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Selling Intelligence (formerly Selling the Cloud)

Selling Intelligence (formerly Selling the Cloud)

By: 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.


© © 2026 Selling the Cloud Economics Leadership Management Management & Leadership
Episodes
  • Ep. 123 -Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 2

    Ep. 123 -Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 2
    Apr 22 2026
    General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of BenchMarket, to go deeper into how companies should measure, operationalize, and compete with agentic AI in go-to-market functions.Ray breaks down why most companies still lack basic GTM measurement discipline, what new AI-specific benchmarks leaders should track, and how legacy SaaS companies can realistically compete with AI-native organizations that are operating at dramatically higher efficiency.The conversation also tackles the hard truth about workforce reduction, the rise of AI operators, and why companies must rethink their entire operating model, not just layer AI on top of existing processes. What You’ll Learn:Measurement Before AI: Why most companies must fix GTM analytics before introducing AI.AI-Specific Benchmarks: The emerging metrics for measuring agentic GTM performance.Competing with AI-Native Companies: Why legacy SaaS teams must rethink their entire playbook.The Role of AI Operators: Why AI expertise is becoming more critical than traditional RevOps.From Pilot to Scale: What success should look like at 90 days and 180 days.Key Topics:Cost per pipeline and cost per ARR before vs after AIAgent cost per opportunity, pipeline, and revenueDesigning modular AI workflows instead of “monster agents”The four-layer framework: productivity, effectiveness, efficiency, and ROIRevenue per FTE gap between SaaS and AI-native companiesWhy legacy SaaS companies struggle to match AI-native efficiencyRadical restructuring: reducing headcount and rebuilding with AI-first processesAI enabling deeper personalization at scale for outbound teamsThe rise of “AI operators” as a new critical roleThe “SaaSpocalypse” and pressure on net revenue retention (NRR)Using AI to improve retention, expansion, and customer insightsBenchmark expectations for agentic SDR performance at 90 and 180 daysGuest Spotlight: Ray RikeRay Rike is the founder and CEO of BenchMarket, a leading provider of B2B SaaS performance benchmarks. With decades of experience as a go-to-market leader, he helps organizations move from intuition to data-driven execution. Ray is also the creator of the AI to ROI newsletter, where he analyzes hundreds of AI developments weekly to help leaders understand what actually drives business outcomes. Resources & Mentions:BenchMarketAI to ROI NewsletterConcept: Agentic AI in go-to-marketConcept: AI-first operating modelsConcept: Revenue per employee as a key efficiency metricConcept: AI operators vs traditional RevOpsConcept: SaaSpocalypse and NRR pressureFramework: Productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI benchmarks, GTM transformation, and building high-performance revenue organizations.Mark (00:26)Excellent. All right, well, Ray, let me bring you back into the days of you and I starting all our research and all the pre-work for data and diagnosis driven selling. So I hope that doesn't cause you to develop a Twitch or anything like that, because as you and I both know, that was hard work. So, but let's, you know.What we really saw right up front is, and we really pushed hard on this, is the idea is you can't manage what you don't measure. And you need external benchmarks, not just internal comparisons to know if your metrics are actually good. You know, it's great. It's great to be able to say, improved this process by 20%. But if you were 45 % behind most of your competitors before that,That 20 % still has you on the back of the pack. So how do you bring that same philosophy to measuring an agentic BDR or an AI-powered deal coaching agent? And we've touched on this, but what's the equivalent of a CAC payback for agents and the entire investment?Ray Rike (01:33)Well, I would start with let's make sure you have your go to market measurements in place, because honestly, we've been talking about these for years. Less than 50 percent of companies have great GTM analytics. ⁓ So things like cost per dollar a pipeline, less than 40 percent of people are measuring cost per dollar a pipeline. So make sure you do that and look at your current state before AI and then measure it post AI introduction. Right.So cost and I'm talking right now, I'm looking very specifically at the customer acquisition process. So cost per dollar pipeline before and after cost per dollar of new AR before and after when rate before and after your average and your contract for you before and after. Cause those are all going to be hopefully much better with AI to your point, Mark. I mean, let's use outreach. Everybody had to have a sales engagement platform, right?How many companies actually said, well, after I invested $1,500 per SCR, I had a better conversion rate or a lower cost per dollar of acquisition? Nobody. You're going to need to do that with AI. So that's my first thing. The second thing, ...
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    25 mins
  • Ep.122 - Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 1

