Selling the Cloud

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 te

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 bu

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 mak

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 prob

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

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? An

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 j

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'

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 objec

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 ha

In Part 2 of this Selling the Cloud conversation, Amy Weber joins KK Anderson and Mark Petruzzi to go deeper into how modern revenue leaders should think about AI, outreach, hiring, and coaching. Amy challenges traditional sales motions like cold outreach and rigid playbooks, and explains how AI should be used to personalize engagement, free up seller time, and enable more meaningful one on one conversations.The discussion also dives into assessment driven hiring and coaching, unpacking why resumes are a poor predictor of success, how to identify true talent signals, and how leaders can reduce friction by understanding identity, motivation, and communication styles across their teams. This episode is a practical guide for CROs who want to build revenue teams that perform, scale, and adapt in a more human centered, AI enabled world.What You’ll Learn:Why cold outreach is losing effectiveness and what CROs should prioritize insteadHow AI can personalize messaging without removing the seller’s individual voiceThe right way to define ICPs based on engagement and impact, not volumeWhy playbooks should act as flexible frameworks, not rigid rulesHow assessment driven hiring reveals true talent signals beyond resumesKey differences between hunter, farmer, and CSM profiles and why misalignment hurts performanceHow leaders can reduce friction between managers and sellers through better coaching and communicationWhy understanding identity, emotional resonance, and motivation matters more than process aloneKey Topics:AI powered personalization in sales outreachICP refinement and engaged account strategiesFreeing up seller time for high value conversationsAssessment driven hiring and role fitCoaching frameworks for sales managers and leadersManaging conflict between sales leaders and individual contributorsIdentity based leadership and communication stylesPositive intelligence and managing saboteurs in high performing teamsGuest Spotlight: Amy WeberAmy Weber is a strategic advisor to growth stage and enterprise revenue teams and the founder of VEDA Sales Consulting. She specializes in aligning people, process, and purpose to drive measurable revenue outcomes. Amy works closely with CROs and executive teams to improve hiring, coaching, and leadership effectiveness using assessment driven insights and practical operating frameworks.🎧 Listen now and follow Selling the Cloud for more conversations on building modern, revenue focused GTM teams in the age of AI.KK Anderson (00:31)if I could kind of double click on that a little bit, what's one of your favorite starting points? Like if you're gonna recommend to a CRO, I know it's obviously where they wanna focus, but what are just some examples of where you would have them start first?Amy Weber (00:46)Yeah. So I think that of the first pieces of it is that, look, I don't think cold emails work anymore. I don't think cold outreach works anymore. think it's figure out your ICP who is already engaged and then how do you automate some outreach to them in a way that makes is impactful to them. So using AI tools to be able to take that outreach and instead of a ⁓ rep,doing what you're saying, making a thousand emails a week or a hundred calls, kind of automating that outreach, whether it's through, and maybe it's a multifaceted approach, right? Getting more information out on LinkedIn. One of the things that I hated when I worked for big companies was that they wanted, like they wanted to silence your individual voice and they wanted it all to be very static and documented. Well, then you're getting the same message over and over again.Mark Petruzzi (01:28)Hmm.Amy Weber (01:34)Using AI to take that static message, but to personalize it based upon who you're going after is a real tool and trick today. And so you're getting out in front of more people and you're getting your message out in more ways. The second part is, like I said, figuring out what your ICP is and what's impactful for them. And then leveraging those AI tools to kind of create a outreach that is not generic.and is not just cold, it's taking the people that you know today that you want to talk to and making it more important to them, you know, in that capacity. ⁓an understanding really kind of that the goal is to free up more time for them to meet with these individuals one-on-one. So automating the things that are getting your message out in a content personalized manner so that the AEs and leadership is getting freed up time so that they can actually engage one-on-one because look,The other thing I think is ridiculous, again, I may get in trouble for saying it, a playbook should just be a framework. If you think there's one answer to how to be successful in sales, you're going to fail. Because you have to understand the client and their business need, and not every need is the same. It doesn't matter if you're selling the same product.or the same service, it's how that product or service is going to impact that end user in a new way. And you can only do that if you actually get in front of them and understand what their business or challenge or issue is, how that solution is going to play.Mark Petruzzi (03:12)Great, well let's move to topic three, which is assessment-driven hiring and coaching. And again, something that's near and dear to AGS's heart and what we do, and we're learning a lot as we've gotten to know Amy ⁓ over the past couple months. So how should a CRO use assessment insights wisely and the most productively? Who do they need to assess?Amy Weber (03:35)Yes.Mark Petruzzi (03:36)what two to three signals matter for this role and how do those signals translate into the right interview questions and then most importantly, the coaching plan for that new hire.Amy Weber (03:48)Yeah, like I said, I'm a huge proponent of this because I do think we hire people or we have historically hired people based upon their resumes. That might be the worst possible thing you could ever do. Now, the resume might get you into the door to talk to the recruiter, to the team or get into the interview process, but it shouldn't be indicative of how successful you're going to be in this role. 85 % of millennials will tell you that they are in the wrong role, but they're afraid to change.And so they're just going to keep taking jobs because that's what they did in the past. It doesn't mean that they're in the right role. And scientifically, 1 % of your past success will dictate your future success. So when we do this, we assess people in three different ways. We assess them during the interview process. So you get through the initial screening to say, ⁓ I think they might be a good fit.What are their really, their talent signals? And you're not gonna figure that out just by interviewing them. Because so many people will interview someone and say, I think there'll be a good culture fit. I like them. I'd like to have a drink with them. Great. That means they're a good person. But are they, do they have the right skills to do the role? Right? I'm glad you like them, but are they going to fit the role? like, you know, talking about the hunter, a hunter needs to have a really high driveand desire to go out and be with people and meet people and drive impact and outcomes. Whereas a CSM needs to have a really high precision to say that I can execute on a vision and I can track and make sure that all of the steps are going, that need to be in place for this person to, their rollout to happen in the right timeframe or their,you know, we're engaging the right individuals from their team on a weekly or bi-weekly basis to ensure that everything is going as planned. Those are different people. so understanding those key characteristics, even your emotional resonance, how you deal ⁓ with emotions. And if somebody has, and we can test for that, if somebody has a really high ER and you put them in a hunting role,it might take them a long time if they lose a deal to deal with the fact that they lost that deal. If they have a lower ER, they're going to be like, okay, I lost it. I can move forward to the next piece. And then we customize through the tools that we work with the interview questions to really pull out those key characteristics and those key identity markers because they're different based upon what you're looking for. From there,Once you've hired the people and you've got your team, then you need to determine who your leader is and kind of what their core identity is and how they individually need to understand managing people. That's going to reduce the conflict. And we build out custom management plans for each of those individuals. So we say either here's your team, here's all your benefits. Here's how you should look at your team overarchingly. And then if they have specificissues with a certain individual, whether they're like, I don't feel like I'm getting the most out of them, or we've got some sort ofconflict for the use of a better word. How do I address this? Because I really want this person to stay and be successful. We build out specific plans for them in that regard.KK Anderson (06:58)Yeah. Well, and kind of where my head is going is around that conflict, like what you just said. Like there is, and even kind of pivoting more toward that coaching aspect of making sure that the new hire is successful. There's very often just natural friction, especially in the sales world, right? When you have sellers who are entrepreneurial,you get a lot of friction between sales managers and individual contributors. And like some things that come to mind are, a sales manager may, be insisting that you're multi-threading and talking to different stakeholders in a prospect where the individual contributor is like, no, I have a champion. I've got this under control. I don't want to go around them. So deal strategy, right. Or, or there might be, like communication style issues, right. Where.Amy Weber (07:38)Correct.KK Anderson (07:43)A manager

