Selling Intelligence (formerly Selling the Cloud)

Mark Petruzzi, KK Anderson
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Selling Intelligence is the evolution of Selling the Cloud and designed for revenue leaders who are navigating the AI era. Hosted by Mark Petruzzi and Kristin "KK" Anderson, the show brings candid conversations with C-suite leaders across sales, marketing, and customer success on how AI is reshaping the way companies grow, sell, and compete. From agentic GTM strategies to AI-powered pipeline and revenue execution, each episode focuses on what’s actually working and how leaders are turning intelligence into performance. If you’re responsible for growth and trying to lead through the fastest shift in go-to-market we’ve ever seen, this podcast is for you.

  1. 2d ago

    Ep. 135 - The Trust Recession, the Death of the BDR, and the Return of the Full Cycle AE with John Tecce - Part 1 General Episode Description:

    In this episode of Selling Intelligence, John Tecce, Vice President of Growth at 2X, joins Mark Petruzzi and KK Anderson to explore why traditional digital outbound is losing effectiveness and what today’s sales organizations must do instead. John shares why B2B selling is facing a “trust recession” fueled by AI-generated communication, rising outreach volume, and declining buyer confidence. As inboxes become saturated and automation reaches its limits, he argues that sales leaders can no longer rely on activity metrics or volume-based prospecting to generate predictable pipeline. The conversation also examines why 2X intentionally built its revenue organization without BDRs, why the full cycle AE is becoming increasingly important, and how timeless sales fundamentals like relationship building, trust, community engagement, and human connection are becoming competitive advantages once again. Mark, KK, and John discuss why quantity is no longer the best predictor of sales success, how experienced sellers can combine AI with classic sales principles, and the mindset required for modern account executives to thrive in an increasingly uncertain market. What You’ll Learn: Understanding the Trust Recession: Why AI-generated communication and digital overload are making buyers increasingly skeptical of outbound sales.Why Digital Outbound Has Changed: How years of automation have created more noise than opportunity and why quality now matters more than quantity.The Return of the Full Cycle AE: Why reducing handoffs creates stronger buyer relationships, better accountability, and more consistent revenue growth.Community Over Cold Outreach: How creating value before buyers enter an active buying cycle builds long-term trust and pipeline.Modern Sales Competencies: The mindset, adaptability, and relationship-building skills today’s sales professionals need to succeed.Key Topics: The trust recession in B2B salesAI-generated communication and declining buyer trustOutreach saturation across email and LinkedInWhy digital outbound is producing lower returnsThe evolution of marketing automationActivity metrics versus quality metricsWhy quantity is no longer the primary sales KPICreativity in outbound prospectingThe VITO letter and direct outreachOld-school sales techniques in modern sellingThe decline of the traditional BDR modelWhy 2X operates without BDRsThe return of the full cycle account executiveReducing buyer handoffs throughout the sales cycleBuilding credibility before the first meetingCommunity-driven pipeline generationBecoming a trusted connectorCreating value without expecting immediate meetingsThe importance of human connection in AI-enabled sellingPresence of mind and relationship mappingAdapting to constant market changeSeparating assumptions from reality during the sales processAI as an enabler, not a replacement for sales fundamentalsGuest Spotlight: John Tecce John Tecce is Vice President of Growth at 2X, where he leads half of the company’s revenue organization with a team of full cycle account executives operating without a traditional BDR model. A third-generation sales professional, John combines classic relationship-driven selling with modern AI-enabled execution. He has become a leading voice on the future of go-to-market strategy, helping organizations rethink outbound sales, trust building, pipeline generation, and revenue operations in an increasingly AI-driven marketplace. Resources & Mentions: 2XKnownwellSixth SenseMarketoSalesforcePredictable RevenueGary VaynerchukLinkedInBob KellySelling to VITOHope Is Not a StrategyThe Go-GiverAGS Academy🎧 Listen now and follow Selling Intelligence for more conversations with today’s leading revenue operators, sales executives, and GTM innovators. Subscribe wherever you get your podcasts. Mark Petruzzi (00:28) Welcome to Selling Intelligence. Our guest today is John TC, Vice President of Growth at 2X, the firm that just its declared itself the first human agentic go-to-market services firm. John runs half of 2x's revenue organization, a team of 12 full-cycle AEs with no BDRs. And he is third generation sales who has spent the last year watching the tools that built his career stop working at scale. Two X recently announced its acquisition of known well, and John has a front row seat to where the market is heading. KK Anderson (01:05) Personal note before we start, when John, Mark and I spoke in preparation, we landed on the same diagnosis from two very different directions and he is living it inside his own team and we are diagnosing it with clients every week. The instinct everyone has is to add more activity. John's answer is the opposite and that's what makes this conversation well worth your time. Mark Petruzzi (01:30) Here are the topics we will cover today. In part one, three things: why Digital Outbound has hit a wall and what that means for every CRO. The death of the BDR and the return of the full cycle AE. And old school fundamentals through new mechanisms, how the best reps apply forever concepts through AI-enabled execution. Then in part two, which drops next week. We will get into two additional topics. What human agentic go-to-market actually means when you combine human agents and tech and the operating model of rethink: what to own, what to outsource, and how to decide. John, welcome to Selling Intelligence. John Tecce (02:13) Great to be here. KK Anderson (02:13) We are thrilled to have you. Okay, let's jump right into it. So much great stuff to cover today. And let's start with this idea of the trust recession and why digital outbound has hit a wall. And we bonded on this topic during the prep session, as I indicated in our introduction. as soon as I said, I said it, the trust recession, which by the way, I picked that up from Bob Kelly, who's the chairman of Sales Management Association. So all credit to him. You immediately reacted to it and we both totally agree that we are in a trust recession right now. And so let's start with you telling us like, what does that mean for you? What does it capture for you? Like, what are you seeing on your team and across your clients that makes that a phrase that really resonates for you? John Tecce (02:58) thing that really sticks out to me is the utilization of AI in all forms of communication that has led to a skepticism on the receiving end. How real the text that I'm receiving, whether it's a LinkedIn post or a message or an email or what have you, actually is from the human being versus how much of it was went through the AI car wash. And inherently, if you think about most of these models are ultimately trying to regress to the mean in terms of what they generate. And so you're ending up with this. copy paste of of phrasing and ways that things are said that strips out a lot of the human nature of it. And I think as a result, as B2B professionals, and when I say B2B professionals, that's under the whole go-to-market lens, everything from BDR to AE to CSM to executive, et cetera. there's the evergreen phrase of people buy from people who they know, like and trust, but it's kind of harder to get to know and trust them if you you have to filter everything they send you through the lens of like how much of this, you know, is really them versus how much of it is Chat GPT or or Copilot or or Claude that they're running these thoughts and communications through. I'm a huge user of AI, to be clear, I'm very AI forward and I encourage my team to be the same. but when you come to the trust recession, I think a lot of it has to do with just a a distance now that exists between two people and the communication between KK Anderson (04:10) and a lot of the noise that it has created, right? It's almost deafening. There's so much noise out there in the market today. It's insane. John Tecce (04:19) It's it's insane. the BDR outreach surge that we've seen in particular, whether it's again BDRs or otherwise, but Sixth Sense put out some research very recently that the baseline touches per contact was was about 17 in 2024. Not that long ago. We're in the middle of 2026. and this research came out a couple of weeks ago. We're now at 34 touches per contact. So it's doubled, number one. Number two, on top of that. KK Anderson (04:39) Ugh. my poor inbox. John Tecce (04:44) It ex well and inboxes, right? So what they found in that research as well was social in particular is the the biggest source of that growth. It went from about four and a half touches in twenty twenty four to now over ten in twenty twenty six. And so your email inbox is already hurting and and kind of getting hammered. And now, LinkedIn kinda used to be the okay, well if you send a a a really strong LinkedIn connect request or a really strong in mail, you had a good chance now But what we're seeing is the volume and just the increase in the noise in in part due to the ability to do it from a scale standpoint, an automation standpoint. but also, you're finding a lot of the inbox tools, both on the LinkedIn side and email, are becoming more intelligent to filtering out that noise. And so it's that's being countered with more noise and just more and more, more, more, and more, and we're at a point where the math just just doesn't math anymore. Mark Petruzzi (05:29) So John, you have been selling a long time now s so you definitely remember when digital outbound was still relatively clean. What has changed at the structural level and how does it show up in the numbers you're watching every day right now? John Tecce (05:44) Yeah, I think you know when I started my career was when marketing automation in its in its current form was really taking shape. my first role out of school was was at Rico for a couple years and helped them launch at the sales level launch Marketo as an example. And it was like super cool that you could put in this template and you could pull and have it personalized by first name and by compan

