Ep. 127 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 2
Ep. 127 - Session Diagnostic: Why should you do a diagnostic before you apply AI to your GTM - Part 2  
Podcast: Selling Intelligence (formerly Selling the Cloud)
Published On: Wed May 20 2026
Description: 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, beginning of their quarter forecast.meaning they don't want to see a team that always comes in 20%, 25 % higher, just tells you you have a sales leadership that doesn't know how to forecast. So at least by the beginning of the quarter, you should be able to define what you do at the end of the quarter. They, of course, don't want to see things that are more, that just tell,show risk and instability as well. So that's where this CRO role has, has changed. Like, early in these more enterprise software space, 20 years ago, you had, know, you had these gunslingers at the senior sales level, you had gunslingers at the rep level. And, they frankly just knew that if they work hard, they were going to make a lot of money.But they really had no idea what their potential was or what they can do. So those are the things that a P team or board on the due diligence side would focus on. They're looking a lot more at the trend than the absolute number. That's something I've seen. They want to see that win rate stay stable, getting better. They want it high.They don't want it to be volatile. They get to learn average deal size, typically trends whether you're in an up market or down market for your product. They wanna really look at cycle time and the trends there, because they really wanna know what kind of process, a selling process this leadership team has driven.⁓ sales leaders, when they're talking to sales managers or sales reps, they're always going to ask for a stretch goal. And I've grown to be okay with that, but I don't want to ever see a board or a CEO asking a CRO for a stretch number. I want them to say, what is the number? I want there to be a lot of technology and AI in identifying that number.We can do a whole nother podcast around the things I've learned working with Clary, Avizo, Collective Eye over the years around forecasting. Same thing, gut process there doesn't work. The data is out there. You just got to have a tool that finds it for you. And then that kind of comes to the final point on this. Forecast accuracy.is the cleanest signal that you can get from just knowing whether you have a business with operational maturity or when you have a business filled with a bunch of gunslingers.KK Anderson (16:05)So you need both layers, right? You need the competency and the board definitely wants to see the metrics, Behaviors and outcomes. And as a side note, one of the free tools that we've built at AGS on our website is a sales cycle diagnostic. It's a mini, if you will, sales cycle diagnostic. I will link that in the show notes as well so that if you're curious, you can go check it out on our online.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.