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Ep. 127 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 2 May 20, 2026

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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 RudolphAlan 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 notsuper 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 thinkyou 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 evendo 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 inmarrying 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 kidsis 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 with your agentic programs and there's a connection, there's a signal, then you get to use your gut and say, okay, out of these hundred companies,These 15 are what I'm going after first. And sometimes you may get a higher rating and you may say, no, that company I'm never going to break into. you say, forget about what the agent is saying. That's where the, so you're kind of doing the same thing I did with my kids. You promote books that they really can get a lot out of, or you promote targets that your team can really get a lot out of as well.So now back to you. So what does the behavioral competency piece tell you that win rate doesn't? Back to OMG, back to the things you figure out within your sales team. What do you get out of all of that side?KK Anderson (08:36)first of all, when I'm thinking about win more, And we're thinking about sales excellence, there's really two core layers and both are required, right? So layer one is that behavioral competency that we've chatted about a little bit today. And that is really what is your team capable of, especially when they're under pressure to perform and to produce revenue, right? That's the objective management group work.Mark that you mentioned the 21 core competencies and layer two is really the outcome metrics. And so that's what do the numbers actually show. win rate, deal size, cycle time, pipeline coverage, forecast accuracy. know, most CROs are measuring some sort of each and each of those behavioral and the actual metrics, but I don't know that.Mark Petruzzi (09:02)Mm-hmm.KK Anderson (09:22)that truly that many of those 600 plus organizations that I've worked with are doing either necessarily well, So for example, they might be measuring calls, activity, meetings, emails, that pipeline stages and things like that, but that's not gonna tell you if your team can actually compress a sales cycle, actually move a deal across that finish line.So it really takes both of those kind of layers. And so when you ask me, what does a behavioral competency tell you that a win rate doesn't, right? It's, competency tells you why, right? And then the win rate, the win rate tells you what's happened. that, I don't know if I'm articulating this the right way, but it's, really two different conversations. two teams can have identical win rates.for completely different reasons. Take team A, right? They win 35 % of their deals. They qualify hard. They walk away from bad deals. They're only investing in real opportunities. And then you've got team B who also has a 35 % win rate because they're discounting aggressively. they're doing everything they can to drag deals across the finish line. And it's a race to the bottom, right? They both have the same win rate.but they have totally different behavioral profiles underneath. And that's why it's so important to know what that behavioral competency is. It's being able to ascertain the health of your sales organization, right?Mark Petruzzi (10:45)I think you hit it right on the mark. I think, and by the way, I've heard Alan kind of name this whole approach, the discount trap. Walk us through it, Alan. The discount trap is exactly where AI applied to a broken motion accelerates the damage.KK Anderson (10:53)Mm-hmm.Alan Rudolph (11:03)often, Mark. mean, that's the problem with a discount trap. And it was just that fascinating discussion in terms of the diagnostics, diagnosis, and behavioral impacts, and all the metrics that KK just threw out. But this discount trap is so critical. And here's another bold statement I'm going make today. How many companies do we know in this broader, softer AI space today that do not have a target price point?Right. Freelancing on every deal. We see it way too often. So the CRO hits his number, his or her number. They outperform on the top line, but they do it by discounting. And we don't even know what the discount is half the time again, because we don't have a price book. And that ripple impact of that discount and the pressure it puts on the downstream systems in terms of time to value, in terms of implementation, in terms of success, in terms of getting toyou know, all the appropriate retention numbers, it just has a huge impact on margin, which ultimately has a huge impact on overall valuation of the firm. And by the time the team has trained itself, about this discounting in terms of getting the deal done, AI just accelerates it. It just makes it that much worse. Right? We get greater proposals out. They look great. They speak great. They talk great. Right. But we don't drive theValue of the solution. Oh, by the way, what am I going to say next goes back to that target ICP, right? So we're discounted because we don't have the target ICP. So how do you fix it? Sell value sell value to this in terms of the solution to that ICP and Don't discount if you sell value you don't have to discount. So you that's how you go about diagnosing that overall competency gap. You have to fix it at the individualcontributor level, you obviously need a price book. And then you can leverage AI appropriately, but don't get caught in that discount trap.KK Anderson (12:56)I couldn't agree more. And Mark, I'm curious for your perspective as well. I know you've sat in a lot of PE diligence conversations. What do investors actually want to see on the deal cycle from yourMark Petruzzi (13:08)Yeah.I'm really excited to answer that question because it's different than what most CROs or sales leaders would think they want to see. They don't want to see you having a history or your team having a history of overperforming in significant ways from their, say, b…

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Ep. 126 - Diagnostic Session: Why should you do a diagnostic before you apply AI to your GTM - Part 1 May 13, 2026

Show notes

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 RudolphAlan 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 canI 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, willMark 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 roomis 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 to be to slow down, take 30 days, diagnose first, make sure you know your numbers.and know where to go in. Do you want to go in solving a find more problem, a win more problem, or a keep more problem? And if you know your baseline, then you know where AI belongs and where AI can help you to solve and have the biggest impact first.Mark Petruzzi (07:23)KK, you, if I can add one additional thing to that. So when we talk about slowing down, the way I look at it, know, 30 days, if we're looking at a football analogy, it's a wide receiver, you know, stopping, looking back at the quarterback for a second, and then go in on that fly pattern afterwards, entirely wide open because the strong safety now, you know, bit on that.So that's really all it is. I do have to admit, early into this gen AI world that we're all in the middle of, this phenomenon, I was just running around all of my CRO friends and relationships and just saying, you gotta move. You're getting beat up by your board every week because you don't have a plan. Jump in, move, make it happen.because your competitors are going to, and if you don't, you're going to lose all those efficiency gains that your competitor is finding. And again, that worked in many cases. Sometimes you can do a quick little diagnostic as you launch, but in a lot of cases now we're seeing some of the damage that can be caused by that type of an approach. So it's a quick move, it's a quick pause, and then it's full out from there.as well.KK Anderson (08:38)Yeah, 100%. And Alan, I'm curious for your perspective. I know you're seeing this from the PE side and from the operating partner seat. Like in your opinion, what's the cost when a CRO scales AI in the wrong area or before they've diagnosed really?Alan Rudolph (08:55)thanks, KK. You know, it's fascinating. It's all about enterprise value creation, right? And, you know, March analogy, you know, on the football field, even though we're in May and it's not football season, still is so relevant. And so, you know, from the operating seat, it's one of the most expensive mistakes I see right now, right? Not doing that diagnosis. So when the CRO scales before they do the work, right? And it's the heavy lifting work.They just think they want to get to, you know, volumes. so the cost is just wasted spend. It's value, value erosion. So every quarter you spend amplifying a broken motion is quarter compressed that compresses that multiple at exit. And who knows where the multiples are today versus tomorrow versus, you know, X months or quarters from now. But the pattern I see most often is AI drives volume, right? We get more leads.Those leads lead to more meetings. That leads to more outreach. The board's excited, right? There's super activity. The CRO feels good. The AI line item gets celebrated. All of a sudden, gross retention starts to erode. And why does it start to erode? Because we filled the pipeline with bad customers. Again, it comes back to that discussion we were having about ICP. And by the time it shows up, you know,You've burned six, eight, 12 months in that value creation runway. So AI doesn't fix the ICP. It amplifies the fact that you need to have discipline. If your ICP is loose, you get the wrong customers. You have to diagnose first. Again, in summary, we all think about AI is going to create the activity, create that volume. What Mark said earlier about less work, get the activity.Drive gross sales, but the wrong gross sales and long-term that impacts the value creation.KK Anderson (10:46)Yep, and that's so well stated and exactly why we always say, you know, again, diagnose before you AI. So the alternative is not slower progress. It's faster regression. Wow.Alan Rudolph (10:58)Yep.KK Anderson (10:59)Mark, let's go into talking about the bow tie go to market and kind of the bow tie framework, if you will. And before we get into the diagnose topics, tell us a little bit about the bow tie framework. It's the structural framework for so much that we do, the anchor, excuse me, for so much of what we do. Why is it so important and why do we talk about it every day?Mark Petruzzi (11:22)Excellent question, And first off, let me give some props and credit to Jaco, the CEO of Winning by Design, who he and his team has built that framework, that bow tie framework that we know and love here at AGS. So what does that do? It extends the traditional funnel, the traditional mindset that many CROs have on just, you you have a great funnel,KK Anderson (11:22)That's it.Mark Petruzzi (11:47)You have good sales and marketing upfront, good BDRs. You'll get leads. You have smart sales team. They're going to close leads over time. as you would hear from and will hear from Alan, that's a part of it. But it's not even 50 % any longer. And when I say that, I of course mean in the reoccurring revenue segments of software.You know, of course we know SaaS is built on that premise, but it's really, really relevant in almost every complex B2B selling organization that I have seen. And I'll give you an example of that. I was fortunate enough to write, I'm selling the cloud. We get a little bit of a group behind that and very strong.level of sales performance, which we never expected when we did it. But then what I would then get is a lot of questions from individuals that were not in the cloud space, the SaaS space, about how can I use these principles in my business? And my answer was always like, you can use it in exactly the same way. Whether you're, unless you're just a company that sells something,once and then you don't sell that again to a client for 20, 25 years. But even if you'…

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Ep. 125 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 2 May 06, 2026