    Ep. 135 - The Trust Recession, the Death of the BDR, and the Return of the Full Cycle AE with John Tecce - Part 1 General Episode Description:

  2. Jul 8

    Ep. 134 – Frontier AI: What the Highest-Performing Sales Organizations Are Doing Differently with Bob Kelly - Part 2

    General Episode Description: In Part 2 of this conversation, Bob Kelly, Founder and Chairman of the Sales Management Association, joins Mark Petruzzi and KK Anderson to examine why AI adoption often fails even when organizations invest in the right technology. Building on research across 111 sales organizations, the discussion moves beyond AI tools and into the operational systems required to create measurable impact. Bob explains why automating a broken sales process only accelerates poor execution, how leaders should distinguish between path problems and insight problems, and why CRM adoption continues to struggle when technology creates work for sellers without delivering value back to them. The conversation also explores the three organizational levers shown to drive AI adoption: leadership endorsement, training investment, and AI proficiency in hiring criteria. Bob shares why AI implementation requires clear decision rights, governance, and process ownership, while Mark and KK examine how AI may finally help revenue organizations break down traditional departmental silos. The episode closes with a candid discussion about AI anxiety, the changing role of sales managers, and why experimentation may become one of the most important leadership practices in the future of sales. What You’ll Learn: Process Before AI: Why automating a broken sales process only creates bad outcomes faster and at greater scale.Path Problems vs. Insight Problems: How leaders can distinguish between work that follows a defined decision tree and work that requires judgment.CRM Data and Seller Productivity: Why salespeople rationally avoid systems that consume selling time without helping them sell.The Three AI Adoption Levers: How leadership endorsement, training investment, and AI-focused hiring criteria influence adoption.AI Governance and Decision Rights: Why organizations must define who builds, owns, instructs, and controls AI agents.Key Topics: The 27-point performance gap between frontier AI adopters and other sales organizationsGeneral-purpose AI, agentic tools, and sales-specific applied AIWhy having ChatGPT open does not mean an organization has adopted AIAI as an amplifier of existing sales processesPath problems versus insight problemsProcess automation and AI-powered decision guidanceWhy “bad fast” can be worse than “bad slow”Using AI to capture CRM data from emails, calls, notes, and conversationsSpeech-to-text technology and sales data captureWhy most CRM implementations fail to create value for salespeopleDocumenting new customer, expansion, and cross-sell sales processesCapturing effective selling messages and value propositionsProcess flexibility and salesperson decision-makingLeadership endorsement as an AI adoption driverThe 36-point AI adoption gap linked to leadership endorsementTraining sales teams to use AI effectivelyAdding AI proficiency to sales hiring criteriaAI governance, security, and decision rightsWho owns and controls AI agents inside an organizationAI’s potential to break down departmental silosCross-functional AI workflowsThe future skills of sales managersAI anxiety and uncertainty across middle managementExperimentation as a sales leadership disciplineGuest Spotlight: Bob Kelly Bob Kelly is the Founder and Chairman of the Sales Management Association, an independent professional organization focused on advancing sales leadership and management effectiveness. Through research, education, and industry events, Bob works with sales leaders to apply evidence-based practices to sales productivity, process design, technology adoption, and organizational performance. He also serves as an adjunct faculty member at multiple business schools and brings an academic, research-driven perspective to the changing role of sales management in the AI era. Resources & Mentions: Sales Management AssociationMicrosoftChatGPTMicrosoft CopilotZapierCRM platformsAgentic AIApplied AIAI governance and securityMiller HeimanTony RobbinsRoman history and leadership researchSales Management Association AI adoption researchKey Takeaway: AI adoption is not primarily a technology problem. It is a leadership, process, and organizational design problem. The sales organizations creating meaningful AI advantage are not simply buying more tools. They are documenting how selling actually works, defining where human judgment belongs, investing in AI skills, and giving leaders clear ownership over how AI is deployed. Technology will continue to change. The organizations that build the discipline to experiment, learn, and redesign their sales systems will be the ones best positioned to adapt. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, sales leadership, revenue operations, and the future of go-to-market execution. #SellingIntelligence #AIforSales #SalesLeadership #RevenueOperations #AgenticAI #AppliedAI #SalesManagement #ArtificialIntelligence #SalesProcess #SalesEnablement #GoToMarket #RevenueLeadership #SalesStrategy #AIAdoption #FutureOfSales Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:31) And I'm KK Anderson. Every week we bring you conversations with operators who have been in the room and come out with something worth using the very next day. Mark Petruzzi (00:40) Our guests today just completed a benchmarking study of 111 sales organizations. And what on? AI adoption. The findings are not what most leaders expect. Only 4% of firms have no one using AI at all. But only 9% qualify as what the research calls frontier adopters. And those 10 firms are outperforming the rest of the field. By on average twenty-seven percent is points on sales objective achievement, nineteen points on individual quota attainment, and nearly double the rate of sufficient selling capacity. The question this research forces is not whether your team is using AI, it is whether they are using it in a way that actually moves the numbers. KK Anderson (01:26) Bob Kelly is founder and chairman of the Sales Management Association, a global, independent, professional organization serving more than ten thousand sales leaders. He has no product to sell and no platform to push, which is exactly why this data matters. Welcome to the show, Bob. We're happy to have you. Bob Kelly (01:43) Thank you so much for having me. It's so nice to be with you. Mark Petruzzi (01:46) So Bob, your research covers over one hundred companies. But before we get into what leaders are doing, give us the honest snapshot. What is the typical sales organization actually doing with AI right now? And how does it compare to what people say they're doing and what the media outlets are saying people are doing as well? Bob Kelly (02:07) the word I would use is dabbling. the typical sales organization is dabbling with AI as opposed to integrating it in a pervasive and sort of formal way in the work streams in the firm. this is a reflection of the uneven nature of how AI affects work in general and including sales work. But the interesting thing is to understand just how few firms are ignoring AI or are untouched by AI. When we look at the adoption curve and history of other technologies, CRM, for example, or other platform technologies, they've taken much, much longer to gain a foothold in most organizations. We're seeing very fast pickup in The use of AI, even if that use is uneven. KK Anderson (02:55) So Bob, when we had our our preparation conversation for this podcast, you used a phrase that I hadn't heard anywhere else and I thought it was fabulous. You said you said there's a lot of machine stench. Right. So walk us through like what is that and why is it showing up so broadly in this research? Bob Kelly (03:07) Machine Yes. Well how is Great term, isn't it? I was just about to think of that term when I heard someone else use it. So I've naturally adopted it as if it were my own, but it is plenty descriptive, right? And I think we all have encountered AI generated content. I mean, the more common term is slop. We see it in social media, but we also see it in our inboxes, we see it in work product within KK Anderson (03:15) It is. Bob Kelly (03:39) the companies that we work for. and its problem is that it represents an inauthentic product. And so this when used inappropriately or i in the wrong context actually I believe does more harm than good. it communicates sort of in auth authenticity rather than clarity and equality. KK Anderson (04:00) Everyone AI it's like AI gave everyone a on the road and no one can move. And everyone sounds the same. So it's figuring out how do you take that superpower and that super intelligence and leverage it in a way to create differentiation rather than Bob Kelly (04:01) We want Yeah, just You know, I KK Anderson (04:15) than the stench of sounding the same, Bob Kelly (04:18) I think the mistake so many make is that they're using AI to substitute for their own voice or work product. And when that happens, ⁓ they're pointing out their own superfluity. do we need a human if we're just gonna have machines generate communication? so I think when used appropriately, we use it to augment our abilities, our voice, our productivity and when we use it poorly we've we make the mistake of y substituting a machine generated product for something that we should have more say in. Mark Petruzzi (04:51) So, Bob, you mentioned in the study that only four to six percent of companies are avoiding AI entirely. That actually concerns me that, there is everybody's diving in. And, only a very small percentage are not. but when it really comes down to it, there's still a huge disparity between those frontier adopters, as you described, and the laggers, the rest of the the Bob Kelly (04:52) Yeah. Mark Petruzzi (05:17) hack is that the gap between the two of them growing and and how fast? How fast is that growing and changing? Bob Kelly (05:27) Well, it the an

