Selling Intelligence (formerly Selling the Cloud)

Mark Petruzzi, KK Anderson
  • 4.4 (8)
  • Management
  • Updated Biweekly

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

    4d ago

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

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

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

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

    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
  6. Ep. 125 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 2

    May 6

    Ep. 125 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 2

    General Episode Description: In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Alan Rudolph, Strategic Advisor at AGS, to explore how sales and marketing alignment, time to value, and retention strategies directly impact enterprise value. Alan breaks down why misalignment between sales and marketing often starts with a lack of shared ICP definition, and how that disconnect destroys both efficiency and effectiveness. He also shares where AI is creating real leverage today across prospecting, coaching, and personalization, while emphasizing that human judgment remains critical in enterprise sales. The conversation closes with a deep dive into time to value, gross versus net retention, and the bow tie revenue model, highlighting how leading organizations connect the full customer lifecycle to long-term value creation.   What You’ll Learn: Sales and Marketing Alignment: Why ICP clarity is the foundation of both quality pipeline and efficient execution.Where AI Actually Works: Practical use cases in prospecting, coaching, and personalization.Time to Value (TTV): Why speed to value is now a critical metric owned by the entire organization.Retention Metrics That Matter: How gross and net retention signal true business health.The Bow Tie Model: How “find, win, keep” connects the full customer journey to enterprise value.Key Topics: Marketing optimizing for volume vs sales needing qualityThe breakdown of lead quality when ICP is not alignedAI enhancing research, call coaching, and content personalizationLimits of autonomous SDRs in enterprise sales todayDefining and reducing time to value (TTV)Gross retention vs net retention and their impact on profitabilityThe hidden cost of poor retention on CAC and EBITDACustomer journey ownership across the entire organizationThe bow tie revenue framework: find more, win more, keep moreWhy traditional funnel thinking ignores retentionThe importance of cross-functional ownership of the customer lifecycleStrategic priorities for CROs: ICP discipline, full revenue ownership, and efficiency as advantage Guest Spotlight: Alan Rudolph Alan Rudolph is a Strategic Advisor at AGS with deep experience advising private equity-backed companies and scaling enterprise sales organizations. With a strong operational background at the COO level, Alan specializes in aligning sales, marketing, and customer success to drive measurable enterprise value and long-term growth.   Resources & Mentions: AGS (Advisory Growth Strategies)Concept: Ideal Customer Profile (ICP) alignmentConcept: Time to Value (TTV)Concept: Gross vs Net Revenue RetentionFramework: Bow Tie Revenue Model (find, win, keep)Concept: AI-assisted sales and marketing workflows🎧 Listen now and follow Selling Intelligence for more insights on enterprise value creation, GTM alignment, and building high-performance revenue organizations. Mark Petruzzi (00:34) Alan, let's talk about the marketing side of this equation. Because in our experience at AGS, sales and marketing misalignment is one of the biggest destroyers of both efficiency and effectiveness. What does a well-aligned value creation oriented sales and marketing motion look like? And where does it usually fall apart? Alan (00:53) So it's fascinating because when it's working, it just works, right? It's invisible. It doesn't matter. But when it starts to fall apart, It's usually, and this is where we start tying all these pieces together in terms of ICP, because it's the definition of that qualified lead or the quality, maybe said another way of that qualified lead, right? So marketing is always going to optimize for volume, right? Throughput. not the quality, right? The actual lead that comes in and making sure it's a good lead. And then sales just starts ignoring it. Sales starts going, doing their own thing and marketing thinks they have this great volume and sales is saying, you no, because they're not matching back to the ICP and that shared definition, that quality of how do I bring a great customer in the door? KK Anderson (01:44) That makes a lot of sense. And Alan, let's pivot to everyone's favorite topic, AI, for a minute here to round out this topic. So AI is reshaping both how we find customers and how we serve them. And so in terms of this kind of efficiency mandate, where are you seeing AI create real measurable leverage for sales and marketing teams right now? like in your port codes that you're working with or have worked with in the past, like where's it working and where is it still mostly noise? Alan (02:14) three areas are where I see it working. First of all, and let's frame this all in the context of making us