankly, you have to identify what data I'm going to ingest, use at the field level for each step, each granular task within that process. And we just haven't re-engineered the process to be optimized for AI centricity yet. And KK, I don't think we're going to until we have a lot of people who have one or two rounds of experience.redesigning a process with an agentic AI first mentality, then then they can do it to third, fourth and fifth time.KK Anderson (06:16)and has that been defined how to have this kind of AI first mindset? Because we've had several people on the podcast talk about this, right? so, and I know I'm going a little bit off of kind of the agenda here, but I'm dying to hear your take on this. When you say AI first mindset versus just a traditional business process mapping,You know, like we're all used to, we all learned in business school, but the data scientists have been doing for decades. Like, what does that mean? What is AI first mindset? talk me through that.Ray Rike (06:54)I wish I could sit here and say, I've done 22 of these. here's here's the playbook. So I don't have the playbook either. I have a lot of ⁓ signals of why it's so difficult. And one of the big signals was OpenAI, what about two plus months ago, formed the Frontier Alliance. And the Frontier Alliance, right, because they said, we're going to get intoKK Anderson (06:57)Right. I know it's all new. No one knows. That's what I'm curious.Mark (06:58)Thank you.Ray Rike (07:17)agentic AI, not just generative AI, right? They first of all introduced, I think in January, the five layer cake of the OpenAI Frontier application map. And then they announced that McKinsey, Accenture, Boston Consulting Group, and maybe it was Ernst & Young, are now forming this Frontier Alliance to partner with OpenAI to help their enterprise customers deploy agentic AI. Why?Mark (07:35)Mm.Ray Rike (07:43)because it had been failing. A lot of the open AI projects to really do process automation using AI agents were not successful. So that's a signal, right? And as far as what's the secret, I don't have one other than try to find a consultant or a third party who's done two or three of these in the domain or the area. Let's say it's SDR.Mark (07:58)Thanks.Ray Rike (08:07)I want to automate the sales development representative function, right? Either you're probably should work with a software company that they specialize in that because they've actually ⁓ embraced and bundled domain expertise in their predefined agents, which then can be customized and or a third party consulting firm that have done it, that have made some of the mistakes and learn from their previous projects.So that's my recommendation. Go with a bundled application that has AI agent specific to that process and a third party. And if you think about vertical AI, KK and Mark, right? That's why I'm so bullish and so are most VCs on vertical AI. Look at a Harvey in legal. They actually are pre-packaging workflows, i.e. agentic AI.specific to the nuances and subtleties of that industry, including regulatory and compliance requirements. And they're making a lot faster headway into driving real return on investment than a horizontal, agentic platform that has to be custom designed for each customer. Did I answer your question okay, KK?KK Anderson (09:17)Makes a ton of sense, 100%.Mark (09:19)Soyou bring me back to the concept you mentioned earlier around BPR, business process, free engineering, and how this isn't that. But it makes me get to a point of like, where is the value going to come from? And to me, I've always seen the value of companies be a part ofor partially driven, if not significantly driven by their competitive advantages, how they differentiate themselves in the market. What I love about agentic AI, when done right, it allows you to build a set of processes in a way that can't be replicated by any of your competitors. You can't just say, great, I went to HubSpot or I went to Salesforce,and that's going to help me win against my top five competitors. Well, it's not because they all have Salesforce and in SaaS models, these systems weren't as flexible as now, know, agentic AI can be infinitely just, you know, infinitely just different than any other model that is out there today. So,I like that connection back to the business process side and ensuring that you have people who know that business process as a consultant, ensuring that you really leverage all the expertise and the tribal knowledge out of the client side because they know how to make this work. And they probably are working within a model today that is not what they would have recommended if they weren't forced to do it.because of the Salesforce process and what the system looks like or SAP or Oracle or whatever. take us a little deeper into that. Like, do you agree, I guess is the first question, like that these processes can now be more competitive advantages for customers and companies than maybe ever before.Ray Rike (11:12)Let me let me double click to the next level and KK I think you asked this question also. So in this framework, right. So one of the things because process redesign is such a critical part of this. Don't boil the ocean. Don't try to look at the entire customer acquisition, retention and expansion process. Let's get really focused and say, let's look at the outbound lead generation process.Constraint right so you redesign that constraint process first with a I centricity you define all the data that you're going to need to use in your existing systems of record like your account data the contact data the Including title you're going to define all I need to bring in this third party data to enrich it So define what data you need at