    Ep. 134 – Frontier AI: What the Highest-Performing Sales Organizations Are Doing Differently with Bob Kelly - Part 2

  3. Jul 1

    Ep. 133 – Frontier AI: What the Highest-Performing Sales Organizations Are Doing Differently with Bob Kelly - Part 1

    In this episode of Selling Intelligence, Bob Kelly, Founder and Chairman of the Sales Management Association, joins Mark Petruzzi and KK Anderson to unpack the findings from one of the most comprehensive benchmarking studies on AI adoption in sales. Drawing from research across 111 sales organizations, Bob reveals why simply using AI is no longer enough. The real advantage belongs to a small group of “frontier organizations” that have moved beyond experimentation and embedded AI into the way sales actually gets done. The conversation explores the current state of AI adoption, why most organizations are still only “dabbling,” and the growing performance gap between companies that integrate AI strategically and those that simply rely on general-purpose tools. Bob also introduces the concept of “machine stench,” explains why authenticity has become more valuable than ever, and shares why sales managers will play an even more important role as AI transforms the revenue organization.   What You’ll Learn: Frontier AI Adoption: What separates the highest-performing AI-enabled sales organizations from everyone else.Beyond AI Experimentation: Why most companies are still dabbling instead of transforming their sales process.The Problem with “Machine Stench”: Why AI-generated content often destroys trust instead of creating efficiency.Applied AI in Sales: How leading organizations are combining general-purpose AI with sales-specific and agentic workflows.The Future of Sales Management: Why coaching, process discipline, and change leadership become even more important in the AI era.Key Topics: Benchmarking 111 sales organizations on AI adoptionThe difference between AI experimentation and AI integrationFrontier organizations outperforming peers on quota attainment and sales objectivesAI adoption compared to historical CRM adoptionThe rise of ChatGPT, Perplexity, and language-based AI tools“Machine stench” and AI-generated content fatigueAuthenticity versus automation in customer communicationTribal knowledge and AI-enabled sales executionGeneral-purpose AI versus sales-specific AI platformsAgentic AI and workflow automationAI embedded inside CRM and revenue platformsSelling capacity and AI-driven productivity gainsWhy AI-created capacity will reshape sales organizationsThe changing role of frontline sales managersAI for coaching, learning, and sales enablementProcess engineering as a future sales leadership competencyLeading organizational change in an AI-first environmentGuest Spotlight: Bob Kelly is the Founder and Chairman of the Sales Management Association, the world’s largest independent professional organization dedicated to advancing sales leadership. Serving more than 10,000 sales leaders globally, Bob has spent decades researching sales management effectiveness, organizational performance, and revenue leadership. His work focuses on helping organizations apply evidence-based practices to improve sales productivity, leadership development, and business performance.   Resources & Mentions: Sales Management AssociationMicrosoftChatGPTPerplexityCRM platformsSales Performance Management (SPM)Sales Enablement platformsEthan Mollick’s “Jagged Frontier”Agentic AIApplied AISales coaching and enablementPipeline managementAI governance and securityComing Next Week: Part 2 dives into why processes must come before AI, the three organizational levers that actually drive successful AI adoption, and how the best sales organizations are redesigning leadership, coaching, and operating models to thrive in the age of AI. 🎧 Listen now and subscribe to Selling Intelligence for more conversations with the leaders shaping the future of AI, sales leadership, revenue operations, and enterprise growth. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi. KK Anderson (00:31) And I'm KK Anderson. Every week we bring you conversations with operators who have been in the room and come out with something worth using the very next day. Mark Petruzzi (00:40) Our guests today just completed a benchmarking study of 111 sales organizations. And what on? AI adoption. The findings are not what most leaders expect. Only 4% of firms have no one using AI at all. But only 9% qualify as what the research calls frontier adopters. And those 10 firms are outperforming the rest of the field. By on average twenty-seven percent is points on sales objective achievement, nineteen points on individual quota attainment, and nearly double the rate of sufficient selling capacity. The question this research forces is not whether your team is using AI, it is whether they are using it in a way that actually moves the numbers. KK Anderson (01:26) Bob Kelly is founder and chairman of the Sales Management Association, a global, independent, professional organization serving more than ten thousand sales leaders. He has no product to sell and no platform to push, which is exactly why this data matters. Welcome to the show, Bob. We're happy to have you. Bob Kelly (01:43) Thank you so much for having me. It's so nice to be with you. Mark Petruzzi (01:46) So Bob, your research covers over one hundred companies. But before we get into what leaders are doing, give us the honest snapshot. What is the typical sales organization actually doing with AI right now? And how does it compare to what people say they're doing and what the media outlets are saying people are doing as well? Bob Kelly (02:07) the word I would use is dabbling. the typical sales organization is dabbling with AI as opposed to integrating it in a pervasive and sort of formal way in the work streams in the firm. this is a reflection of the uneven nature of how AI affects work in general and including sales work. But the interesting thing is to understand just how few firms are ignoring AI or are untouched by AI. When we look at the adoption curve and history of other technologies, CRM, for example, or other platform technologies, they've taken much, much longer to gain a foothold in most organizations. We're seeing very fast pickup in The use of AI, even if that use is uneven. KK Anderson (02:55) So Bob, when we had our our preparation conversation for this podcast, you used a phrase that I hadn't heard anywhere else and I thought it was fabulous. You said you said there's a lot of machine stench. Right. So walk us through like what is that and why is it showing up so broadly in this research? Bob Kelly (03:07) Machine Yes. Well how is Great term, isn't it? I was just about to think of that term when I heard someone else use it. So I've naturally adopted it as if it were my own, but it is plenty descriptive, right? And I think we all have encountered AI generated content. I mean, the more common term is slop. We see it in social media, but we also see it in our inboxes, we see it in work product within KK Anderson (03:15) It is. Bob Kelly (03:39) the companies that we work for. and its problem is that it represents an inauthentic product. And so this when used inappropriately or i in the wrong context actually I believe does more harm than good. it communicates sort of in auth authenticity rather than clarity and equality. KK Anderson (04:00) Everyone AI it's like AI gave everyone a on the road and no one can move. And everyone sounds the same. So it's figuring out how do you take that superpower and that super intelligence and leverage it in a way to create differentiation rather than Bob Kelly (04:01) We want Yeah, just You know, I KK Anderson (04:15) than the stench of sounding the same, Bob Kelly (04:18) I think the mistake so many make is that they're using AI to substitute for their own voice or work product. And when that happens, ⁓ they're pointing out their own superfluity. do we need a human if we're just gonna have machines generate communication? so I think when used appropriately, we use it to augment our abilities, our voice, our productivity and when we use it poorly we've we make the mistake of y substituting a machine generated product for something that we should have more say in. Mark Petruzzi (04:51) So, Bob, you mentioned in the study that only four to six percent of companies are avoiding AI entirely. That actually concerns me that, there is everybody's diving in. And, only a very small percentage are not. but when it really comes down to it, there's still a huge disparity between those frontier adopters, as you described, and the laggers, the rest of the the Bob Kelly (04:52) Yeah. Mark Petruzzi (05:17) hack is that the gap between the two of them growing and and how fast? How fast is that growing and changing? Bob Kelly (05:27) Well, it the answer is very, very fast. The study that we did was concluded I guess about three months ago. It's likely out of date. so we see these adoption and the development of the products that we're even talking about moving so quickly. the the the thing to keep in mind is that or a relevant Point here is that so many AI products are freely available and they are in the general population. In fact, the most widely adopted tools are those that anyone can pick up, chat GPT or perplexity or any of these sort of language-based chat uh-based tools. And so we see lots of people picking them up, fooling around with them. And this is unlike other technology. platforms that we've seen impacting the sales organization like CRM or SPM or sales enablement or any many many other tools. So this does beg the question, will this be a phenomenon driven by consumers? personal adoption? will it be democratized in that way or will companies be required to adopt sort of institution wide, highly controlled platforms to provision AI. KK Anderson (06:37) really interesting and one of the incredible benefits of leveraging AI in your sales organization is that you can take that tribal knowledge of your best your your top sales performer and figure out what it what is it that makes them the