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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 advantageGuest Spotlight: Alan RudolphAlan 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 theReally, 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, butHow 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 retentionis 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 haveGross 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 net retention, this comes back to the way you phrased the question, KK, if we see that net retention staying that 110 plus, but the gross retention slipping, for example, into the 80s, maybe even only 90, that means we're putting inToo much pressure on net new sales, right? Too much pressure on selling that more, selling additional, and we're losing that gross retention. And what happens when you lose gross retention, number one is what I just said, too much pressure on the organization overall to get that add on sale. Number two, the overall cost of acquisition goes up. And so inherently, the EBITDA for the organization is getting impacted because I'm selling net new.and I'm not retaining my bass.Mark Petruzzi (08:59)And you know, Alan, I've seen over the years, there's almost this kind of machismo sort of looking at new opportunities and new revenue. And everyone wants to be that hunter that leaves the village and comes back with an antelope on their back, carrying it back to the entire village and everyone gets to eat. But we find in a lot of ways,It's really the individuals who are out there foraging and growing and doing things in the village are the ones that really keep a village alive much more than the big celebrated hunter that comes in. So it's amazing how that mindset just, it still hasn't gone away. Everybody still thinks a new logo is worth more than additional revenue and an old logo. And it just really doesn't.Okay, so let's switch to the Bowtie revenue architecture and go a little deeper here. The whole concept of find more, win more, keep more. That's the framework that ties the full customer lifecycle into that single value creation narrative that we started this entire podcast on. How do you use that framework when you walk into a port co or leadership offsite andAlan (09:52)Okay.Mark Petruzzi (10:13)What does it unlock in that conversation that traditional funnel thinking just absolutely messes?Alan (10:19)It misses the keep more, right? The whole premise is, you know, find and win. That just is the beginning of the journey. And I can't lose sight of that keep more, right? The whole discussion we have, and we spent a lot of time in off-sites talking about this is what is the customer journey? to, think about it from a RACI standpoint, right?Who touches the customer throughout the lifecycle, throughout the customer journey to ensure that the customer is ready, willing, and able to buy more throughout, again, that customer journey, that customer lifecycle? And that's why the bow tie in terms of find, win, keep is so critical and intertwined with this whole discussion of gross and net retention and making sure that theWhole organization drives value to the customer throughout the entire journey.KK Anderson (11:13)Really interesting. Okay, so as we round out this last topic, let's bring it home with a forward looking question, Alan. ⁓ So if you're advising a chief revenue officer or a CEO heading into a new fiscal year, right? They're still navigating a tough SaaS environment, PE pressure on EBITDA, and buyers who are more cautious now than they were three years ago.Alan (11:20)Mm-hmm.KK Anderson (11:36)What would you say are the two or three moves that separate the leaders who will create enterprise value from those who will just survive?Alan (11:44)I sound like so repetitive on number one. Ruthless, ruthless ICP discipline, right? That will just drive tremendous value as we look forward. Number two, and this might be a little bit controversial, own CRO, Chief Revenue Officer. Revenue, not sales, revenue. So own the entire revenue lifecycle. So let's, I don't want to.KK Anderson (11:44)Alan (12:09)We're have a whole other podcast about ⁓ how should a port co be organized. But suffice it to say that an executive leader that owns revenue needs to own that whole lifecycle, needs to own find more, win more, keep more, needs to own the customer journey of driving great value through TTV, as well as making sure we get the renewal signed. And then lastly, if you remember,half a dozen questions or so ago, we talked about efficiency and effectiveness. Make efficiency a competitive advantage, right? Drive the value. Make sure we understand where the buyers are coming from. Why are they coming through us? How do we drive through the sales cycle as quickly as possible? How do we leverage AI? Right? So you said it, KK. This is the culmination of what we've been talking about throughout this podcast. And it's aboutspeed and efficiency and effectiveness and pulling that all together into a competitive advantage.KK Anderson (13:09)I mean, it all comes together, right? It all comes together. Okay, Alan, we are gonna move on to our favorite part of every podcast we do, the rapid fire questions. And I'm gonna kick us off and then we'll, Mark, you can take the next one, okay? And I can't wait to see what you're gonna say for this first one. Okay, the metric you think every CRO should have tattooed on their wrist.Alan (13:29)Net Net retention.KK Anderson (13:30)at rest.Mark Petruzzi (13:32)Great, so okay, growth or profitability? If you can only optimize one for the next 12 months, which do you pick and why?Alan (13:40)So these are all mature companies. So it has to be profitability. I'm not in startup mode, right? So it has to be profitability with an asterisk optimizing for profitable growth, right? So we've talked throughout this podcast about, you know, a successful organization historically was at least rule Now those that that's even, you know, with AI with everything that's going on in the world around us, even growing more. So it's got to be profitable.And it's got to be growth. And you t…

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Ep. 124 - Enterprise Value Creation, ICP Discipline, and Building Efficient Revenue Engines with Alan Rudolph - Part 1 Apr 29, 2026

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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 valueGuest Spotlight: Alan RudolphAlan 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 driveincreases 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 teamsMark Petruzzi (05:56)It actually seems betterKK 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 Isee 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 becauseFor whatever reason, there's a gap between the solution sold versus the expectation of the customer. So it's just really when we come back to that question about how can a CRO destroy enterprise value overall, is get that right customer base that truly understand the value we drive, that can benefit from the solution.Mark Petruzzi (08:11)is really important for me to come back to that question.Alan (08:26)We know it's a very small world out there that will talk to their peers in their respective industry about the solution. So again, it's all about getting to the right customer.Mark Petruzzi (08:37)Excellent, excellent points, Alan. So one of the things we hear constantly from P E operating partners is that founders and early sales leaders are often great at the hunt, but man, do they struggle to build the system when they really have to take it past founder led growth. You have described this as the difference between being the lead salesperson and being a sales leader who builds organizational capacity.Alan (08:54)Mmm.Mark Petruzzi (09:02)Walk us through that ⁓ transition, typically breaks and what really does have to change to make it successful.Alan (09:09)mean founders are phenomenal, right? Because they build, they grow, they have personal relationships with that first set of customers. And by the way, they know what they can and cannot sell, right? They know where the product does or does not break. The discussions I have with founders in earlier stage companies really boils down to one primary aspect. Definition of the ICP.Who is my target customer? Right? So comes back to what I said earlier about whether it's finding customers or selling to the wrong customers, et cetera. It's all about the ICP. So I have a well-defined solution. And I know that that solution is relevant to a target set of customers. So how do I define that ICP? That's what will drive an organization to go from a founder-led sale that he or she canbasically make whatever decisions need to be made and can drive that solution into a much broader sales team that needs to understand what is that profile of the customer that I'm looking for? How do I drive the solution into that customer and win those deals?KK Anderson (10:23)You know, ICP is the cornerstone of everything really. And even now this week, we've been having a lot of conversations around agentic workflows and go to market and all of it hinges on the ICP. If the ICP is not effective, then none of the agentic workflows are effective. And it sounds like it's the cornerstone of our value creation as well, huh?Alan (10:43)KCAD, add to that, without the definition and the adherence to the ICP, the firm, the company, the SaaS provider will not get to its target valuation. I would be very bold in making that statement, but I'd stand behind it.KK Anderson (10:58)Well, and you might somehow weave this into my next question here. so, you know, thinking about making this concrete and you know, we like to measure everything. if I'm a CRO at a PE back SaaS company and I'm going into a board meeting next month, what are the two or three metrics that I should be walking in with that signal? I understand enterprise value. My team understands enterprise value. So.Like beyond just ARR and pipeline coverage, like what are those metrics?Alan (11:27)net revenue retention. It comes back to ICP. Am I selling to the right customer that continues to buy more from me? And so let's be clear for a second. Net revenue retention, everybody gets this messed up. Net revenue retention is I start the year, let's call it $1. And if at the end of the year I have $1.10, that means I grew at 110%.KK Anderson (11:30)Right. Yeah.Alan (11:49)revenue retention is the combination of my gross, what I'm renewing, plus the additional sales, cross-sell, up-sell, et cetera, into that customer. So first and foremost, a clear understanding of that revenue retention. Number two, and I talked about this briefly earlier, is the payback period for our customer, right? We know that the costs are higher in the first months and the first year of managingimplementing owning a customer. So again, this comes back to ICP sell to the right customer, right? It's I spent a lot of my career middle part of my career in outsourcing. We didn't actually make any money in large complex outsourcing deals to year two, three or four. So right, it's all about making sure you have the right ICP, the right solution selling into that customer. And then lastly, TTV time to value in this day and age.Customers want value as soon as they sign the contract. So we all know that in a SaaS world, customers sign the contract, they get an invoice, they pay us upfront for a year. Well, they want value immediately from that. So we want to make sure we're continuing to address time to value and how much we are decreasing the implementation time frame number one.Mark Petruzzi (13:09).Alan (13:09)and or number two for depending on the solutions and the more complex solutions that we're segmenting that implementation so that we get piecesof the solution implemented as quickly as possible so the customer is getting value out of the money they're spending with us.Mark Petruzzi (13:26)Good stuff. So let's move on to topic two. Effectiveness versus efficiency. Building the team that is able to move the needle. So the era of growth at any cost is over. It's way over, right? It's, you know, we've moved much more to the rule of 40, which means you have to have a growth rate plus a profit margin that is 40 or greater.and it's probably going to be moving past that metric as well pretty soon because, you know, was the good old days, right? It was, we, we had to grow each year. A sales leader was asked or was told what the number is and th…

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Ep. 123 -Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 2 Apr 22, 2026

