13h ago

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

23 min

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

26 min

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

22 min

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

17 min

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

27 min

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

31 min

May 20

Ep. 127 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 2

General Episode Description: In this continuation of the Selling Intelligence Diagnostic Session, Mark Petruzzi, KK Anderson, and Alan Rudolph go deeper into what happens when AI is layered onto a broken go-to-market system. The team explores real-world examples of companies that accelerated pipeline volume with AI, only to later discover collapsing win rates, longer sales cycles, and poor ICP alignment. They also unpack the critical difference between sales activity metrics and true behavioral competency, highlighting why qualification skill remains one of the biggest hidden weaknesses inside modern sales organizations. The conversation closes with a deep dive into the “discount trap,” forecasting discipline, and the operational signals private equity firms use to evaluate the maturity and long-term value of a revenue organization. What You’ll Learn: AI on Top of Broken GTM Systems: Why more pipeline volume can actually create worse outcomes.Qualification Competency Matters: How weak qualification destroys sales efficiency and forecast reliability.AI Done Right: What happens when strong ICP discipline and human judgment combine with AI-driven signals.The Discount Trap: How discounting erodes enterprise value and creates downstream operational pressure.Forecasting as a Maturity Signal: Why investors care more about predictability than heroic overperformance.Key Topics: AI lead scoring increasing volume while lowering win ratesWeak qualification competency as a hidden scaling bottleneckOMG sales competency assessments and qualification benchmarksAI-powered signal intelligence for outbound prospectingUsing hiring patterns, LinkedIn activity, and market signals to prioritize outreachHuman judgment combined with AI-assisted targetingBehavioral competency vs outcome metrics in sales organizationsTwo teams with identical win rates but completely different operational healthThe “discount trap” and the dangers of unmanaged pricingWhy selling value matters more than discounting to win dealsForecast accuracy as a signal of operational maturityThe shift from “gunslinger” sales cultures to data-driven revenue organizationsPE diligence around trends, forecast reliability, CAC efficiency, and sales disciplineGuest Spotlight: Alan Rudolph Alan Rudolph is the leader of the private equity division at AGS and a strategic operator with extensive experience building and scaling enterprise revenue organizations. With a background spanning sales, operations, and enterprise value creation, Alan helps organizations diagnose GTM inefficiencies, improve operational discipline, and build scalable growth systems. Resources & Mentions: AGS (Advisory Growth Strategies)Objective Management Group (OMG) sales assessmentsConcept: Diagnose Before You AIConcept: Qualification competency in enterprise salesConcept: The Discount TrapMetrics: Win rate, cycle length, forecast accuracy, CAC efficiencyAI-powered signal intelligence for outbound prospectingClari, Aviso, and Collective[i] forecasting platformsAGS Sales Cycle Diagnostic Tool🎧 Listen now and follow Selling Intelligence for more diagnostic sessions, AI strategy insights, and practical frameworks for scaling modern revenue organizations. Mark Petruzzi (00:38) So KK, what does AI applied to a broken front of funnel motion look like? What are the ramifications of getting that? KK Anderson (00:47) Mark, let me share with you an actual real live case study, a real customer of ours. this is a growth stage SaaS company. They invested heavily in AI lead scoring and outreach. And they were ecstatic because, their pipeline jumps up 40 % in one quarter. The amount of leads coming in the door was just through the roof. leadership was celebrating and what happened and when they ended up calling us is that six months later, all of a sudden, their win rate is collapsing and their sales cycle is just getting longer and longer and longer and deals keep getting pushed out into other quarters. And so it got worse. And the reason why, once we did the diagnosis is because what it turned out is that the underlying qualifying motion of the sales team, when it comes to win more, was weak. It was deplorable weak. And to the point that Alan made earlier, the ICP was not the correct ICP and that was not disciplined. But because the sales team had a weak qualification competency, they were not prepared to be able to accept more of anything, even if it was the right ICP. And so it's interesting, just a note on that qualification competency, objective management group who is a partner of ours here at AGS, they have assessed it's got to be close to three million salespeople by now and interesting fact that of all of those three million people only 27 % are strong in