In this episode of Selling the Cloud, Mark and KK sit down with Amy Weber, founder of Vetta Sales Consulting and strategic advisor to GrowthStage and Enterprise revenue teams. Amy specializes in aligning people, process, and purpose so strategy translates into real performance. She shares why many revenue organizations stall not because of tools or plans, but because of role confusion, misaligned talent, and leadership gaps.Amy breaks down how to design roles that reflect reality, how to hire and coach based on true behavioral identity, and why companies must stop promoting top reps into leadership without assessing desire and capability. She also explains how AI can power a stronger customer experience by removing low value tasks and freeing sellers to focus on discovery, executive access, and relationship building.This conversation hits the core of modern revenue growth: the right people in the right roles, operating in a healthy, human selling system.What You’ll Learn:The three fastest tells that your people or role design are brokenHow to distinguish hunters, farmers, and CSMs without relying on personality stereotypesWhy top performers burn out in “Frankenstein” job descriptionsHow to test for core sales behaviors using identity based assessmentWhy leadership is not a reward and should not be given based on quota attainmentHow AI can support human selling by automating research, follow up, and content prepHow to create operating rhythms that ensure AI actually frees time, not adds more dashboardsKey Topics:Role design and talent fit for revenue teamsBehavioral identity vs personality in hiringMisaligned promotions and the manager IC divideWhy customer success is undervalued and misunderstoodModern client experience and relationship driven sellingPractical, tool agnostic ways to use AI for research and personalizationOperating cadence changes that make AI adoption realAvoiding analysis paralysis when implementing new technologiesGuest Spotlight: Amy WeberAmy Weber is the founder of Vetta Sales Consulting and an advisor to high growth revenue organizations. She helps CROs and CEOs fix the people's side of revenue through role clarity, talent fit, and leadership development. Her work replaces outdated activity goals with clear rhythms and systems that actually change behavior, increase productivity, and create healthier teams. Amy also advises organizations building AI for talent decisions.Resources and Mentions:Cisco sales story on customer experienceMedium content repurposing with LLMsTalent identity and psychometric assessmentsOperating rhythms for revenue teamsRelationship led selling frameworks🎧 Listen now and follow Selling the Cloud for more GTM insights from leaders driving the future of revenue. Subscribe wherever you get your podcasts.Mark Petruzzi (00:31)Welcome to Selling the Cloud podcast. Today we're joined by Amy Weber, a strategic advisor to GrowthState, Stage and Enterprise Revenue teams and the founder of VEDA Sales Consulting. Amy's work centers on aligning people, process and purpose. So strategy turns into the most powerful performance. She's known for helping CROs fix the people side of revenue, writing roles that match reality, hiring for fit.not just overall pedigree, and coaching managers to run simple weekly systems that actually change behavior and drive the highest level of productivity. Amy Kevin Lee serves as a strategic advisor to organizations building useful AI for people decisions. And she's led transformations that replaced the old fashioned ad hoc activity goals with clear operating rhythms.This allows there to be a freeing up of more human time for discovery, executive access, and relationship building. Her lens is tool agnostic and outcomes first. What should change on Monday morning and how do we start measuring it? We'll cover three topics today. People and with the focus on them being greater than tools, roles, fit, and real leadership.Why growth stalls when the wrong people sit in the wrong roles, and how leaders create clarity and accountability. AI plus a strong experience culture, freeing time for human selling, using AI to take low value work off the team's plate so sellers could spend more time with customers, and assessment-driven hiring and coaching, really tool agnostic but practical ways to use talentdata to hire coach and fix manager IC friction without turning it into a tech commercial. So most people who know us and are on this ⁓ podcast with us every week know that's all things that are near and dear to KK and my heart and to what we do at AGS as well. So in another way, we're bringing an opportunity to get a...a different perspective or another perspective, but I think we're going to agree on a lot of things here based on the stuff we know about Amy already. So Amy, thank you so much for joining us and welcome to Selling the Cloud.Amy Weber (02:43)Thank you both. really appreciate it and I'm looking forward to the conversation today.Mark Petruzzi (02:46)Excellent. Cool. So first question, lots of teams have the right strategy and plenty of software, but the people role fit isn't right and results off install. As a CRO, what are the three fastest tells that role design or fit is the real problem and that it's not the plan or the overall tech as well?Amy Weber (03:04)Yeah, it's great because everybody steps back and they're like, what tool can I put in place? What new playbook can I roll out? What's our strategy? But they forget about the fact that the number one thing that they need to determine is do we have the right people in place and are we managing them correctly? So number one is, are your top performers miserable? Are they out there driving sales, but they are updating their LinkedIn? They're telling you that they're unhappy. They show up and they are on Monday mornings.you can just see that the energy is drained out of them. Because they're driven individuals, they're going to go out and they're high achievers, they're going to go focus on success, but you can just see that they're deflated. So number one, top performers are just absolutely miserable. You the second thing I see is that you see the same mistakes over and over again. You're providing individual or team coaching. You're giving a...guidance, you're rolling the playbook out, but you're seeing that the mistakes are just compounding. That's just repeating themselves. And then really the third one is we're promoting people incorrectly. So promotions are causing problems. I tell people that leadership is not a reward, it's a responsibility. So we're taking top sales performers. We're like, oh my God, they killed it. They were 300 % of their number again, and they've made club every year. So we're going to make them the manager.a director. And they may be a phenomenal sales individual, but they have both not the desire nor the actual skills to lead a team. And that desire component is really important. You could be the best sales rep in the world, but really not have the desire to want to manage, train, create empathy, you know, in other situations. So for me, those are the three glaring ones that I see that when I go into organizations, I'm like,They say we can't grow or we're stagnant or we've got a lot of they say culture problems. It's it's not culture. It's people you people problemsKK Anderson (04:56)That's so interesting. what we see with our clients and sales organizations is that the quote unquote job description for the sales roles, I mean, they're conflicting. You've got this mandate to go out and hunt and prospect and build new business, must hunt. And yet they need to be also an account manager and running projects and programs and keeping the relationship of the...keeping everybody happy, right? And then, you know, some of them are also part-time analysts. And so it's just like a lot of conflicting roles. And I think that probably leads to what you described with that burnout almost, right?Amy Weber (05:37)Exactly.I call those Frankenstein job descriptions because they're like, I want a self-starter who's a good collaborator. And I'm like, what? You know, I need somebody who's going to really go out and drive revenue and has the executive relationship that's good at doing the research. OK, well.KK Anderson (05:41)Yes.Mark Petruzzi (05:46)Ha!Amy Weber (05:54)They're just, they're putting together these, what they think the requirements are and they really need to hire for the key components of what they're looking for. A hunter role is different than a farmer role. A customer success manager, and sadly we see that get cut from companies all the time. It is cheaper to maintain a good client than it is to find a new one. And I could repeat that over and over again, but people don't understand it. And they're like, well, they,Accounting executives as Hunter can be the CSM as well. You know what? They probably don't have the right skills because a good CSM is going to be somebody who really wants to be a collaborator, can hide behind the scenes, is very detail oriented, likes to follow a process, right? A good salesperson thrives in chaos. There's somebody who goes out and can just drive opportunities because they're listening to the business needs.and they can kind of pivot and determine how to pitch the right solution, but they're not following a step one, step two, step three mentality that a good CSM really needs to do. That's why I don't think, and I get in trouble all the time, and I'm going to say it and just throw it out there. Most SDRs are not salespeople and should not report to sales. SDRs are operations people. They are good at following a script and setting an appointment, but they're not doing the key coreKK Anderson (06:53)Right.Amy Weber (07:10)attributes of sales, is listening to the business problem and creating a solution.KK Anderson (07:14)Right. So I follow up on that real quick though. So once we get those kind of roles rewritten and we figure out like wha