    Ep.122 - Measuring Agentic AI, ROI, and the Future of GTM Benchmarks with Ray Rike - Part 1
    Apr 15 2026
    General Episode Description:In this episode of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Ray Rike, founder and CEO of Benchmarkit, to tackle one of the most critical questions in enterprise AI today: how do you actually measure success in agentic AI programs?Ray shares why most AI initiatives are stuck in “pilot purgatory,” the common mistakes companies make when trying to automate broken processes, and why an AI-first mindset requires a complete rethink of data, workflows, and metrics. The conversation also explores how go-to-market teams should define ROI, what benchmarks matter in an AI-driven world, and why traditional SaaS metrics are no longer enough. What You’ll Learn:Why AI Projects Stall: The real reasons most agentic AI initiatives never scale beyond pilots.AI-First vs Human-First Thinking: How redesigning processes for AI fundamentally changes outcomes.Data Readiness Matters: Why poor CRM data and lack of governance derail AI success.Measuring AI ROI: The new metrics leaders must track to justify AI investment.The Shift in GTM Economics: Why cost structures and efficiency benchmarks are changing fast.Key Topics:“Pilot purgatory” and lack of enterprise-wide AI focusThe importance of data hygiene and enrichment for AI successRedesigning processes with AI at the center, not as an add-onThe rise of vertical AI and pre-built agent workflowsDefining success with leading, mid-term, and lagging metricsCAC ratio vs AI-driven efficiency benchmarks“COGS is the new CAC” and shifting cost structures in AI-native companiesRevenue per employee as a proxy for AI productivityToken consumption and cost predictability challengesBuilding smaller, modular agents instead of large monolithic systemsThe four-layer measurement framework: productivity, effectiveness, efficiency, and ROIGuest Spotlight: Ray RikeRay Rike is the founder and CEO of Benchmarkit, a leading source of B2B SaaS performance benchmarks with data from over 1,800 companies. He is also the host of the AI to ROI podcast and a founding member of the SaaS Metric Standards Board. With decades of experience as a go-to-market operator and executive, Ray focuses on helping companies move from intuition to data-driven decision-making in both SaaS and AI-driven environments. Resources & Mentions:BenchMarkitAI to ROI podcastConcept: Agentic AI in go-to-marketConcept: “Pilot purgatory” in AI adoptionConcept: AI-first process designConcept: COGS as the new CACOpenAI Frontier AllianceVertical AI platforms (example: Harvey for legal)Metrics framework: productivity, effectiveness, efficiency, ROI🎧 Listen now and follow Selling Intelligence for more insights on AI measurement, GTM strategy, and building data-driven revenue engines.Mark (00:31)Welcome to Selling Intelligence. We're joined today by someone who might have had the honor and privilege of calling both a collaborator and a friend. Ray Reich is the founder and CEO of BenchMarket, the industry's most comprehensive source of B2B SaaS performance benchmarks with data from over 1,800 companies.Ray is also the host of the AI to ROI podcast. He's a founding member of the SAS Metric Standards Board. And full disclosure, my co-author on data and diagnosis driven selling, Ray has spent decades as a go-to-market operator, having served as president of Simply Learn, CEO at Higher Mojo, SVP at Moment Feed,and multiple times SVP market and sales and SaaS companies before founding Benchmark it roughly five years ago. And they have a singular mission, give every B2B reoccurring revenue software operator access to data driven benchmarks so they stop flying blind. Today, we're going, well, first off, let me welcome you, Ray. Thanks so much for joining us.Ray Rike (01:43)Thank you, Mark. Sorry that I'm so old that you had it took that long to read everything I've done.Mark (01:47)Exactly. Well, you know what? That's also a good thing because you've done some amazing things throughout your career and you're not that old. So, yes, let me tell you, let's talk a little bit about today and where we're going to go on this podcast. ⁓ What we'd like to do is tackle what might be the most important and for sure most underserved question in enterprise AI right now.How do you actually measure the success of agentic AI programs? And even more specifically, what does that look like for go-to-market functions? We'll dig into what benchmark its data, what is it revealing, where the industry is setting the bar, and what separates teams that are generating real ROI from those stuck in pilot purgatory. Ray, welcome to Selling Intelligence.Ray Rike (02:36)Okay, excited to be here. Let's dive into it.Mark (02:39)All right, so Ray, you've been collecting SAS performance data for years, and now you're turning that lens on AI. From what you're seeing at Benchmark and in hearing on your podcast, what's the core reason most agentic AI programs never graduate from pilot stage? Is it a data problem, ...
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    26 mins
  • Ep. 121 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 2