the field level?Make sure you know where that data is coming from and how you cleanse and enrich. Think about the governance. I call this AI explainability, right? And you're going to need this, especially in regulated industries, but even if you're doing outbound sales for a software company, right? What's my government governance and policy? Who actually makes the determination that I should reach out to these people? Right? Is that in my ICP?What do I do different with a non-ICP member? That doesn't sound like governance, but it is in a way governance. You also need to pre-define human interaction and engagement points. Am I really going to just have that SCR agent do everything or I'm going to have some points pre-defined where human interaction, including maybe reinforcement, maybe ongoing coaching and mentoring, learning of the AI agent.You want to define those right up front. So you're prepared for that not only from a process perspective, but a resource availability perspective. Right. And then this is the major thing, KK and Mark, that I see so many people not doing is defining the criteria of success using metrics. What are my leading indicators? Maybe a leading indicator, since we're talking SDRs right now, maybe it is myengagement per transaction or outreach, right? How many times does somebody respond to the email, et cetera? Maybe it's the conversion rate from a agent interaction to a true discovery call or a sales call. And ultimately, you're going to want to carry that all the way through. What are my measurements as measured by pipeline generated per dollar of agent invested ordollar of new ARR generated by dollar of agent investment that I make, or agent investment plus human ⁓ reinforcement and learning. So you've got to really understand the leading indicators, the midterm, and then the long-term measurements that are going to impact the income statement. And I can go on and on about this, but I'll stop it here. If your CFO can't go to you and say you spent $100 million on AI agents last year,What did we get for it? And if you say, we got 20 % better sales calls, we got 30 % better sales call. Nah, not good enough. maybe I got 20 % more ACV. I just did a podcast with Amanda Kalo, who's the founder of OneMine, which is a great sales AI agent. And they've compressed on average their customer cell cycle time by about 35 % and increased ACV by 25%. SoThose are real tangible things that you as the executive owning your AI initiative, you got to be ready to share with your CFO.KK Anderson (14:43)And you know, and I have this on my list of questions here to ask you because we read that Gartner is predicting 40 % of agentic AI projects are going to be canceled by 2027 because of exactly what you've described, lack of clear value guardrails, know, change management. Maybe they're focusing on the wrong or an invalid process. So there's going to be a lot ofups and downs over the next couple of years as teams begin to roll out agentic AI. And so from your research there at Benchmarkit, and I know you mentioned Amanda as well and some of the KPIs that she's achieving, but what do you think the single leading KPI should be for a CRO? What should they be focusing on? To see if their program is on track to be successful or to fail? Where would you guide?a CRO to look first.Ray Rike (15:36)Well, in the traditional world, I think one of the most important metrics is called the CAC ratio, cost-requisition cost ratio. And this is how much money do I invest in sales and marketing to get $1 of new revenue, ARR in the recurring world, right? And it's around $1.50, up to $2, depending if it's a higher ACV product you spend more for traditional.recurring revenue software companies, SaaS companies. So $1.50 to $2.00. These new AI native software companies, it's 50 cents to a dollar. So it's one third to one half cheaper. if you're a legacy SaaS company or you're a CRO who is going into a AI native software company, you got to think about your CAC ratio with different benchmarks. The other thing that I would sayMark (16:09)ThankYeah.Ray Rike (16:26)It's outcome per dollar of AI investment. So an outcome might be new deals worth $50,000 per $25,000 of AI agent. So always be thinking about what's the input. It's my investment in the, used to be people and all the tools and stuff. Now it's more in AI tools and agents. And what do I get for that?That is ROI when you compare the output and outcome received to the input invested.Did I answer your question okay?KK Anderson (16:59)You sure did. Absolutely.Ray Rike (17:01)Now I will tell you there's another metric and the CROs don't need to be aware of this, but your CFO is going to start asking this because I don't know if you've heard it here first, but cost of goods sold is the new CAC. What do I mean by that? A lot of AI native software companies are seeing 30, 40, 50 % gross margin. What that means is for every dollar revenue, they're spending 70 centsKK Anderson (17:15)Mmm.Mark (17:16)So, so.Ray Rike (17:28)on delivering the product, paying for AI inference, playing for your cloud infrastructure, paying for your AI agents, right? Well, that used to be 20 cents. Well, I'm not, I can't be less profitable as a company. So what do need to do? I need to decrease my investment in sales and marketing, or it can be fancy and call it go to market, right? Well, in most SaaS companies, even larger SaaS companies, like, you know, Salesforce is 35%.an early stage, it can be 50, 75, 100 percent, right? So you're going to have to take your sales and marketing or GTM investments down by an amount kind of equal to what your cost of goods sold has went up as a percent of revenue. So that's why I'm saying COGS is the new