humans better, not replacing us humans. let's start there. That's first and foremost. so number one, prospecting and research, right? Who should I be talking to? Who should I be reaching out to? Right? That time spent in building those lists, et cetera. Number two is call intelligence and coaching. And I can remember, my God, one of the port codes I was working with probably five-ish years ago, actually in the middle of COVID, we started doing call recording. And the value prop around what I can, the takeaway from our calls, right? What worked? What didn't work? How should I change the script, et cetera? Just a huge opportunity for training, for coaching, for getting much more effective results out of our calls. you know, again, huge in terms of intelligence and coaching. lastly, content personalization at scale, right? Using AI to tailor the case study, to tailor the solution definition, to tailor, the whole presentation, to make sure that it matches specifically, you know, to that, that prospect we're going, going after. So it's not noise. It is real. AI is real. The one thing I would stay away from, right, in terms of what's not working is sort of these autonomous SDRs, right? Because it just, it's not there yet. know, tomorrow is, we don't know, but it's just not there yet. Again, it comes back to, it makes us all better. It makes humans better, but it doesn't replace that human judgment. That is so important in a high stakes enterprise class sale. Mark Petruzzi (04:02) Excellent, Alan. All right, well, let's move us into our final topic, time to value retention and the revenue bow tie. Earlier on, Alan, you introduced us to the concept of time to value, TTV, as a critical metric that most sales leaders do not own, but absolutely should. Please define TTV for our audience and make the case for why it belongs on the sales leader scorecard. not just customer success. Alan (04:29) Absolutely. So TTV is, as you said, Mark, time to value. It's how quickly can I get from that contract signature to value from the solution, whatever that means, right, in terms of the solution up and running. And I can remember going back in my career, we'd be talking six, nine, 12 months. And customers want 15, 30, 45 days. So it's just so critical that the Really, and I'm going to broaden it between customer, beyond just customer success and sales, the whole organization, the whole executive leadership team needs to get focused in on how do I define a solution, sell a solution and drive that solution to quote unquote live to value with the customer as quickly as possible. And that's what TTV is all about. And that's why it needs to be both on the seller scorecard as well as the success scorecard. And it's going to tie right back into the bow tie. So it's just, it's, it's, you think about a customer journey, right. And I'm drawing a circle here because the customer journey is in fact, is a circle, right? We find a customer, we win the customer, we keep the customer. And it's so important that the, that whole journey. that the executive leadership team is, you know, it's on the scorecard. They're evaluated on the success of driving TTV as low as possible. KK Anderson (05:55) That makes a lot of sense. so building on TTV, right? And thinking about, you know, gross retention versus net retention. So walk us through, if you would, the gross retention versus net retention, you know. Alan (06:04) Mm-hmm. KK Anderson (06:11) concepts, right? So thinking, you know, at AGS, we see this constantly. A team will sell aggressively. They'll hit their new logo acquisition number. But gross retention is quietly eroding in the background, right? So what does that diagnostic conversation sound like with the CEO or a board of directors when those two numbers start to diverge? And I know, know TTV fits into that for sure, but How do you fix that? How do you fix it when your gross retention is not aligned with your net retention? Alan (06:43) Sure. So let's go back to definitional, right? So gross retention is I open my doors on day one of the year. If I have a dollar and I renew that dollar, that's 100 % gross retention. So let's be clear on definitions here. And then net retention is how much additional do I sell? And depending on how the scorecard is kept, that additional can be everything from a CPI increase, 4%, 5%, 6%, or whatever the number is that you choose. to true add on to increase in the actual pricing so that when I take the dollar, I renew the dollar. But if I have, you know, an, an, an extra 10 cents, excuse me, of add on now it's a dollar 10. And now I have a net retention of 110%. This whole conversation you hear us talking about this through this whole podcast comes back to selling value. selling value to my ICP, my ideal customer profile, and making sure the customer is getting that value vis-a-vis the previous topic around TTV as quickly as possible. The more we can tighten in on the combination of the solution along with the ICP and driving that value to the customer, the customer is going to renew, the customer is going to buy more. World class metrics have Gross retention in the mid to upper 90s. World class metrics have net retention, 110 % plus. That's world class. What happens is if we see

