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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. 132 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 2

    Ep. 132 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 2
    Jun 24 2026
    General Episode Description:In Part 2 of this conversation, Jared Zelman, Founder and CEO of Othello AI, explores what happens when AI moves beyond helping individual sellers and begins transforming entire sales organizations.Jared shares his perspective on the future of sales management, explaining how AI can handle repetitive coaching, call analysis, and execution consistency while allowing managers to focus on higher-value leadership activities. The conversation examines how AI-powered coaching systems are changing the role of frontline managers and why sales leaders must rethink how they develop and scale teams.The discussion also dives into Jared’s founder-led go-to-market journey. From cold-emailing executives, investors, and industry leaders to building relationships with some of the most influential business figures in the world, Jared explains how disciplined outreach, persistence, and deep personalization helped accelerate Othello’s growth from startup to seven-figure ARR.The episode concludes with practical lessons for founders, CROs, and sales leaders on scaling efficiently, shortening sales cycles, achieving product-market fit, and balancing the art and science of selling in an increasingly AI-driven world. What You’ll Learn:• The Future of Sales Management: How AI changes the role of frontline sales leaders.• AI-Augmented Coaching: Moving from repetitive coaching activities to strategic leadership.• Founder-Led Sales at Scale: How deliberate outreach can build customers, investors, and mentor networks.• Product-Market Fit First: Why founders should focus on learning and validation before scaling teams.• The Art and Science of Selling: Understanding what AI can teach and what remains uniquely human.Key Topics:• Managing AI-augmented sales organizations• The future role of sales managers• AI-powered diagnostics and coaching• CRM automation and systems of record• Salesforce versus next-generation CRM experiences• MEDDPICC automation and sales process intelligence• Sales velocity as a growth metric• Founder-led go-to-market strategies• Building relationships through cold outreach• Howard Schultz and executive networking stories• Product-market fit versus revenue growth• Shortening sales cycles• Why founders should delay hiring sales teams too early• The science versus art of selling• Human trust and relationship-building in sales• Scaling enterprise SaaS companiesGuest Spotlight: Jared ZelmanJared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Prior to Othello, Jared founded Cicero, an AI-powered celebrity avatar platform. Through Othello, he is helping organizations scale elite sales behaviors while preserving the human elements of trust, empathy, and relationship-building that drive long-term success. Resources & Mentions:• Othello AI• Salesforce• HubSpot• Notion• MEDDPICC• Howard Schultz• Steve Ballmer• Sam Altman• Paul Graham• Dale Carnegie• Costco• Lenovo• Science of Scaling by Mark Roberts• Entrepreneur.comKey Takeaway:AI can automate coaching, surface insights, and improve execution consistency, but it cannot replace the human side of selling. The organizations that win will combine AI-driven discipline with authentic relationships, strong leadership, and a relentless focus on understanding customers.🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, sales leadership, revenue growth, founder-led scaling, and the future of enterprise sales.KK Anderson (00:38)Okay, so you are, and we're gonna wrap up the second topic here with this question. You're reporting 10 to 15% win rates improvement, 8 to 10% reduction in sales cycle length, which is huge. ⁓ a lot of AI tools are making, some some pretty large claims like that. so like generally speaking, just w help us understand a little bit, like what what are you measuring over what time period?Jared Zelman (00:51)Crazy.KK Anderson (01:02)how was work to some of your success?Jared Zelman (01:04)Yeah.These are like guess depends, because ⁓ like some of these numbers are pointing time numbers, some of these are ⁓ like over a period of time. so if it's a period of time, these are like over a course of twelve months. what's unique is these are all for large enterprise, these are for Fortune one hundreds. When you see AI companies quoting crazy growth or performance metrics, it's because they're selling to a two person business in YC. in other words, bullcrap.Right. ⁓ these are metrics that are proven at some of the biggest companies in ⁓ multi-sectors. that said, the bar for the expectation the expectation of buyers these days is kind of ridiculous. frankly, if you're a sales tool and you're affecting win rates and you're not improving them by over 10%, that you're a failure.our minimum is like fifteen, ...
