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General Episode Description: In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of BenchMarket, to go deeper into how companies should measure, operationalize, and compete with agentic AI in go-to-market functions. Ray breaks down why most companies still lack basic GTM measurement discipline, what new AI-specific benchmarks leaders should track, and how legacy SaaS companies can realistically compete with AI-native organizations that are operating at dramatically higher efficiency. The conversation also tackles the hard truth about workforce reduction, the rise of AI operators, and why companies must rethink their entire operating model, not just layer AI on top of existing processes.   What You’ll Learn: Measurement Before AI: Why most companies must fix GTM analytics before introducing AI.AI-Specific Benchmarks: The emerging metrics for measuring agentic GTM performance.Competing with AI-Native Companies: Why legacy SaaS teams must rethink their entire playbook.The Role of AI Operators: Why AI expertise is becoming more critical than traditional RevOps.From Pilot to Scale: What success should look like at 90 days and 180 days.Key Topics: Cost per pipeline and cost per ARR before vs after AIAgent cost per opportunity, pipeline, and revenueDesigning modular AI workflows instead of “monster agents”The four-layer framework: productivity, effectiveness, efficiency, and ROIRevenue per FTE gap between SaaS and AI-native companiesWhy legacy SaaS companies struggle to match AI-native efficiencyRadical restructuring: reducing headcount and rebuilding with AI-first processesAI enabling deeper personalization at scale for outbound teamsThe rise of “AI operators” as a new critical roleThe “SaaSpocalypse” and pressure on net revenue retention (NRR)Using AI to improve retention, expansion, and customer insightsBenchmark expectations for agentic SDR performance at 90 and 180 daysGuest Spotlight: Ray Rike Ray Rike is the founder and CEO of BenchMarket, a leading provider of B2B SaaS performance benchmarks. With decades of experience as a go-to-market leader, he helps organizations move from intuition to data-driven execution. Ray is also the creator of the AI to ROI newsletter, where he analyzes hundreds of AI developments weekly to help leaders understand what actually drives business outcomes.   Resources & Mentions: BenchMarketAI to ROI NewsletterConcept: Agentic AI in go-to-marketConcept: AI-first operating modelsConcept: Revenue per employee as a key efficiency metricConcept: AI operators vs traditional RevOpsConcept: SaaSpocalypse and NRR pressureFramework: Productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI benchmarks, GTM transformation, and building high-performance revenue organizations. Mark (00:26) Excellent. All right, well, Ray, let me bring you back into the days of you and I starting all our research and all the pre-work for data and diagnosis driven selling. So I hope that doesn't cause you to develop a Twitch or anything like that, because as you and I both know, that was hard work. So, but let's, you know. What we really saw right up front is, and we really pushed hard on this, is the idea is you can't manage what you don't measure. And you need external benchmarks, not just internal comparisons to know if your metrics are actually good. You know, it's great. It's great to be able to say, improved this process by 20%. But if you were 45 % behind most of your competitors before that, That 20 % still has you on the back of the pack. So how do you bring that same philosophy to measuring an agentic BDR or an AI-powered deal coaching agent? And we've touched on this, but what's the equivalent of a CAC payback for agents and the entire investment? Ray Rike (01:33) Well, I would start with let's make sure you have your go to market measurements in place, because honestly, we've been talking about these for years. Less than 50 percent of companies have great GTM analytics. ⁓ So things like cost per dollar a pipeline, less than 40 percent of people are measuring cost per dollar a pipeline. So make sure you do that and look at your current state before AI and then measure it post AI introduction. Right. So cost and I'm talking right now, I'm looking very specifically at the customer acquisition process. So cost per dollar pipeline before and after cost per dollar of new AR before and after when rate before and after your average and your contract for you before and after. Cause those are all going to be hopefully much better with AI to your point, Mark. I mean, let's use outreach. Everybody had to have a sales engagement platform, right? How many companies actually said, well, after I invested $1,500 per SCR, I had a better conversion rate or a lower cost per dollar of acquisition? Nobody. You're going to need to do that with AI. So that's my first thing. The second thing, which haven't been defined yet, but I'm working with some VCs on this right now, is AI specific customer acquisition efficacy. So I'm looking at agent costs per opportunity. Agent cost per dollar pipeline, agent cost per dollar of new ARR, agent dollar per cost of retained ARR. So you can think about your gross revenue retention and agent cost per dollar of expansion ARR. Now I'm projecting that we're going to be using agentic AI a lot in those processes or sub processes. And by the way, that's the other best practices. When you design a process, it's better to design a lot of subprocesses underneath so you don't have one large unwieldy AI agent. You have a lot of subprocesses that you have different people auditing and evaluating. KK Anderson (03:28) All right. Let's dig into that design a little bit. So walk us through, and I know this is new, as we've said multiple times for so many of us, what a well-instrumented, agentic, you know, GTM for the purposes of our audience, pilot could look like. You just gave us one great clue, which is, you know, don't make monster agents and, and to break them up so that you can, you know, be more agile and and predictable with those. You've walked us through some baseline metrics that you want to set before you launch, things that haven't necessarily been done in the past with programs like our outreach launches over the years. But what does the pilot to scale gate look like? And how do you separate the agent did something from the agent created revenue attributed value? Ray Rike (04:14) Well, let me go to the baseline metrics first, KK. So I think I have four levels of metrics I like to see in any initiative, including the Gentic AI. So one is a productivity metric, and that is outputs per time, you know, whether it's outputs per human hour, outputs per day or time spent per activity. That's what we've been measuring for the last year and a half and AI in marketing and sales. But that's what then you have effectiveness. How effective is my AI enabled process going to be? ⁓ How many desired outputs am I getting versus the inputs? Hey, for every hundred emails my agent sending, how many meetings do I get set up? Right. Then there's efficiency. That's the cost per outcome. And then there's actual ROI, which is outcome value divided by the AI investment. So productivity, effectiveness, efficiency, and ROI. I'm not going to go into detail what that's like for just an SDR program, but at least it gives you a framework and a layer approach to designing those four layers of metrics you need to measure. Mark (05:19) Excellent. All right, let's move into topic three, the benchmarked view, and tell us a little bit about what the data has been telling you and your team at Benchmarkit. And let's go with, guess, a baseline of that. Some of your initial benchmarks that you have been working on are showing AI native companies hitting two to three times higher ARR per FTE. than a legacy SaaS, as