    20 min
  7. Ep. 124 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 1

    Apr 29

    Ep. 124 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 1

    General Episode Description: In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Alan Rudolph, Operating Partner at AGS, to break down what enterprise value creation really means for modern sales leaders. Alan shares why CROs must move beyond just hitting quota and start thinking like operators responsible for long-term enterprise value. The conversation explores how retention, expansion, deal velocity, and cost of acquisition directly influence valuation, and why aligning go-to-market execution with investor expectations is now critical. They also dive into the shift from founder-led growth to scalable sales organizations, the importance of ICP discipline, and why effectiveness and efficiency must now coexist in every revenue team.   What You’ll Learn: Enterprise Value Creation Explained: What it actually means for CROs and sales leaders beyond hitting quota.The ICP Foundation: Why defining and sticking to your ideal customer profile drives valuation.Efficiency vs Effectiveness: How modern sales teams must balance both to compete.Destroying Value Without Knowing It: Common mistakes like discounting, churn masking, and selling to the wrong customers.From Founder-Led to Scalable Sales: What must change to build repeatable revenue systems.Key Topics: Value creation plans and their connection to company valuation multiplesThe four drivers of enterprise value: retention, expansion, deal velocity, and acquisition costThe “discount trap” and its impact on profitability and valuationNet revenue retention as a core board-level metricCustomer acquisition payback and time to value (TTV)The bow tie revenue model: find, win, and keep customersTransitioning from founder-led sales to structured go-to-market systemsLeading indicators of inefficiency: activity without outcomes, extended sales cycles, poor handoffsThe role of ICP in both agentic workflows and traditional GTM executionWhy misalignment between sales and delivery destroys trust and value Guest Spotlight: Alan Rudolph Alan Rudolph is a Strategic Advisor at AGS with decades of experience working with growth-stage and private equity-backed companies. Known for operating at the COO level, Alan specializes in aligning sales, marketing, and operations with investor expectations, helping organizations build scalable revenue engines that drive long-term enterprise value.   Resources & Mentions: AGS (Advisory Growth Strategies)Concept: Enterprise Value Creation (EVC)Concept: Ideal Customer Profile (ICP) disciplineConcept: Rule of 40 and evolving efficiency benchmarksFramework: Bow tie revenue model (find, win, keep)Metrics: Net Revenue Retention, CAC payback, Time to Value (TTV)🎧 Listen now and follow Selling Intelligence for more insights on scaling revenue, aligning with investors, and building high-performance go-to-market teams. Mark Petruzzi (00:28) Welcome to Selling Intelligence. I'm Mark Petruzzi, joined as always by my co-host, KK Anderson. Today we have a guest who sits at a genuinely rare intersection. Someone who has operated inside growth stage companies, advised P backboards, and built sales and marketing engines from the ground up. and also from the COO, Chief Operating Officer, Level, which has been his core focus. He's also a close friend and a member of our team here at AGS. Please welcome Alan Rudolph, Strategic Advisor at AGS. So, Alan (01:03) Thanks, Mark. to be on the podcast today. Mark Petruzzi (01:06) Great, we're happy to have you, Alan. So Alan brings decades of experience across boardrooms, PA backed operators and enterprise deal cycles. He's known for helping leadership teams connect the dots between investor readiness, revenue acceleration and overall sales team performance. And also for making the case that great sales leadership is not just about hitting a number. It's about building a machine that creates lasting enterprise value. That is exactly where we would like to go today. We're going to talk about what enterprise value creation actually means for the sales leader, why efficiency now sits alongside effectiveness as a C-suite mandate, and how the boat-time revenue model, finding, winning, and keeping customers, maps directly to the metrics P investors care most about. Three topics we'll cover. EVC, enterprise value creation, what it is, why sales leaders need to understand it and own it. Effectiveness versus efficiency, the dual mandate for modern sales and marketing leaders and why building an efficient team is no longer optional. The third one is time to value retention and the revenue bow tie. How customers onboard focus on gross retention and how important net retention is to the overall enterprise value and what the best senior operators do about it. Again, Alan, we're so happy to have you here. Let's jump right in. So, okay, first topic, enterprise value creation. You know, really what a sales leaders get wrong here. And let's start with a framing question because this concept of enterprise value creation gets talked about in boardrooms, but rarely makes it onto the whiteboard in a sales QBR in plain