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    26 mins
  • Ep. 131 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 1

    Ep. 131 – Fixing the 80/20 Sales Problem with Real-Time AI Coaching with Jared Zelman - Part 1
    Jun 17 2026
    General Episode Description:In this episode of Selling Intelligence, Jared Zelman, Founder and CEO of Othello AI, joins Mark Petruzzi and KK Anderson to challenge one of the most accepted assumptions in sales leadership: that 20% of sellers will always generate 80% of the results.Jared argues that the 80/20 problem is not a talent issue. It is a systems issue. Drawing from millions of minutes of sales conversations and real-world customer deployments, he explains how modern AI can capture the behaviors of top performers and deliver coaching in the moment when it matters most: during live customer conversations.The discussion explores why traditional coaching models fail to scale, the limitations of post-call analysis, and how real-time AI guidance can improve discovery quality, qualification, and win rates across entire sales organizations. Jared also shares insights into how AI is uncovering new patterns in selling behavior, including why Sandler-style methodologies continue to outperform across modern B2B sales environments. What You’ll Learn:The 80/20 Sales Problem: Why performance gaps are often driven by systems, not talent.Real-Time Coaching vs. Post-Call Coaching: Why feedback during the conversation matters more than feedback after the fact.Discovery Done Right: How top performers uncover deeper pain points and create stronger buying urgency.AI-Powered Sales Execution: Using AI to replicate the behaviors of elite sellers at scale.The Future of Sales Methodologies: How AI is identifying winning patterns across millions of sales interactions.Key Topics:The Pareto Principle in sales organizationsWhy most CROs attack the wrong coaching problemReal-time AI coaching inside customer callsImproving discovery conversationsThe “question behind the question” frameworkWin rate improvement versus productivity improvementWhy CRM automation alone does not improve revenue performanceAI-assisted coaching and behavioral reinforcementThe difference between efficiency and effectivenessRote versus rogue selling behaviorsPersonalized coaching versus scripted sellingSandler methodology and AI pattern recognitionCustom sales methodologies powered by organizational dataUsing AI to scale top-performer behaviorsThe future of AI-enabled sales leadershipGuest Spotlight: Jared ZelmanJared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Built by the team behind Cicero, Othello helps organizations scale elite selling behaviors across entire teams through contextual, in-the-moment coaching. Since launching in 2025, Othello has rapidly grown to support thousands of users across Fortune 500 companies and high-growth technology organizations. Resources & Mentions:Othello AISalesforceHubSpotGongSalesloftClariMicrosoft TeamsZoomSandler Sales MethodologyCiceroDan LawrenceLenovoCostcoHome DepotGeneral ElectricComing Next Week:Part 2 explores how sales leaders should manage AI-augmented teams, how coaching changes when AI handles execution consistency, and Jared’s founder-led go-to-market playbook for building a venture-backed company through strategic cold outreach and relationship-driven selling.🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, revenue leadership, enterprise sales, and the future of go-to-market execution.Mark Petruzzi (00:28)Welcome to Selling Intelligence. I am Mark Petruzzi, and I am joined as always by my co host, KK Anderson. Our guest today built the company on a number every CRO already knows and hates. Those numbers are the 20% of reps drive 80% of the results. The question is, what do you do about it? Most leaders throw more coaching hours at the problem.Build out their enablement team, and then just hope it scales and gets more productive. Jared Zellman did something a little different. He went out and he built an AI that sits inside the call and fixes it in real time and on every call. Jared is the founder and CEO of Othello AI, a real-time AI sales coaching platform that guides reps before, during, and after every call.Built by the team behind Cicero, Othello launched in July of 2025 and reached over 5,000 users and 1 million in revenue within its first six months, with clients spanning Fortune 500 companies and high-growth startups. Othello integrates with the go-to-market stack you already have, whether it's Salesforce, HubSpa, Gong, SalesLoft, Clary's, Zoom, or Teams.And sits as the execution layer that makes sure what happens on the call matches what the playbook says.KK Anderson (01:55)What I love about Jared's story is that he is not just a founder talking about sales AI. He is a practitioner of the exact skills he built Othello to teach. He built his entire investor base, his early customers, and his mentor network through deliberate, personalized cold outreach to some of the most senior people in the business. Howard Schultz, CEO...
