Selling Intelligence (formerly Selling the Cloud)

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

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

    2D AGO

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

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

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

    APR 29

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

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

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

    APR 22

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

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

    25 min
  4. Ep.122 - Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 1

    APR 15

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

    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 Rike Ray 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 was email 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 experience of 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 s****y 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 is fundamentally 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 into KK 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

    26 min
  5. Ep. 121 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 2

    APR 9

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

    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 Parsons Sabrina 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, that You 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 some issues 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) for Sabrina 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 watched the 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 my KK 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) Now Super Mario Brothers. Mark Petruzzi (07:11) Hahaha Sabrina 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. Be

    25 min
  6. Ep.120 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 1

    APR 1

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

    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 engagement Guest Spotlight: Sabrina Parsons Sabrina 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, Google still 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 preferring when 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 people are 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 using AI 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 want to 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 i

    19 min
  7. Ep. 119 – Running Uphill at Full Speed When AI Keeps Raising the GTM Bar with Sunil Rao – Part 2

    MAR 25

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

    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 engagement Guest Spotlight: Sunil Rao Sunil 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 the the 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

    22 min
  8. Ep. 118 – Running Uphill at Full Speed When AI Keeps Raising the GTM Bar with Sunil Rao – Part 1

    MAR 18

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

    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 sprawl Guest Spotlight: Sunil Rao Sunil 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 efficient isn'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

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

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