In this episode of Selling the Cloud, Drew Sechrist, CEO and co-founder of Connect the Dots and longtime Salesforce veteran, joins Mark Petruzzi and KK Anderson to unpack what it really means to build a relationship intelligence layer that changes how your team goes to market.Drew shares why his own career win stories at Salesforce led him to build Connect the Dots, and how mapping real relationship strength can turn stalled enterprise deals into closed revenue. He breaks down the nuance of activating networks at scale, aligning incentives around introductions, and embedding relationship data directly into the existing workflow so new processes do not die on the vine. From Monday pipeline reviews to executive access and stuck late stage opportunities, Drew explains how the best revenue teams treat relationship intelligence like the air they breathe.What You’ll Learn:Relationship Intelligence Fundamentals: What it really means to build a relationship intelligence layer and why it is a different go to market motion than cold outbound.Incentives and Activation: Why simply seeing who knows whom is only half the game and how incentive alignment, compensation, and context determine whether relationships actually get activated.Workflow, Not Side Quest: Practical ways to embed relationship data in tools like Salesforce, Slack, and email so managers naturally coach around it in pipeline reviews.From Story to Playbook: How one trusted introduction at Salesforce unlocked a seven figure deal and how that kind of magic can be turned into a repeatable team playbook.Modern Deal Strategy: How to use relationship maps and heat maps to unblock late stage deals stuck with finance, legal, or executive signoff instead of just hoping the contract gets approved.Key Topics:Building a relationship intelligence layer for GTM and revenue teamsThe nuance of relationship activation and incentive alignmentWhere relationship intelligence should live in the RevOps and sales tech stackUsing Salesforce embedded views, alerts, and APIs instead of forcing new UI and heavy change managementDesigning Monday pipeline reviews that start with “who do we know” and “have we connected the dots”Why LinkedIn connections alone are noisy and how signal based relationship scoring changes the gameMoving from manual “who knows who” exercises to scalable, AI powered relationship mappingGuest Spotlight: Drew SechristDrew Sechrist is the CEO and co founder of Connect the Dots and a former Salesforce executive who rose through the ranks during the company’s hyper growth era. His experience closing large, relationship driven enterprise deals at Salesforce inspired him to build a platform that operationalizes the power of real networks for modern revenue teams. Today, Drew helps companies turn hidden relationship capital into measurable improvements in win rates, cycle times, and deal size.Resources and Mentions:Company: Connect the DotsConcept: Relationship intelligence and relationship heat maps for GTMBook: The Tipping Point by Malcolm GladwellPlatform Ecosystem: Salesforce, Slack, email, and RevOps systems as primary surfaces for relationship data🎧 Listen now and follow Selling the Cloud for more GTM, sales leadership, and AI driven revenue insights from leading voices in enterprise growth. Subscribe wherever you get your podcasts.KK Anderson (00:31)And this really feeds into our second topic, which is around building that kind of relationship intelligence layer. What you've been describing, right? That is, it really is a different approach to like, to go into market. And so like, and if you think about like, let's say we do, you do this 90 day plan, it's working, like your team is,show this team that you're piloting this with is showing success. You build kind of the playbook and the process for how you could repeat it or scale it. Does this become something then that your managers start coaching? Does your pipeline meeting sound differently? What happens then?Drew Sechrist (01:08)Absolutely. So do anything except use our network to go to market. That's it. That's all we do. I can't actually say it's entirely true. It's like we do some events. We'll go out. I was at Dreamforce last week. We hosted the Salesforce alumni reunion. So we do things like that. But that's also kind of relationship based as well. But we don't do anything else. So we're kind of like this purist in this new motion.So the answer is absolutely yes. But I will say we don't have it all figured out yet. We have some of it figured out. The challenge, think, is really like.The challenge is a lot about protocol. Protocol and aligning incentives for everybody. Just because you can see everybody that knows everybody in the world and how well. Just imagine there's some magic way for you to see everybody that we collectively as a company know and all the people that they know and how well they know them so that we could say, great, Mark's got this really strong, looks like he's got a strong relationship with the CEO of this.Fortune 500 companies, let's leverage Mark to get to that person. How do you do that? Like it depends on, there's a lot of nuance. Who is Mark? Is Mark one of our senior executives? Is Mark an investor? Is he an advisor? Is he just a friend from the gym? Is he my neighbor? What are his incentives aligned with us? Is he a customer of ours? You know, like all of this.those things play into the, how do we activate Mark's relationship with this person? Just because we can see that it exists. That's, that's like, call it 50 % of game. But then the other 50 % of game is how do we actually activate this in a way that Mark feels good about that's going to be effective. That's going to, know, he's going to facilitate the introduction. one of the big challenges I think on this is like, the incentive alignment thing, like, let's just talk about compensation here.Let's talk about compensation for a moment, if I can take it that direction. If you really want to unlock the network, then everybody's got to be compensated somehow. Now, I don't want to be too capitalistic about this. I don't want to be too capitalistic because many moons ago when I was starting my career at Salesforce, it was around that time.I read Malcolm Gladwell's The Tipping Point. you've read it, KK. Mark, have you read that? Yeah. So deep in our brains, right? And I definitely identify it as a connector, even at that young age. And I was like, I'm a connector, and I love this. And so no surprise that years later, I started Connect the Dots. And I do make connections for,Mark Petruzzi (03:09)I certainly have,Drew Sechrist (03:25)Many like Matt, vast majority of the connections that I facilitate in my life are not, I'm not expecting any kind of, know, compensation for that. let's say certainly not any monetary compensation. might like, would, I might like, Hey, thanks a lot, Drew. That was really nice. You helped me out a lot here by introducing me to this person. I like that. makes me feel good. So.But if you want to do this at scale, you got to figure out like, what is the compensation that everybody's in the network is going to have? and it could be straight up, just, you feel good doing it. Like I'm a connector and I do feel good doing it. KK, if you wanted to get to get to somebody, let's say, totally random idea. Like you're, you're going to go to Dublin and that came up and you're like, I really wish I knew great.whatever pubs in this little town outside of Dublin, cause that's where I'm going to be. like, you know what? know somebody from that town. Let me introduce you to, I'd feel good. You go to some cool pub and have a great time. And that person that I connected you to probably would be like, yeah, that's kind of neat. Somebody's going to my town. And so my compensation on that one is, you know, it's, basically, it's a dopamine hit. I feel good that I've connected to people and their lives are going to be a little bit better because of that connection. But KK, if you hit me up like.40 times a day, every day for introductions to various people, for various reasons. At some point I'll break and I'll be like, KK, I got a day job, I'm sorry. You know, like I can't help you with, you know, 40 introductions a day. Now, if you hit me up with 40 at and say, Drew, I'd like you to make 40 introductions a day for me. And these are the introductions I'd like you to make. And it's good for the person that you introduced me to.And by the way, Drew, for every introduction that you make, I'm going to give you $10,000. I'd be like, hmm, all right, KK, you only want 40 a day? you like 50 a day? Would like 60 a day? I'll see what I can do. Right? So incentive alignment and compensation are important here, it's so nuanced. mean, think about it. Like, you're getting paid to make an introduction to somebody, you're a friend. That doesn't feel...KK Anderson (04:58)Yeah, or 400. Yeah.Mark Petruzzi (04:59)YeahDrew Sechrist (05:14)Right? Does it? You know, it feels, that feels wrong. Like if, he's, if KK you say, Hey, Drew, could you introduce me to one of your friends who is a good prospect for us? And if they buy, or even if they don't buy, I'm going to give you a thousand dollars or something like that. then I don't know. just, it feels weird. that feels weird. Now, if I were an advisor for your company, KK, you're CEO of company andYou say, Drew, it looks like you've got a great network into the companies that we want to sell to. would you be an advisor for us? We're going give you some equity and we'd like some advice from you. We'd like you to open some doors for us so that we can get in and sell our product and get feedback and grow and become a successful customer. That doesn't feel bad in the same way as getting paid with cash, right? so there's a ton of nuance here.Candidly, we don't have it all figured out yet. I think this is like this whole space is taking shape right now. It's like there are tools that are making it possib