CAC.Mark (17:53)Mm-hmm.youI love it.KK Anderson (18:09)Heardit here first. ⁓Mark (18:12)Yep,I love it. Great, why don't we move over to topic two. KK, do want to kick us off there?KK Anderson (18:17)Sure. okay, you, have built in your illustrious career the SaaS industry's most trusted benchmark database. We've talked about CAC, Payback, NRR, Magic Number, and you're moving into AI measurement. You've talked about COGS as the new CAC, right? And so that's clearly one of the emerging KPIs that you're convinced are going to become standard benchmarks.in the next 24 months, what else? What else is there to be focused on?Ray Rike (18:45)Right now, it's hard to get benchmarks for AI native software company productivity because they're too new, right? So even large enterprises who are implementing agentic AI, let's use a GE, for example, because I worked for GE for almost 10 years. They're not typically saying on their earnings calls, I invested five million in this AI agent and it saved me 20 million dollars. So.The number one proxy that I've started benchmarking and I went back now 12 quarters is revenue per employee. Because as I become more efficient and require less human resources, hopefully that means my revenue per employee is going to be increasing. And hell, let's just look at it today. The median revenue per employee for a public SaaS company today is $395,000. The outlier is Palantir at about $800,000.But if you look at Anthropic, they're around $3 million per employee. If I look at Cursor, I think they're at $1.7 million per employee. Even if I look at one of the least ⁓ efficient, Harvey, the legal AI, they're at $804,000 of revenue per employee. So revenue per employee is going to be something everybody needs to look at. I'd mentioned I want to start looking at the evolution of my COGS.KK Anderson (19:39)Wow.Ray Rike (20:00)I'm compared to OPEX. My token consumption, everyone's talking about when everyone. CFOs, I just did a state of AI pricing from the buyer's perspective. The number one issue for CFOs and CIOs is predictability of my AI cost. I have no idea how much it's going to cost because it's all over the board. I don't have enough history. So token consumption per outcome, because you're going to know your token cost.That's going to become a new metric that whether you're a customer and you're paying the L.M. Ford or you're the head of R &D and you're using an L.M. in your product, you only need to know token consumption per outcome. And outcome achieve per agent interaction. Let's just say it's an inbound customer service call. Hey, for 100, my AIA agent is solving 84 % first interaction.We used to call that resolution rate in the old human days, right? And then the last thing is cost per outcome in an agentic AI world. I resolved that customer service call. It cost me 50 cents last quarter per resolve call. And I spent $1.80 for human resolve calls. So cost per outcome is going to be important. When I say cost, start with your AI cost.and then you can look at your fully loaded custom.And I'm working on an entire AI metrics framework for this that I'm going to be publishing hopefully in the next month.Mark (21:19)I love it.Excellent. All right, well, Ray, let me bring you back into the days of you and I starting all our research and all the pre-work for data and diagnosis driven selling. So I hope that doesn't cause you to develop a Twitch or anything like that, because as you and I both know, that was hard work. ⁓ So, but let's, you know.What we really saw right up front is, and we really pushed hard on this, is the idea is you can't manage what you don't measure. And you need external benchmarks, not just internal comparisons to know if your metrics are actually good. You know, it's great. It's great to be able to say, improved this process by 20%. But if you were 45 % behind most of your competitors before that,That 20 % still has you on the back of the pack. So how do you bring that same philosophy to measuring an agentic BDR or an AI-powered deal coaching agent? And we've touched on this, but what's the equivalent of a CAC payback for agents and the entire investment?Ray Rike (22:33)Well, I would start with let's make sure you have your go to market measurements in place, because honestly, we've been talking about these for years. Less than 50 percent of companies have great GTM analytics. ⁓ So things like cost per dollar a pipeline, less than 40 percent of people are measuring cost per dollar a pipeline. So make sure you do that and look at your current state before AI and then measure it post AI introduction. Right.So cost and I'm talking right now, I'm looking very specifically at the customer acquisition process. So cost per dollar pipeline before and after cost per dollar of new AR before and after when rate before and after your average and your contract for you before and after. Cause those are all going to be hopefully much better with AI to your point, Mark. I mean, let's use outreach. Everybody had to have a sales engagement platform, right?How many companies actually said, well, after I invested $1,500 per SCR, I had a better conversion rate or a lower cost per dollar of acquisition? Nobody. You're going to need to do that with AI. So that's my first thing. The second thing, which haven't been defined yet, but I'm working with some VCs on this right now, is AI specific customer acquisition efficacy. So I'm looking at agent costs per opportunity.Agent cost per dollar pipeline, agent cost per dollar of new ARR, agent dollar per cost of retained ARR. So you can think about your gross revenue retention and agent cost per dollar of expansion ARR. Now I'm projecting that we're going to be using agentic AI a lot in those