one example. From our listeners who are operators inside non-AI native companies that are trying to deploy these agentic go-to-market programs we're describing, how do they close that gap? What are the structural differences they need to address? Not just the tooling, but the operating model as well. Ray Rike (06:02) In the let's be real. It's going to be real hard. And the reason being is a lot of the AI native companies are getting new budget. They're getting experimentation budgets. They're getting budget from labor versus budget from I.T. investments. Right. So I hate to say it, but it's going to be hard. But hey, there's a lot of people out there in legacy says companies that they need to get there. Right. So number one is you've got to be laser focused on number one, the effectiveness. Can AI help you get more conversions? Can they get higher ACV? Can they increase your win rate? And you got to go right to cost per. If AI is not getting you a reduced cost per dollar of new ARR, it's going to be really hard. And honestly, Mark, The hardest part is for me, if it was me and he brought me into a $50 million SaaS company, I would say we got to throw out the old playbook and start from scratch. But I don't have the new playbook based upon years and years of experience. So it's going to be really hard to throw out the old playbook and build the new one. So that's why I bring in someone who's got maybe six, 12, 18 months of experience and an AI first culture. and have them do it with you or hire a third party consultant. KK Anderson (07:22) Wow. And it's quite the conundrum that we're all faced with right now. All of these native SaaS leaders trying to compete with these AI native companies who are just crushing it. Ray Rike (07:33) I mean, when you're talking about your best in class, SaaS companies are doing 600 ⁓ to 800,000 revenue per FTE and Anthropics doing three to four. How do you compete with that? It's a little bit like saying, how did JCPenney compe

General Episode Description: In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of Benchmarkit, to tackle one of the most critical questions in enterprise AI today: how do you actually measure success in agentic AI programs? Ray shares why most AI initiatives are stuck in “pilot purgatory,” the common mistakes companies make when trying to automate broken processes, and why an AI-first mindset requires a complete rethink of data, workflows, and metrics. The conversation also explores how go-to-market teams should define ROI, what benchmarks matter in an AI-driven world, and why traditional SaaS metrics are no longer enough.  What You’ll Learn: Why AI Projects Stall: The real reasons most agentic AI initiatives never scale beyond pilots.AI-First vs Human-First Thinking: How redesigning processes for AI fundamentally changes outcomes.Data Readiness Matters: Why poor CRM data and lack of governance derail AI success.Measuring AI ROI: The new metrics leaders must track to justify AI investment.The Shift in GTM Economics: Why cost structures and efficiency benchmarks are changing fast.Key Topics: “Pilot purgatory” and lack of enterprise-wide AI focusThe importance of data hygiene and enrichment for AI successRedesigning processes with AI at the center, not as an add-onThe rise of vertical AI and pre-built agent workflowsDefining success with leading, mid-term, and lagging metricsCAC ratio vs AI-driven efficiency benchmarks“COGS is the new CAC” and shifting cost structures in AI-native companiesRevenue per employee as a proxy for AI productivityToken consumption and cost predictability challengesBuilding smaller, modular agents instead of large monolithic systemsThe four-layer measurement framework: productivity, effectiveness, efficiency, and ROIGuest Spotlight: Ray Rike Ray Rike is the founder and CEO of Benchmarkit, a leading source of B2B SaaS performance benchmarks with data from over 1,800 companies. He is also the host of the AI to ROI podcast and a founding member of the SaaS Metric Standards Board. With decades of experience as a go-to-market operator and executive, Ray focuses on helping companies move from intuition to data-driven decision-making in both SaaS and AI-driven environments.  Resources & Mentions: BenchMarkitAI to ROI podcastConcept: Agentic AI in go-to-marketConcept: “Pilot purgatory” in AI adoptionConcept: AI-first process designConcept: COGS as the new CACOpenAI Frontier AllianceVertical AI platforms (example: Harvey for legal)Metrics framework: productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI measurement, GTM strategy, and building data-driven revenue engines. Mark (00:31) Welcome to Selling Intelligence. We're joined today by someone who might have had the honor and privilege of calling both a collaborator and a friend. Ray Reich is the founder and CEO of BenchMarket, the industry's most comprehensive source of B2B SaaS performance benchmarks with data from over 1,800 companies. Ray is also the host of the AI to ROI podcast. He's a founding member of the SAS Metric Standards Board. And full disclosure, my co-author on data and diagnosis driven selling, Ray has spent decades as a go-to-market operator, having served as president of Simply Learn, CEO at Higher Mojo, SVP at Moment Feed, and multiple times SVP market and sales and SaaS companies before founding Benchmark it roughly five years ago. And they have a singular mission, give every B2B reoccurring revenue software operator access to data driven benchmarks so they stop flying blind. Today, we're going, well, first off, let me welcome you, Ray. Thanks so much for joining us. Ray Rike (01:43) Thank you, Mark. Sorry that I'm so old that you had it took that long to read everything I've done. Mark (01:47) Exactly. Well, you know what? That's also a good thing because you've done some amazing things throughout your career and you're not that old. So, yes, let me tell you, let's talk a little bit about today and where we're going to go on this podcast. ⁓ What we'd like to do is tackle what might be the most important and for sure most underserved question in enterprise AI right now. How do you actually measure the success of agentic AI programs? And even more specifically, what does that look like for go-to-market functions? We'll dig into what benchmark its data, what is it revealing, where the industry is setting the bar, and what separates teams that are generating real ROI from those stuck in pilot purgatory. Ray, welcome to Selling Intelligence. Ray Rike (02:36) Okay, excited to be here. Let's dive into it. Mark (02:39) All right, so Ray, you've been collecting SAS performance data for years, and now you're turning that lens on AI. From what you're seeing at Benchmark and in hearing on your podcast, what's the core reason most agentic AI programs never graduate from pilot stage? Is it a data problem, a change management problem, or something else? Ray Rike (02:59) I think it's an evolutionary problem. So I did some research with scale venture partners last year about what the state of AI and GTM adoption was. And what we found, Mark, was it was primarily individuals adopting generative AI tools like Clot or Chat GPT to help them with individual tasks. Things like maybe it was an image creation for an ad campaign. Maybe it was email messages for outbound campaigns, et cetera. And the primary benefit was personal productivity. Hey, I can do this much more research quicker for each account, or I can generate this many more campaigns in a month. Now, when we get to process automation, which is really where agentic AI is going to be used, ⁓ we're just at the very beginning there, and we don't have enough experience of actually deploying agentic AI to have a lot of success stories on a production basis, especially the enterprise, because most of the enterprises, and I'm talking about companies a