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

In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrain, joins KK Anderson and Mark Petruzzi for a compelling conversation on how modern sales leaders can use AI to coach more effectively, eliminate wasteful pipeline rituals, and build real self-leadership within their teams.Paul outlines how high-performing sales managers are shifting from performative metrics to meaningful enablement; using AI to flag risk, generate insights, and equip reps to close complex deals. He also shares how sales leaders can establish operating rhythms, drive accountability, and lead with trust; all while reporting to the board with metrics that prove the business value of relationships.What You’ll Learn:AI-Enhanced Coaching: How to pair red/yellow flag systems with AI insights to pinpoint stalled deals and coach with precisioCadence of Accountability: How to replace unproductive pipeline calls with actionable, written commitments that build trust and executionManager Enablement: Why coaching the coach is the next evolution in sales performance systemsBoard-Ready Metrics: Which numbers matter most to prove relationships and strategic selling actually move the needlePractical AI Use Cases: Where AI drives effectiveness now (e.g., summarization, follow-up, personalization), and where it still falls shortKey Topics:Operationalizing AI in pipeline reviews and deal strategyMoving from activity tracking to outcome coachingSystems for continuous manager developmentReal intelligence vs. performative sales theaterCRO priorities in the AI era: focus, trust, proofEnabling full-cycle reps with better content, follow-up, and insightsMeasuring relationship impact: customer engagement, strategic touches, lifetime valueGuest Spotlight: Paul FullerPaul Fuller is Chief Revenue Officer at Membrain, where he brings structure, strategy, and coaching to complex B2B sales organizations. A strong advocate for elevating leadership and execution within sales teams, Paul focuses on embedding process, insights, and AI into daily workflows to help reps and managers improve continuously.Resources & Mentions:• Company: Membrain• Book Recommendations:– The Greatest Sales Question Ever Asked by Brent Long– A Mind for Sales by Mark Hunter– The Speed of Trust by Stephen M.R. Covey– Mere Christianity by C.S. Lewis• Sales leader to follow: Matt Green (Sales Assembly)🎧 Listen now and follow Selling the Cloud for more real conversations with revenue leaders building tomorrow’s go-to-market playbooks.KK Anderson (00:31)So building on that, Paul, from a sales manager's perspective, let's say they're in a coaching call with the rep and there's deal after deal that's stalled. And we know that stalled deals kill quarters, right? And so what are some ways you see top sales leaders leveraging AI?or AI signals, to help coach through some of those common challenges that sellers have.Paul Fuller (00:55)we personally, do it by, coaches that managers that use our system and, are doing, but we have a really robust flagging system and a really robust ability to, look at a pipeline by a variety of factors.then you can start to layer the AI in top of it. So we've built a flagging system for years. So something has been in stage more than 15 days. Let's check this out. Let's understand it. Let's, let's figure out and based on the profile of the customer and the actions that we've taken, red, yellow, red, yellow, let's categorize those flags. where you start to get into the AI stuff is that AI can then start to deliver based on that framework, very specific things based onto other reps that have been successful and move things based on situations that have happened across the organization and based on that rep behavior itself. If you do things like tie in, tie in recordings and fathom and gong and those types of things. So you can do some really cool work there. What I found is it's best for the flags and the AI to bring up suggestions to a manager saying, Hey, here is threethree or four deals ⁓ that are specifically, let's talk these through, right? Bring up those flags. I do believe a hundred percent that it is on the manager then to dive in into those deals, understand them and human to human get that coaching on what are the barriers that are, are specifically in the way and how we're then improving.the skills, the who and the who of what we want to be and how we want to act. How are we improving that on ongoing basis? So we have a platform called Elevate within our tool set that is a, it's a cadence to coaching and cadence rhythm platform. So it ensures that we're doing the right work. we can set goals in that platform. It can bring insights from our pipeline. It can flag deals that we need to discuss.But if we don't actually have the meeting, I'm still a huge fan of that. Like we have to have those one-on-ones and dive in, discover and understand. And so for the sales manager, the most important thing data is about half of it. The other half of it as a sales manager is how am I improving as a leader in my ability to coach these deals? And they need to have a cadence on those. need to understand howCause information is not the, we need the information and we need to have it highlighted. But if there's not a rhythm by which you're continuing to improve your coaching skills and ability and dive into deals and those types of things, the sales manager, doesn't matter how much information I give them. because the sales manager in that, that is coaching a lot of times, we'll just do the same things over and over again. It's a man.why aren't you closing this? I would have closed it. that's a lot of the coaching that happened that happens today. Well, I would have done this. And that doesn't that doesn't cut it. So I think that that layer of those sales managers and those coaches really need to work on that skill.Mark Petruzzi (03:44)Right on. So Paul, let's kind of anchor this maybe around like a mini cadence. So if we're reviewing pipeline for 12 weeks at a client, you if you're doing it within your CRO role for your own company, what are the three weekly review items and the three actions that you'd mandate and who owns each and when do they need to be done?which are the ones that really drive behavior to become sticky?Paul Fuller (04:14)That's a great question. Do I have to limit it to three?Mark Petruzzi (04:16)You do not.Paul Fuller (04:18)All right. Well, again, I can only go from my experience.And, this is weird because we've been talking so much about, the who and the, core of the people that we need to become and those types of things. and then the processes, and I am going to give you an answer that I think is completely outside of that. and it's a very simple answer that I think doesn't happen, across just about everyone.I've seen there needs to be and I don't care what system you're using. don't care if you're using Excel. I don't care if you're using a membrane. I don't care if you're using a pad and paper, but on a weekly basis, every rep and every manager of that rep needs to have a full understanding and picture of an updated pipeline and the deals in those pipeline in that pipeline.And, again, our system makes this easy. makes it much more, much easier and gives the ability to do it, and flags and pulls information out of it and all that stuff. But that habit in and of itself on a weekly basis for a sales manager, is something that is skipped so often and it changes everything. second.is the cadence of, if you have that, then you can effectively coach and have a cadence and rhythm to that. And I call it a cadence of accountability. The cadence of accountability is just as important to the sales manager as it is to the sales person, as it is to the VP of sales, as it is to the CEO, right? It is.What are we committing to this week that we're going to get done for each other? And that goes back. It does go back to that who like self leadership and the ability to be a self leader, but that cadence of accountability is critical and it needs to be written down. It just, it just has to, Hey rep one, I'm a sales manager. I am going to dive in and review through your accounts and I'm going to do this for you.Okay, and I'll do it by Friday or I'll do it by next Tuesday.Do you know how you're in sales? So you know this and you're in leadership and coaching and you know this is that how frequently that gets missed and pushed to the side and in favor of busyness is, is crushing. It's crushing to a sales team. It's crushing to a sales leader and it's crushing to a forecast ultimately. All right. And the third thing that a sales, I would say that's incredibly, incredibly important.And again, we, going back to the basis, you could do this on a pad and paper is, what are the things that I am accountable to my prospects and customers for this week? My top five, right? And in, and I might, I'm going to complete those. I think just those three things, absolutely.It's why I harp so much on, the self leadership and I, what I call the real intelligence, the leadership, the service, the way if I have accepted and we've defined that together, those three things don't become necessarily easier, but they become something that I will commit to, as, a person and as a manager and as a sales team member. and they become so, so important. And so again,Our systems, everything is a glorified system around that, quite frankly, but those things are so incredibly important to make an impact and to move forward together, lead well, serve well, and to really ⁓ drive performance.Mark Petruzzi (07:28)Yeah, and you know what's really cool, Paul, about what you just walked us through is you really define what the items that are really important in the selling process as compared to things that we have done for so long. For example, we've relied on a CRM and we all know a CRM doesn't do anything to make a sales rep more effective or even more productive.And so, okay, so we spent a lot of