processes or sub processes. And by the way, that's the other best practices.When you design a process, it's better to design a lot of subprocesses underneath so you don't have one large unwieldy AI agent. You have a lot of subprocesses that you have different people auditing and evaluating.KK Anderson (24:27)All right. Let's dig into that design a little bit. So walk us through, and I know this is new, as we've said multiple times for so many of us, what a well-instrumented, agentic, you know, GTM for the purposes of our audience, pilot could look like. You just gave us one great clue, which is, you know, don't make monster agents and, and, and to break them up so that you can, you know, be more agile andand predictable with those. You've walked us through some baseline metrics that you want to set before you launch, things that haven't necessarily been done in the past with programs like our outreach launches over the years. But what does the pilot to scale gate look like? And how do you separate the agent did something from the agent created revenue attributed value?Ray Rike (25:15)Well, let me go to the baseline metrics first, KK. So I think I have four levels of metrics I like to see in any initiative, including the Gentic AI. So one is a productivity metric, and that is outputs per time, you know, whether it's outputs per human hour, outputs per day or time spent per activity.That's what we've been measuring for the last year and a half and AI in marketing and sales. But that's what then you have effectiveness. How effective is my AI enabled process going to be? ⁓ How many desired outputs am I getting versus the inputs? Hey, for every hundred emails my agent sending, how many meetings do I get set up? Right. Then there's efficiency. That's the cost per outcome. And then there'sactual ROI, which is outcome value divided by the AI investment. So productivity, effectiveness, efficiency, and ROI. I'm not going to go into detail what that's like for just an SDR program, but at least it gives you a framework and a layer approach to designing those four layers of metrics you need to measure.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore the human side of leadership, trust, and AI adoption in today’s rapidly evolving business landscape.Sabrina shares her perspective on diversity in leadership, the realities of building a career as a working parent, and why creating an “integrated life” leads to stronger teams and better business outcomes. The conversation also dives into how trust has become the ultimate differentiator in an AI-driven world, and how companies must rethink how they show up as human, credible, and authentic.The episode closes with practical insights on how leaders should approach AI, where it delivers real value, and how to use it as a tool for thinking, not replacing human judgment. What You’ll Learn:Diversity as a Competitive Advantage: Why different perspectives lead to better decisions and stronger organizations.The Integrated Life Approach: How flexibility and trust improve retention, loyalty, and performance.Human Trust in an AI World: Why authenticity and real human interaction are becoming the new moat.Practical AI Usage: How to use AI for preparation, critique, and efficiency without losing credibility.Leading Through AI Disruption: How leaders can guide teams to experiment with AI while setting the right guardrails.Key Topics:The impact of diversity and inclusion on business performanceSupporting working parents and creating flexible, human-centered workplacesThe myth of “doing it all” and redefining success in leadershipWhy trust is harder to earn in a world of AI-generated contentReal vs artificial experiences in customer interactionsThe role of influencer trust and community platforms like RedditUsing real people and authentic content to build credibilityWhere AI overpromises and where it delivers real efficiencyAI as a tool for critique, feedback, and preparationUnderstanding how LLMs perceive your product and brand through consensus signalsThe shift from SEO authority to AI-driven consensus and reputationGuest Spotlight: Sabrina ParsonsSabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, and a leader with deep experience across sales, marketing, and executive leadership. She is a strong advocate for women in leadership and brings a unique perspective on building resilient organizations, fostering trust, and navigating multiple waves of technological change. Resources & Mentions:Palo Alto SoftwareLivePlanConcept: AI trust gap and authenticity in digital interactionsConcept: Integrated life vs traditional work-life balanceConcept: Consensus-driven reputation in AI search and LLMsBook: Into Thin Air by Jon KrakauerBook: Superintelligence by Nick Bostrom🎧 Listen now and follow Selling Intelligence for more insights on leadership, AI adoption, and building trust in modern go-to-market teams.Mark Petruzzi (00:31)So Sabrina, you're a strong advocate for women in sales and leadership. In your experience, what do women bring to the sales equation that often gets undervalued? And what does the data actually show?Sabrina Parsons (00:43)Yeah, that's a great question. I think that we've, well, hopefully people have, there's been a lot of data over the years that just shows a few things, I know these days, you know, talking about diversity is, you know, a hot topic and not something everybody wants to hear. But if you actually go and look at the data,Any time you're bringing different viewpoints in, it actually turns out the data shows that that's really good for an organization. That when you have six people who all come from the same background, who went, you know, got similar educations, have the same experiences, you're