billion dollars and over, I see an average of 20 or more simultaneous AI proof of concepts going on, and they're not really getting the focus of the centralized IT executive team, they're departmental. Maybe it's just customer service or maybe it's just development with a code assisting tool. So my answer is I'm not seeing enough organizational wide enterprise focus on true agentic AI initiatives yet. KK Anderson (04:32) And Ray, welcome to Selling Intelligence. glad you're here. And I just want to jump on top of what you just said there. It seems like the concern would also be that they're trying to put some agentic AI solutions onto maybe processes that should not be automated or were not the right process to begin with. Ray Rike (04:52) of the most common mistakes, and I've kind of built this framework of the variables that help ⁓ indicate success and agentic AI deployments. But one is the data is a mess, right? Think about today for what, 20 years we've been talking about how bad CRM data is and have we cleaned it up? No, we still have s****y CRM data, but the SDR or the AE will say, well, that's not the right information. Joe doesn't work at company A, Joe's a company B or that's the wrong title, right? So a lot of data hygiene, data prep needs to be done. So that's number one. And then to your point, we're thinking like old fashioned business process re-engineering. Well, yeah, maybe we map current state process and we want to map future state process, but we're doing it with a human first orientation and an AI first orientation is fundamentally going to change each step along the way of that process. Quite frankly, you have to identify what data I'm going to ingest, use at the field level for each step, each granular task within that process. And we just haven't re-engineered the process to be optimized for AI centricity yet. And KK, I don't think we're going to until we have a lot of people who have one or two rounds of experience. redesigning a process with an agentic AI first mentality, then then they can do it to third, fourth and fifth time. KK Anderson (06:16) and has that been defined how to have this kind of AI first mindset? Because we've had several people on the podcast talk about this, right? so, and I know I'm going a little bit off of kind of the agenda here, but I'm dying to hear your take on this. When you say AI first mindset versus just a traditional business process mapping, You know, like we're all used to, we all learned in business school, but the data scientists have been doing for decades. Like, what does that mean? What is AI first mindset? talk me through that. Ray Rike (06:54) I wish I could sit here and say, I've done 22 of these. here's here's the playbook. So I don't have the playbook either. I have a lot of ⁓ signals of why it's so difficult. And one of the big signals was OpenAI, what about two plus months ago, formed the Frontier Alliance. And the Frontier Alliance, right, because they said, we're going to get into KK Anderson (06:57) Right. I know it's all new. No one knows. That's what I'm curious. Mark (06:58) Thank you. Ray Rike (07:17) agentic AI, not just generative AI, right? They first of all introduced, I think in January, the five layer cake of the OpenAI Frontier application map. And then they announced that McKinsey, Accenture, Boston Consulting Group, and maybe it was Ernst & Young, are now forming this Frontier Alliance to partner with OpenAI to help their enterprise customers deploy agentic AI. Why? Mark (07:35) Mm. Ray Rike (07:43) because it had been failing. A lot of the open AI projects to really do process automation using AI agents were not successful. So that's a signal, right? And as far as what's the secret, I don't have one other than try to find a consultant or a third party who's done two or three of these in the domain or the area. Let's say it's SDR. Mark (07:58) Thanks. Ray Rike (08:07) I want to

General Episode Description: In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore the human side of leadership, trust, and AI adoption in today’s rapidly evolving business landscape. Sabrina shares her perspective on diversity in leadership, the realities of building a career as a working parent, and why creating an “integrated life” leads to stronger teams and better business outcomes. The conversation also dives into how trust has become the ultimate differentiator in an AI-driven world, and how companies must rethink how they show up as human, credible, and authentic. The episode closes with practical insights on how leaders should approach AI, where it delivers real value, and how to use it as a tool for thinking, not replacing human judgment.  What You’ll Learn: Diversity as a Competitive Advantage: Why different perspectives lead to better decisions and stronger organizations.The Integrated Life Approach: How flexibility and trust improve retention, loyalty, and performance.Human Trust in an AI World: Why authenticity and real human interaction are becoming the new moat.Practical AI Usage: How to use AI for preparation, critique, and efficiency without losing credibility.Leading Through AI Disruption: How leaders can guide teams to experiment with AI while setting the right guardrails.Key Topics: The impact of diversity and inclusion on business performanceSupporting working parents and creating flexible, human-centered workplacesThe myth of “doing it all” and redefining success in leadershipWhy trust is harder to earn in a world of AI-generated contentReal vs artificial experiences in customer interactionsThe role of influencer trust and community platforms like RedditUsing real people and authentic content to build credibilityWhere AI overpromises and where it delivers real efficiencyAI as a tool for critique, feedback, and preparationUnderstanding how LLMs perceive your product and brand through consensus signalsThe shift from SEO authority to AI-driven consensus and reputationGuest Spotlight: Sabrina Parsons Sabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, and a leader with deep experience across sales, marketing, and executive leadership. She is a strong advocate for women in leadership and brings a unique perspective on building resilient organizations, fostering trust, and navigating multiple waves of technological change.  Resources & Mentions: Palo Alto SoftwareLivePlanConcept: AI trust gap and authenticity in digital interactionsConcept: Integrated life vs traditional work-life balanceConcept: Consensus-driven reputation in AI search and LLMsBook: Into Thin Air by Jon KrakauerBook: Superintelligence by Nick Bostrom🎧 Listen now and follow Selling Intelligence for more insights on leadership, AI adoption, and building trust in modern go-to-market teams. Mark Petruzzi (00:31) So Sabrina, you're a strong advocate for women in sales and leadership. In your experience, what do women bring to the sales equation that often gets undervalued? And what does the data actually show? Sabrina Parsons (00:43) Yeah, that's a great question. I think that we've, well, hopefully people have, there's been a lot of data over the years that just shows a few things, I know these days, you know, talking about diversity is, you know, a hot topic and not something everybody wants to hear. But if you actually go and look at the data, Any time you're bringing different viewpoints in, it actually turns out the data shows that that's really good for an organization. That when you have six people who all come from the same background, who went, you know, got similar educations, have the same experiences, you're missing out. You're not getting some of these other alternate viewpoints that... could actually give you different insights and make your company better. So from that perspective, be it women or people of color, people from different cultural backgrounds, every time you have