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General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of BenchMarket, to go deeper into how companies should measure, operationalize, and compete with agentic AI in go-to-market functions.Ray breaks down why most companies still lack basic GTM measurement discipline, what new AI-specific benchmarks leaders should track, and how legacy SaaS companies can realistically compete with AI-native organizations that are operating at dramatically higher efficiency.The conversation also tackles the hard truth about workforce reduction, the rise of AI operators, and why companies must rethink their entire operating model, not just layer AI on top of existing processes. What You’ll Learn:Measurement Before AI: Why most companies must fix GTM analytics before introducing AI.AI-Specific Benchmarks: The emerging metrics for measuring agentic GTM performance.Competing with AI-Native Companies: Why legacy SaaS teams must rethink their entire playbook.The Role of AI Operators: Why AI expertise is becoming more critical than traditional RevOps.From Pilot to Scale: What success should look like at 90 days and 180 days.Key Topics:Cost per pipeline and cost per ARR before vs after AIAgent cost per opportunity, pipeline, and revenueDesigning modular AI workflows instead of “monster agents”The four-layer framework: productivity, effectiveness, efficiency, and ROIRevenue per FTE gap between SaaS and AI-native companiesWhy legacy SaaS companies struggle to match AI-native efficiencyRadical restructuring: reducing headcount and rebuilding with AI-first processesAI enabling deeper personalization at scale for outbound teamsThe rise of “AI operators” as a new critical roleThe “SaaSpocalypse” and pressure on net revenue retention (NRR)Using AI to improve retention, expansion, and customer insightsBenchmark expectations for agentic SDR performance at 90 and 180 daysGuest Spotlight: Ray RikeRay 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 andand 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'sactual 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 compete with Amazon? ⁓ I'll bring in a guy from Apple who created the Apple retail experience and that's going to fix it. We saw how that worked, right?KK Anderson (07:42)blue.really is.Ray Rike (07:57)Sometimes it's just nice being part of the next generation versus trying to reinvent the current generation. I'm being honest here.KK Anderson (08:04)you know, and I know it's hard to answer that, but if you were a CRO in one of these old school SaaS companies, what, aside from calling a consultant, like what, where do think you would go first? Like what would you, what would you do? How would you that gap?Ray Rike (08:17)I would completely get rid of my SDR team and make it 100 % agent based. I would reduce my number of salespeople by probably 50 % and say, okay, now that we got 50 % less staff, how do I manage more of their task with AI agents, research discovery, etc. So I would just basically look at what the AI native companies are doing, and then burn the ships and say, we got to do this with 50 % less people.Having a bandaid, I don't think helps. You got to rip it off. So even customer success, right? I do a lot of work with Gainsight. It's like AI is the best retention vehicle in the world because you can look at things that humans can't, kind of like usage patterns, et cetera. And they can predict churn faster than any CSM can. But when you've got 10 CSMs, they're like, that's my job.Well, if I only have three CSMs, I'm not going to be able to do this much, right? So I'm forced to try AI and automation.KK Anderson (09:11)Yep. And just since we're talking about the sensitive topic of AI replacing humans, is something, you know, questions we get a lot of, right? And we are firmly of the belief that yes, of course AI is going to replace some humans, but it can also make humans, that super intelligence can have an exponential impact on their effectiveness, sellers in particular, on their effectiveness if they're using AI correctly.So if you've got the three BDRs instead of the 10, what are some ways that, I don't know, talk to me about how AI can help them be more effective in these roles where there's less people.Ray Rike (09:48)I'll give you BDRs for example is research and doing a lot more targeted research and personalized outreach to those contacts in your ICP at scale. Where maybe I could do 20 or 30 emails that were personalized, best case now maybe I can do 50 a day or 75 a day. So research, highly targeted. That'd be one thing I'd be doing as a BDR every day.I would be using AI to say, how do I follow up with this person who I talked to three months ago? What's the best approach? Let's look at their LinkedIn profile. Let's look at the latest corporate articles out there in the ethos, you know, and on the internet, and let's tailor my next follow up based upon my AI agent helping me get more personal and personalized.KK Anderson (10:32)And what's interesting is more and more we are hearing about this kind of crisis of sameness, right? Where AI has enabled, know, everyone's got the same content, everyone's saying the same things, everyone's sending the same emails. Like you can tell if it's AI, you know, from a mile away. And then we also are also hearing this theme around how now, you know, your humanness is your uniqueness.And people are loving when they see a typo in an email or a message or a, hey, by the way, this is really me. This is not a bot.Ray Rike (11:04)So, you know, I don't know if this is good for this podcast, but I have to call, say it the way I see it. So I don't know if we saw the New York Times research from about a month ago, where 54 % of people prefer AI written communication versus human written communications. 54%, right? AndKK Anderson (11:11)Yep.Mark (11:23)Yep.Ray Rike (11:25)that's going to increase as AI becomes more, more able to personalize the communication to KK versus Mark, right? Which humans are going to have a harder time doing that. So ask me the question again, KK, I went on a tangent.KK Anderson (11:28)normal.What,when I was just thinking, you know, we're hearing now that your humaneness is your uniqueness. And so,Ray Rike (11:42)yeah.So an enterprise class sells, I think it's going to continue to be the case. But, know, I think even having, you know, children who are early career people, right. So and I hate these type of generic comments, but be the person who knows how to use AI in your function better than anyone. Everyone should be spending at least an hour a day on their own, learning how to use AI in their role.They should be learning a new tool at least once per quarter, if not once per month. So that's one thing, because for the next few years, those who know how to use AI in your function, whether it just is your assistant to do your function better, or you become what I call the AI operations guru, you can go into any company and say, I'm going to improve your sales development process by 5X.by doing this, that, this, this, and this that I've done four times before. So doing it as a practitioner and then be able to do it as a consultant, you're going to have job security for quite a while.So that would be my advice. Learn it and be better than anyone else. And by the way, make sure that your boss knows that you're the person who knows it better than anyone else. Because when it comes time to get rid of people, like, I can't get rid of Joe. Joe knows more about this AI agent than anyone in the company. So that's why, Kay, I think you asked me this earlier. I believe that AI operations is going to be much more strategic and important.Mark…

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Ep.122 - Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 1 Apr 15, 2026

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General Episode Description:In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of Benchmarkit, to tackle one of the most critical questions in enterprise AI today: how do you actually measure success in agentic AI programs?Ray shares why most AI initiatives are stuck in “pilot purgatory,” the common mistakes companies make when trying to automate broken processes, and why an AI-first mindset requires a complete rethink of data, workflows, and metrics. The conversation also explores how go-to-market teams should define ROI, what benchmarks matter in an AI-driven world, and why traditional SaaS metrics are no longer enough. What You’ll Learn:Why AI Projects Stall: The real reasons most agentic AI initiatives never scale beyond pilots.AI-First vs Human-First Thinking: How redesigning processes for AI fundamentally changes outcomes.Data Readiness Matters: Why poor CRM data and lack of governance derail AI success.Measuring AI ROI: The new metrics leaders must track to justify AI investment.The Shift in GTM Economics: Why cost structures and efficiency benchmarks are changing fast.Key Topics:“Pilot purgatory” and lack of enterprise-wide AI focusThe importance of data hygiene and enrichment for AI successRedesigning processes with AI at the center, not as an add-onThe rise of vertical AI and pre-built agent workflowsDefining success with leading, mid-term, and lagging metricsCAC ratio vs AI-driven efficiency benchmarks“COGS is the new CAC” and shifting cost structures in AI-native companiesRevenue per employee as a proxy for AI productivityToken consumption and cost predictability challengesBuilding smaller, modular agents instead of large monolithic systemsThe four-layer measurement framework: productivity, effectiveness, efficiency, and ROIGuest Spotlight: Ray RikeRay Rike is the founder and CEO of Benchmarkit, a leading source of B2B SaaS performance benchmarks with data from over 1,800 companies. He is also the host of the AI to ROI podcast and a founding member of the SaaS Metric Standards Board. With decades of experience as a go-to-market operator and executive, Ray focuses on helping companies move from intuition to data-driven decision-making in both SaaS and AI-driven environments. Resources & Mentions:BenchMarkitAI to ROI podcastConcept: Agentic AI in go-to-marketConcept: “Pilot purgatory” in AI adoptionConcept: AI-first process designConcept: COGS as the new CACOpenAI Frontier AllianceVertical AI platforms (example: Harvey for legal)Metrics framework: productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI measurement, GTM strategy, and building data-driven revenue engines.Mark (00:31)Welcome to Selling Intelligence. We're joined today by someone who might have had the honor and privilege of calling both a collaborator and a friend. Ray Reich is the founder and CEO of BenchMarket, the industry's most comprehensive source of B2B SaaS performance benchmarks with data from over 1,800 companies.Ray is also the host of the AI to ROI podcast. He's a founding member of the SAS Metric Standards Board. And full disclosure, my co-author on data and diagnosis driven selling, Ray has spent decades as a go-to-market operator, having served as president of Simply Learn, CEO at Higher Mojo, SVP at Moment Feed,and multiple times SVP market and sales and SaaS companies before founding Benchmark it roughly five years ago. And they have a singular mission, give every B2B reoccurring revenue software operator access to data driven benchmarks so they stop flying blind. Today, we're going, well, first off, let me welcome you, Ray. Thanks so much for joining us.Ray Rike (01:43)Thank you, Mark. Sorry that I'm so old that you had it took that long to read everything I've done.Mark (01:47)Exactly. Well, you know what? That's also a good thing because you've done some amazing things throughout your career and you're not that old. So, yes, let me tell you, let's talk a little bit about today and where we're going to go on this podcast. ⁓ What we'd like to do is tackle what might be the most important and for sure most underserved question in enterprise AI right now.How do you actually measure the success of agentic AI programs? And even more specifically, what does that look like for go-to-market functions? We'll dig into what benchmark its data, what is it revealing, where the industry is setting the bar, and what separates teams that are generating real ROI from those stuck in pilot purgatory. Ray, welcome to Selling Intelligence.Ray Rike (02:36)Okay, excited to be here. Let's dive into it.Mark (02:39)All right, so Ray, you've been collecting SAS performance data for years, and now you're turning that lens on AI. From what you're seeing at Benchmark and in hearing on your podcast, what's the core reason most agentic AI programs never graduate from pilot stage? Is it a data problem, a change management problem, or something else?Ray Rike (02:59)I think it's an evolutionary problem. So I did some research with scale venture partners last year about what the state of AI and GTM adoption was. And what we found, Mark, was it was primarily individuals adopting generative AI tools like Clot or Chat GPT to help them with individual tasks. Things like maybe it was an image creation for an ad campaign. Maybe it wasemail messages for outbound campaigns, et cetera. And the primary benefit was personal productivity. Hey, I can do this much more research quicker for each account, or I can generate this many more campaigns in a month. Now, when we get to process automation, which is really where agentic AI is going to be used, ⁓ we're just at the very beginning there, and we don't have enough experienceof actually deploying agentic AI to have a lot of success stories on a production basis, especially the enterprise, because most of the enterprises, and I'm talking about companies a billion dollars and over, I see an average of 20 or more simultaneous AI proof of concepts going on, and they're not really getting the focus of the centralized IT executive team, they're departmental.Maybe it's just customer service or maybe it's just development with a code assisting tool. So my answer is I'm not seeing enough organizational wide enterprise focus on true agentic AI initiatives yet.KK Anderson (04:32)And Ray, welcome to Selling Intelligence. glad you're here. And I just want to jump on top of what you just said there. It seems like the concern would also be that they're trying to put some agentic AI solutions onto maybe processes that should not be automated or were not the right process to begin with.Ray Rike (04:52)of the most common mistakes, and I've kind of built this framework of the variables that help ⁓ indicate success and agentic AI deployments. But one is the data is a mess, right? Think about today for what, 20 years we've been talking about how bad CRM data is and have we cleaned it up? No, we still have shitty CRM data, but the SDR or the AE will say, well, that's not the right information.Joe doesn't work at company A, Joe's a company B or that's the wrong title, right? So a lot of data hygiene, data prep needs to be done. So that's number one. And then to your point, we're thinking like old fashioned business process re-engineering. Well, yeah, maybe we map current state process and we want to map future state process, but we're doing it with a human first orientation and an AI first orientation isfundamentally going to change each step along the way of that process. Quite frankly, you have to identify what data I'm going to ingest, use at the field level for each step, each granular task within that process. And we just haven't re-engineered the process to be optimized for AI centricity yet. And KK, I don't think we're going to until we have a lot of people who have one or two rounds of experience.redesigning a process with an agentic AI first mentality, then then they can do it to third, fourth and fifth time.KK Anderson (06:16)and has that been defined how to have this kind of AI first mindset? Because we've had several people on the podcast talk about this, right? so, and I know I'm going a little bit off of kind of the agenda here, but I'm dying to hear your take on this. When you say AI first mindset versus just a traditional business process mapping,You know, like we're all used to, we all learned in business school, but the data scientists have been doing for decades. Like, what does that mean? What is AI first mindset? talk me through that.Ray Rike (06:54)I wish I could sit here and say, I've done 22 of these. here's here's the playbook. So I don't have the playbook either. I have a lot of ⁓ signals of why it's so difficult. And one of the big signals was OpenAI, what about two plus months ago, formed the Frontier Alliance. And the Frontier Alliance, right, because they said, we're going to get intoKK Anderson (06:57)Right. I know it's all new. No one knows. That's what I'm curious.Mark (06:58)Thank you.Ray Rike (07:17)agentic AI, not just generative AI, right? They first of all introduced, I think in January, the five layer cake of the OpenAI Frontier application map. And then they announced that McKinsey, Accenture, Boston Consulting Group, and maybe it was Ernst & Young, are now forming this Frontier Alliance to partner with OpenAI to help their enterprise customers deploy agentic AI. Why?Mark (07:35)Mm.Ray Rike (07:43)because it had been failing. A lot of the open AI projects to really do process automation using AI agents were not successful. So that's a signal, right? And as far as what's the secret, I don't have one other than try to find a consultant or a third party who's done two or three of these in the domain or the area. Let's say it's SDR.Mark (07:58)Thanks.Ray Rike (08:07)I want to automate the sales development representative function, right? Either you're probably should work with a software company that they specialize in that because they've actually ⁓ embraced and bundled domain expertise in their predefined agents, which then can be customized and or a third party consulting firm that have done it, that have made some of the mistakes and learn from their previous projects.So that's my recommendation. Go with a bundled application that has AI agent specific to that process and a third party. And if you think about vertical AI, KK and Mark, right? That's why I'm so bullish and so are most VCs on vertical AI. Look at a Harvey in legal. They actually are pre-packaging workflows, i.e. agentic AI.specific to the nuances and subtleties of that industry, including regulatory and compliance requirements. And they're making a lot faster headway into driving real return on investment than a horizontal, agentic platform that has to be custom designed for each customer. Did I answer your question okay, KK?KK Anderson (09:17)Makes a ton of sense, 100%.Mark (09:19)Soyou bring me back to the concept you mentioned earlier around BPR, business process, free engineering, and how this isn't that. But it makes me get to a point of like, where is the value going to come from? And to me, I've always seen the value of companies be a part ofor partially driven, if not significantly driven by their competitive advantages, how they differentiate themselves in the market. What I love about agentic AI, when done right, it allows you to build a set of processes in a way that can't be replicated by any of your competitors. You can't just say, great, I went to HubSpot or I went to Salesforce,and that's going to help me win against my top five competitors. Well, it's not because they all have Salesforce and in SaaS models, these systems weren't as flexible as now, know, agentic AI can be infinitely just, you know, infinitely just different than any other model that is out there today. So,I like that connection back to the business process side and ensuring that you have people who know that business process as a consultant, ensuring that you really leverage all the expertise and the tribal knowledge out of the client side because they know how to make this work. And they probably are working within a model today that is not what they would have recommended if they weren't forced to do it.because of the Salesforce process and what the system looks like or SAP or Oracle or whatever. take us a little deeper into that. Like, do you agree, I guess is the first question, like that these processes can now be more competitive advantages for customers and companies than maybe ever before.Ray Rike (11:12)Let me let me double click to the next level and KK I think you asked this question also. So in this framework, right. So one of the things because process redesign is such a critical part of this. Don't boil the ocean. Don't try to look at the entire customer acquisition, retention and expansion process. Let's get really focused and say, let's look at the outbound lead generation process.Constraint right so you redesign that constraint process first with a I centricity you define all the data that you're going to need to use in your existing systems of record like your account data the contact data the Including title you're going to define all I need to bring in this third party data to enrich it So define what data you need at the field level?Make sure you know where that data is coming from and how you cleanse and enrich. Think about the governance. I call this AI explainability, right? And you're going to need this, especially in regulated industries, but even if you're doing outbound sales for a software company, right? What's my government governance and policy? Who actually makes the determination that I should reach out to these people? Right? Is that in my ICP?What do I do different with a non-ICP member? That doesn't sound like governance, but it is in a way governance. You also need to pre-define human interaction and engagement points. Am I really going to just have that SCR agent do everything or I'm going to have some points pre-defined where human interaction, including maybe reinforcement, maybe ongoing coaching and mentoring, learning of the AI agent.You want to define those right up front. So you're prepared for that not only from a process perspective, but a resource availability perspective. Right. And then this is the major thing, KK and Mark, that I see so many people not doing is defining the criteria of success using metrics. What are my leading indicators? Maybe a leading indicator, since we're talking SDRs right now, maybe it is myengagement per transaction or outreach, right? How many times does somebody respond to the email, et cetera? Maybe it's the conversion rate from a agent interaction to a true discovery call or a sales call. And ultimately, you're going to want to carry that all the way through. What are my measurements as measured by pipeline generated per dollar of agent invested ordollar of new ARR generated by dollar of agent investment that I make, or agent investment plus human ⁓ reinforcement and learning. So you've got to really understand the leading indicators, the midterm, and then the long-term measurements that are going to impact the income statement. And I can go on and on about this, but I'll stop it here. If your CFO can't go to you and say you spent $100 million on AI agents last year,What did we get for it? And if you say, we got 20 % better sales calls, we got 30 % better sales call. Nah, not g…