    Ep. 133 – Frontier AI: What the Highest-Performing Sales Organizations Are Doing Differently with Bob Kelly - Part 1

  4. Jun 24

    Ep. 132 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 2

    General Episode Description: In Part 2 of this conversation, Jared Zelman, Founder and CEO of Othello AI, explores what happens when AI moves beyond helping individual sellers and begins transforming entire sales organizations. Jared shares his perspective on the future of sales management, explaining how AI can handle repetitive coaching, call analysis, and execution consistency while allowing managers to focus on higher-value leadership activities. The conversation examines how AI-powered coaching systems are changing the role of frontline managers and why sales leaders must rethink how they develop and scale teams. The discussion also dives into Jared’s founder-led go-to-market journey. From cold-emailing executives, investors, and industry leaders to building relationships with some of the most influential business figures in the world, Jared explains how disciplined outreach, persistence, and deep personalization helped accelerate Othello’s growth from startup to seven-figure ARR. The episode concludes with practical lessons for founders, CROs, and sales leaders on scaling efficiently, shortening sales cycles, achieving product-market fit, and balancing the art and science of selling in an increasingly AI-driven world.   What You’ll Learn: • The Future of Sales Management: How AI changes the role of frontline sales leaders. • AI-Augmented Coaching: Moving from repetitive coaching activities to strategic leadership. • Founder-Led Sales at Scale: How deliberate outreach can build customers, investors, and mentor networks. • Product-Market Fit First: Why founders should focus on learning and validation before scaling teams. • The Art and Science of Selling: Understanding what AI can teach and what remains uniquely human. Key Topics: • Managing AI-augmented sales organizations • The future role of sales managers • AI-powered diagnostics and coaching • CRM automation and systems of record • Salesforce versus next-generation CRM experiences • MEDDPICC automation and sales process intelligence • Sales velocity as a growth metric • Founder-led go-to-market strategies • Building relationships through cold outreach • Howard Schultz and executive networking stories • Product-market fit versus revenue growth • Shortening sales cycles • Why founders should delay hiring sales teams too early • The science versus art of selling • Human trust and relationship-building in sales • Scaling enterprise SaaS companies Guest Spotlight: Jared Zelman Jared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Prior to Othello, Jared founded Cicero, an AI-powered celebrity avatar platform. Through Othello, he is helping organizations scale elite sales behaviors while preserving the human elements of trust, empathy, and relationship-building that drive long-term success.   Resources & Mentions: • Othello AI • Salesforce • HubSpot • Notion • MEDDPICC • Howard Schultz • Steve Ballmer • Sam Altman • Paul Graham • Dale Carnegie • Costco • Lenovo • Science of Scaling by Mark Roberts • Entrepreneur.com Key Takeaway: AI can automate coaching, surface insights, and improve execution consistency, but it cannot replace the human side of selling. The organizations that win will combine AI-driven discipline with authentic relationships, strong leadership, and a relentless focus on understanding customers. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, sales leadership, revenue growth, founder-led scaling, and the future of enterprise sales. KK Anderson (00:38) Okay, so you are, and we're gonna wrap up the second topic here with this question. You're reporting 10 to 15% win rates improvement, 8 to 10% reduction in sales cycle length, which is huge. ⁓ a lot of AI tools are making, some some pretty large claims like that. so like generally speaking, just w help us understand a little bit, like what what are you measuring over what time period? Jared Zelman (00:51) Crazy. KK Anderson (01:02) how was work to some of your success? Jared Zelman (01:04) Yeah. These are like guess depends, because ⁓ like some of these numbers are pointing time numbers, some of these are ⁓ like over a period of time. so if it's a period of time, these are like over a course of twelve months. what's unique is these are all for large enterprise, these are for Fortune one hundreds. When you see AI companies quoting crazy growth or performance metrics, it's because they're selling to a two person business in YC. in other words, bullcrap. Right. ⁓ these are metrics that are proven at some of the biggest companies in ⁓ multi-sectors. that said, the bar for the expectation the expectation of buyers these days is kind of ridiculous. frankly, if you're a sales tool and you're affecting win rates and you're not improving them by over 10%, that you're a failure. our minimum is like fifteen, we're aiming for like twenty five, thirty in some cases. Yeah, I mean w the buy the buyers are just so damn pro snickety these days. People's standards have gone through the roof. KK Anderson (01:49) wow. Mark Petruzzi (01:57) Beautiful. All right, let us move from topic two to topic three. Topic three is from rep consistency to overall CRO intelligence and how that impacts the overall management of an AI augmented team. And the first question I have on that is once your technology is levered across a team. What what changes for the manager? Because if the AI is handling execution consistency, prompting the right questions, catching objective handling in real time, the manager's job needs to change as well. So what does a great sales manager do differently when they have a productive and effective AI layer between them and the team? Jared Zelman (02:43) So we try to do three things in a closed up cycle. So we try to diagon it's kind of similar to like a I'll use like doctors as an analogy. We try to diagnose what's working, what's not working. So pretty much diagnosing what happens in sales calls, that stink. We then report that right back to the ⁓ to the managers and we give them a prescription. We'll actually give managers direct suggestions on what they should be doing differently to coach their team. Specifics, because managers they need specifics, they have a lot of other stuff going on. We will then actually implement that prescription. We'll then create the cure, hopefully, and reinforce those best practices in every single call. Right? And that system goes on, it's a close-up system. The way the manager job changes though is threefold. They now don't need to do all the diagnostics, they don't need to listen to 300 call recordings to identify the trends and what's working and what's not working. They don't even need to then draw the conclusions to how to fix that. Right? They can always be a human diluent director, but they don't have to do it from scratch anymore because of Thela's helping. Most significantly, they don't need to reinforce that training. They don't need to actually be sitting there coaching reps every single day, every single day. I mean, sorry, every single week. Because Thelo is doing that for them. So it's it's threefold. it's interesting. It's a point solution in that it's focused on sales calls. but it's doing every single part of that cycle such that the manager's job is similar, but it's not menial anymore. There is very little repetition in the manager's job when they have effectively an AI agent that is doing their journey work for them. KK Anderson (04:05) I would think that, as someone who has managed sales teams for many years, I find myself saying the same things, and as a sales coach, right, with our clients, I find myself saying the same thing to this, over and over again, like a broken record. And ⁓ it could be really interesting if you have to take away some of the fundamental that some of the repetitive stuff, like you said, it could be really interesting how those how that value of that coaching conversation would change. So ⁓ and I'm curious to get your take on this as we're evolving. Like what do you see the future of of CRM? Right? We know every salesperson, hates logging CRM. I had this conversation with the CRO just today, like, our CRM is a mess. And it's it but it's still the crux of everything. I imagine that what you're what you're Jared Zelman (04:29) Yeah. KK Anderson (04:49) the notes you're pulling and the insights you're pulling on these calls are are feeding into CRM. Like what do you see the future of of CRM? Is it gonna be more in the background? Is it gonna be a big part of of the future? Jared Zelman (05:02) I think a system of record in general will always be a very important part of the future. It's also a good data layer which you need then to use AI on top of. ⁓ so it will always exist. I do think it'll look different. I will think it is good. I do think it will be one of the l last things to change though, and evolve. ⁓ I just like one prediction is ⁓ like look at Notion. I don't know if you guys have have you guys used Notion before? Great. we started to use Notion as our CRM. We use Salesforce and Notion. Kind of for different things. KK Anderson (05:08) No. Yeah, yeah. Mark Petruzzi (05:22) Do. Jared Zelman (05:27) Notion, although you cannot do 95% of the stuff you can do Salesforce, and you can do Salesforce with, ⁓ the 5% that you do have overlap is the most important 5%, which is like the standard, CRM part. ⁓ and it's so goddamn easy. Like, there's gotta be a way to have like notion level experience, but with the level of like complexity that you can have like a CRM today, like maneuver with. Like, I think that KK Anderson (05:50) Give me an example. Jared Zelman (05:52) Like like here, like with Notion you can just copy and paste like