missing out. You're not getting some of these other alternate viewpoints that...could actually give you different insights and make your company better. So from that perspective, be it women or people of color, people from different cultural backgrounds, every time you have different people in a room, you're gonna win because they're gonna bring different information to the table. And then I think that, you know.Even though it's 2026 and I wish we were in a different place with women in leadership, the reality is that we still live in a world where, you know, there aren't as many women in technology. ⁓ And the numbers just show that and there aren't as many women in technology and leadership. And so women who are there and have made it all the way through, particularly in a leadership role, have probably worked really hard to get there.and probably have some really good insights. From my perspective, one of the things that I think is most powerful and I think can bring a lot of value to a company is recognizing particularly working moms and working parents, but as a working mom, I'm not a working dad, so I won't talk for working dads, thatYou know, there's a lot of very motivated, super smart women who want to work for a place. They don't want to have to jump from job to job to job. And if you can give them an opportunity to stay in one place, to continue to move up, if you can be the kind of boss that recognizes that there's going to be some peaks and valleys that a woman with young kids might have someissues with my kid is sick, my kid is going to the doctor, but at the end of the day, if you help them with flexibility, not making their job easier, not giving them less job, but giving them the ability to be flexible and do their job when they can, you're actually going to retain women longer. They're going to be more loyal. if, you know, loyalty and retention, we all know is, you know,There's nothing better for your bottom line, particularly in software and tech sales where people are your biggest asset.KK Anderson (03:36)You preach into the choir. Could not agree, could not agree more. I would love to hear about some of your, know, pursuits with women in sales and leadership and would love to, AGS would love to support you in those as well. Really cool.Sabrina Parsons (03:38)Thank you.Mark Petruzzi (03:47)forSabrina Parsons (03:48)you. I appreciate that. it's been a really, it's interesting. I think when Mark and I first caught up prior to the podcast, we talked about it a little bit, but being a Gen Xer and having grown up in the 80s and early 90s, I am of the generation that watchedthe women's lib movement, And watched all these really strong women come out of the 70s and early 80s, the Gloria Steinmans, This very powerful.movement and we were kind of fed this idea that like you can do it all women can be super women and you can do it all and I bought it I was like I am gonna be superwoman I am gonna do it all and didn't really think anything of it until I had my first child and that's when like the brakes come on and you're like wait what what does this actually mean?And you know, just this reality that like, wait a minute, this is a myth. Like you can't do it all, right? And there's a reason why very successful men were never expected to do it all. And yet we still have this place in 2026 where there's still a lot of judgment with women as mothers, like, you know,Why aren't you there at drop off? Why aren't you there at pick up? Somehow you're a bad mother and all these kind of, know, guilt woven into, you know, being this working parent and how do you deal with it? And what does that mean? And as I had one child and then two and then my third as I was running the business for me really understanding that myKK Anderson (05:14)Guilts.Sabrina Parsons (05:32)take on this, my approach is very much about leaning into who I am, not leaning into the structure that exists today, which I think a lot of us were still being told even 10 years ago when Sheryl Sandberg came out with her lean in ⁓ kind of autobiography, it was all about leaning into the current structure, right? It wasn't, wait a minute, does that actually work? And for,KK Anderson (05:54)Mm-hmm.Sabrina Parsons (05:59)from for me what's worked and what I like to mentor and what I like to, you know, really.do here at Palo Alto Software is to say that doesn't work and I have what I call an integrated life and my kids are older now and I've got two in college but when they were little that meant bringing kids on business trips with me and my mom would come with me. That meant kids in the office after school or on a snow day. It meant having appropriate places in the office.so that they could have coloring books and homework areas. you know, I mean, we often laugh because we have a very old, ⁓ I think it's a Nintendo PlayStation, but it's a very old one. I don't even know if it's called a PlayStation, but it's a very old one where it isn't actually wireless. The console that the game console, like the player that the kids, the controller that the kids play with is actually plugged into the gaming.console. Well, kids love the old thing ever when they come in. but they always break it because they keep unplugging the controllers because they're like they're charged. And it's like, no, these are old school. And they don't even get that, which is always funny. I mean, from my perspective, that's what I've done for myself and for people here in the company is to say,KK Anderson (06:57)NowSuper Mario Brothers.Mark Petruzzi (07:11)HahahaSabrina Parsons (07:20)I'm not going to pretend you don't have kids. I'm not going to make you apologize for having kids. I'm also not going to pretend that if