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Ep. 121 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 2 Apr 09, 2026

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General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore the human side of leadership, trust, and AI adoption in today’s rapidly evolving business landscape.Sabrina shares her perspective on diversity in leadership, the realities of building a career as a working parent, and why creating an “integrated life” leads to stronger teams and better business outcomes. The conversation also dives into how trust has become the ultimate differentiator in an AI-driven world, and how companies must rethink how they show up as human, credible, and authentic.The episode closes with practical insights on how leaders should approach AI, where it delivers real value, and how to use it as a tool for thinking, not replacing human judgment. What You’ll Learn:Diversity as a Competitive Advantage: Why different perspectives lead to better decisions and stronger organizations.The Integrated Life Approach: How flexibility and trust improve retention, loyalty, and performance.Human Trust in an AI World: Why authenticity and real human interaction are becoming the new moat.Practical AI Usage: How to use AI for preparation, critique, and efficiency without losing credibility.Leading Through AI Disruption: How leaders can guide teams to experiment with AI while setting the right guardrails.Key Topics:The impact of diversity and inclusion on business performanceSupporting working parents and creating flexible, human-centered workplacesThe myth of “doing it all” and redefining success in leadershipWhy trust is harder to earn in a world of AI-generated contentReal vs artificial experiences in customer interactionsThe role of influencer trust and community platforms like RedditUsing real people and authentic content to build credibilityWhere AI overpromises and where it delivers real efficiencyAI as a tool for critique, feedback, and preparationUnderstanding how LLMs perceive your product and brand through consensus signalsThe shift from SEO authority to AI-driven consensus and reputationGuest Spotlight: Sabrina ParsonsSabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, and a leader with deep experience across sales, marketing, and executive leadership. She is a strong advocate for women in leadership and brings a unique perspective on building resilient organizations, fostering trust, and navigating multiple waves of technological change. Resources & Mentions:Palo Alto SoftwareLivePlanConcept: AI trust gap and authenticity in digital interactionsConcept: Integrated life vs traditional work-life balanceConcept: Consensus-driven reputation in AI search and LLMsBook: Into Thin Air by Jon KrakauerBook: Superintelligence by Nick Bostrom🎧 Listen now and follow Selling Intelligence for more insights on leadership, AI adoption, and building trust in modern go-to-market teams.Mark Petruzzi (00:31)So Sabrina, you're a strong advocate for women in sales and leadership. In your experience, what do women bring to the sales equation that often gets undervalued? And what does the data actually show?Sabrina Parsons (00:43)Yeah, that's a great question. I think that we've, well, hopefully people have, there's been a lot of data over the years that just shows a few things, I know these days, you know, talking about diversity is, you know, a hot topic and not something everybody wants to hear. But if you actually go and look at the data,Any time you're bringing different viewpoints in, it actually turns out the data shows that that's really good for an organization. That when you have six people who all come from the same background, who went, you know, got similar educations, have the same experiences, you're missing out. You're not getting some of these other alternate viewpoints that...could actually give you different insights and make your company better. So from that perspective, be it women or people of color, people from different cultural backgrounds, every time you have different people in a room, you're gonna win because they're gonna bring different information to the table. And then I think that, you know.Even though it's 2026 and I wish we were in a different place with women in leadership, the reality is that we still live in a world where, you know, there aren't as many women in technology. ⁓ And the numbers just show that and there aren't as many women in technology and leadership. And so women who are there and have made it all the way through, particularly in a leadership role, have probably worked really hard to get there.and probably have some really good insights. From my perspective, one of the things that I think is most powerful and I think can bring a lot of value to a company is recognizing particularly working moms and working parents, but as a working mom, I'm not a working dad, so I won't talk for working dads, thatYou know, there's a lot of very motivated, super smart women who want to work for a place. They don't want to have to jump from job to job to job. And if you can give them an opportunity to stay in one place, to continue to move up, if you can be the kind of boss that recognizes that there's going to be some peaks and valleys that a woman with young kids might have someissues with my kid is sick, my kid is going to the doctor, but at the end of the day, if you help them with flexibility, not making their job easier, not giving them less job, but giving them the ability to be flexible and do their job when they can, you're actually going to retain women longer. They're going to be more loyal. if, you know, loyalty and retention, we all know is, you know,There's nothing better for your bottom line, particularly in software and tech sales where people are your biggest asset.KK Anderson (03:36)You preach into the choir. Could not agree, could not agree more. I would love to hear about some of your, know, pursuits with women in sales and leadership and would love to, AGS would love to support you in those as well. Really cool.Sabrina Parsons (03:38)Thank you.Mark Petruzzi (03:47)forSabrina Parsons (03:48)you. I appreciate that. it's been a really, it's interesting. I think when Mark and I first caught up prior to the podcast, we talked about it a little bit, but being a Gen Xer and having grown up in the 80s and early 90s, I am of the generation that watchedthe women's lib movement, And watched all these really strong women come out of the 70s and early 80s, the Gloria Steinmans, This very powerful.movement and we were kind of fed this idea that like you can do it all women can be super women and you can do it all and I bought it I was like I am gonna be superwoman I am gonna do it all and didn't really think anything of it until I had my first child and that's when like the brakes come on and you're like wait what what does this actually mean?And you know, just this reality that like, wait a minute, this is a myth. Like you can't do it all, right? And there's a reason why very successful men were never expected to do it all. And yet we still have this place in 2026 where there's still a lot of judgment with women as mothers, like, you know,Why aren't you there at drop off? Why aren't you there at pick up? Somehow you're a bad mother and all these kind of, know, guilt woven into, you know, being this working parent and how do you deal with it? And what does that mean? And as I had one child and then two and then my third as I was running the business for me really understanding that myKK Anderson (05:14)Guilts.Sabrina Parsons (05:32)take on this, my approach is very much about leaning into who I am, not leaning into the structure that exists today, which I think a lot of us were still being told even 10 years ago when Sheryl Sandberg came out with her lean in ⁓ kind of autobiography, it was all about leaning into the current structure, right? It wasn't, wait a minute, does that actually work? And for,KK Anderson (05:54)Mm-hmm.Sabrina Parsons (05:59)from for me what's worked and what I like to mentor and what I like to, you know, really.do here at Palo Alto Software is to say that doesn't work and I have what I call an integrated life and my kids are older now and I've got two in college but when they were little that meant bringing kids on business trips with me and my mom would come with me. That meant kids in the office after school or on a snow day. It meant having appropriate places in the office.so that they could have coloring books and homework areas. you know, I mean, we often laugh because we have a very old, ⁓ I think it's a Nintendo PlayStation, but it's a very old one. I don't even know if it's called a PlayStation, but it's a very old one where it isn't actually wireless. The console that the game console, like the player that the kids, the controller that the kids play with is actually plugged into the gaming.console. Well, kids love the old thing ever when they come in. but they always break it because they keep unplugging the controllers because they're like they're charged. And it's like, no, these are old school. And they don't even get that, which is always funny. I mean, from my perspective, that's what I've done for myself and for people here in the company is to say,KK Anderson (06:57)NowSuper Mario Brothers.Mark Petruzzi (07:11)HahahaSabrina Parsons (07:20)I'm not going to pretend you don't have kids. I'm not going to make you apologize for having kids. I'm also not going to pretend that if you've got a kid who's sick, that you're actually going to be at the office doing any sort of productive work because I made you come in. Like, okay, you can come in and you're not going to like me and you're not going to be productive and you're going to be worried about your kid. And so why don't we treat people like humans and say, you know what, your kid is sick, go home.Because if I do that, that person is going to work harder for me and be more loyal and be happy. And if you're happy, you're more creative and you're more innovative.KK Anderson (07:58)You know, in a weird way, like it's like a, whole world is coming full circle and our, our humanness, even in this AI world, mean, specifically there are humaneness is now our uniqueness. No, which is wild. And, and so, you know, kind of going back to that, how sales and marketing teams are using AI, you know, it can.You know, we've all seen it simulate preparation and personalization. mean, we were on vacation last week and we took a family picture of the four of us, my husband and my two kids and myself. And we're sitting at a table and there were, you know, dirty dishes in front of us. And my husband just, and his AI, and next thing you know, there's no dirty dishes in front of us. Right? And then, you know, I sent the picture to my mom.Mark Petruzzi (08:40)Ha ha.KK Anderson (08:44)And she was like, that's so great, whatever. And then my husband goes and sends it right back and we're all in like, you know, he's wearing a tuxedo and I'm wearing a ball gown and whatever. He's like, you didn't get invited to the wedding? And you're like, just making it like in five seconds, what? Right? And so, you know, we see that AI can simulate all of these things, right? And there's just, you know, the sky is the limit, the videos, the empathy, the personalization, that it's hard to know. So like,And building off the conversation that we were just having around women in particular, like is, is humaneness like the new moat? that what, you know, what's your perspective on that?Sabrina Parsons (09:18)I mean, that's a great question. I think it is. I mean, it's been interesting too, because not only is it trying to figure out how do you integrate AI into how your employees are using it so that they're using it appropriately and it doesn't come out like all of our communications are robots, right? So like the humanness of interactions. One of the things we do is right now we don't have chat bots. It's all real people.And it's all real people that we employ here in our headquarters. They're not outsourced because of that ability to say we are humans and real people. We're not just bots. ⁓ I think that's really important. I think that the trust that people need, I think they always needed trust, but it was easier to get their trust. And now it's like, because we've all seen,pictures that are different. We've all seen videos that are AI. We've all seen essays that are written with purely AI. I think there's that constant question, is this real? Are you a human? Is this true? And so anything that you can do to help alleviate that fear of what's a fact and what's not a fact.Right? Even now, like we talk about it a lot, like when you think about Instagram and you're scrolling through, most of us have probably made the mistake of that product that you're like, this is awesome. It's just for me. And then you order it and you know, it was supposed to be like a dress that fits me and it's a dress that fits a doll. You've heard all these stories. So I think all of us now know, like you don't trust that on Instagram.Right. This is why influencer marketing is so big because you do trust the person, right? You don't trust the company and the random product. You do trust the person. And so I think that's where we're back. Like, and how do you do that beyond influencer marketing? Right. Why is Reddit such a huge resource for people?KK Anderson (11:01)trust that person.Sabrina Parsons (11:13)because people perceive that Reddit is moderated, that people get kicked out of Reddit if they're bad and they do bad things. And so somehow, at least at this point, people trust that it's real people on Reddit. That's why people go to Reddit.KK Anderson (11:27)And so how are you using that specifically within your team?Sabrina Parsons (11:29)youwe, I mean, first of all, it's changing all the time, but, you know, we really try to emphasize in a lot of our educational videos, we use, you know, I'm in a lot of them, real people at the company, people that, you know, we have personalities. we've just recently even started to put out some blooper videos so people can see us as real people that we aren't just AI bots.KK Anderson (11:54)and not the radio.Mark Petruzzi (11:56)Yeah.Sabrina Parsons (11:57)And really leaning into, you know, the way that we have all figured out how we trust things. And I think that's really important when you think about and work with sales teams is to really get people to reflect like you're out there, you're a consumer, you know the things that you won't trust. You know the things that are kind of that gray material you're not sure. And you know the things that you do trust. And so,the more that you can get your own employees to embrace their own experiences and bring those, I think that brings a lot of value.Mark Petruzzi (12:30)Well, Sabrina, we should really put out some selling intelligence bloopers because there's been some big ones over the years, but probably more me than anyone else. So maybe I'll hold back on that one. Never blooper. All right, let's move into our final topic, leading through this world that we live in today that is just rife with...KK Anderson (12:42)No.Never, never been a blooper.Mark Petruzzi (12:57)AI disruption everywhere. So as CEO, you're managing AI disruption on two fronts, inside your business and in the general…

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Ep.120 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 1 Apr 01, 2026