    Ep. 132 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 2

  5. Jun 17

    Ep. 131 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 1

    General Episode Description: In this episode of Selling Intelligence, Jared Zelman, Founder and CEO of Othello AI, joins Mark Petruzzi and KK Anderson to challenge one of the most accepted assumptions in sales leadership: that 20% of sellers will always generate 80% of the results. Jared argues that the 80/20 problem is not a talent issue. It is a systems issue. Drawing from millions of minutes of sales conversations and real-world customer deployments, he explains how modern AI can capture the behaviors of top performers and deliver coaching in the moment when it matters most: during live customer conversations. The discussion explores why traditional coaching models fail to scale, the limitations of post-call analysis, and how real-time AI guidance can improve discovery quality, qualification, and win rates across entire sales organizations. Jared also shares insights into how AI is uncovering new patterns in selling behavior, including why Sandler-style methodologies continue to outperform across modern B2B sales environments.   What You’ll Learn: The 80/20 Sales Problem: Why performance gaps are often driven by systems, not talent.Real-Time Coaching vs. Post-Call Coaching: Why feedback during the conversation matters more than feedback after the fact.Discovery Done Right: How top performers uncover deeper pain points and create stronger buying urgency.AI-Powered Sales Execution: Using AI to replicate the behaviors of elite sellers at scale.The Future of Sales Methodologies: How AI is identifying winning patterns across millions of sales interactions.Key Topics: The Pareto Principle in sales organizationsWhy most CROs attack the wrong coaching problemReal-time AI coaching inside customer callsImproving discovery conversationsThe “question behind the question” frameworkWin rate improvement versus productivity improvementWhy CRM automation alone does not improve revenue performanceAI-assisted coaching and behavioral reinforcementThe difference between efficiency and effectivenessRote versus rogue selling behaviorsPersonalized coaching versus scripted sellingSandler methodology and AI pattern recognitionCustom sales methodologies powered by organizational dataUsing AI to scale top-performer behaviorsThe future of AI-enabled sales leadershipGuest Spotlight: Jared Zelman Jared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Built by the team behind Cicero, Othello helps organizations scale elite selling behaviors across entire teams through contextual, in-the-moment coaching. Since launching in 2025, Othello has rapidly grown to support thousands of users across Fortune 500 companies and high-growth technology organizations.   Resources & Mentions: Othello AISalesforceHubSpotGongSalesloftClariMicrosoft TeamsZoomSandler Sales MethodologyCiceroDan LawrenceLenovoCostcoHome DepotGeneral ElectricComing Next Week: Part 2 explores how sales leaders should manage AI-augmented teams, how coaching changes when AI handles execution consistency, and Jared’s founder-led go-to-market playbook for building a venture-backed company through strategic cold outreach and relationship-driven selling. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, revenue leadership, enterprise sales, and the future of go-to-market execution. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I am Mark Petruzzi, and I am joined as always by my co host, KK Anderson. Our guest today built the company on a number every CRO already knows and hates. Those numbers are the 20% of reps drive 80% of the results. The question is, what do you do about it? Most leaders throw more coaching hours at the problem. Build out their enablement team, and then just hope it scales and gets more productive. Jared Zellman did something a little different. He went out and he built an AI that sits inside the call and fixes it in real time and on every call. Jared is the founder and CEO of Othello AI, a real-time AI sales coaching platform that guides reps before, during, and after every call. Built by the team behind Cicero, Othello launched in July of 2025 and reached over 5,000 users and 1 million in revenue within its first six months, with clients spanning Fortune 500 companies and high-growth startups. Othello integrates with the go-to-market stack you already have, whether it's Salesforce, HubSpa, Gong, SalesLoft, Clary's, Zoom, or Teams. And sits as the execution layer that makes sure what happens on the call matches what the playbook says. KK Anderson (01:55) What I love about Jared's story is that he is not just a founder talking about sales AI. He is a practitioner of the exact skills he built Othello to teach. He built his entire investor base, his early customers, and his mentor network through deliberate, personalized cold outreach to some of the most senior people in the business. Howard Schultz, CEO of Lenovo, CEO of Costco. All started as cold emails, which is incredible. And that kind of disciplined, researched, human first selling approach is what Othello reinforces at scale. So this interview will be a part of a two-series, a two-part series overcome excuse me, reviewing four topics. today we're gonna get into the first two topics. Topic one, that 80-20 problem that Mark mentioned. And why the performance gap between your best and average reps is not a talent issue. It is a systems issue. And why most CROs are solving the wrong problem. Excited to get into that. And the second topic for today's episode is real-time AI coaching and what it actually means to have AI inside the call, how the live cue cards and pre-call briefs work, and the results that the teams are seeing. And this modern, AI run, coaching platform, which is really interesting. Now, next week, when you tune back in, we'll talk about topic number three, managing an AI augmented team. what a CRO's job looks like when AI handles execution consistency. and topic number four, the founder go to market playbook. And this is one I can't wait to get into. So tell us exactly how, Jared, you went from being a new college grad with no network to ⁓ VC back CEO with Fortune 500 clients in under a year. So we got a lot to dig into today. Jared, welcome to Selling Intelligence. Jared Zelman (03:46) Thank you for having me. I'll try not to bore you guys. Mark Petruzzi (03:48) No, you would never. So Jared, ⁓ you built Othello on the premise around twenty eighty. Twenty percent of reps driving eighty percent of the results. And that this is a solvable problem. Most CROs have lived with that ratio for their entire career and has accepted it as a fact of selling life. Please make the case for us that it is not a talent problem. Jared Zelman (03:55) Mm-hmm. Yep. Mark Petruzzi (04:12) What is actually happening structurally in the calls of average reps that top performers are doing differently? And how do you make sure those those top performer practices actually get leveraged into the rest of the team, those eighty percent of reps that we we all know? Jared Zelman (04:30) It's the Pareto principle, right? So the Paretto principle isn't it's it's not a law, like things don't need to adhere to it, but it's a commonality. So most sales organizations will suffer from the 80-20 problem. Doesn't mean they have to. I was just chatting with a mentor and advisor to our company, a guy named Dan Lawrence, one the most lovely and impressive sales leaders I know. He's the GM of America's at Nebbius. Nebbius does not suffer from the 80-20 problem. Right? Like a rising tide lists all ships. He's been able to upscale all of his reps to be so effective that they're all ⁓ top performers, especially if you compare them to any competitors. I believe it's a systems problem, not a talent problem. I actually think you can turn the middle sixty percent into the top twenty percent. The bottom twenty percent is a different story, but at the very least you can get to performing better. KK Anderson (05:12) And it's all by being there in the moment. Jared Zelman (05:15) Well, like it's it's interesting. It's like a like let's let's use like basketball as an analogy. Practice is obviously crucial. No one's gonna tell you that practice isn't important, right? And that's preparation, right? In sales, it's the same thing as going, Tuesday afternoon after school practicing ⁓ shooting hoops, right? But what's also crucial and you can't live without is having your coach screaming at you when you're shooting hoops in a game. Live, right? we try to bring that into sales. ⁓ similar to how if you guys are in sales or have been in sales, your sales manager perhaps would have been slacking you on the side telling you what you should be saying, or even like hooking up to your call with headphones, kind of like whispering in your ear what you should say instead. We try to replicate that experience with AI. KK Anderson (05:54) So but you're not the ma you're not the coach screaming at you from the sideline. Jared Zelman (05:58) We ⁓ no, we can't. It's when you're dealing with salespeople, it's a b it's an art and a science, right? Like on paper, what does work doesn't always actually work ⁓ in practice. ⁓ sales reps are dealing with very high pressure sensitive environments. So ⁓ I mean that's like one of the reasons why a lot of engineers fail at building sales tools is you need empathy for the user experience, which is very different from the UX and other products. KK Anderson (06:03) It is. It's ⁓ So when you went went deep on this problem before building your platform, what like what did you find in your research that surprised you the most? I think I read in one of your articles that you were starting with a different like something about celebrity avatars or something, and then you quickly pivoted when you saw the market. Like te