the qualification and competency. So I said 27, two seven. So that means that if you're a CRO listening to this, it is likely that your team is not super effective at qualification. Right. And these are the things that you need to know before you start deploying a lead gen system that's going to against an ICP that's not disciplined with a sales team that doesn't qualify effectively. So AI on top of we qualifying is just expensive amplification of the wrong thing. Mark Petruzzi (02:50) I think you hit it right on there. KK Anderson (02:52) now, Mark, back to you on this one. tell us a story of when AI applied to the type of funnel works, right? We know we've got the horror stories, right? But tell us when it actually delivers. Give us an example of where you've seen it work. Mark Petruzzi (03:07) before I even do that, I'm going to give you a little bit of props here that you would always be too humble to share. But Objective Management Group is a company that KK has been working with for over 10 years. She has done more of these SEIAs, which are those as their assessments, the biggest in sales. There's nobody who does the does more of them than OMG. And there's nobody who has done more of them over the last eight, 10, 12 years than KK. she knows this space. She's got a lot of personal data in addition to all the metrics and everything else we track. So, okay, let's go to, let's talk a little bit about another story if you all don't mind. B2B Services Company that we work with, 40 reps. And in general, the first thing we noticed, they're in the top quartile on qualifying competency. They were really good. They knew it. The data confirmed it as well. They had a pretty tight ICP discipline. And they tried to work with AI a little bit on the prequel research, account intelligence side of the equation. But then they really picked this up. in the standpoint of really understanding signals. What would happen out there in social media, in their TAM that they're going after. Things like job changing, changes, hiring patterns, general press, LinkedIn activity, all of that. What then happened is that their outbound conversion went through the roof. they're able to go in there and really figure out how to be, and this is really so much of what almost every one of my clients struggle with today. You know, it's great to reach out to companies that could be part of your TAM. It's really great to reach out to companies in your TAM that have some sort of signal of why they may need your services at that point. It's kind of like this. If you're in your late twenties, whatever you're at, and you really want to get married in the next couple of years, well, what would you do? Would you reach out to every woman you've met ever? And would you reach out to the ones that are married already and said, would you go on a date with me? No. would you reach out to every woman throughout the world to see if they are interested in marrying some American from New York City? No, you would find the right Tam. And then if you, not that we can get to this level in our personal lives, but if you knew women that were out there, they've kind of spent time with the, they've dated enough and they're kind of like, I'd like to settle down in the next three to five years. Well, wouldn't that be something? Right? So, and that works for every side from men looking for women, women looking for men, men looking for men, women looking for women, all four. It goes everywhere. But the same thing, that's the it just it really blows. It's just amazing what it can do. And what we saw is that their outbound conversion went up to 60 percent. Their cycle length dropped. And it just turned the signals that AI can bring into pipeline for that company. KK Anderson (06:20) I love it. So basically the AI didn't replace the human judgment. The AI just gave that like use signals, pattern analysis to be able to figure out where even more of their ideal customer was and then brought into a sales team that had the competency and the ability to act on it compounding results. Mark Petruzzi (06:40) And you know what? And what the AI did? This it's some kind of a thing that I've done that we're really covering the personal side in a number of areas here. But I have most of you all know I have two amazing children. I have an amazing wife as well. But so we got a great, great family. Right. And one of the things that I did from the beginning with my kids is I've given them a lot of latitude. I know some people that are like, I want my kids to be an amazing student or want them to be an amazing athlete or whatever you do. And then you kind of push your child in that direction. I tried to be open with that. The one thing I did orchestrate a little bit is the books that I propose that they read and not like, you this is you have to get this done by the end of the week. It was always more of what I was reading. read this book talking to my, you know, and whether there were classics, whether there were new books, but it's the same thing in all of this. Like if you're looking at the right lists of companies and know that these have all been vetted through the process that you built