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General Episode Description:In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore how AI is rapidly reshaping buyer behavior and forcing a complete rethink of how companies sell, market, and build trust.Sabrina shares how search behavior has fundamentally shifted toward AI-generated answers, reducing click-throughs and changing how buyers consume information. She explains why this creates new challenges in clarity, especially around the “build vs buy” decision, and why sales teams must now work harder to guide buyers through uncertainty.The conversation also dives into the growing importance of trust, the evolving relationship between sales and marketing, and how organizations can use AI effectively without losing the human connection that ultimately drives decisions. What You’ll Learn:The New Buyer Behavior: How AI-driven search and LLMs are reducing clicks and changing how buyers gather information.The “Muddy Middle” Problem: Why AI has blurred clarity around what buyers actually need and whether they should build or buy.Selling in an AI World: How sales teams must adapt when buyers are more informed but also more uncertain.Sales and Marketing Alignment: Why tighter collaboration is critical to address buyer confusion and build trust earlier.Using AI Without Losing Trust: Where AI enhances the sales process and where it can damage credibility.Key Topics:Shift from keyword search to question-based search behaviorAI-generated answers reducing traditional website trafficAEO vs SEO: optimizing for AI engines, not just search enginesBuyers arriving more educated but with incomplete or misleading contextThe disruption of the “why change” conversation in salesBuild vs buy vs AI: a more complex decision landscape for buyersMarketing’s role in answering buyer questions upfront and building trustThe risk of poor AI experiences damaging brand perceptionUsing AI for preparation versus customer-facing interactionsTurning AI efficiency into better personalization and human engagementGuest Spotlight: Sabrina ParsonsSabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, a leading business planning and financial forecasting platform. With experience leading both sales and marketing, she brings a unique perspective on how companies build sustainable revenue engines. Sabrina is also a strong advocate for women in leadership and technology, and has guided her company through multiple waves of technological change. Resources & Mentions:Palo Alto SoftwareLivePlanConcept: AEO (AI Engine Optimization) vs traditional SEOConcept: Build vs Buy vs AI decision-makingConcept: Trust equation in modern salesExample: Customer experience with AI chatbots (Oura Ring case)🎧 Listen now and follow Selling Intelligence for more insights on AI, modern buyer behavior, and building high-performing revenue teams.Mark Petruzzi (00:31)Welcome to Selling Intelligence. Our guest today is Sabrina Parsons, CEO of Palo Alto Software, makers of LivePlan, one of the world's leading business planning and financial forecasting platforms. Sabrina has been the helm at the company, this company that has over four decades of history leading through multiple waves of technology disruption.Before stepping into the CEO role, she ran both sales and marketing, giving her a uniquely integrated view of how companies grow, how buyers decide, and what it really takes to build a revenue engine that lasts. She is a passionate advocate for women in leadership and technology, a thread we'll weave in throughout today's conversation as well. So three topics we'd like to cover with you and with Sabrina today.how AI is reshaping buyer behavior and what that means for how you sell. We've covered that many times on our podcasts already, but we really are excited about Sabrina's perspective and her experiences in that area as well. The second one is why the human element, why trust, story building and storytelling.And relationships are the only sustainable differentiators that we really can build in today's business climate. And third and finally, what sales and marketing leaders must do differently today and how that integrates into the CEO role and also the board of directors. What can the boards be doing to help their sales and marketing leaders evolve in the way that they need to?Sabrina, welcome to Selling Intelligence.Sabrina Parsons (02:13)Great, thanks Mark, I'm really happy to be here.Mark Petruzzi (02:15)All right, let's dive right into topic one. ⁓ Topic one, AI and the changing buyer. So Sabrina, you've described the buyer behavior online as having shifted more dramatically in the last 18 months than in the prior decade. What are you actually seeing? Why does it matter so much for how we sell and how we need to sell in the future?Sabrina Parsons (02:35)that's a great question. And I'm pretty sure as soon as I start talking, all the listeners are going to say, because we've all experienced, I think, a very similar change in how we interact online. In the last 18 months and even more so in the last 12 months, we have all seen the way our interaction on search has changed.particularly with these new AI synopsis that you see at the top of the page.And while there will be articles and sites that are cited in this AI, what's happened is that fewer people are clicking through because they go, they have a question, they type it into Google, and they're typing questions now into Google. used to be that we would type keywords, right? And then you'd see what happened. And now people are typing questions into Google and then the or whatever search engine, but, Googlestill probably the most used. And then what they're getting back, it scratches the itch for the most part. And so they're getting this information and then maybe they're moving on, right? So that's one huge change in behavior and we're all seeing it, right? You have interacted and chosen not to go forward because your question is answered or you found what you need. ⁓ So that new way that we're getting...all of this information displayed, it means fewer click-throughs, and so companies that are selling have to deal with that. The other thing is that search engines are really leaning on and preferringwhen you can put content out there that actually gives answers, because that's what people are looking for, right? It's how do I, those types of questions, how do I do this? How do I sell? How do I market? How do I, all of these how do I's, that's what people are doing. ⁓ And then the other thing that I think we all know is that people are for the most part, very familiar with LLMs, right? With all these AI chat box. And many peopleare using them instead of search engines, which I will say if you are, think about it because it's a very expensive search engine. It uses a lot of energy to do an AI query. And every time we're usingAI when you could just use a search engine, we're wasting energy. So it's something that, you know, not everybody always knows, but there's an appropriate use for AI, but it doesn't matter, right? Behavior has changed, and we're all trained now in this new behavior. And it feels like it's just been like instant, like in the last 12 months, because changing behavior used to be a huge thing, right?From a sales perspective, people like you would teach salespeople how to help change behavior. And like we have seen behavior change just so quickly this time around.KK Anderson (05:23)overnight. so how does that change how we sell?Sabrina Parsons (05:27)So that's a great question. I mean, it has to, right? Because when you're selling, used to be that your marketing team could just make sure like, are search results going to come up on first page versus second page? And if not, let's just buy pay-per-click ads and make sure that they come up.in those results. And it's like that doesn't work anymore. So a lot of what you have to do in terms of how to change how you're selling is address this new way that content is consumed. So you really have to think through, am I providing answers? And it's not just content that fits keywords, right? It's content that's actually giving answers. And then in the way you format your content, if you wantto be AEO forward, right? It used to be just SEO, search engine optimized. Now we're AI chat bot optimized. If you want to be AEO forward, you really have to rethink how you're putting your content together, what kind of sort of synopsis you have that's easy for AEO to grab.Do you have the right FAQ schema? It's just a, you know, it's a different way that the LLMs are crawling through information. And so you just have to make those changes.KK Anderson (06:46)Right. And I'll just add to that. It's all about that trust equation. Right. And so that's what our prospects for all of us, you who are running businesses and running sales organizations, they're all looking to, they're looking for value and that value is what's driving trust. And that trust equation ⁓ is going to what finally converts. And so when your buyers do get on the phone with you finally,They're going to be so much more educated. going to know so much more. They will probably have an LLM, create a table stack ranking, the three top options to solve their problem. And so they're going to be so much more educated when they get on the phone with your team as well, which is another, when you get sort of that sales process behavior that it just, all the changes at top of funnel are filtering down.into that as well. Everything changes.Sabrina Parsons (07:37)and I think that's important, right? And salespeople know this because they're getting confronted. It's like they used to have their process, the information, they've done their homework on the prospect. And now you have to be prepared to understand what are they seeing in chatbots, what is coming through, what kind of, because the other part is that it doesn't necessarily, itThere are opportunities to help someone understand that the landscape may be more nuanced than the AI LLM has put out there, right? But you have to do your homework ahead of time. You have to understand what they're seeing, how much more research, so to speak, they think they have, and then how do you address that, particularly, KK, like you said, just from that trust side of the equation.KK Anderson (08:25)And Mark, I'll give the next one to you here in a second, but just to kind of cap that off, it makes the concept of selling to your customers' outcomes even more important because it's not necessarily about educating them on your product or your service or what you're doing. It's how do you take that, how do you take what they think they know or they don't know or the absence or the void and convert that into something that's important to them, which is the outcome that they're trying to achieve.Sabrina Parsons (08:50)Exactly.Mark Petruzzi (08:50)Excellent. So Sabrina, at AGS, we talk about a two-sale mentality. The first sale is just why change. The second sale is why you and why now. If you're not accomplishing both of these processes within a selling model, then you're not winning the deal.You know, there are companies that are really good in understanding clients, understanding why they want to change, but they're not as good on the, you know, differentiating themselves in the market. There are even more companies that are the other way around that really just don't spend enough time understanding, you know, what are the risks here? Why change it all? And their pipelines get bloated and then get very, very lean quickly.because they have a lot of clients that just say, or prospects that just say, I don't need to change and I'd rather not write out another $3 million check. So where does AI driven buyer behavior disrupt that first sale the most in your opinion?Sabrina Parsons (09:56)You know, I think number one, it's disrupting in terms of what that client thinks they need help with, right? It was very clear. think there's now, it used to be very clear, this is what my tool might do. And I very much understand how I can help the client. And the client...for the most part understands what they need and how you can help them. And I think AI has blurred all the edges, right? As we're all learning how to use it, it's blurred all of that where it's like, well, do I need that tool? What can AI do for me instead? Should I change my process and adopt this new tool or do I just need to get better at prompts for AI or should somebody in my organization vibe code something and dosomething that's more internal and specific to us. And so it's almost like the buy birth versus build is a much murkier, muddier question, right? Because, and it doesn't always mean that the tool isn't actually the best thing for them. It's just that your buyer is now.confused and wondering like, maybe I don't need the tool, maybe AI can just do it for me. And so I think we've just that clarity that used to be a little bit easier with those two things like, you know, what do I need and how does your tool help me? Like that's just muddy now. It's now like, I don't know what I need. Do I need your tool or do I just need, you know?some internal AI expert or maybe I need both. And so I think thatit's just made things muddier. And so the salesperson has to help that prospect understand that and see and clarify and then show them those benefits of like, you don't want the pain of learning all of this. We've got you. We have done it and we've integrated this into our tools. So you get the best of all the worlds without having to figure it out.KK Anderson (12:00)really insightful. You are spot on with that. so you and you've kind of seen this from both the market. I know the world is changing every day, every month. It's different than it was yesterday with every recording and every time we publish a podcast, something else has changed, right? But you've seen this from both the marketing head of marketing seat and the head of sales seat, know, at LivePerson. So in this new world,that we're in, like how did these two function, sales and marketing? how, I mean alignment between the two has always been a problem, right? And so what are some ways that you're seeing like that overlap, that handshake to happen more effectively in this new era? Like talk to me about that.Sabrina Parsons (12:38)that's a really good question because I think you you're right. There's always a little bit of headbutting, and sales is sometimes out selling things. I mean even headbutting with product as well, right? Where sales will sometimes sell things the product doesn't have yet and sales will say well marketing you're not keeping up. We need these materials you don't have. So I think that's always been a little bit more, you know, that's always been something thatdepartments have butted heads against. think right now marketing and sales have an opportunity ⁓ to really understand when you have this much gray area and fuzziness around, what is it that the client actually thinks they need? You can very much...be in a space where you believe you have the best tool and they actually need you, but now the client's not sure they need you. So marketing has to help make that case, right? Marketing has to be playing this new AEO game. Marketing has to also understandWhat are the things that these clients think they mi…

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Ep. 119 – Running Uphill at Full Speed When AI Keeps Raising the GTM Bar with Sunil Rao – Part 2 Mar 25, 2026