    Ep. 121 - AI-Driven Buyer Behavior, Trust, and the New Sales Playbook with Sabrina Parsons - Part 2
    Apr 9 2026
    General Episode Description:In this continuation of Selling Intelligence, Mark Petruzzi and KK Anderson sit down with Sabrina Parsons, CEO of Palo Alto Software, to explore the human side of leadership, trust, and AI adoption in today’s rapidly evolving business landscape.Sabrina shares her perspective on diversity in leadership, the realities of building a career as a working parent, and why creating an “integrated life” leads to stronger teams and better business outcomes. The conversation also dives into how trust has become the ultimate differentiator in an AI-driven world, and how companies must rethink how they show up as human, credible, and authentic.The episode closes with practical insights on how leaders should approach AI, where it delivers real value, and how to use it as a tool for thinking, not replacing human judgment. What You’ll Learn:Diversity as a Competitive Advantage: Why different perspectives lead to better decisions and stronger organizations.The Integrated Life Approach: How flexibility and trust improve retention, loyalty, and performance.Human Trust in an AI World: Why authenticity and real human interaction are becoming the new moat.Practical AI Usage: How to use AI for preparation, critique, and efficiency without losing credibility.Leading Through AI Disruption: How leaders can guide teams to experiment with AI while setting the right guardrails.Key Topics:The impact of diversity and inclusion on business performanceSupporting working parents and creating flexible, human-centered workplacesThe myth of “doing it all” and redefining success in leadershipWhy trust is harder to earn in a world of AI-generated contentReal vs artificial experiences in customer interactionsThe role of influencer trust and community platforms like RedditUsing real people and authentic content to build credibilityWhere AI overpromises and where it delivers real efficiencyAI as a tool for critique, feedback, and preparationUnderstanding how LLMs perceive your product and brand through consensus signalsThe shift from SEO authority to AI-driven consensus and reputationGuest Spotlight: Sabrina ParsonsSabrina Parsons is the CEO of Palo Alto Software, makers of LivePlan, and a leader with deep experience across sales, marketing, and executive leadership. She is a strong advocate for women in leadership and brings a unique perspective on building resilient organizations, fostering trust, and navigating multiple waves of technological change. Resources & Mentions:Palo Alto SoftwareLivePlanConcept: AI trust gap and authenticity in digital interactionsConcept: Integrated life vs traditional work-life balanceConcept: Consensus-driven reputation in AI search and LLMsBook: Into Thin Air by Jon KrakauerBook: Superintelligence by Nick Bostrom🎧 Listen now and follow Selling Intelligence for more insights on leadership, AI adoption, and building trust in modern go-to-market teams.Mark Petruzzi (00:31)So Sabrina, you're a strong advocate for women in sales and leadership. In your experience, what do women bring to the sales equation that often gets undervalued? And what does the data actually show?Sabrina Parsons (00:43)Yeah, that's a great question. I think that we've, well, hopefully people have, there's been a lot of data over the years that just shows a few things, I know these days, you know, talking about diversity is, you know, a hot topic and not something everybody wants to hear. But if you actually go and look at the data,Any time you're bringing different viewpoints in, it actually turns out the data shows that that's really good for an organization. That when you have six people who all come from the same background, who went, you know, got similar educations, have the same experiences, you're missing out. You're not getting some of these other alternate viewpoints that...could actually give you different insights and make your company better. So from that perspective, be it women or people of color, people from different cultural backgrounds, every time you have different people in a room, you're gonna win because they're gonna bring different information to the table. And then I think that, you know.Even though it's 2026 and I wish we were in a different place with women in leadership, the reality is that we still live in a world where, you know, there aren't as many women in technology. ⁓ And the numbers just show that and there aren't as many women in technology and leadership. And so women who are there and have made it all the way through, particularly in a leadership role, have probably worked really hard to get there.and probably have some really good insights. From my perspective, one of the things that I think is most powerful and I think can bring a lot of value to a company is recognizing particularly working moms and working parents, but as a working mom, I'm not a working dad, so I won't talk for working dads, thatYou know, there's a lot of very motivated, super smart ...
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    25 mins
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