    Ep. 131 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 1

  6. Jun 10

    Ep. 130 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 2

    General Episode Description: In Part 2 of this conversation, Scott Stollwerk returns to Selling Intelligence to explore one of the most important questions facing modern sales leaders: what happens when AI becomes excellent at execution, but human performance remains the deciding factor? As AI continues to improve outreach, forecasting, coaching, scoring, and productivity, Scott argues that the real competitive advantage is no longer process or technology. It is the human being operating behind the tools. Drawing on the Tao of Sales framework, Scott explains why resilience, self-awareness, creativity, intuition, and personal growth remain irreplaceable in high-performance sales organizations. The conversation explores the limits of AI, the dangers of over-automation, and why leaders must continue investing in human development even as technology becomes more powerful. Through practical stories, leadership lessons, and personal experiences, Scott demonstrates why sales success ultimately comes down to overcoming the internal barriers that technology cannot solve.   What You’ll Learn: What AI Cannot Fix: Understanding where technology excels and where human performance still matters most.The Human Edge in Sales: Why creativity, intuition, emotional resilience, and connection remain irreplaceable.Overcoming Self-Limiting Beliefs: How internal dialogue often creates bigger obstacles than external challenges.AI as an Amplifier: Why AI accelerates both strengths and weaknesses within sales organizations.Developing the Individual Seller: Why long-term sales success requires personal growth, not just process improvement. Key Topics: The limits of AI in enterprise salesWhy buyers still trust humans for high-stakes decisionsAI productivity gains versus human connectionThe “crisis of sameness” created by AI-generated contentIntuition, creativity, and human decision-makingStrengthening the mind like a muscleThe role of spirituality, mindfulness, and self-awareness in performanceThe famous arrow-breaking exercise and overcoming fearInternal dialogue and self-limiting beliefsAI as an amplifier of organizational alignment or dysfunctionUsing AI as a brainstorming tool instead of a replacement for thinkingLeadership responsibility in developing human potentialProtecting individuality and creativity in an AI-driven world Guest Spotlight: Scott Stollwerk Scott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Combining Eastern philosophy, neuroscience, martial arts principles, and human performance science, Scott helps individuals and organizations build resilience, self-awareness, and sustainable performance. As part of the leadership team at Pest Share, he continues to develop sales cultures that prioritize human growth alongside business results.   Resources & Mentions: Tao of Sales FrameworkTony Robbins’ Six Human NeedsAbraham MaslowRobert CialdiniGongZoomAsk ElephantPhil JacksonMichael JordanDennis RodmanThe Five Love LanguagesEastern Philosophy and Tai ChiConcept: AI Amplifier Principle Key Takeaway: AI can improve productivity, automate execution, and accelerate workflows. But it cannot replace resilience, courage, creativity, judgment, or human connection. The organizations that win in the AI era will not be the ones that develop technology alone. They will be the ones that continue developing people. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, AI, human performance, and enterprise growth. #SellingIntelligence #AIforSales #SalesLeadership #HumanPerformance #SalesCoaching #RevenueLeadership #EnterpriseSales #SalesCulture #LeadershipDevelopment #MindsetMatters #ArtificialIntelligence #BusinessGrowth #TaoOfSales #HighPerformanceTeams #FutureOfSales Mark Petruzzi (00:38) I'll move us into topic two. and that is what AI cannot fix the human edge in sales. So I guess I what I want to share is in sales, AI cannot fix everything. I mean you heard it here, you know, everybody thinks every board thinks like any problem we can fix with AI. I don't believe that's the case. So what it can do, it is now writing outreach, coaching calls, scoring deals, forecasting pipeline. Those examples it does really, really well. And in most cases, almost all cases, it does it better than humans can individually, certainly for the at the productivity levels that it can do it at. That's good because a lot of our listeners have made significant bets on it, and that's going to be a great thing for your Salesforce effectiveness and productivity. but what does AI get right about sales performance? And Scott, where does it just hit that wall that no amount of compute is going to break through? what's your point of view on that? Scott Stollwerk (01:40) It's a it's the mo the it's the Peloton question of this year, right? and I wanna get it right and I wanna start with a compliment for AI in just in case it's listening. So I'm always gonna laugh at my own jokes, but that was very okay, that was very generous of you. I appreciate the smile and the chuckle. KK Anderson (01:54) Yeah. Scott Stollwerk (01:57) I have the same fears that everybody else does. I don't want it to lock my bank accounts and give me a hundred dollars every time I do what it tells me to do. the fact is, look, we're all way more productive today than we were last year or the year before at this time. Cause I get messages to follow up, which maybe I would have forgotten before AI. I get instruction on how you might follow up. We get coaching. After every single call. And there's a tremendous amount that it does well. But I think if everybody just empties your mind of all these benefits of AI for one second and do a little mindfulness, a little awareness. Imagine that we're sitting in a room with one other voice, artificial or human. It doesn't matter. Buy something from it in your imagination. For fifty dollars. And then buy something from it based on what it's telling you. about your life and how this object or solution or thing is going to benefit you as a person. And then go to a thousand dollars. And then go to ten thousand dollars. It doesn't take long for sentient human beings that are not AI code writers to say, no, right there, that's it, $1,000. I'm not buying something from a machine if it's more than $1,000. That's just one exercise. But yeah, within it, yeah, the implications for my answer to you, Mark. In the enterprise, I may use AI to research everything. KK and Mark told me on a Zoom call like this about their solution. I may go and ask multiple AI sources well, is this the right solution in this for this problem set? But there's no way I'm buying it from the robot. And there's a lot like that when it comes to What has been traditionally human to human. my the best one of the best examples, my daughter's an artist. She's a concept artist for video game makers. And they tried AI. Here's the Nordic warrior princess that we need for our video game. She's got a horned helmet and a skull atop her spear. And go, give me the rest of it. These are these are very artistic, very aware designers of video games. And when they compare the human versus the AI content, it's humanity every time. You just don't have sentience yet in AI. And that's the difference. KK Anderson (04:07) Well, and it's also the core of what makes a seller successful is their relationship. And we always we always talk about, you know, on this podcast that that AI has really I mean, as much as we love AI, clearly, it is incredible you're right, how how much more productive we are. it is incredible what agentic workflows can do to completely transform a business. I'm not doubting that at all. Scott Stollwerk (04:07) Okay, Exactly. KK Anderson (04:29) But it is also AI has also created this crisis of sameness where everyone sort of sounds the same, right? We've all, you know, you you you can recognize AI slop or AI content you know, just like you used to be able to recognize a, you know, a stock photo on a website when the internet first came out, right? ⁓ and so so so people are getting sort of you know immune to that as well. And so Scott Stollwerk (04:36) Mm-hmm. Exactly right. KK Anderson (04:54) one of the things, Scott, that I've heard you say before is that you're you're thinking, and you talked about this quite a bit in topic one, but your personal thinking, your personal drive, it's not a gene or a chromosome, it's more like a muscle. And and the reality is that AI can't build that muscle, right? That development of that muscle has to come from. your consistent practice, your consistent mindset, your consistent state of mind, you know, consistently showing up as as one of my old mentors used to say, time to make the donuts every day. You got to wake up and you got to make the donuts, right? Every single day. and so like when you think about as I know you are thinking about it, we've talked about this, like what can be automated? Scott Stollwerk (05:28) That's right. KK Anderson (05:35) you know, in your business and what could not be automated, like where does your head go? Like what are those things that you're gonna protect no matter what for for the humans on your team? Scott Stollwerk (05:44) Well, and I think I I definitely want to help protect that those things. And it's our individuality. And and it's our humanness. And creativity falls in there. You know, I don't know. You're teaching me what AI can and can't do ultimately. But I know today I have intuition and I have feelings. However you carve them up, Tony Robbins, Socrates or otherwise. And it always feels better to have connections like we're having right now, like-minded people on important topics and and what might be tomorrow. One of one of Michael Jordan's coaches, I forget his name offhand, but he said to succeed you have to be stronger than your feelings. Today, that's what all of us need to do to def