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In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson continue their conversation with Sunil Rao, founder and CEO of Tribble, diving deeper into SaaS fatigue, agentic execution, and the challenge of scaling institutional knowledge in enterprise sales.Sunil breaks down how AI agents are reshaping the way work gets done by becoming the interface across systems, eliminating the need for constant tool-switching, and enabling teams to operate from a single layer of intelligence. He also shares how modern GTM teams can capture and scale expertise across conversations, documents, and internal knowledge to improve performance over time.The discussion closes with a look at the human side of selling, where trust, collaboration, and real customer engagement remain irreplaceable even as AI automates more of the workflow. What You’ll Learn:SaaS Fatigue and the Shift to Agents: Why the future interface is not more tools, but a single AI layer that connects everything.Agentic Execution in Practice: How AI can capture context across calls, RFIs, and RFPs to generate smarter, more personalized responses.Scaling Institutional Knowledge: How to turn tribal knowledge, conversations, and documents into a usable system of intelligence.The Failure of Static Content Systems: Why traditional enablement platforms fall behind the speed of modern business.Human + AI Collaboration: Where automation should take over and where human judgment, trust, and relationships still win.Key Topics:“Kiss your apps goodbye” and the rise of agents as the new interfaceEliminating tool-switching and browser tab overload for GTM teamsCapturing context across the full sales lifecycle, not just at the RFP stageUsing AI to coach reps in real time during customer interactionsBuilding knowledge graphs from calls, documents, and internal conversationsDenoising and validating data from sources like Slack, Gong, and CRM systemsWhy knowledge bottlenecks exist due to limited subject matter expertsThe limits of traditional enablement programs and static content librariesDesigning AI systems with humans in the loop for approval and quality controlReallocating 30% of seller time from admin work to customer engagementGuest Spotlight: Sunil RaoSunil Rao is the founder and CEO of Tribble, an AI-native platform that helps enterprise sales teams automate and optimize go-to-market workflows. With a background as an engineer at SAP and a leader at Salesforce, Sunil brings a unique perspective on both the technical and human sides of enterprise selling. At Tribble, he focuses on building systems that scale knowledge, improve response quality, and enable teams to operate more efficiently with AI. Resources & Mentions:TribbleConcept: Agentic workflows in go-to-marketKnowledge graphs for sales and GTM intelligenceSaaS consolidation and interface shift to AIThe Hard Thing About Hard Things by Ben HorowitzSuperintelligence by Nick BostromConcepts: “SaaS fatigue” and “tribal knowledge” in enterprise organizations🎧 Listen now and follow Selling the Cloud for more insights on AI-driven GTM strategy, enterprise sales transformation, and the future of work.Mark Petruzzi (00:31)So Sunil, let's talk about the SaaS fatigue problem. Companies are drowning in tools, licenses, and unused platforms. If you built a company in the enterprise software space going right at all of that overflow, how did you design Tribble to be part of the solution rather than be another product out there that's part of the problem and the challenges?Sunil Rao (00:54)I think from the very early days, one of the things we thought about deeply was, hey, where is this all going? If I think for two, three, five years, what do we think happens? And it was very clear to us that there's a consolidation that's going to take place across where people want to go to get their information.when we see what was happening with ChatGPT and you think about how this kind of AI can be pervasive across systems, this is one of the things I was telling someone recently. If you go back on the internet, you go to the Wayback Machine, which is a website that allows you to go back in time, you can go see the 2023 December page for Tripple. It says, kiss your apps goodbye at the very top. Say hello to agents. And that, I think, was very indicative of, this is what's going to happen. We probably did that message too early because no one knew what an agent was in 2023.But I think that's where we are right now, right? It's like, hey, there's this new interface, right? I can talk to an agent or I can talk to software and I can give it access to all the other systems I work with. So I kind of don't need to go to all those systems again, right? I can do the work through this proxy.And the way that we always describe it is like in the future, you know, when you onboard a new employee, what do you do? You say, here's your license to system one, system two, system three, system four. And they're sitting on their chair and their browser tabs and they're swiveling from one to another, to another, to another.That kind of all goes away. So I think when I think about SaaS fatigue, think agents actually are going to change and become the interface. And Trivel, for us, when we think about go-to-market technology, we want that to be the interface when we think about the respond process and the engage process. That's our bet. And underneath the hood, we have many systems we integrate with. But I had a prospect ask me this the other day. They're like, hey, if we're using your tool, do I need to go to these other systems? And the short answer is no, you don't.Get everything you need right over here.KK Anderson (02:35)So walk us through like what an agentic execution actually looks like in practice. So like when a sales team sends triple an RFP, what's happening behind the scenes? Like how much is automated versus augmented, if you will.Sunil Rao (02:49)Yeah, so I'll give you two examples, KK. I think one, let's think about a company that responds heavily to RFPs and that's a big portion of their business. The RFP coming to you isn't the first point of contact with the customer, right? And depending on the size of the organization and how big this engagement is, it might be something more like, hey, we've had an initial call with the team and they shared with us that they're going to issue an RFP. So there's some discovery being done. We learned some requirements. We learned some players at the table, the different business units that are relevant here.Fast forward a week, another call takes place. Different team members at both organizations are on a call. Information is shared. Then you get to another call and then they issue an RFI, which is the precursor to the RFP.So it's one document that gets sent over and then you got to answer a bunch of questions. Then you finally get to the RFP, which then ends up becoming a bigger proposal. But we think about the journey across all these touch points as opportunities to collect context. So one of the things we do is we show up on the call for each of these touch points. We collect context. We coach the folks live on the call on what data to collect.and how to think about this so that when it comes time to build the response, it's contextual on all the data we've collected for this specific prospect, but every other conversation we've had and where we've won bids and where we've lost them. And that way we can see, historically, when you've answered no to this question for this type of company, you've lost the deal. So one of two things, either explain you can do it because it's on your roadmap or actually put it on your roadmap. Right. And these are the kinds of insights we can glean because we're integrated to thethe systems behind the scene, as we come across these insights, we can go write the data back directly. The agent will go and update a ticket in JIRA, or it'll go make an update in Salesforce directly. And it's done throughout the journey, throughout the process. So that's kind how we think about it across the lifecycle.Mark Petruzzi (04:30)that's excellent. Excellent. So let's go to topic three here, scaling institutional knowledge. We use this, the term kind of tribal knowledge and a lot of the work we do in engendric space ourselves. So yeah, let's dive into that. One of the most interesting things about Tribble, that it's not just about speed, it's about scaling the...the expertise, scaling the process, making those processes better over time as well. You've described the problem of a limited number of experts having the necessary knowledge. In your experience at Salesforce and now at Tribble, why is knowledge scaling such a massive bottleneck in most enterprise organizations, particularly within their sales function?Sunil Rao (05:15)Depending on how big the organization is and what products you sell, historically for me, one of the things that I've experienced firsthand, when you're selling a complex product or you're selling into a vertical where the business processes are very specific and non-standard and it's not something everyone knows, you usually will have a gap in terms of the understanding of the field team and what it is that the customer wants. So how do you speak the language of the customer is always a term that we used a lot in my career.And whether you're in financial services, health, whether you're in CPG, retail, manufacturing.There are processes that are very specific to that industry. So how do you enable the field teams to know what it is the customer's pains are and what they need? And how do you build the right software to meet those needs? So I think that ends up in, thinking back five, 10 years ago, how do you scale that within a company? Well, you create these enablement organizations. You create enablement programs. You take everyone to Vegas for kickoff, and you show them 800 bajillion PowerPoint presentations and hope they remember it for the year. And of course they do, because that works every single time.Right? And when you show up, you've now enabled everyone and they're talking about the product. I think that that kernel, it.The one consistent theme that we've seen and I've experienced it firsthand is you still need to leverage these SMEs during the sales process and you tap them on the shoulder and bring them in. And whether they're sales engineers, they're industry experts, technical architects, program architects, whatever you call them, they all have some level of knowledge and there's too few of them in the organization. So that's what I think about when I think about the scarcity of that type of resource and how do you scale it? So for us, we've always thought of, you've got data in docs.Those documents will inform a certain amount of the business process. You've got knowledge now in these large language models that we can tap into.And there's tribal knowledge, right? We know that Mark actually is really, really good at this one feature in that product that no one else in the company knows, but it's not written down anywhere. It's in Mark's brain, right? So like, has Mark mentioned that on a call? Is that something that's come out in calls with customers? How do you tap into that kernel, right? So we take that data from the calls. We take the data from the documents and everything we're observing across all the calls in the company. And we create a graph of the experts in the company and who has what tribal knowledge and what documents.have what knowledge. So we're trying to solve it in that way Mark of how do you scale the expert? Will you create a backup of them and you try to understand in the organization where you can go to for what.KK Anderson (07:36)And so that's, does that one explain why you're, you're ingesting all kinds of secondary information like Slack conversations or conversations between engineering or product or sales teams? That is that part of how you do that?Sunil Rao (07:49)that you before something becomes a document people are usually talking about it on slack or on callsKK Anderson (07:54)So how do you, like a couple of things come to mind. Number one, like how do you ingest that much information without just having a lot of junk? know, like 80 % of gong conversations are junk and there's a maybe a golden nugget in there. you, mean, it seems like a lot of memory, a lot of space.Sunil Rao (08:11)You haveto compress it. You have to de-noise it, and then you have to compress it. So we actually have, it's funny, when I was geeking out with the engineers on this, we were thinking, look, and I've done sales as well. Sometimes people say things on calls that are not necessarily factual, right? So we have to attribute for the fact that it happens, and especially with gone calls, you have a lot of salespeople saying a lot of stuff on calls.But then you have this idea of ground truth, which pertains to your product information that we're connected to systems of record that we pull data. So we'll look at the data that's coming in and the really noisy stuff, which is gone calls call transcripts, and we'll cross check it. We'll almost fact check it with what we know is in the main store. And if there's anything new gleaned, we will pull that out and denoise and get rid of all the back and forth that's not necessary to store. But we try to pull out the key facts. We try to understand, hey, who was on this call? What were they discussing?which people were saying which things, what regions, locations, product lines, segments were discussed. So anything that pertains to go to market is what we try to pull out of this and then we store it in what we call our knowledge graph. And that allows us to like pull out the signal from the noise if you will, KK. And then we will fact check some of that.And we'll also use the folks using the product to actually validate if information is correct or not. So that way we move from this vast ocean of noise to a usable data set that's otherwise really hard to get to.KK Anderson (09:28)it's really, reallyMark Petruzzi (09:29)most companies, as we all know here, have invested heavily in content libraries, knowledge bases, sales enablement platforms. Yet somehow the right answer is not there when the rep needs it. Why do traditional knowledge management systems fail in high-velocity sales environments? And again, how does Tribble andthe things that you do overcome some of those challenges.Sunil Rao (09:55)It's almost like a short circuit cheat code, right? Because I remember the Russian December.to get high spot loaded with all of our content. When I was at Salesforce working with marketing and it was like the stretch going into Christmas and we're all building the 40 different variations of first call decks and second call decks and these subvertical plays and you'd create and it's this one moment in time where all the content gets created gets uploaded to these systems and it's not any one system. It's just the way it was done, right? You have to have a central place where people can download this content.But the problem with that is you do it at some frequency that's not fast enough for the speed of the business. Information is changing at the rate at which product is being released at the company. And there are just new pieces of information that are coming out. So tapping into the higher velocity data sources, like conversational data, whether it's coming from Slack, whether it's come from Teams, or it's coming from call t…

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Ep. 118 – Running Uphill at Full Speed When AI Keeps Raising the GTM Bar with Sunil Rao – Part 1 Mar 18, 2026