you've got a kid who's sick, that you're actually going to be at the office doing any sort of productive work because I made you come in. Like, okay, you can come in and you're not going to like me and you're not going to be productive and you're going to be worried about your kid. And so why don't we treat people like humans and say, you know what, your kid is sick, go home.Because if I do that, that person is going to work harder for me and be more loyal and be happy. And if you're happy, you're more creative and you're more innovative.KK Anderson (07:58)You know, in a weird way, like it's like a, whole world is coming full circle and our, our humanness, even in this AI world, mean, specifically there are humaneness is now our uniqueness. No, which is wild. And, and so, you know, kind of going back to that, how sales and marketing teams are using AI, you know, it can.You know, we've all seen it simulate preparation and personalization. mean, we were on vacation last week and we took a family picture of the four of us, my husband and my two kids and myself. And we're sitting at a table and there were, you know, dirty dishes in front of us. And my husband just, and his AI, and next thing you know, there's no dirty dishes in front of us. Right? And then, you know, I sent the picture to my mom.Mark Petruzzi (08:40)Ha ha.KK Anderson (08:44)And she was like, that's so great, whatever. And then my husband goes and sends it right back and we're all in like, you know, he's wearing a tuxedo and I'm wearing a ball gown and whatever. He's like, you didn't get invited to the wedding? And you're like, just making it like in five seconds, what? Right? And so, you know, we see that AI can simulate all of these things, right? And there's just, you know, the sky is the limit, the videos, the empathy, the personalization, that it's hard to know. So like,And building off the conversation that we were just having around women in particular, like is, is humaneness like the new moat? that what, you know, what's your perspective on that?Sabrina Parsons (09:18)I mean, that's a great question. I think it is. I mean, it's been interesting too, because not only is it trying to figure out how do you integrate AI into how your employees are using it so that they're using it appropriately and it doesn't come out like all of our communications are robots, right? So like the humanness of interactions. One of the things we do is right now we don't have chat bots. It's all real people.And it's all real people that we employ here in our headquarters. They're not outsourced because of that ability to say we are humans and real people. We're not just bots. ⁓ I think that's really important. I think that the trust that people need, I think they always needed trust, but it was easier to get their trust. And now it's like, because we've all seen,pictures that are different. We've all seen videos that are AI. We've all seen essays that are written with purely AI. I think there's that constant question, is this real? Are you a human? Is this true? And so anything that you can do to help alleviate that fear of what's a fact and what's not a fact.Right? Even now, like we talk about it a lot, like when you think about Instagram and you're scrolling through, most of us have probably made the mistake of that product that you're like, this is awesome. It's just for me. And then you order it and you know, it was supposed to be like a dress that fits me and it's a dress that fits a doll. You've heard all these stories. So I think all of us now know, like you don't trust that on Instagram.Right. This is why influencer marketing is so big because you do trust the person, right? You don't trust the company and the random product. You do trust the person. And so I think that's where we're back. Like, and how do you do that beyond influencer marketing? Right. Why is Reddit such a huge resource for people?KK Anderson (11:01)trust that person.Sabrina Parsons (11:13)because people perceive that Reddit is moderated, that people get kicked out of Reddit if they're bad and they do bad things. And so somehow, at least at this point, people trust that it's real people on Reddit. That's why people go to Reddit.KK Anderson (11:27)And so how are you using that specifically within your team?Sabrina Parsons (11:29)youwe, I mean, first of all, it's changing all the time, but, you know, we really try to emphasize in a lot of our educational videos, we use, you know, I'm in a lot of them, real people at the company, people that, you know, we have personalities. we've just recently even started to put out some blooper videos so people can see us as real people that we aren't just AI bots.KK Anderson (11:54)and not the radio.Mark Petruzzi (11:56)Yeah.Sabrina Parsons (11:57)And really leaning into, you know, the way that we have all figured out how we trust things. And I think that's really important when you think about and work with sales teams is to really get people to reflect like you're out there, you're a consumer, you know the things that you won't trust. You know the things that are kind of that gray material you're not sure. And you know the things that you do trust. And so,the more that you can get your own employees to embrace their own experiences and bring those, I think that brings a lot of value.Mark Petruzzi (12:30)Well, Sabrina, we should really put out some selling intelligence bloopers because there's been some big ones over the years, but probably more me than anyone else. So maybe I'll hold back on that one. Never blooper. All right, let's move into our final topic, leading through this world that we live in today that is just rife with...KK Anderson (12:42)No.Never, never been a blooper.Mark Petruzzi (12:57)AI disruption everywhere. So as CEO, you're managing AI disruption on two fronts, inside your business and in the general market as a whole. Where have you found real efficiency gains and where has AI disappointed you or just over-promised along the way?Sabrina Parsons (13:15)that's a great question. I mean, I feel like AI is constantly ⁓ over-promising. I think that's a constant of like, you know, always thinking and I think everybody else thinking how much AI can actually do. It's been an interesting thread because I have two kids in college right now and working with them for them. So my oldest is a senior, AI did not exist when he was in high school.Mark Petruzzi (13:20)HaSabrina Parsons (13:39)and didn't even exist the first two years that he was in college. It's really just been the last two years. ⁓ And kind of working with him on how do you use it? What's the appropriate use? How is it beneficial to how you study? How is it not beneficial?KK Anderson (13:42)tomorrow.Sabrina Parsons (14:01)He's in a situation where he knows people where entire classes have been caught for AI and how do professors have to rethink things. So I bring it up because I think it's important for us to see as people are coming out of college what their experiences are going to be. So you're back to Blue Book essays in colleges right now.But it's all kinds of issues, right? Kids can't even write because they've been on computers for so long. no one did. Like, if you want to puzzle, you know, a Gen Z person, write something in cursive. Like, it's like code. Yes, they didn't learn cursive. They don't.KK Anderson (14:28)Well, my kids never learned cursive.Sabrina Parsons (14:40)They don't actually, they can't write very quickly or write very well. And so that's been an interesting experience.KK Anderson (14:47)line that's gonna show up under the blue book and say, you stop.Sabrina Parsons (14:49)exactly. So I think that's an interesting thing to think about as you think about where, you know, how people are going to be coming into the workforce and some expectations. The fact that people find that like, if you've written it down, it's somehow authentic and right, which is an interesting idea. But yeah, I mean, I think for me, as we look at these AI challenges, thebiggest thing and what I tell employees and what I tell my kids is you actually just have to be using it all the time and constantly challenging yourself on was that the right use? Did I get what I needed out of that or did it lead me astray? And if it did, why? And maybe that's not the right use for it. You know, so like learning where those guardrails are today and then being open to the fact thatthose guardrails will probably change in two months. And so very much encouraging everybody to not be afraid of it, experience it, but with your eyes wide open.KK Anderson (15:48)one of the things that, one of the ways I love to use AI is just asking it to poke holes in my proposals and in my approach. if you're a CFO or a board member looking at this proposal, tell me all of the ways that it sucks, quite frankly, right? And then just making it bulletproof from there.Sabrina Parsons (16:06)that's, mean, it's one of the ⁓ ways that I've really worked with both my college kids using AI appropriately and not writing their essays for them, but to actually say, hey, this is like a one-on-one tutor who can give you critical feedback.on your essay, in the past this would be like if I paid for a writing tutor to like read your papers and give you feedback, this is how you should use AI. You don't want to use AI to write your paper because you're going to get caught and then when you have to do the blue book you're not going to know it, but it can be used to give you that critical feedback and I think within your company as well, right?Mark Petruzzi (16:34)Mm-hmm.Sabrina Parsons (16:49)Don't have it write your proposals, have it critique it. Don't have it write all your emails, have it help you theme them or schedule them or those things that take a lot of time but don't necessarily need the human element.KK Anderson (17:04)And so what would you do to kind of build off of that? Like what would you say to a founder or a CRO who's listening right now? What would be the first thing you would do to change how they're selling or approaching sales right now using AI?Sabrina Parsons (17:19)Whoa, there's so many things. You know, I think that really living in all the LLMs to see how the LLMs are perceiving your product. I think it's really important because people are going to LLMs to research. And so how is your product being portrayed? How's it coming up?KK Anderson (17:35)Uh-huh.Sabrina Parsons (17:43)If you don't know that, then that's a problem. And a lot of times people don't realize and that is really important. You need to be, and there's tools that can help you ⁓ kind of gauge that and see how many times am I showing up? Is it in positive ways? Is it in negative ways? ⁓ LLMs are referencing different kind of data. It used to be that, you know,the way you showed up and the way customers found you had to do with your search engine optimization. And while there was always all this kind of behind the scenes, Google's not going to tell you if you were really an SEO expert. You knew. And there was the next Google release. And people kind of knew what they had to do to appear in the right places.and Google would assign page ranks and they would say, that HubSpot is great at this, they are the expert. Well, that's gone now. The way that now, know, truth is assigned is through consensus. It's not because we've chosen one thing and said that's the expert piece, it's through consensus. So the LLMs are going out there and