17 min

May 13

Ep. 126 - Diagnostic Session: Why should you do a diagnostic before you apply AI to your GTM - Part 1

General Episode Description: In this first-ever Selling Intelligence Diagnostic Session, Mark Petruzzi, KK Anderson, and Alan Rudolph go deep on one of the biggest questions facing revenue leaders today: where does AI actually belong inside the go-to-market motion? Rather than a traditional guest interview, this episode introduces a new format focused on unpacking real operational challenges from inside the work AGS does every day with CROs, CEOs, and private equity-backed companies. The team explores why “diagnose before you AI” has become a core principle in modern GTM strategy, and how AI can either accelerate enterprise value creation or amplify existing operational problems. The conversation also dives into the bow tie revenue framework, ICP discipline, and why retention and customer outcomes matter far more than simply generating more pipeline activity. What You’ll Learn: Diagnose Before You AI: Why AI amplifies both strengths and weaknesses inside your GTM engine.The Cost of Moving Too Fast: How scaling AI without operational diagnosis creates value erosion.The Bow Tie Framework Explained: Why “find more, win more, keep more” changes how leaders think about revenue.ICP Discipline Matters More Than Ever: How weak ICP alignment destroys CAC efficiency, retention, and enterprise value.Why Gut Feel Is No Longer Enough: The growing importance of data-driven decision-making in AI-enabled sales organizations.Key Topics: AI increasing productivity while amplifying broken processesThe pressure CROs face from boards, CFOs, and AI vendorsWhy “slowing down” can actually accelerate long-term resultsEnterprise value creation and AI investment decisionsThe hidden danger of filling pipelines with the wrong customersThe relationship between ICP discipline and long-term retentionThe bow tie model: find more, win more, keep moreWhy investors care more about post-sale execution than contract signatureCustomer onboarding, time to value, and retention as core valuation driversThe evolution from founder-led growth to scalable GTM systemsCAC payback, pipeline coverage, and modern SaaS benchmarkingThe rise of data-driven CRO leadership in the AI eraGuest Spotlight: Alan Rudolph Alan Rudolph is the leader of the private equity division at AGS and a strategic operator with deep experience across growth-stage companies, enterprise sales, and operational leadership. With a unique background operating at the COO level, Alan specializes in enterprise value creation, GTM transformation, and aligning revenue organizations with board-level priorities. Resources & Mentions: AGS (Advisory Growth Strategies)Concept: Diagnose Before You AIFramework: Bow Tie Revenue Architecture (Find More, Win More, Keep More)Concept: Ideal Customer Profile (ICP) disciplineMetrics: CAC payback, pipeline coverage, gross retention, net retentionWinning by Design bow tie frameworkRay Rike and SaaS benchmark analyticsConcept: Founder-led growth vs scalable revenue operations🎧 Listen now and follow Selling Intelligence for more diagnostic sessions, GTM insights, and practical frameworks for AI-driven revenue growth. Mark Petruzzi (00:00) Welcome to Selling Intelligence. I'm Mark Petruzzi, joined as always by my co-host KK Anderson, and in a very special way today, joined by Alan Rudolph, who is the architect and the leader of our private equity division at AGS. Alan has been a guest on Selling Intelligence before, so our regular listeners will know him already. He brings a rare lens to the revenue conversation. He's operated inside growth stage companies. He's advised PE boards time and again, and he's built sales and go-to-market engines from the ground up. But most importantly for us today, he's built those engines from the CIO level, which gives us a really distinct and important vantage point to. really how boards and CEOs and COOs need to balance these initiatives when we're looking at growing faster or building our revenue. He's also a close friend and I'm really happy to have him with us here today. Quick note for our listeners, today we're trying something entirely new. We're calling this format Diagnostic Sessions. No traditional guest interview. just three operators going deep on a single revenue topic from inside the work that we do every single day. We've been getting so many questions from our listeners about what we actually mean when we say, diagnose before you AI, because that mantra has been showing up in nearly every CRO conversation we are having. So we decided to spend the full session unpacking it, and Alan is joining us from the operating. side of this conversation because we really feel it an operator's voice as well. KK Anderson (01:44) Thank you, Mark. We're so excited to be here, Alan. We're so excited to have you. And we're going to keep bringing you the amazing guests and the revenue leaders and the business operators that you've come to know and expect on the show. Don't worry. But from time to time, when there is a topic that we really want to go deep on, when we start getting a lot of questions from our audience, as we have been lately, we're going to drop in. a diagnostic session like this one. And we'd love your feedback on the format. So please leave us a comment, send us a note, tell us what you think. So today's session is all about where AI belongs in your sales motion. And just as