Show notes

In this episode of Selling Intelligence Podcast, Mark Petruzzi and KK Anderson sit down with Sunil Rao, founder and CEO of Tribble, to explore how AI is reshaping enterprise sales, go-to-market execution, and the future of software itself. Sunil shares why AI-driven productivity alone is no longer enough to create advantage, how the rise of agents is changing what software should do, and why trust, personalization, and institutional knowledge are becoming even more important in a world flooded with AI-generated noise.The conversation dives into the productivity paradox, the coming consolidation of fragmented SaaS tools, and the shift from software that assists humans to systems that can actually take action on their behalf. What You’ll Learn:The Productivity Paradox: Why AI makes everyone faster at the same time, raising the bar instead of creating instant advantage.AI and New Work Creation: How efficiency gains in one part of the workflow can create new review, oversight, and decision-making work elsewhere.Differentiation in an AI World: Why personalization, timing, and relevance matter more now that everyone has access to the same tools.From SaaS to Agents: What separates AI-assisted software from agentic systems that can actually do the work.Trust in Autonomous Systems: Why transparency, confidence, and clear decision logs are critical when AI operates inside core business systems.Key Topics:The treadmill problem in modern sales productivityWhy AI has upgraded everyone at the same timeThe flood of low-quality outbound and the need for precision engagementUsing digital exhaust and customer signals to guide better sales conversationsWhy traditional scaling models relied on people because software could not solve the problem yetHow fast-moving foundation models are changing product designThe coming consolidation of SaaS point solutionsWhy the future interface may be lighter, with more approvals and fewer manual workflowsBuilding AI-native products that can evolve with each new model releaseReducing SaaS fatigue by designing for orchestration, not more app sprawlGuest Spotlight: Sunil RaoSunil Rao is the founder and CEO of Tribble, an AI-native platform built to help enterprise sales teams scale knowledge and automate critical go-to-market workflows. Before founding Tribble, Sunil began his career as a software engineer at SAP and later held leadership roles at Salesforce, including GM of Consumer Goods. Tribble was founded in 2023 and has quickly gained traction for helping companies automate RFP responses and improve GTM efficiency with AI-native workflows. Resources & Mentions:TribbleSalesforce Ventures generative AI fundRFP automation and response workflowsAI agents versus traditional SaaS applicationsSaaS consolidation and platform orchestrationThe role of trust and transparency in AI adoption🎧 Listen now and follow Selling Intelligence Podcast for more conversations on AI, modern go-to-market strategy, and the future of enterprise sales.Mark Petruzzi (00:31)Welcome to today's episode of Selling Intelligence Podcast. I'm thrilled to welcome Sunil Rao, founder and CEO of Tribble, an AI native platform that's fundamentally changing how enterprise sales teams scale knowledge and automate critical go-to-market workflows. Sunil's journey has been fascinating. He started as a software engineer at SAP.moved into leadership roles at Salesforce, including and general manager of consumer goods, and then founded Tribble in 2023. Tribble was quickly added to Salesforce's ventures, $500 million generative AI fund, and has since revolutionized RFP automation, helping companies like Clary, Sword Health, and others slash response times by up to 80%.Today we're exploring a critical challenge facing every sales leader. AI is making us more productive, but the bar keeps rising. It's like running on a treadmill at full speed and just when you your stride, the incline keeps going up. How do you stay ahead when everyone else has access to the same productivity gains? We're gonna focus on four critical themes. The productivity paradox, why AI-driven efficientisn't enough to win anymore. From software to agents, building AI that actually does the work, not just assists, scaling institutional knowledge, the hidden competitive mode in enterprise go-to-market, and the human element, where AI should take over and where it must step back. Sunil.First off, we're really happy to have you here. Thank you for taking the time with us and welcome.Sunil Rao (02:10)Thanks for having me. It's nice to be with you all.Mark Petruzzi (02:12)Excellent. So topic one, the productivity paradox. Let's start with what you have called the treadmill problem. Every sales team now has access to AI tools, chat GPT, co-pilot, all these niche engagement and enablement platforms. And all sales teams are getting more productive, or at least the ones that are investing in this. But here's the thing, if everyone's running faster, you're not actually getting ahead. You're keeping up with the pack.And worse, buyers' expectations are rising because they know that you have these tools. So how do you think about this productivity paradox?Sunil Rao (02:47)Productivity paradox, it's interesting because I think there's a couple of ways that I like to think about it. You obviously have this tremendous technology. It's almost magical. It's been distributed to everyone almost simultaneously. And they're all able to see how much productivity it brings into all aspects of their job. But I back to beginning of when we started Tribble, and this is when Chat GPT has just come out, November of 2022.And everyone had that aha moment of, whoa, this thing can write coherently for such a long time. It can actually write code. It can write snippets of code. And it just started to become a way for you to use in your workflow versus going to Google, searching for information. This thing can synthesize knowledge. So when you look at that and that impact,It already was a tremendous time saver for a lot of smaller jobs. But I think what's been going on and what's been happening over the last few years with these foundation models getting better and better, it gets to the point now where these systems can run for hours on end and complete much more complex tasks. And that's where it's more interesting where, you know, what was not possible to solve with software three years ago.is possible today. And that's where agents come in and everything comes in. it's interesting because like you have that happening in one side and it's really magical technology. But then at the same time, you kind of create new work.when you have access to this technology, because now everyone's a creator. And I see this a lot in the engineering side. Everyone's writing more code, and then it's the question of who's reviewing it. If everyone's writing more content to go in documents, who is doing the human check? So you have this trade-off of, yes, there is efficiency in one part of the process, but you end up creating some work elsewhere. So I think it's the paradox, because it actually changes the distribution of where work is being done.KK Anderson (04:30)Really, really interesting. So when we think about it from, you know, a sales or revenue perspective, right? It's, you know, for, for so many years, it was, do you have this Salesforce CRM? Do you have this outreach, you know, program set up? Do you have this automation set up? And it was, you were always running to keep ahead and to keep up to pace with all of the different technologies that were available. And that was just sort of table stakes.Right? And now with AI, as you just said, like everybody has it. And so now it's how you use AI is, is, and how you become a, differentiator using AI is the new game. Because otherwise it's this, we, you know, ⁓ as Doug Landis, one of our good friends and colleagues says is we're in a culture of sameness right now.Sunil Rao (05:15)Mm-hmm.KK Anderson (05:16)an era of sameness, I think is what he says. So talk to us a little bit about that. So now here we are, we all overnight got Chappie, GBT and these amazing programs. How do we differentiate ourselves in this world of AI?Sunil Rao (05:30)it's an interesting way to think about it, right? It's almost like everyone got upgraded, but exactly to the same level. So then how do you differentiate is the It's how do you stand out from the pack? And, you know, and I take the example of outbound and emails. Like I think what's happened, it's both a gift and curse.KK Anderson (05:37)Yes.Sunil Rao (05:45)I mean, I'd it's more of a curse because now there's so much garbage when it comes to outbound, right? In terms of mass generation of emails that are not personalized, that are not targeted. And I still think that the age old, you know, what makes you really good about that style of top of the funnel engagement is when you are very personalized and targeted. think that just actually gets even more amplified as an important way to stand out, right? Don't, don't try to sell something to the masses. Really think about what signals.indicate that this may be a buyer that's interested and engage with them on the journey at the right time becomes way more important. Because otherwise, you're just feeding into the sea of noise that's being generated because we have these tools that can mass create this content. So I think there's that aspect of it. How can we be much more tailored on the engagement side? And I think about it at different parts of the funnel. For us at Tribble, we think deeply about this problem.when we talk about our customers using our products and how they engage with their customers. So we look at it from two sides of that coin. Mark, you'd shared our respond product, which is all about responding to RFPs, responding to customers. You have to be very particular about what it is you do as a business, how you differentiate.And that's informed by your conversations, your knowledge basis and all this stuff internally allows you to differentiate against your competition. But then on the engaged side, where we have software that helps BDRs, SDRs and others engage with their customers. Like we think really about what is the information that we have captured in all the digital exhaust with all the touch points we've had with this customer that indicate that this is in fact something that they're interested in. And how can we in real time kind of guide that conversation and coach it? So we get to the.And I think customers really want that level of detail and personalization because otherwise you're kind of feeding the sea of noise like you've said.KK Anderson (07:29)All of a sudden to be human is to be cool.Mark Petruzzi (07:30)Yeah.Sunil Rao (07:32)I mean, I think people arepurposefully putting spelling mistakes in LinkedIn posts because it's like now become a sea of, and you see it, right? When you look at the posts and you see the dashes, the end dashes or the dead giveaway of ChatGP, everyone's using them now.KK Anderson (07:43)yeah. The dashes,Mark Petruzzi (07:44)100KK Anderson (07:45)I can't, emojis make my blood curl now. I'm like, ⁓ you know?Sunil Rao (07:50)KK,like, here's a funny question. I actually thought about this the other day. I actually don't know how to type the dash on the keyboard. So it's like, where is it coming from?KK Anderson (07:55)I don't know.Mark Petruzzi (07:56)That is great. You know what, Sunil, when you mentioned the top of funnel and what's happening there, that's an area that KK and I spend a lot of time with our clients to make sure that they don't fall into this AI paradox where five years ago, before we were in the,KK Anderson (07:57)really don't? That's awesome!Mark Petruzzi (08:18)Gen. AI era before it even had a name. You saw that there was so much outbound going to prospects and customers. And what we found is there's been more damage in that than benefit in a lot of companies, meaning they are pushing more potential clients away than in some cases they're ever bringing through the door.So taking you back to your time at Salesforce and when you were running your go-to-market operations initiatives there and seeing all the inefficiencies that were happening with customers of Salesforce but also right in with Salesforce as well, what was the breaking point for you that made you realize traditional approaches to sales productivity were just fundamentally broken?Sunil Rao (09:07)You know, I think it's.Once again, this comes back to the point earlier of what is now solvable by software simply wasn't solvable five years ago, right? So what did you do? The problem was solved by hiring humans and kind of building processes, building checks, building scaling functions, building these expert groups within the company that house knowledge that would scale the rest of the organization. You invest heavily in resources like that and all the supporting functions and resources to keep them going. And I think, you know, thatthat goes far and frankly if you don't have the technology you have today, that's the only way to do it at the time.For me, the inflection point clearly was the rate of change of the technology outside that was indicative that, hey, if I had to build a company from scratch today, I would probably not staff it the same way, given where tech is at this moment in time. That was 2022, right? And then you go forward in time one year, the number of people factors down even further because the technology is now improving at an exponential rate. And you fast forward another two years and it's crazy how fast things are moving. So I think, like I would saythe tools and capabilities and what it is that you are building from a scaling standpoint, as more is becoming available outside, really how quickly can you factor that into the organization and how quickly can you grow? Like this has to be top of mind for every executive at every company right now, right? And I think that that is changing at such a fast pace that folks are just open to having those conversations now and like really thinking, how do we build this differently?KK Anderson (10:32)And it, does it become less fragmented? Right. Or more fragmented. You're adding in, there's a big one million AI products and solutions out there. And there's one, you know, go to market inside this, this, this company. Right. Like, how do you even begin to look at and think about.you know, how you're gonna weave in and out all of these products and how they're gonna talk to each other and I don't know, talk to me a little bit about that.Sunil Rao (10:55)Our thesis on this is there's a mass consolidation coming. And I don't think that that is a very unique point of view. I think most people realize it. The general purpose nature of the underlying technology serves itself very well to addressing many use cases. And what I mean by that is when we started the company, thought about a category and we were, the vision was always to do something much broader and go to market, but then you kind of say, hey, what's the thing I'm going to do tomorrow really, really well?And we picked RFP. And the reason for that was it's a known problem. People knew how to buy software in that domain. And there's a lot of pain there. But that being carved out as a product category, and this is true for any other category of software, these are artificial boundaries created as, this is a category of software. There's a level of functional kind of capability…

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