    Ep. 130 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 2

  7. Jun 3

    Ep. 129 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 1

    General Episode Description: In this episode of Selling Intelligence, Scott Stollwerk, creator of the Tao of Sales framework and member of the leadership team at Pest Share, joins Mark Petruzzi and KK Anderson to explore a topic becoming increasingly important in modern sales organizations: developing the human behind the salesperson. As AI continues to automate outreach, scoring, sequencing, and administrative tasks, the true differentiator is no longer the technology stack. It is the individual seller’s mindset, emotional resilience, self-awareness, and ability to perform under pressure. Drawing from Eastern philosophy, Tai Chi, neuroscience, human performance science, and more than 15 years of leadership experience, Scott explains why traditional sales training often fails when real-world pressure arrives. He shares how the Tao of Sales helps individuals develop the internal foundation required to navigate rejection, uncertainty, and growth while building stronger sales organizations from the inside out. The conversation explores why progress matters more than speed, how leaders can create resilient teams, and why personal growth is often the missing ingredient in sales performance.   What You’ll Learn: The Tao of Sales Framework: How Eastern philosophy can create stronger, more resilient sales professionals.Beyond Techniques and Playbooks: Why most sales training breaks down when pressure increases.Progress Over Speed: Understanding the importance of building foundations before pursuing rapid growth.Human Performance in Sales: How mindset, self-awareness, and emotional regulation impact results.Coaching the Individual: Why great leaders develop people first and salespeople second.Key Topics: The origins of the Tao of SalesEastern philosophy and enterprise sellingWhy attachment to outcomes creates frustration and poor performanceThe role of resilience in sales successSales training versus skill developmentTai Chi principles applied to business and leadershipBuilding strong sales foundations before scalingGrowth, progress, and long-term performanceLeadership lessons from Phil Jackson, Michael Jordan, and Dennis RodmanDeveloping confidence under pressureCoaching through beliefs, fears, and behavioral patternsThe psychology behind high-performing sales teamsGuest Spotlight: Scott Stollwerk Scott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Over the past 15 years, he has developed a unique framework that combines Eastern philosophy, neuroscience, martial arts principles, and human performance science to help sales professionals thrive under pressure. As part of the leadership team at Pest Share, Scott continues to focus on developing high-performing individuals and teams by strengthening the human foundations that drive sustainable success.   Resources & Mentions: Tao of Sales FrameworkPhil JacksonMichael JordanDennis RodmanTony RobbinsAbraham MaslowRobert CialdiniThe Five Love LanguagesA Fighter’s MindDavid HortonEthics of Our FathersTai Chi and Eastern Philosophy Coming Next Week: Part 2 of this conversation dives deeper into belief systems, behavior change, leadership development, and building a high-performance culture that can sustain growth in an increasingly AI-driven sales environment. 🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, human performance, AI, and enterprise growth. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi and I'm joined as always by my co-host KK Anderson. Our guest today has spent more than a decade building sales team from the inside out. Not with just another playbook or a new stack of tools, but with something most sales organizations have really never thought to develop. The human being behind the rep. Scott Stolwerk is part of the leadership team at Pest Share. And the creator of a methodology known as the Tao of Sales. The Tao of Sales is a framework that draws on Eastern philosophy, neuroscience, and human performance science to develop sellers who results hold when the pressure comes. He has been doing this work for 15 years and the results follow him everywhere he goes. KK Anderson (01:12) Scott's framework could not be more timely. Everyone in this audience is navigating the same tension right now. AI is handling more of the execution layer, the outreach, the sequencing, the scoring. And that means that the gap to determine who wins is not just the tool anymore. It's the person. And it's what they believe, it's how they manage their state of mind. Whether they can stay present in a hard conversation. And it's really coming back to some of those more human elements that were present before technology took a hold. Now, Scott has been working on exactly this problem for a long time. And today we're excited to dig in with Scott and find out what he's learned and how he implements this within his teams. Now, this is part one of a two-part conversation, and we'll be back with Scott. For part two to go deeper on belief science, culture building, and what it actually takes to install this inside a sales organization next week. So be sure to tune back in next week as well. Now, for today's episode, here is what we're going to be covering: four key topics. Number one, the Tau of Sales. What is it? Where did it come from? And why Eastern philosophy maps and how it maps onto modern sales better than most Western methodologies. Topic number two, what AI cannot fix and why the human edge is the last defensible advantage, and what that means for how you can develop your team as a sales leader. And then part two will be topic three, which will be beliefs, behaviors, and the six inches between the ears. And topic four building a high performance culture from the inside out. And what leaders are getting wrong about development and what Scott does differently, and things you can take back and do within your own sales organization today. Mark Petruzzi (02:59) Thank you, KK. Scott, welcome to Selling Intelligence. Scott Stollwerk (03:03) Thank you so much for having me. Really a pleasure to be here. Mark Petruzzi (03:04) Awesome. Always a pleasure to be with you as well. Topic one, the DAO of sales, what is it and why does it work so well? So, Scott, most sales methodologies come with a deck, a framework, and sometimes a certification. Yours came from Eastern Philosophy, Tai Chi, and the decade of watching what actually holds under pressure. Walk us through the origin story of the DAO of sales. And what did you see happening to sellers that made you go in this direction at the beginning instead of down a more traditional path? Scott Stollwerk (03:36) Wow, terrific question. And it's so long ago. it's been an amazing journey. And I'll tell you, look, the early days, you may even remember when you were a consultant and and working with enterprise software sales teams, the early days in in our profession they I don't know if it's very complimentary to To these organizations. But you know, I used to hear a lot of things like, hey Scott, I thought you were smart on team weekly calls, like, okay, this is at stage one and this is at stage two. And you really weren't, the point is, you really weren't a human being. To the higher up you went in the corporate hierarchy, you were more and more a number. And Sales to me wasn't something that I started. I went to law school and I practiced as a class action consumer side class action attorney for a little bit. It was miserable. I needed to talk to people. so really the Dow of sales is the way I think I didn't invent it. I didn't create these things. They're just discoverable as you go. Certainly if you're being treated like a number, certainly if it's never too fast, like building a revenue team for a venture-backed company or private equity, you will find the Dow. And I think each of us that have sold in these negative environments, you know it's there. It it's ours to pull it out and when we get the opportunity to turn things around. And try and convince those that are that are either in charge or making up the rules where you are, that there is a better way, that there's a more humanistic, nicer but more effective. I don't want to say faster, but more effective way of succeeding. And that could be in anything. If it's in sales, great, if it's playing the piano, If it's speaking in public, the main tenant of the Tao of sales is that we practice sales to be better people first. And you can put whatever qualifier before people: husband, people, sons, daughters, sales, whatever it is, we practice that first to be better people and to hit our number second. And therein lies in that simple motto, probably the first. Eastern philosophy tenet that will cover, and that is detaching from your goals. Attachments create pain, they create frustration, they create impatience at the very least. And Phil Jackson treats that beautifully in his books. Just so everybody knows, he's the guy that got Michael Jordan and Dennis Rodman in the same room to meditate and contemplate eternity. So You know, all veneration, all credit goes to the the teachers, the masters that came before us in the Dow. KK Anderson (06:08) Really interesting. And I've heard you use a phrase, probably stop our listeners in their tracks. And that is that everyone is a black belt until they get hit in the face. Or maybe you said punched in the face, right? and that's really the whole problem with sales training right there. And I've been in the sales training industry specifically for 20 years myself. So Scott Stollwerk (06:09) Really interesting. I I've heard you use our KK Anderson (06:29) What what does conventional sales development get wrong about how people actually change and this kind of this human approach? Like how does that pivot? Scott Stollwerk (06:40) There's so much. And it's an it's an excellent question because of it. KK, there's litera