different people in a room, you're gonna win because they're gonna bring different information to the table. And then I think that, you know. Even though it's 2026 and I wish we were in a different place with women in leadership, the reality is that we still live in a world where, you know, there aren't as many women in technology. ⁓ And the numbers just show that and there aren't as many women in technology and leadership. And so women who are there and have made it all the way through, particularly in a leadership role, have probably worked really hard to get there. and probably have some really good insights. From my perspective, one of the things that I think is most powerful and I think can bring a lot of value to a company is recognizing particularly working moms and working parents, but as a working mom, I'm not a working dad, so I won't talk for working dads, that You know, there's a lot of very motivated, super smart women who want to work for a place. They don't want to have to jump from job to job to job. And if you can give them an opportunity to stay in one place, to continue to move up, if you can be the kind of boss that recognizes that there's going to be some peaks and valleys that a woman with young kids might have some issues with my kid is sick, my kid is going to the doctor, but at the end of the day, if you help them with flexibility, not making their job easier, not giving them less job, but giving them the ability to be flexible and do their job when they can, you're actually going to retain women longer. They're going to be more loyal. if, you know, loyalty and retention, we all know is, you know, There's nothing better for your bottom line, particularly in software and tech sales where people are your biggest asset. KK Anderson (03:36) You preach into the choir. Could not agree, could not agree more. I would love to hear about some of your, know, pursuits with women in sales and leadership and would love to, AGS would love to support you in those as well. Really cool. Sabrina Parsons (03:38) Thank you. Mark Petruzzi (03:47) for Sabrina Parsons (03:48) you. I appreciate that. it's been a really, it's interesting. I think when Mark and I first caught up prior to the podcast, we talked about it a little bit, but being a Gen Xer and having grown up in the 80s and early 90s, I am of the generation that watched the women's lib movement, And watched all these really strong women come out of the 70s and early 80s, the Gloria Steinmans, This very powerful. movement and we were kind of fed this idea that like you can do it all women can be super women and you can do it all and I bought it I was like I am gonna be superwoman I am gonna do it all and didn't really think anything of it until I had my first child and that's when like the brakes come on and you're like wait what what does this actually mean? And you know, just this reality that like, wait a minute, this is a myth. Like you can't do it all, right? And there's a reason why very successful men were never expected to do it all. And yet we still have this place in 2026 where there's still a lot of judgment with women as mothers, like, you know, Why aren't you there at drop off? Why aren't you there at pick up? Somehow you're a bad mother and all these kind of, know, guilt woven into, you know, being this working parent and how do you deal with it? And what does that mean? And as I had one child and then two and then my third as I was running the business for me really understanding that my KK Anderson (05:14) Guilts. Sabrina Parsons (05:32) take on this, my approach is very much about leaning into who I am, not leaning into the structure that exists today, which I think a lot of us were still being told even 10 years ago when Sheryl Sandberg came out with her lean in ⁓ kind of autobiography, it was all about leaning into the current structure, right? It wasn't, wait a minute, does that actually work? And for, KK Anderson (05:54) Mm-hmm. Sabrina Parsons (05:59) from for me what's worked and what I like to mentor and what I like to, you know, really. do here at Palo Alto Software is to say that doesn't work and I have what I call an integrated life and my kids are older now and I've got two in college but when they were little that meant bringing kids on business trips with me and my mom would come with me. That meant kids in the office after school or on a snow day. It meant having appropriate places in the office. so that they could have coloring books and homework areas. you know, I mean, we often laugh because we have a very old, ⁓ I think it's a Nintendo PlayStation, but it's a very old one. I don't even know if it's called a PlayStation, but it's a very old one where it isn't actually wireless. The console that the game console, like the player that the kids, the controller that the kids play with is actually plugged into the gaming. console. Well, kids love the old thing ever when they come in. but they always break it because they keep unplugging the controllers because they're like they're charged. And it's like, no, these are old school. And they don't even get that, which is always funny. I mean, from my perspective, that's what I've done for myself and for people here in the company is to say, KK Anderson (06:57) Now Super Mario Brothers. Mark Petruzzi (07:11) Hahaha Sabrina Parsons (07:20) I'm not going to pretend you don't have kids. I'm not going to make you apologize for having kids. I'm also not going to pretend that if you've got a kid who's sick, that you're actually going to be at the office doing any sort of productive work because I made you come in. Like, okay, you can come in and you're not going to like me and you're not going to be productive and you're going to be worried about your kid. And so why don't we treat people like humans and say, you know what, your kid is sick, go home. Be

General Episode Description: In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore how AI is rapidly reshaping buyer behavior and forcing a complete rethink of how companies sell, market, and build trust. Sabrina shares how search behavior has fundamentally shifted toward AI-generated answers, reducing click-throughs and changing how buyers consume information. She explains why this creates new challenges in clarity, especially around the “build vs buy” decision, and why sales teams must now work harder to guide buyers through uncertainty. The conversation also dives into the growing importance of trust, the evolving relationship between sales and marketing, and how organizations can use AI effectively without losing the human connection that ultimately drives decisions.  What You’ll Learn: The New Buyer Behavior: How AI-driven search and LLMs are reducing clicks and changing how buyers gather information.The “Muddy Middle” Problem: Why AI has blurred clarity around what buyers actually need and whether they should build or buy.Selling in an AI World: How sales teams must adapt when buyers are more informed but also more uncertain.Sales and Marketing Alignment: Why tighter collaboration is critical to address buyer confusion and build trust earlier.Using AI Without Losing Trust: Where AI enhances the sales process and where it can damage credibility.Key Topics: Shift from keyword search to question-based search behaviorAI-generated answers reducing traditional website trafficAEO vs SEO: optimizing for AI engines, not just search enginesBuyers arriving more educated but with incomplete or misleading contextThe disruption of the “why change” conversation in salesBuild vs buy vs AI: a more complex decision landscape for buyersMarketing’s role in answering buyer questions upfront and building trustThe risk of poor AI experiences damaging brand perceptionUsing AI for preparation versus customer-facing interactionsTurning AI efficiency into better personalization and human engagement Guest Spotlight: Sabrina Parsons Sabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, a leading business planning and financial forecasting platform. With experience leading both sales and marketing, she brings a unique perspective on how companies build sustainable revenue engines. Sabrina is also a strong advocate for women in leadership and technology, and has guided her company through multiple waves of technological change.  