In this episode of Selling the Cloud, Paul Fuller, Chief Revenue Officer at Membrane, joins KK Anderson and Mark Petruzzi to reframe how revenue teams win in complex, multi-stakeholder deals. Paul explains why many orgs over index on apps and one-off skills while under investing in operating rhythms, leadership habits, and relationship-driven execution. He introduces the idea of real intelligence as the who and why that guide the how, and shows how process plus AI inside the workflow can coach managers, focus reps, and change what happens every Monday morning.What You’ll Learn:Defining real intelligence: moving beyond tools to leadership, service, and wayfindingBuilding operating rhythms: weekly coaching, clean pipelines, and a cadence of accountabilityEmbedding insights in the workflow: checklists that coach, not just boxes to tickActivating AI where it matters: individualized multi-stakeholder follow ups and manager signalsProving what boards fund: focusing on measurable behaviors that move win rate and cycle timeKey Topics:Systems over one-off training for durable behavior changeProcess plus AI to guide day-to-day actions in CRMCoaching frameworks that reinforce who, why, then howMulti-threading effectively and right-sizing stakeholder engagementFrom performative pipeline calls to meaningful operating reviewsGuest Spotlight: Paul FullerPaul is the Chief Revenue Officer at Membrane. He helps complex sales organizations operationalize process, coaching, and buyer-centric execution so managers can coach and reps can execute without bouncing across tools.Resources & Mentions:Fathom and Gong for call capture and summarizationMembrane workflow checklists and coaching cadenceWINS framework for servant leadership based sellingBooks: The Greatest Sales Question Ever Asked by Brent Long; A Mind for Sales by Mark Hunter; The Speed of Trust by Stephen M. R. CoveyLeader to follow: Matt Green of Sales Assembly🎧 Listen now and follow Selling the Cloud for more GTM insights from enterprise operators and CROs. Subscribe wherever you get your podcasts.Mark Petruzzi (00:31)Today on Selling the Cloud, we're joined by Paul Fuller, Chief Revenue Officer at Membrane. Paul spent years helping complex sales organization operationalize process and coaching, bringing structure to multi-stakeholder deals while keeping sellers focused on what moves outcomes. At Membrane, he's championed approach that layers insights and prescriptive guidance inside the workflow so managers can coach and reps can execute.KK Anderson (00:40)youMark Petruzzi (01:00)without bouncing across tabs. We'll dig into Paul's thesis on real intelligence, the durable leadership practices that operate, rhythm sales teams need to thrive amid AI tool bloat and rising partner competition. We have three topics we'd like to cover with you today. From skills to real intelligence, why systems, leadership habits and operating rhythms be one-off training.Process plus AI, kind of day-to-day actions, putting insights inside the workflow so reps and managers change what they do on Monday morning and every single day of the week. Focus, trust, and proof. Leading in the AI era, keeping teams competent, and proving to the board, CFO, CEO, that relationships and systems move the numbers. Welcome, Paul. We're so happy to have you with us here today.Paul Fuller (01:50)Thanks so much for having me. really appreciate being here. I'm pumped. I'm excited.Mark Petruzzi (01:55)Beautiful. We love it, All right. Let me open with a question here in topic one. So Paul, you've argued that revenue orgs over index on apps and one-off skills while under investing in the systems and leadership habits that drive outcomes. In your words, what is real intelligence for a sales org? And how is it different from adding another tool or another skill module?Paul Fuller (02:17)Yeah, great question. And I think you've, everybody's been there. in terms of we love in the sales world to focus on the how, And how do we get things done more efficiently and quicker and better and put more numbers on a rep and make sure that they get, things done more appropriately. LikeThe whole revolution of the past 25 years has focused on that. Let's, make sales and manufacturing line. Let's get an SDR. Let's get to an AE to an AE that does, another thing at a sales engineer to the next, to the next, to the next, right? How do we make this more efficient? there's, there's an interesting concept though, that I I'm really finding that more and more as we, today's world and what we're dealing with.is we have skipped some certain things. We have skipped some of the fundamentals that it takes us to operate as sales professionals as a human and really make a continual impact in the market. We have skipped things and pushed them to the side. Things like relationships, things like how we work on those relationships together, things like a long-terma relationship that is going to drive impact for your business for years to come instead of, and instead in much of what we focused on, have you gotten a conversation and is there an opportunity? So when I talk about real intelligence and building that into a company, I'm focusing more on the who we want to choose to be. And then the why that we choose to be this instead of, and then move into the how. And I think that focuses on three things that we choose to be in sales.how we choose to lead, how we choose to serve. And I have a word that it's wayfinding, but how we choose to problem solve and find a way to work with companies and, do that core to who we are and define the, make those choices about who we want to be in those actions. We can always figure out the how another app, another thing. andSo many of us just focus on that. How let's just, my gosh, I got this, I got this for data. got this for this scraping. got this for this. And you focus on that so much that you've seen tech bloat. You've seen confused reps. You've seen reps promoted to AEs that just cause they know how to book a meeting, but they couldn't, they couldn't discover and ask a question for the life of them. Or they don't even know who they are and what a sales motion is. So that's what I.Mean when I'm talking about real intelligence.KK Anderson (04:27)So the real intelligence as my daughter would call it is like the invisible thread, right? That connects everything. It is the common denominator that must be there to be able to make a sale. And that's a true relation. It's a human-based relationship. that what I'm hearing?Paul Fuller (04:45)Yeah. Amen. and let's make it real with like one word that you hear a lot in sales today and you hear people throwing up their hands about accountability, right? I can't get my reps to be accountable to leadership or customers. And so how did most people solve that? Well, I'm going to throw, I'm going to throw test management at this. Right. I'm going to throw check boxes that they have to do in their CRM. I'm going to throw.And they think that's solving the problem. Well, the problem lies much deeper than that. Yeah, the problem is much deeper than that, right? The problem is that you haven't invested in your team and built leaders on your team that know how to lead themselves and lead others. So why don't you start? Why don't we start with core components of self leadership as a team and say, that's how we want to sell and what that means to us before we then create this in the line thing wall andKK Anderson (05:10)another box to click.Paul Fuller (05:33)of accountability, because you have so many see I was on a CRO forum the other day and they're like, I just can't get these Gen Z errs or whatever to be accountable. Well, quite frankly, look at the system they've grown up in look at a lot of things that has happened. I think you need to go back to the real intelligence part of this. Let's talk about what it means we want to hire leaders, have leaders in our culture and what that looks like for us here. Let's start there and how that can impact your life.Therefore, you know, so you start a little earlier in the cycle, get rid of that. You do the how, but start with the who.KK Anderson (05:57)Yeah.Mark Petruzzi (06:03)So Paul, where do teams get stuck in this? What's kind of a common anti-pattern? Something that looks smart, feels good, shiny AI, but doesn't translate into consistent behavioral change.Paul Fuller (06:17)well, I'll use, we, are heavily, we love sales process. I love sales process. I actually really appreciate, our, platform is built around sales process, and how we're able to do that. sales process is a wonderful thing. and, let's say it's created in the mind of, the sales process is created in the mind of the medic expert that knows everything and has been.been in there for 30 years and knows exactly the questions to ask and all of those things, right? And then I put that out there and I put it into an organization. I find out, why isn't this working? It should be. I mean, we had an expert design it. it was perfect. It's in a system, right? There are gaps in the people I think don't see where they say, okay, let's fundamentally go back to this. And I put this concept of real intelligence, butlet's go back to these fundamentals of leadership there that are embedded into it. Let's agree on those and gain agreement for our team that that's what we're to practice. And then let's look at that in the context of a sales process. What are the actions that we're going to do continually and how is that going to, how are we going to craft reminders of that initial who that initial agreement, who do we want to be? Right? How do we're going to craft those in the sales process that actually helps us execute?cause if we have our who and our why figured out our how, we can systemize that really well. Right. So I think people get stuck in the anti thing is, well, I'm just going to put it in a sales process. Okay. If, if you just do that, you're going to get a bump. You're not going