    Ep. 129 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 1

  8. May 27

    Ep. 128 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 3

    In this episode of Selling Intelligence, KK Anderson, Mark Petruzzi, and Alan Rudolph continue their Diagnostic Session series by focusing on the most underinvested side of the go-to-market bow tie: customer retention and expansion. The conversation explores why enterprise value is built not just through acquiring customers, but through keeping, expanding, and delivering value to them over time. Alan breaks down the difference between gross retention and net revenue retention, why time to value has become one of the most critical metrics in modern SaaS, and how broken retention models create pressure that sales teams can never fully outrun. The team also discusses the dangers of applying AI to flawed systems, why bad data and weak customer alignment create compounding problems at scale, and how CROs can build healthier, more profitable businesses through stronger metrics, ICP discipline, and operational alignment. What You’ll Learn: Gross vs. Net Revenue Retention: Why both metrics matter and how world-class SaaS companies measure customer health.Time to Value as a Growth Driver: Why TTV belongs on the CRO scorecard and how faster customer outcomes drive expansion.The Cost of Poor ICP Alignment: How selling to the wrong customers destroys retention, profitability, and scalability.Diagnose Before You AI: Why AI amplifies broken systems and how to avoid accelerating bad processes.Metrics That Protect Enterprise Value: The KPIs every CRO should monitor to improve retention, forecasting, and operational efficiency.Key Topics: Customer retention and expansion strategyGross retention vs. net revenue retentionTime to value and customer onboardingDiagnosing broken retention models before implementing AIICP alignment and customer fitEnterprise SaaS growth metricsAI-driven forecasting and operational efficiencyData quality and AI readinessCustomer churn and expansion motionsBuilding scalable revenue operationsGuest Spotlight: Alan Rudolph Alan Rudolph is a strategic advisor at AGS with deep expertise in enterprise software, revenue operations, customer retention, and scaling go-to-market organizations. He has worked closely with growth-stage companies and executive leadership teams to improve operational discipline, retention performance, and enterprise value creation. Resources & Mentions: AGS Revenue Blueprint DiagnosticBenchMarketKey Metrics Discussed:Gross RetentionNet Revenue Retention (NRR)Time to Value (TTV)CAC PaybackWin Rate by ICPTopics: Diagnose Before You AICustomer Health MetricsAI Readiness in Revenue Organizations🎧 Listen now and follow Selling Intelligence for more insights on AI, revenue growth, enterprise operations, and go-to-market strategy from today’s leading operators and advisors. Subscribe wherever you get your podcasts. KK Anderson (00:29) Welcome back to another exciting episode of our diagnostic sessions. And today we're going to pick up right where we left off with the last one in chatting with Mark and Alan about the go to market bow tie and specifically the last, the right side of the bow tie, what we call Keetmore, which is all around customer retention and expansion. And I know Alan will agree with this when we say that This is really the most under invested side of the bow tie and where enterprise value truly has the opportunity to compound. so, Mark, I'll hand it over to you to kick us off and we're excited to have another great session. Mark Petruzzi (01:08) great. So Alan, that last segment of the bow tie that KK is describing, that customer retention expansion, this is your home turf. So what does diagnosis look like here? And why is this side the side most CROs just under invest in? Alan Rudolph (01:25) Do we have enough time? I'll be here for hours. ⁓ No, think it's just there needs to be a focus on gross retention, on net retention, on the whole structure of how does sales and account management and customer success, how do all these pieces come together? And we know that it drives growth and it drives value overall for the company. But the under investment mark to your point, I probably have two, three, four conversations today. I was just talking to an exec this morning from a leading research firm and he was telling about one of his clients and their churn numbers are down, their sales numbers are off and obviously they're not growing. And if your churn numbers are too high, i.e. lack of gross retention, then it puts undue pressure. on the sales team because we think, we can just go sell our way out of the box. And we know that doesn't work, right? We know for a healthy software company, we need to keep the gross retention north of, ideally north of 90%. Best in class is 95 % to 97%. And so this is where the pieces need to come together, right, in terms of selling, account management. Oh, let's not forget about product because it's all about driving value to the customer. So it's definitely the art of the deal, right? It's more than just science. There's art here, in other words, in terms of finessing to ensure that we have the right overall gross retention driven into the organization. Mark Petruzzi (03:04) Yeah, and Alan, you are right on with that because when you then try to sell your, just sell out of that kind of churn challenge that you're describing, what happens is you really need to overextend the sales team and all the sales capabilities. And guess what that gets you? At the end of the day, that gets you a higher churn and a lower retention. Alan Rudolph (03:27) Right, right, right. Mark Petruzzi (03:28) So you think you can do this and everyone, every CRO I know loves to go back and say, yes, I can do that for us. But you can't just offer to do it without making sure your board and your executive team, your CEO knows what's likely gonna happen after doing so. Alan Rudolph (03:48) Right. Right. KK Anderson (03:49) So Alan, walk us through net revenue retention specifically, because this is the metric that most leaders mess up. And a lot of times ownership of that falls on the CSM side of the business, which is perhaps why it is not as visible, right? Everyone's focusing on the logo. Alan Rudolph (04:06) Yeah, spot on, KK. And it's fascinating. People just get messed up a little bit. So gross retention is just that. I start the year with $1 of business. I finish the year with $1.10. I'm sorry. I finish the year. I renew the dollar. That's 100 % gross retention. If I increase that dollar to $1.10, whether it's And again, different companies count things a little differently. But if it's, if it's a CPI increase, if it's another product going into that customer, right? If there's a price increase separate from CPI, right? So all those factors go into gross retention. I started with a dollar. I finished with a dollar. That's 100 % net retention. I start with a dollar and with 110, that's 110%. Right. And again, coming back to what I said earlier about you know, world class kind of metrics, gross retention in the 90 to 95 range, obviously 95, 97 will be world class. Net retention north of 120, it varies a little bit by industry. You get to 115, 120, it's that much more powerful. It puts less pressure, as I said previously then, on the sales force in terms of bringing in new logos because you have a healthy recurring revenue business that continues to drive success into the install base of customers. That's really how to think about those two numbers in terms of gross and net retention. But they are key metrics and they need to be calculated consistently, month in, month out, quarter in, quarter out, because they are key metrics that need to be not only reported across the company, reported to the board on a regular basis. Mark Petruzzi (05:49) Yeah. And you know what, Alan, I've always, I've never been a fan of net retention, net revenue retention, because I really like to look at these numbers separately. And I guess companies like that opportunity to put them together because they can hide something in it as well. But I mean, there's two things. You really want to look at your churn and understand what that is. Alan Rudolph (06:01) Mm-hmm. Right? Mark Petruzzi (06:16) Then you want to look at your revenue growth and your growth versus the targets that were set at the beginning of the year. And those are separate things. So if there's anyone out there with my kind of brain that just feels more comfortable in that space, think it's fine. It's good to have even more clarity and detail than just combining those two numbers. Alan Rudolph (06:40) Correct. Yep. Mark Petruzzi (06:40) So Alan, you also talk a lot about just time to value as one of the most underappreciated metrics. Please make the case for why TTV belongs on the sales leader scorecard, not just customer success. Alan Rudolph (06:55) we go back in time, for us folks that have been around this enterprise software space for a while. And we can all remember, and not that far back in time, less than 10 years, where enterprise application took months and months and quarters and years to get implemented. And in this day and age with all of the new technologies, with all of the changes that we all know about going on in the world around us in terms of, the autonomous world that we're about to live in or we're living in already. A customer signs a contract and they want value tomorrow. And so that's why it's so important from a selling standpoint that the outcomes are clearly laid out for the prospect, you know, soon to be customer. And they understand what they're getting, when they're getting it. And again, that time to value metric, i.e. how quickly can we get that new solution implemented? and the customer getting value out of the solution is in, I'm gonna call it days, soon we're gonna be in hours, but let's call it days, not months and quarters. And that's why TTV is so critical. That's why it needs to be on the CRO, the CCO, the COO, so Chief Revenue Officer, Chief Custo

    Ep. 128 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 3
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Selling Intelligence is the evolution of Selling the Cloud and designed for revenue leaders who are navigating the AI era. Hosted by Mark Petruzzi and Kristin "KK" Anderson, the show brings candid conversations with C-suite leaders across sales, marketing, and customer success on how AI is reshaping the way companies grow, sell, and compete. From agentic GTM strategies to AI-powered pipeline and revenue execution, each episode focuses on what’s actually working and how leaders are turning intelligence into performance. If you’re responsible for growth and trying to lead through the fastest shift in go-to-market we’ve ever seen, this podcast is for you.

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