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    22 mins
  • Ep. 130 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 2

    Ep. 130 – Building Resilient Salespeople in the Age of AI with Scott Stollwerk - Part 2
    Jun 10 2026
    General Episode Description:In Part 2 of this conversation, Scott Stollwerk returns to Selling Intelligence to explore one of the most important questions facing modern sales leaders: what happens when AI becomes excellent at execution, but human performance remains the deciding factor?As AI continues to improve outreach, forecasting, coaching, scoring, and productivity, Scott argues that the real competitive advantage is no longer process or technology. It is the human being operating behind the tools. Drawing on the Tao of Sales framework, Scott explains why resilience, self-awareness, creativity, intuition, and personal growth remain irreplaceable in high-performance sales organizations.The conversation explores the limits of AI, the dangers of over-automation, and why leaders must continue investing in human development even as technology becomes more powerful. Through practical stories, leadership lessons, and personal experiences, Scott demonstrates why sales success ultimately comes down to overcoming the internal barriers that technology cannot solve. What You’ll Learn:What AI Cannot Fix: Understanding where technology excels and where human performance still matters most.The Human Edge in Sales: Why creativity, intuition, emotional resilience, and connection remain irreplaceable.Overcoming Self-Limiting Beliefs: How internal dialogue often creates bigger obstacles than external challenges.AI as an Amplifier: Why AI accelerates both strengths and weaknesses within sales organizations.Developing the Individual Seller: Why long-term sales success requires personal growth, not just process improvement.Key Topics:The limits of AI in enterprise salesWhy buyers still trust humans for high-stakes decisionsAI productivity gains versus human connectionThe “crisis of sameness” created by AI-generated contentIntuition, creativity, and human decision-makingStrengthening the mind like a muscleThe role of spirituality, mindfulness, and self-awareness in performanceThe famous arrow-breaking exercise and overcoming fearInternal dialogue and self-limiting beliefsAI as an amplifier of organizational alignment or dysfunctionUsing AI as a brainstorming tool instead of a replacement for thinkingLeadership responsibility in developing human potentialProtecting individuality and creativity in an AI-driven worldGuest Spotlight: Scott StollwerkScott Stollwerk is a sales leader, coach, and creator of the Tao of Sales methodology. Combining Eastern philosophy, neuroscience, martial arts principles, and human performance science, Scott helps individuals and organizations build resilience, self-awareness, and sustainable performance. As part of the leadership team at Pest Share, he continues to develop sales cultures that prioritize human growth alongside business results. Resources & Mentions:Tao of Sales FrameworkTony Robbins’ Six Human NeedsAbraham MaslowRobert CialdiniGongZoomAsk ElephantPhil JacksonMichael JordanDennis RodmanThe Five Love LanguagesEastern Philosophy and Tai ChiConcept: AI Amplifier PrincipleKey Takeaway:AI can improve productivity, automate execution, and accelerate workflows. But it cannot replace resilience, courage, creativity, judgment, or human connection. The organizations that win in the AI era will not be the ones that develop technology alone. They will be the ones that continue developing people.🎧 Listen now and subscribe to Selling Intelligence for more conversations on sales leadership, AI, human performance, and enterprise growth.#SellingIntelligence #AIforSales #SalesLeadership #HumanPerformance #SalesCoaching #RevenueLeadership #EnterpriseSales #SalesCulture #LeadershipDevelopment #MindsetMatters #ArtificialIntelligence #BusinessGrowth #TaoOfSales #HighPerformanceTeams #FutureOfSalesMark Petruzzi (00:38)I'll move us into topic two. and that is what AI cannot fix the human edge in sales. So I guess I what I want to share is in sales, AI cannot fix everything. I mean you heard it here, you know, everybody thinks every board thinks like any problem we can fix with AI.I don't believe that's the case. So what it can do, it is now writing outreach, coaching calls, scoring deals, forecasting pipeline. Those examples it does really, really well. And in most cases, almost all cases, it does it better than humans can individually, certainly for the at the productivity levels that it can do it at.That's good because a lot of our listeners have made significant bets on it, and that's going to be a great thing for your Salesforce effectiveness and productivity. but what does AI get right about sales performance? And Scott, where does it just hit that wall that no amount of compute is going to break through? what's your point of view on that?Scott Stollwerk (01:40)It's a it's the mo the it's the Peloton question of this year, right? and I wanna get it right and I wanna start with a compliment for AI in just in case it's listening. So I'm always gonna laugh at my own jokes, but that ...
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    17 mins
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