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    Business

    Selling Intelligence (formerly Selling the Cloud)

    Selling Intelligence is the evolution of Selling the Cloud and designed for revenue leaders who are navigating the AI era.

    Hosted by Mark Petruzzi and Alan Rudolph, the show brings candid conversations with C-suite leaders across sales, marketing, and customer success on how AI is reshaping the way companies grow, sell, and compete.

    From agentic GTM strategies to AI-powered pipeline and revenue execution, each episode focuses on what’s actually working and how leaders are turning intelligence into performance.

    If you’re responsible for growth and trying to lead through the fastest shift in go-to-market we’ve ever seen, this podcast is for you.

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    Copyright: © © 2023 Selling the Cloud

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    Latest Episodes:
    Ep. 117 – Escaping the Crisis of Sameness in Modern Sales with Doug Landis – Part 2 Mar 11, 2026
    Show notes

    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 p…

    Full show notes at the publisher

    Ep. 116 – Escaping the Crisis of Sameness in Modern Sales with Doug Landis – Part 1 Mar 03, 2026
    Show notes

    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 sa…

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    Ep. 115 - Building Repeatable Sales Success in Enterprise B2B with Glenn Poulos - Part 2 Feb 24, 2026
    Show notes

    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,…

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    Ep. 114 - Building Repeatable Sales Success in Enterprise B2B with Glenn Poulos - Part 1 Feb 17, 2026
    Show notes

    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 si…

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    Ep. 113 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 2 Feb 10, 2026
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    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, y…

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    Ep. 112 – From CRO to CEO: What Boards Really Look for in Sales Leaders with Jason Baumgarten - Part 1 Feb 03, 2026
    Show notes

    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…

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    Ep. 111 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman - Part 2 Jan 27, 2026
    Show notes

    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. Y…

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    Ep. 110 – Building AI Fluency, Trust, and Modern Sales Leadership with Cherilynn Castleman – Part 1 Jan 20, 2026
    Show notes

    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…

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    Ep. 109 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 2 Jan 13, 2026
    Show notes

    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…

    Full show notes at the publisher

    Ep. 108 - Scaling the Right Way: Product Market Fit, Retention, and Go to Market Readiness with Mark Roberge - Part 1 Jan 06, 2026
    Show notes

    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…

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