seeing.How are people talking about you on Reddit? Where are your reviews? What are they saying? What are the common threads? And they're finding that consensus. And then that's how they're figuring out which solution to recommend. And so I would say that's the number one thing is really understand how are you being portrayed when people are looking and asking questions. And then keep doing that because it's going to continue to change.KK Anderson (19:21)and then use AI to get you into more places. Right, yeah. So Mark, what do you think? Do you wanna take us to rapid fire?Sabrina Parsons (19:24)Exactly.Mark Petruzzi (19:28)Sure, let's kick it off. Perfect. So Sabrina, thanks for all these great observations. So RapidFire goes right into first thing you have ever sold.Sabrina Parsons (19:37)I was thinking about that, I was like, oh wow, was it like a literal lemonade stand, which I think it was. But I thought what I really talk about was when I was in high school, my junior and senior year, I worked at a yogurt shop in Palo Alto right across the street from Stanford campus. And...I actually became at the ripe old age of 17 the manager of the yogurt shop because it was run by two Stanford MBAs, one of whom her dad had bought her the yogurt shop.that she could have experience while she was an MBA and she really didn't want to do it. And so I ended up being like the manager of the yogurt shop doing all of the decisions of like, what are the flavors? Which ones do we put next to each other? Understanding like, if I put these two flavors together next to each other, we sell more. And then at the end of the day, I don't have to clean the machines in the same way and it's better for me.KK Anderson (20:24)the house.Sabrina Parsons (20:36)Europe.KK Anderson (20:36)You're leaningon that experience every day,Mark Petruzzi (20:39)Well, Sabrina, have, I mean, think about that. You were destined to be a CEO because you had two Stanford MBAs tell you you were management material at 17 years old. It's awesome.KK Anderson (20:50)HahahaSabrina Parsons (20:52)Well,I think it was by default more than else, but I definitely took it and ran with it.Mark Petruzzi (20:56)HahaKK Anderson (20:58)If youwere like, I'm going to Princeton. A leader, you know, a leader or communicator that you admire.Sabrina Parsons (21:00)I'm sorry.right, I thought about it a lot and I feel like right now I have to say I love Eileen Gough. If you watch the Winter Olympics at all, ⁓ you know, this phenomenal athlete woman and her leadership and her ability to talk to the press about her experiences.She was embroiled in some controversies because she was raised in the Bay Area, a Chinese immigrant mom, and at these Olympics she decided to compete for China. Very smart, very well-spoken, crazy accomplished athlete who had to deal with a lot of questions that I think women often have to deal with. They're in this place where you're like, she's like the most decorated freestyle.Olympian and you're going to ask her these questions and I just I love how quickly she responds, how she doesn't apologize, how hard she works. Yeah, so for right now I'm going to say Eileen Gough because I think she's earned it.Mark Petruzzi (22:08)Very cool. So one practice every sales leader should adopt this quarter or even better that today.Sabrina Parsons (22:14)One practice, I would say just embrace AI, all of it. Do not be afraid of it, embrace it, figure out all the places you can be using it because it is the future and the more you know, you're gonna have an advantage.KK Anderson (22:29)It's like the, you you can just see the lower third, the more you know, dot, dot, dot, right? my favorite question, advice that you would give to your 21 year old self.Sabrina Parsons (22:34)Exactly.You know, I think I would go back to that, my 21 year old self to say, you don't have to do it all and that's okay. That you actually can think about what you love and focus in on it and you don't have to be everything for everyone. ⁓ That's what I would tell myself back then.Mark Petruzzi (23:01)and your favorite.Sabrina Parsons (23:02)It would have reducedstress in my late 20s and early 30s, I think.Mark Petruzzi (23:06)for sure, your favorite non-business book.Sabrina Parsons (23:09)I do a lot of reading. was really trying to think about, because it depends on when you ask me, but I think I will go back to, I love Into Thin Air. I love that book. I'm an avid outdoors person, do a lot of backpacking and skiing and mountain biking and.water sports and ⁓ I'm fascinated by the story by people who climb Everest, but I'm also fascinated by the decision making and how this whole disaster on Everest actually happened. ⁓ It's just, and it's such a well-written story.KK Anderson (23:49)definitely we need it.Mark Petruzzi (23:50)Yes, andSabrina and I bonded right from our first discussions on rowing as well. we both had children who were rowers and ⁓ we both had done some rowing over the years as well. I love it. And hopefully you get out on the water more often than I do, because I just seem to always be ⁓ on a rowing machine, not an actualSabrina Parsons (24:15)Yo!KK Anderson (24:15)say onMark Petruzzi (24:15)well, that's for sure. I'm going to start rowing on our podcast. That's what I'm going to do to get a little bit of multitasking in. So Sabrina, thanks so much for taking the time with us today. Thank you just for all your great observations and your insights. Thank you, KK, and thank you to our wonderful audience for being with us here every week.You are all amazing.Sabrina Parsons (24:38)Thank you guys, this has been lots of fun.KK Anderson (24:40)It's a lot of fun. Thank you, Sabrina.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.