Resources & Mentions: Palo Alto SoftwareLivePlanConcept: AEO (AI Engine Optimization) vs traditional SEOConcept: Build vs Buy vs AI decision-makingConcept: Trust equation in modern salesExample: Customer experience with AI chatbots (Oura Ring case)🎧 Listen now and follow Selling Intelligence for more insights on AI, modern buyer behavior, and building high-performing revenue teams. Mark Petruzzi (00:31) Welcome to Selling Intelligence. Our guest today is Sabrina Parsons, CEO of Palo Alto Software, makers of LivePlan, one of the world's leading business planning and financial forecasting platforms. Sabrina has been the helm at the company, this company that has over four decades of history leading through multiple waves of technology disruption. Before stepping into the CEO role, she ran both sales and marketing, giving her a uniquely integrated view of how companies grow, how buyers decide, and what it really takes to build a revenue engine that lasts. She is a passionate advocate for women in leadership and technology, a thread we'll weave in throughout today's conversation as well. So three topics we'd like to cover with you and with Sabrina today. how AI is reshaping buyer behavior and what that means for how you sell. We've covered that many times on our podcasts already, but we really are excited about Sabrina's perspective and her experiences in that area as well. The second one is why the human element, why trust, story building and storytelling. And relationships are the only sustainable differentiators that we really can build in today's business climate. And third and finally, what sales and marketing leaders must do differently today and how that integrates into the CEO role and also the board of directors. What can the boards be doing to help their sales and marketing leaders evolve in the way that they need to? Sabrina, welcome to Selling Intelligence. Sabrina Parsons (02:13) Great, thanks Mark, I'm really happy to be here. Mark Petruzzi (02:15) All right, let's dive right into topic one. ⁓ Topic one, AI and the changing buyer. So Sabrina, you've described the buyer behavior online as having shifted more dramatically in the last 18 months than in the prior decade. What are you actually seeing? Why does it matter so much for how we sell and how we need to sell in the future? Sabrina Parsons (02:35) that's a great question. And I'm pretty sure as soon as I start talking, all the listeners are going to say, because we've all experienced, I think, a very similar change in how we interact online. In the last 18 months and even more so in the last 12 months, we have all seen the way our interaction on search has changed. particularly with these new AI synopsis that you see at the top of the page. And while there will be articles and sites that are cited in this AI, what's happened is that fewer people are clicking through because they go, they have a question, they type it into Google, and they're typing questions now into Google. used to be that we would type keywords, right? And then you'd see what happened. And now people are typing questions into Google and then the or whatever search engine, but, Google still probably the most used. And then what they're getting back, it scratches the itch for the most part. And so they're getting this information and then maybe they're moving on, right? So that's one huge change in behavior and we're all seeing it, right? You have interacted and chosen not to go forward because your question is answered or you found what you need. ⁓ So that new way that we're getting... all of this information displayed, it means fewer click-throughs, and so companies that are selling have to deal with that. The other thing is that search engines are really leaning on and preferring when you can put content out there that actually gives answers, because that's what people are looking for, right? It's how do I, those types of questions, how do I do this? How do I sell? How do I market? How do I, all of these how do I's, that's what people are doing. ⁓ And then the other thing that I think we all know is that people are for the most part, very familiar with LLMs, right? With all these AI chat box. And many people are using them instead of search engines, which I will say if you are, think about it because it's a very expensive search engine. It uses a lot of energy to do an AI query. And every time we're using AI when you could just use a search engine, we're wasting energy. So it's something that, you know, not everybody always knows, but there's an appropriate use for AI, but it doesn't matter, right? Behavior has changed, and we're all trained now in this new behavior. And it feels like it's just been like instant, like in the last 12 months, because changing behavior used to be a huge thing, right? From a sales perspective, people like you would teach salespeople how to help change behavior. And like we have seen behavior change just so quickly this time around. KK Anderson (05:23) overnight. so how does that change how we sell? Sabrina Parsons (05:27) So that's a great question. I mean, it has to, right? Because when you're selling, used to be that your marketing team could just make sure like, are search results going to come up on first page versus second page? And if not, let's just buy pay-per-click ads and make sure that they come up. in those results. And it's like that doesn't work anymore. So a lot of what you have to do in terms of how to change how you're selling is address this new way that content is consumed. So you really have to think through, am I providing answers? And it's not just content that fits keywords, right? It's content that's actually giving answers. And then in the way you format your content, if you want to be AEO forward, right? It used to be just SEO, search engine optimized. Now we're AI chat bot optimized. If you want to be AEO forward, you really have to rethink how you're putting your content together, what kind of sort of synopsis you have that's easy for AEO to grab. Do you have the right FAQ schema? It's just a, you know, it's a different way that the LLMs are crawling through information. And so you just have to make those changes. KK Anderson (06:46) Right. And I'll just add to that. It's all about that trust equation. Right. And so that's what our prospects for all of us, you who are running businesses and running sales organizations, they're all looking to, they're looking for value and that value is what's driving trust. And that trust equation ⁓ is going to what finally converts. And so when your buyers do get on the phone with you finally, They're going to be so much more educated. going to know so much more. They will probably have an LLM, create a table stack ranking, the three top options to solve their problem. And so they're going to be so much more educated when they get on the phone with your team as well, which is another, when you get sort of that sales process behavior that it just, all the changes at top of funnel are filtering down. into that as well. Everything changes. Sabrina Parsons (07:37) and I think that's important, right? And salespeople know this because they're getting confronted. It's like they used to have their process, the information, they've done their homework on the prospect. And now you have to be prepared to understand what are they seeing i