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

In Part 2 of our conversation with Neil Graham, Chief Revenue Officer at Disqo, we dive deeper into how modern CROs must rethink their org design, marketing execution, and AI integration strategies to stay competitive in 2025 and beyond. Neil shares why curiosity, humility, and bias for action are now non-negotiables; and how his team is operationalizing those values inside a flat, fast-moving GTM system.From building AI-generated deal strategy sessions to deploying 24/7 agents on the website, Neil unpacks the real-world tools and team behaviors that are reshaping sales and marketing execution. This episode is packed with tactical insights for CROs leading through change.What You’ll LearnFlatter Orgs, Bolder Execution: How Disqo’s three-layer model speeds up decisions and drives alignment across marketing, sales, and delivery.Non-Negotiables in Revenue Teams: Why curiosity, humility, and action orientation matter more than ever, and how to screen for them.AI as a Revenue Multiplier: How Disqo uses AI for outbound personalization, content creation, and automated deal intelligence.Coaching in the AI Era: How Neil’s RevOps team leads enablement through data-driven strategy docs and always-on insights.Creating New Roles for the AI Age: Why Disqo now has a dedicated AI strategy lead embedded in RevOps, and how other CROs can follow suit.Key TopicsScaling outbound without bloating headcountRedefining RevOps to include data, process, enablement, and AI ownershipDesigning a leadership team that balances vision and executionThe future of SDR and BDR roles in an AI-enabled GTMUsing AI agents for 24/7 coverage and real-time buyer insightsBuilding culture through feedback, modeling, and EQ-based hiringGuest Spotlight: Neil GrahamNeil Graham is the Chief Revenue Officer at Disqo. A proven growth operator and revenue architect, Neil has helped scale iconic brands like Salesforce, Siebel, and Jive. At Disqo, he’s building a flat, AI-accelerated GTM machine that prizes speed, ownership, and alignment over legacy hierarchy.Resources & MentionsCompany: DisqoFrameworks: MedPick, DSF (Disqo Success Framework)Sales Tools: Gong, Clay, ChatGPT, AI agentsLeadership Inspiration: Carl Schachter, Eli Cohen, John BarrowsBook: Emotional Intelligence by Daniel Goleman🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.KK Anderson (00:32)to drill into this topic, topic three, talking a little bit more about the flat org and the expanding CRO role, we've had this conversation quite a bit on our podcast about how CROs are now...taking responsibility of the marketing org, of the customer success org, of the sales org, of the entire go-to-market revenue system. And one of the things we see every day in our customer conversations is how disjointed marketing can be from sales disjointed product and from product management as well. And soas marketing is kind of folded in under you and this kind of this new flatter org and you mentioned that the alignment that you're having with your SLT every week but tell me a little bit about how this is helping to kind of bridge that gap between marketing sales customer success like the whole go-to-marketNeil (01:24)So I am a big fan of the CMO role in today's modern company and organization and, I know the SaaS and sort of technology world really well. So I'll speak from that perspective.I can't really make a comment on other industries, but I am a big fan of, the CMO's role, and, sort of ownership of a modern AI driven marketing strategy. that said, we're trying to innovate quite a bit and do some really cool disruptive stuff and shift the focus of our marketing strategy here. And my CEO is a big vision behind that as well. And,hoping that I'm actually a pretty good impact on that. and we've got some great leadership on our marketing team that's doing an awesome job thinking big and bold and in a differentiated way, but also really good at execution. And I think, this is a little bit of a side point, but I do believe in, making sure that on your management team, you've got a good, portfolio of leadership skills.from vision to execution oriented people. So you can do both. And we've been really careful to kind of put together our leadership team on the marketing team and the sales team. I don't own the success side of the business here, as you mentioned. We've got a whole, Chief Customer Officer owns all of our post-sale delivery and customer success functions, implementation consultants, all that kind of stuff. But doing a great job there.creating a leadership team that spans between visionary and execution oriented and has skills and that can kind of augment each other and kind of take both to market. That said, in marketing, I think what we've done a really good job at especially the last nine to 12 months, is shifting the focus to data-driven ROI creation activities and initiatives and making sure that everything thateverybody's focused on has proven results when it comes to lead creation and continued pipeline development of those leads into high converting opportunities. Right. And so we look at the data constantly in terms of how many leads, how many stage one pipeline deals were created, what conversion rates are going on and how much closed business happened from the marketing activities we're doing and dropping the stuff that doesn't have higher ROI.And for us, some of the traditional things that most people in this industry think drive a ton of output are things that we've actually cut. And just from a perspective keeping our own sort of information and strategies a little bit behind the scenes, like I'll just leave it at that, butin a pretty severe direction from less inbound and more outbound pipeline creation strategies with our marketing team and our marketing skill. that's been a lot more focused on demand gen, content, sales-facing, market-facing content, and overall product marketing.And those are the skills that we've really built out on the team. because, you know, getting into like the final subject a little bit, but we can dive deeper into AI. But I mean, because of AI, it's like, it's allowed us to do this. there's mass personalization that we can do at scale, truly. And people have always said, you know, mass personalization at scale. like today with the tools that are available in the market for us to understand the ICP.that we're focused on, our ideal customer profile and the key personas at those companies that have challenges that we solve for in a unique way. That data is all now massively in our CRM and with other tools, it makes it easy to augment a message to those people at those companies based on specifically what they care about and specifically what the business issues and challenges are at that company at scale.so we can get out the best prospecting that the most senior BDR and or sales professional would do because they know this account and they know these people and they've worked with them the last 20 years, that's starting to happen at scale in an automated AI based way. So we can get a message out there to the market that's hyper contextualized for the person in the company that we're targeting.And create awareness and pipeline that way. So mass personalization. The other thing we're doing in marketing, like creative content factories, like we're getting with AI, we're getting five, 10 times the output and a consistent brand voice.through creative and through content creation than we did before. And it's all kind of wrapped around what I'd call before that curiosity culture, that experimentation culture, getting a lot of velocity there with, auto-generated hypotheses and variants and insights into how to create better content, have better creative, do better outbound at scale. And that's what the whole marketing team's focused on right now.Mark Petruzzi (05:58)Excellent. Neil, very cool.Mark Petruzzi (06:02)So Neil, what are the non-negotiables?Neil J (06:05)The non-negotiables. All right. Quick question back. Are you talking about what non-negotiables exist in terms of how I run my business, my team, the operation itself?Mark Petruzzi (06:14)Yeah, I mean, would say kind of yes, yes, yes, all three. Just what are the things you have to do for success in this business?Neil J (06:17)Okay,KK Anderson (06:18)as well.Neil J (06:21)Ah, that's a great question. I think they all, to me they all ladder back to, and maybe this is for other leaders too, they ladder back to the core values of the company that you're at. And hopefully as a business you've done a good job or as a business or a business leader flushing those core values out and making them applicable to the unique attributes of your culture and your company and the space you're in and all that kind of stuff. Because they shouldn't just be words that are up on a wall, right?here we've got four core values at Disco. I'm not going to go into each one of them. They're actually on our website. They are up on a wall, but at other companies they've been slightly different. And I think about, I go back them quite a bit in the way that I lead, in way that I help my leaders lead the organization. If we keep kind of connecting things back to, as we talked about before, the DSF, the overall objectives of the company, for us it's our Disco success framework. Or if it's...the core value of the employee experience and the culture itself, right? One of ours is together, win together as one team. Another is pursuing outsized impact. So delivering exceptional results, being relentlessly all in as a third. There's more, but I think those are really impactful for, especially for a customer facing organization that are driven by numbers and that have clear objectives in terms of what good performance is and what it isn't. Like having those three things be.kind of non-negotiable to me and the rest of our core values non-negotiable and we try and bring things back to that quite a bit, right? We do a lot as a busin

