Ep. 117 – Escaping the Crisis of Sameness in Modern Sales with Doug Landis – Part 2
Ep. 117 – Escaping the Crisis of Sameness in Modern Sales with Doug Landis – Part 2  
Podcast: Selling Intelligence (formerly Selling the Cloud)
Published On: Wed Mar 11 2026
Description: 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.