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson continue their conversation with Sunil Rao, founder and CEO of Tribble, diving deeper into SaaS fatigue, agentic execution, and the challenge of scaling institutional knowledge in enterprise sales. Sunil breaks down how AI agents are reshaping the way work gets done by becoming the interface across systems, eliminating the need for constant tool-switching, and enabling teams to operate from a single layer of intelligence. He also shares how modern GTM teams can capture and scale expertise across conversations, documents, and internal knowledge to improve performance over time. The discussion closes with a look at the human side of selling, where trust, collaboration, and real customer engagement remain irreplaceable even as AI automates more of the workflow.  What You’ll Learn: SaaS Fatigue and the Shift to Agents: Why the future interface is not more tools, but a single AI layer that connects everything.Agentic Execution in Practice: How AI can capture context across calls, RFIs, and RFPs to generate smarter, more personalized responses.Scaling Institutional Knowledge: How to turn tribal knowledge, conversations, and documents into a usable system of intelligence.The Failure of Static Content Systems: Why traditional enablement platforms fall behind the speed of modern business.Human + AI Collaboration: Where automation should take over and where human judgment, trust, and relationships still win.Key Topics: “Kiss your apps goodbye” and the rise of agents as the new interfaceEliminating tool-switching and browser tab overload for GTM teamsCapturing context across the full sales lifecycle, not just at the RFP stageUsing AI to coach reps in real time during customer interactionsBuilding knowledge graphs from calls, documents, and internal conversationsDenoising and validating data from sources like Slack, Gong, and CRM systemsWhy knowledge bottlenecks exist due to limited subject matter expertsThe limits of traditional enablement programs and static content librariesDesigning AI systems with humans in the loop for approval and quality controlReallocating 30% of seller time from admin work to customer engagement Guest Spotlight: Sunil Rao Sunil Rao is the founder and CEO of Tribble, an AI-native platform that helps enterprise sales teams automate and optimize go-to-market workflows. With a background as an engineer at SAP and a leader at Salesforce, Sunil brings a unique perspective on both the technical and human sides of enterprise selling. At Tribble, he focuses on building systems that scale knowledge, improve response quality, and enable teams to operate more efficiently with AI.  Resources & Mentions: TribbleConcept: Agentic workflows in go-to-marketKnowledge graphs for sales and GTM intelligenceSaaS consolidation and interface shift to AIThe Hard Thing About Hard Things by Ben HorowitzSuperintelligence by Nick BostromConcepts: “SaaS fatigue” and “tribal knowledge” in enterprise organizations🎧 Listen now and follow Selling the Cloud for more insights on AI-driven GTM strategy, enterprise sales transformation, and the future of work. Mark Petruzzi (00:31) So Sunil, let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and unused platforms. If you built a company in the enterprise software space going right at all of that overflow, how did you design Tribble to be part of the solution rather than be another product out there that's part of the problem and the challenges? Sunil Rao (00:54) I think from the very early days, one of the things we thought about deeply was, hey, where is this all going? If I think for two, three, five years, what do we think happens? And it was very clear to us that there's a consolidation that's going to take place across where people want to go to get their information. when we see what was happening with ChatGPT and you think about how this kind of AI can be pervasive across systems, this is one of the things I was telling someone recently. If you go back on the internet, you go to the Wayback Machine, which is a website that allows you to go back in time, you can go see the 2023 December page for Tripple. It says, kiss your apps goodbye at the very top. Say hello to agents. And that, I think, was very indicative of, this is what's going to happen. We probably did that message too early because no one knew what an agent was in 2023. But I think that's where we are right now, right? It's like, hey, there's this new interface, right? I can talk to an agent or I can talk to software and I can give it access to all the other systems I work with. So I kind of don't need to go to all those systems again, right? I can do the work through this proxy. And the way that we always describe it is like in the future, you know, when you onboard a new employee, what do you do? You say, here's your license to system one, system two, system three, system four. And they're sitting on their chair and their browser tabs and they're swiveling from one to another, to another, to another. That kind of all goes away. So I think when I think about SaaS fatigue, think agents actually are going to change and become the interface. And Trivel, for us, when we think about go-to-market technology, we want that to be the interface when we think about the respond process and the engage process. That's our bet. And underneath the hood, we have many systems we integrate with. But I had a prospect ask me this the other day. They're like, hey, if we're using your tool, do I need to go to these other systems? And the short answer is no, you don't. Get everything you need right over here. KK Anderson (02:35) So walk us through like what an agentic execution actually looks like in practice. So like when a sales team sends triple an RFP, what's happening behind the scenes? Like how much is automated versus augmented, if you will. Sunil Rao (02:49) Yeah, so I'll give you two examples, KK. I think one, let's think about a company that responds heavily to RFPs and that's a big portion of their business. The RFP coming to you isn't the first point of contact with the customer, right? And depending on the size of the organization and how big this engagement is, it might be something more like, hey, we've had an initial call with the team and they shared with us that they're going to issue an RFP. So there's some discovery being done. We learned some requirements. We learned some players at the table, the different business units that are relevant here. Fast forward a week, another call takes place. Different team members at both organizations are on a call. Information is shared. Then you get to another call and then they issue an RFI, which is the precursor to the RFP. So it's one document that gets sent over and then you got to answer a bunch of questions. Then you finally get to the RFP, which then ends up becoming a bigger proposal. But we think about the journey across all these touch points as opportunities to collect context. So one of the things we do is we show up on the call for each of these touch points. We collect context. We coach the folks live on the call on what data to collect. and how to think about this so that when it comes time to build the response, it's contextual on all the data we've collected for this specific prospect, but every other conversation we've had and where we've won bids and where we've lost them. And that way we can see, historically, when you've answered no to this question for this type of company, you've lost the deal. So one of two things, either explain you can do it because it's on your roadmap or actually put it on your roadmap. Right. And these are the kinds of insights we can glean because we're integrated to the the systems behind the scene, as we come across these insights, we can go write the data back directly. The agent will go and update a ticket in JIRA, or it'll go make an update in Salesforce