In this episode of Selling the Cloud, we’re joined by Neil Graham, Chief Revenue Officer at Disqo and a seasoned revenue leader whose career spans Salesforce, Siebel, Jive, and Telem. Neil shares a ground-level view of what it takes to lead, scale, and modernize revenue organizations in an era where traditional sales playbooks are no longer enough.From breaking out of funnel-stage rigidity to building flat organizations that prioritize curiosity, Neil walks through the changes CROs must embrace to stay ahead. He also shares how Disqo is rethinking GTM structure and leveraging AI to drive personalization, speed, and operational clarity; without drowning in tools.What You’ll LearnWhy the Playbook is Obsolete: What Neil really means when he says the old models no longer work, and what replaces them.Lightweight Rigor at Scale: How to build process and alignment without slowing teams down.From Bottoms-Up to Top-Down TAM: How Disqo blends relationship selling with TAM-led targeting for scale.Curiosity as Culture: Why curiosity is a non-negotiable leadership trait in flat, fast-moving GTM orgs.Leading Through Change: How to coach teams to self-govern, move fast, and stay mission-aligned in a no-layer org model.Key TopicsBuilding sales organizations without bureaucracy or bloatAligning marketing, sales, and success teams around business outcomesUsing AI to power real-time customer insight and hyper-relevant outboundFlattening GTM structures for speed, ownership, and clarityCreating cultures where experimentation and impact are rewardedGuest Spotlight: Neil GrahamNeil Graham is the Chief Revenue Officer at Disqo and a proven sales leader with decades of experience scaling GTM organizations from Series A to post-IPO. Known for his ability to bring structure without red tape, Neil has helped some of the most recognized B2B SaaS names balance scale with agility in high-growth phases.Resources & MentionsCompany: DisqoFramework: DSF (Disqo Success Framework)Sales Tools: Gong, Clay, ChatGPTBooks & Influence: MedPick methodology, Salesforce early days, AI-led sales enablement🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.Mark Petruzzi (00:33)Welcome to today's episode of Selling the Cloud Podcast. We're excited today to welcome Neil Graham, Chief Revenue Officer of Disco. Neil is a proven revenue leader who has helped scale organizations at Salesforce, Siebel, Jive, Telem, and now Disco, the best name of them all. At Disco, Neil leads a go-to-market organization of about 45 inside a nearly 300-person company.KK Anderson (00:33)Thank you.Mark Petruzzi (01:00)His career spans taking companies public, guiding series A to series F growth, and balancing early stage venture backed and private equity operating models. Today, Neil will share what it looks like to lead and scale revenue organizations when the old playbook is obsolete, which pretty much is all the time nowadays. Covering agility,operational discipline, and why CROs must embrace a new approach to building revenue in 25 and beyond. Here are the four themes we'll explore. First, when the old playbook is obsolete. So when these old legacy models no longer fit, no longer work, how do leaders adapt? Scaling from 10 to 100 million, that sweet spot, especially in the SaaS and ISV world.And then, the concept of lightweight operational rigor, like how to combine a sleeves rolled up selling model with really good process and tools, but not too many process and tools slow How flat orgs need to be structured and how they work and how that really puts more pressure and responsibility on the CRO.and also sprinkling AI into the go-to-market mix. How Neil is experimenting with AI to augment productivity and rethink traditional roles. Neil, thank you so much for joining us. Welcome to Selling the Cloud.Neil (02:26)Thank you, Mark. Appreciate it. Thanks for having me.Mark Petruzzi (02:30)Happy to have you here. All right, topic one, when the old playbook is obsolete. So, Neil, I've heard you say, don't even know what the playbook is right now. It's all getting disrupted. Tell us a little bit about what you meant by that.Neil (02:43)thanks for the introduction. That was great. look, privileged to be at a lot of great companies through the years and hopefully caught on to a little infrastructure and kind of prioritization through the years in terms of how I approach things. we're in a really unique age today.the traditional playbooks from the last, I'd say 20, 25 years in a way, are going out the window in a way they're still there. And I think if you think about what's happening with AI and with how that impacts operational structures, go to market strategies, people and process skills.And overall playbooks, it's like you really have to kind of reconsider the way you're operating at every step of the way yet continue to operate and make sure that you put one foot in front of the other and execute. And so what does that look like? we've spent a lot of time. I think about the back in the days at Oracle in the early days and then at Salesforce, where we really scaled some organizations from small to large.the playbooks that we created around, marketing and sales and customer success became kind of a standard. And it's like, if you think about the processes from lead development, MQLs to SQLs to, early stage pipeline and the sales process from stage one to being selected at stage four or five and getting into a negotiation, the process of value selling along the way where you identify.the customer's business issues and challenges, you map your solution to that. You think about trying to position how you're unique against the competition or the status quo and quantify that, that value and articulate that really well to the client. A lot of that was put on our people and we would train and enable around these processes and these plays, try to roll out frameworks like, every part of the sales process, dissecting it.providing people visibility and information into what it takes to be successful, whether it comes to discovery, whether it comes to running a great demo, whether it comes to positioning the differentiated value prop, whether it comes to building the business case of the impact that you're going to make at the organization in terms of driving business outputs, whether it comes to scoping and professionally delivering a plan to make the customer successful, whether it comes to the negotiation, the objection handling, the competitive intel.All that stuff's still there. And our customer facing people and processes need to execute flawlessly on that. At the end of the day, it's just that the information is so readily available and we'll talk more about it later with AI have to do everything that I just said, but it's so flat in terms of being able to access that information, position that information on the fly.and make it part of your cadence that some of the traditional models of the playbooks and the enablement plans and the objection handling frameworks and all that kind of stuff literally go out the window and they become kind of almost in the moment. So I don't like at the end of the day, I think the old playbook being obsolete, I don't know. I think from my point of view, customer value still wins,the modern model starts with the customer's business case, knowing their business issues and challenges, understanding the pressures and constraints they have, and your people being able to flush that out and have that information at their fingertips when they come into a conversation. Then being able to articulate how the solution that they bring to market is differentiated and tie that differentiation to the measurable outcomes.It's just doing it in a more productive and higher impact and flatter and faster way. But every interaction that you have should clarify, how you come back to the business issue and challenge the customer has. So I think second, the AI tech that's out there puts these answers within reach and, we're able to have this information quicker and faster than ever before. And then I think third, just creating a culture and sort of a overall.go-to-market system that is rooted in curiosity. So your people and your processes continue to evolve quicker and faster than the competition is really important for every company.KK Anderson (06:30)I echo everything you said, Neil. this morning, as a matter of fact, I pulled out my phone and I wrote it in my notes thought exactly what you just said. The activities, what's changed now is that the activities aren't the work. Going into CRM and working in CRM, that is what's obsolete. Right? You can't do the same things every day and expect to have a differentiatedcustomer focused, customer obsessed approach, right? it's all about leveraging all of this super intelligence, leveraging AI, what's at our fingertips to do the hard. And so sales, in my view, is going back to what it was originally, the beginning of the sales profession, right? Where it was all about solving problems asking great questions and getting to know people and relationships.And then we had all of these years of playbooks here's what you do, here's what you say, here's how you handle this objection, here's how you position this, here's how you differentiate this. And it's almost now, like the second something gets turned into a PDF, it's no longer relevant, right? And so it is interesting. All of this is allowing sellers to do the hard things, which is if you go a day or a week,God forbid, and you don't feel that anxiety of what am I gonna say on this call or how am I gonna approach that person, then you're not doing the hard things. Ticking off tasks is old school. That's the old playbook, right? Anyhow, so as you think about this kind of seismic shift that's happening, what are the principles that are guiding you as you lead today? If you're going back to basics,back to you were just talking about, like what are those principles? Like h