language. What is an EVC and why should every CRO SVP of sales and VP of sales have it front of mind, not just the CFO in the board. Alan (03:04) Thanks, Mark. Great question. So EVC or value creation or value creation plans has been the buzzword, as you say, of boardrooms, of private equity firms. And at the end of the day, a value creation plan, also a transformation plan, simply drives to whatever that target multiple is. And so everybody thinks, it's just about the multiple. pick the day and age, pick the year, pick whatever time frame you want to pick in terms of what are target valuations. But let's forget about the number for a second. And again, let's talk about what the CRO needs to worry about. And so as you said previously, CROs think, it's just the number, right? I got a quota. What percent of quota? How am I doing against my sales forecast, et cetera? When I think about a value creation plan for a CRO, I think about things like customer retention, right? How am I doing? How am I driving value across my install base? Because we know the higher the gross retention, that drives into expansion capabilities. That drives into a broader opportunity to sell more of what I have in my toolbox, number one. So that's retention and expansion. Then add to that deal velocity. Again, the deeper relationship, the clearer understanding, I have faster deal velocity. And then lastly, think about it from what does it cost me to win that deal? That's what's so critical for the CRO. these are, if you take, just take those four things I just said, retention, expansion, deal velocity, and costs of acquisition and you put that into a value creation plan. Okay, so what does that really mean? Let's dig into that for a second. When I think about a value creation plan around retention, I'm going to have a key set of initiatives that I'm going to drive across my sales team, hunters, farmers, whether it's customer success or account management. I'm going to have key initiatives that drive increases in overall retention. That's what a value creation plan is. Separate and distinct from my quarterly forecast as the CRO. Right? So it's the combination when I think about what does a good CRO look like when he or she steps into the boardroom and starts talking about how am I doing this? How did I do this past quarter? What's the forecast for the next three quarters? How am I going to do for the year? And how am going to improve that overall value prop into the value creation plan, which ultimately drives the multiple in terms of the overall valuation of the. KK Anderson (05:50) So as you think about, am I echoing by the way? Alan (05:53) You are. Mark Petruzzi (05:53) You are, yes. KK Anderson (05:55) Okay. Hang on. that better? Okay. I think it might be gone. Okay. Sorry about that. so as you think about these, these specific value creation plans, you know, and you think about sellers in general, right? Salespeople. What would you say are the top two or three places where sales teams Mark Petruzzi (05:56) It actually seems better KK Anderson (06:13) or sellers unknowingly destroy enterprise value, even though they may be hitting their top line number? What are some things to look out for where they're inadvertently impacting in a negative way? Great question. Alan (06:23) Great question and I see it too often and don't laugh too much when I give you the first comment. The discount trap as I call it. Right? We get to the number, we outperform, but I do that by discounting and we know that that discounting inherently puts challenges all throughout the organization because now our profitability numbers, our bottom line isn't where we need them to be. So we just really need to be careful in terms of selling value that we're, have a, you know, I've walked into companies that don't even have a target price book, right? And so it's important that we understand what our price structure is, how to drive value with that price structure and not to ultimately fall into the discount trap. That's number one. Number two is the, I'm gonna call it the yin and the yang or the tie between, and this comes back to, find, and keep more is churn versus new business. So is a ⁓ lower retention massed by net new business. And we know the cost of acquiring new business versus the profitability of a long-term customer is dramatically different. And so we don't want to overachieve revenue numbers because we're bringing more in the door net new. but we're losing or reducing on gross retention. then lastly, and again, I'm an ops guy, right? And so I need to manage and maintain customers throughout the life cycle. It's selling to the wrong customers. And the hardest thing we all can do in an enterprise SaaS company is fire a customer. But we know that sometimes we just need to do that because For whatever re

    19 min
  8. Ep. 123 -Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 2

    Apr 22

    Ep. 123 -Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 2

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

    25 min
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About

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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