directly. And it's done throughout the journey, throughout the process. So that's kind how we think about it across the lifecycle. Mark Petruzzi (04:30) that's excellent. Excellent. So let's go to topic three here, scaling institutional knowledge. We use this, the term kind of tribal knowledge and a lot of the work we do in engendric space ourselves. So yeah, let's dive into that. One of the most interesting things about Tribble, that it's not just about speed, it's about scaling the... the expertise, scaling the process, making those processes better over time as well. You've described the problem of a limited number of experts having the necessary knowledge. In your experience at Salesforce and now at Tribble, why is knowledge scaling such a massive bottleneck in most enterprise organizations, particularly within their sales function? Sunil Rao (05:15) Depending on how big the organization is and what products you sell, historically for me, one of the things that I've experienced firsthand, when you're selling a complex product or you're selling into a vertical where the business processes are very specific and non-standard and it's not something everyone knows, you usually will have a gap in terms of the understanding of the field team and what it is that the customer wants. So how do you speak the language of the customer is always a term that we used a lot in my career. And whether you're in financial services, health, whether you're in CPG, retail, manufacturing. There are processes that are very specific to that industry. So how do you enable the field teams to know what it is the customer's pains are and what they need? And how do you build the right software to meet those needs? So I think that ends up in, thinking back five, 10 years ago, how do you scale that within a company? Well, you create these enablement organizations. You create enablement programs. You take everyone to Vegas for kickoff, and you show them 800 bajillion

In this episode of Selling Intelligence Podcast, Mark Petruzzi and KK Anderson sit down with Sunil Rao, founder and CEO of Tribble, to explore how AI is reshaping enterprise sales, go-to-market execution, and the future of software itself. Sunil shares why AI-driven productivity alone is no longer enough to create advantage, how the rise of agents is changing what software should do, and why trust, personalization, and institutional knowledge are becoming even more important in a world flooded with AI-generated noise. The conversation dives into the productivity paradox, the coming consolidation of fragmented SaaS tools, and the shift from software that assists humans to systems that can actually take action on their behalf.  What You’ll Learn: The Productivity Paradox: Why AI makes everyone faster at the same time, raising the bar instead of creating instant advantage.AI and New Work Creation: How efficiency gains in one part of the workflow can create new review, oversight, and decision-making work elsewhere.Differentiation in an AI World: Why personalization, timing, and relevance matter more now that everyone has access to the same tools.From SaaS to Agents: What separates AI-assisted software from agentic systems that can actually do the work.Trust in Autonomous Systems: Why transparency, confidence, and clear decision logs are critical when AI operates inside core business systems.Key Topics: The treadmill problem in modern sales productivityWhy AI has upgraded everyone at the same timeThe flood of low-quality outbound and the need for precision engagementUsing digital exhaust and customer signals to guide better sales conversationsWhy traditional scaling models relied on people because software could not solve the problem yetHow fast-moving foundation models are changing product designThe coming consolidation of SaaS point solutionsWhy the future interface may be lighter, with more approvals and fewer manual workflowsBuilding AI-native products that can evolve with each new model releaseReducing SaaS fatigue by designing for orchestration, not more app sprawl Guest Spotlight: Sunil Rao Sunil Rao is the founder and CEO of Tribble, an AI-native platform built to help enterprise sales teams scale knowledge and automate critical go-to-market workflows. Before founding Tribble, Sunil began his career as a software engineer at SAP and later held leadership roles at Salesforce, including GM of Consumer Goods. Tribble was founded in 2023 and has quickly gained traction for helping companies automate RFP responses and improve GTM efficiency with AI-native workflows.  Resources & Mentions: TribbleSalesforce Ventures generative AI fundRFP automation and response workflowsAI agents versus traditional SaaS applicationsSaaS consolidation and platform orchestrationThe role of trust and transparency in AI adoption🎧 Listen now and follow Selling Intelligence Podcast for more conversations on AI, modern go-to-market strategy, and the future of enterprise sales. Mark Petruzzi (00:31) Welcome to today's episode of Selling Intelligence Podcast. I'm thrilled to welcome Sunil Rao, founder and CEO of Tribble, an AI native platform that's fundamentally changing how enterprise sales teams scale knowledge and automate critical go-to-market workflows. Sunil's journey has been fascinating. He started as a software engineer at SAP. moved into leadership roles at Salesforce, including and general manager of consumer goods, and then founded Tribble in 2023. Tribble was quickly added to Salesforce's ventures, $500 million generative AI fund, and has since revolutionized RFP automation, helping companies like Clary, Sword Health, and others slash response times by up to 80%. Today we're exploring a critical challenge facing every sales leader. AI is making us more productive, but the bar keeps rising. It's like running on a treadmill at full speed and just when you your stride, the incline keeps going up. How do you stay ahead when everyone else has access to the same productivity gains? We're gonna focus on four critical themes. The productivity paradox, why AI-driven efficient isn't enough to win anymore. From software to agents, building AI that actually does the work, not just assists, scaling institutional knowledge, the hidden competitive mode in enterprise go-to-market, and the human element, where AI should take over and where it must step back. Sunil. First off, we're really happy to have you here. Thank you for taking the time with us and welcome. Sunil Rao (02:10) Thanks for having me. It's nice to be with you all. Mark Petruzzi (02:12) Excellent. So topic one, the productivity paradox. Let's start with what you have called the treadmill problem. Every sales team now has access to AI tools, chat GPT, co-pilot, all these niche engagement and enablement platforms. And all sales teams are getting more productive, or at least the ones that are investing in this. But here's the thing, if everyone's running faster, you're not actually getting ahead. You're keeping up with the pack. And worse, buyers' expectations are rising because they know that you have these tools. So how do you think about this productivity paradox? Sunil Rao (02:47) Productivity paradox, it's interesting because I think there's a couple of ways that I like to think about it. You obviously have this tremendous technology. It's almost magical. It's been distributed to everyone almost simultaneously. And they're all able to see how much productivity it brings into all aspects of their job. But I back to beginning of when we started Tribble, and this is when Chat GPT has just come out, November of 2022. And everyone had that aha moment of, whoa, this thing can write coherently for such a long time. It can actually write code. It can write snippets of code. And it just started to become a way for you to use in your workflow versus going to Google, searching