In Part 2 of our conversation with Josh Hoffman, we explore the leadership mindset required to thrive in moments of high-pressure change, like mergers, long enterprise cycles, and AI-driven disruption.Josh shares how sales teams can stay grounded in customer value, build trust through co-created plans, and lead with consistency; regardless of who owns the company or what the logo says.We also talk about the real-world impact of AI on sales effectiveness, onboarding, and go-to-market readiness.What You’ll Learn:Leading Through Change: How to stabilize culture and focus teams during M&A, leadership transitions, or high-stakes GTM shiftsMutual Action Plans that Work: Why aligning around a co-created calendar is a simple but powerful tool for accountability and momentumConsistency Over Chaos: How sticking to your core value proposition helps drown out internal and external noiseReal AI Use Cases: How Josh and his team use AI for onboarding, writing, analysis, and market research—without replacing human judgmentLeadership in Modern Sales Orgs: The behavioral traits that inspire performance, loyalty, and resilienceKey Topics:Sales leadership in high-pressure, transitional environmentsUsing backward-planning and mutual calendars for deal velocityStaying aligned on value across long sales cyclesCultural consistency across internal and client-facing teamsAI for productivity, market intelligence, and GTM strategyEmbracing humility and continuous learning as a CROGuest Spotlight: Josh HoffmanJosh is Chief Revenue Officer at Totus Rx and a long-time leader in B2B revenue organizations. He’s built and led sales teams across tech, telecom, and compliance industries, with a focus on building high-trust teams and delivering real value to customers. Josh is known for his practical, human-centered leadership style, especially in complex, high-stakes environments.Resources & Mentions:Book: The Challenger SaleBook: SPIN SellingLeaders Mentioned: Mark Anderson, Russ Reeder, Todd Abbott, Mike Jenner, Joe BurtonFollow Josh Hoffman on LinkedIn for more insights on sales leadership and culture.🎧 Listen now and subscribe to Selling the Cloud to hear more from enterprise GTM leaders shaping the future of sales.KK Anderson (00:31)our third topic is around leading teams in a time of change. And so where I wanna take us. All the pressure of a change. You know, it can be a pressure cooker. All the accountability, which we know sales is famous for. The behaviors and the mindsets and the relationship and the building trust. All the things, right, that go into being an exceptional salesperson. Like when you're...going through like some of these acquisitions or mergers or whatnot, people are under the microscope, like how do you get your reps to believe and act the right way on the same side of the table in these high pressure environments?Joshua Hoffman (01:07)It comes back to me to the word consistency. You have to maintain a consistent value based approach on what you're delivering to your partners and clients. That shouldn't change. Even in times of mergers, acquisitions, whatever they might be. I don't know that I've been through any of those situations where the value proposition of the company changed at all. There might have been something added to it.There might have been something taken away from it based on that. But the general value proposition, if you believe in the organization that you're a part of, who owns it doesn't really matter. If the value of what you're delivering to your client or partner has remained the same, the rest of it is noise. And you have to remain focused on the outcomes. I really can't think of a time that I've been forced to say, oh my gosh, the value of our organization or the value of what we'rewhat we're providing to our clients has changed so dramatically that we've got to make a shift in who we are with them. Now, there may be other shifts that take place inside the organization. There's changes in leadership, there's changes in locations, there's changes in potentially having another strategy that has to come into the business because two things are coming together. But what doesn't have to change is that your approach with your clients and partners, it's still the same.you're still there to be a part of a team that's driving an outcome. And if you can remain consistent in that approach, you can help people remove the noise from the system and say, you know what? I don't have to worry about that. I don't have to worry about whether our company name changed. I don't have to worry about whether headquarters is in Dallas or Michigan. ⁓ It doesn't matter because I'm still doing the same thing every day. Now that's a lot easier, I think, for salespeople.than it may be for others in other parts of the organization. I don't want to paint it that it always works the same way, but for the pieces of the business that I've been the most part of over the years, sales, sales operations, marketing, very much consistency is an opportunity to make things a lot smoother and a lot better for people and to make sure that culture remains a consistent, strong, positive force in people's lives.Mark Petruzzi (03:11)Very cool. so let's talk a little more process here for a few minutes. What kind of role does a mutual account plan or an action plan that you may create with your team, what did they play in making sure both seller and customer are aligned and accountable? How much do you use them? What kind of value do you get out of them? And are there times thatthings like that are a distraction and not really productive.Joshua Hoffman (03:37)so first of all, I'm a little nervous answering this question with you because you've literally written the book on some of these things. I feel I might be a little bit on my heels, but let me try and answer the question as best I can. First of all, the idea that you're sitting on the same table with a client, with a partner, with both of them simultaneously, by default, that should mean that you have a mutual action plan. It should mean that you have a mutual calendar that you're working off of.It should mean that the outcome that you're trying to drive is identical because you've coordinated that you've co-created it. You've, but you know, back to my co words, right? You have co decided what those things should be. Now, whether you're a value selling person, a challenger salesperson, maybe even a spin selling person, there's all of these different models that are sitting out there. there are some attributes that those things have that are in common.And I always like to quote one of my favorite people. So I had this person in my life for a long time named Marcel Brunel. And Marcel was at this organization that did great work when it came to helping people work through the process of selling. And one of the focus areas that Marcel brought to me, it was a learning for me at the time, and that I've carried with me throughout these years, is about having that calendar in place. And for me, when I talk to aclient or partner, it's about having a backwards-facing calendar. And so let's start at the end. Where is the end here? What is the date? What is the outcome? What is the goal that we share in? And let's work our way backwards and establish goals and milestones that are going to help us achieve that. And then let's hold ourselves accountable to that. And as soon as we have alignment on the end of the line,it becomes much easier to fill in everything that works backwards. And if you miss a date, you need to catch up and you need to come up with a co-created action plan to do that. And that kind of collaboration, it really solves not everything, but it solves an awful lot. And it's not that things don't go wrong, things do. But if you build the action plan the right way, if you build the outcome the right way, you also try and provide yourself with the opportunity.for things to potentially not go the way you expect. You build in a potential buffer. Maybe there's an extra day or two here. Maybe, depending on how complex it is, there's an extra week that's baked into that that allows you to still achieve the outcome. And so that kind of planning is something that I talk about consistently, whether it's with a person on our team, whether it's with somebody that's working inside of an organization that's actually delivering the product or service or with a partner or client.Let's start at the end and let's work our way backwards and make sure we're in alignment.KK Anderson (06:16)it occurs to me as well, especially if you're in any kind of a, you know, complex sale where, or a longer sales cycle, right? Where you may have different people coming in and out of the sales process. If you have a mutual action plan or mutual account plan, whatever you want to call it, you can always lead with that outcome, lead the conversation with that value that everyone is synthesized there together to accomplish. And whoever's new to the call just falls right in place.Right?Joshua Hoffman (06:42)That's right. You get onto a call of you. If you had that co-created action plan and you've decided on the outcomes and the dates and you're having, you know, let's pretend it's a longer sales cycle, so to speak for that. And maybe it's a two month sales cycle when you're having that series of meetings to get there. The first slide should be that calendar. What have we agreed to already? Are we on track or are we not on track?and let's make sure that we're in this together. And that way, when new people do enter the conversation, they walk right into a framework that allows you to be successful, that allows you to introduce other people into the process.KK Anderson (07:18)What allows them to have the confidence that the conversation has been effective and aligned so that when you're at the wire and procurement comes in and starts asking questions, you've built the value. So you don't need to worry about getting slashed