importantly, where it doesn't across the full revenue cycle from finding new customers to winning deals and to keeping and growing them. There is an AI technology out there that can I to fix everything at every stage, I promise you. And the question is whether AI actually delivers or whether it amplifies problems that your team already has. And so we're gonna talk about this in four different areas. Number one, what we actually mean when we say diagnose before you AI. Number two, the bow tie framework that anchors how we think about revenue and how we think about the go-to-market architecture. And number three, how to diagnose each part of your go-to-market funnel. And we'll walk through specific examples of actual clients that have done it the right way and sometimes the wrong way. And then finally, the fourth thing that we'll talk about are four things that every CRO should do this quarter before scaling AI investment. So we have got an action-packed diagnostic session today. Alan, Mark. Welcome back to Selling Intelligence. Alan Rudolph (03:28) Thanks, KK. Great to be here today. I think one of our challenges is going to be, can we clearly say diagnose how many times throughout this podcast? Because the diagnose before you AI conversation is so critical, as KK just said. And we're going to keep unpacking it as we go through this session. And I think you, as our listeners, will Mark Petruzzi (03:37) No, no, no. Alan Rudolph (03:50) be intrigued with what we say and hopefully challenge us through the journey. Because the pattern is real, the cost of getting it wrong is real, but the opportunity to get it right is even bigger. So looking forward to going deep with you on this topic throughout the session. KK, where do you want to start? KK Anderson (04:06) Okay, Mark, let's start with you. So you have been saying for over a year, since I can remember honestly, AI doesn't solve, AI amplifies. So what do you actually mean by that? Mark Petruzzi (04:19) Yeah, KK, thank you for that question. For me, and you hear this word out of me very often, and so we'll be saying diagnose and we'll be saying productivity and efficiency. And those are the things I focus on and talk about with my clients every single day. And so what does that mean? know, AI amplifies, it just amplifies the productivity of everything you do. everything you do gets more efficient and when done right, it can get more effective. However, when it's there isn't that diagnosis up front, you have, you just start to amplify your problems and challenges you already have in your go-to-market process. you know, think about it that way. It makes you more effective at all the bad things you do. You know, makes you more effective in finding clients that would never buy your products. And maybe they'll listen to you for a couple of meetings, but they're not, they're not a good ICP. It makes you reach out to more individuals. You know, as you're targeting and lead Jen and the people who just really would be a huge uphill climb to be able to get them excited about making an investment in your product. So. It's got to be done right up front to really get the productivity. Productivity comes together when there's something that really helps you that gets amplified rather than more challenges being amplified out there every day. So KK, you're in CRO conversations every week as well. Why are so many leaders rushing AI before doing the diagnostic work? KK Anderson (05:55) That's a great question. Every CRO I talk to is getting pitched by AI vendors 30 times a week, not even kidding. And the pitches are all very similar. We promise a shorter sales cycle, more closed deals, a better forecast. And at the same time, they're under pressure from their boards asking, what's the AI strategy? And the CFO saying, prove your ROI before you AI, right? And from vendors, of course, saying just buy this like I just mentioned. And so they're really getting it from all sides. And I just attended a transformation event last week in Houston with about 30 CROs in the room. And every single one of them had the same questions. They wanted to know how do they measure AI? How do they validate it? Where do they apply it? And I think what became abundantly clear in that room is that the one consistent thing is that there are, there's just a million unknowns. The one consistency is that nobody really knows yet, right? There's so many unknowns. And so I feel like the pressure is there to be decisive and to make a decision. And, you know, our perspective has been and will continue

27 min

Selling Intelligence (formerly Selling the Cloud)

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Ep. 126 - Diagnostic Session: Why should you do a diagnostic before you apply AI to your GTM - Part 1

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Selling Intelligence (formerly Selling the Cloud)

Episodes

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

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

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

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

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

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

Ep. 127 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 2

Ep. 126 - Diagnostic Session: Why should you do a diagnostic before you apply AI to your GTM - Part 1

Ratings & Reviews

About

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