for information. This thing can synthesize knowledge. So when you look at that and that impact, It already was a tremendous time saver for a lot of smaller jobs. But I think what's been going on and what's been happening over the last few years with these foundation models getting better and better, it gets to the point now where these systems can run for hours on end and complete much more complex tasks. And that's where it's more interesting where, you know, what was not possible to solve with software three years ago. is possible today. And that's where agents come in and everything comes in. it's interesting because like you have that happening in one side and it's really magical technology. But then at the same time, you kind of create new work. when you have access to this technology, because now everyone's a creator. And I see this a lot in the engineering side. Everyone's writing more code, and then it's the question of who's reviewing it. If everyone's writing more content to go in documents, who is doing the human check? So you have this trade-off of, yes, there is efficiency in one part of the process, but you end up creating some work elsewhere. So I think it's the paradox, because it actually changes the distribution of where work is being done. KK Anderson (04:30) Really, really interesting. So when we think about it from, you know, a sales or revenue perspective, right? It's, you know, for, for so many years, it was, do you have this Salesforce CRM? Do you have this outreach, you know, program set up? Do you have this automation set up? And it was, you were always running to keep ahead and to keep up to pace with all of the different technologies that were available. And that was just sort of table stakes. Right? And now with AI, as you just said, like everybody has it. And so now it's how you use AI is, is, and how you become a, differentiator using AI is the new game. Because otherwise it's this, we, you know, ⁓ as Doug Landis, one of our good friends and colleagues says is we're in a culture of sameness right now. Sunil Rao (05:15) Mm-hmm. KK Anderson (05:16) an era of sameness, I think is what he says. So talk to us a little bit about that. So now here we are, we all overnight got Chappie, GBT and these amazing programs. How do we differentiate ourselves in this world of AI? Sunil Rao (05:30) it's an interesting way to think about it, right? It's almost like everyone got upgraded, but exactly to the same level. So then how do you differentiate is the It's how do you stand out from the pack? And, you know, and I take the example of outbound and emails. Like I think what's happened, it's both a gift and curse. KK Anderson (05:37) Yes. Sunil Rao (05:45) I mean, I'd it's more of a curse because now there's so much garbage when it comes to outbound, right? In terms of mass generation of emails that are not personalized, that are not targeted. And I still think that the age old, you know, what makes you really good about that style of top of the funnel engagement is when you are very personalized and targeted. think that just actually gets even more amplified as an important way to stand out, right? Don't, don't try to sell something to the masses. Really think about what signals. indicate that this may be a buyer that's interested and engage with them on the journey at the right time becomes way more important. Because otherwise, you're just feeding into the sea of noise that's being generated because we have these tools that can mass create this content. So I think there's that aspect of it. How can we be much more tailored on the engagement side? And I think about it at different parts of the funnel. For us at Tribble, we think deeply about this problem. when we talk about our customers using our products and how they engage with their customers. So we look at it from two sides of that coin. Mark, you'd shared our respond product, which is all about responding to RFPs, responding to customers. You have to be very particular about what it is you do as a business

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 Learn Why 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 because It'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 say KK Anderson (03:09) Yes. 1,000. Mark Petruzzi (03:17) Excel. you KK 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) Thank Mark 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 gotta get good at telling stories on the Doug 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. So Imagine 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 the things 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, righ

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 Landis Doug 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 a Doug 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 wh

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 Poulos Glenn 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 of what 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 or KK 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 the you 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, I I 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 before where lost like a manufacturer's gun direct Glenn 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 mi

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 mastery Key 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 leaders Guest Spotlight: Glenn Poulos Glenn 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 firms with 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 buy Right. 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, so or 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? Rig

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 Baumgarten Jason 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 of claiming 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 not if 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?

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 Baumgarten Jason 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 what separates 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 have thought 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 deeply interested 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 with Mark 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 into Jason Baumgarten (07:15) Sure. You know, 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 w

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 Castleman Cherilynn 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 intense change. 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 see in 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 that the 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) human Cherilynn 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 meaningful outreach, 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) and KK 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 make to 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 vers

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 Castleman Cherilynn 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 of B2B 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 up And 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 me KK 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) Thank Cherilynn 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

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 growth Key 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 models Guest Spotlight: Mark Roberge Mark 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 to a 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 is You'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 and Mark (04:45) Thank Mark 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