Agentic AI Episodes

Chris Carter — technologist, keynote speaker, and SAP ecosystem veteran — joins Lee to unpack what it actually means to use AI well in enterprise selling. From using Gemini to simulate discovery conversations to the Peloton analogy that woke up a room of Oracle salespeople, this episode is about preparation, strategy, and making your own rules. If you're firing off AI-generated emails and wondering why nobody's responding, this one's for you.

Enterprise sales is under pressure to adopt AI sales strategies. But...in enterprise sales, the mindset of the sales rep still dictates success or failure.

James Stephan-Usypchuk brings 15 years of AI development experience and a psychology degree to a conversation about what machines can and can't replace in sales. We explore why trust still requires a human face, how predictive algorithms should be used as filters rather than closers, and why likability remains the ultimate competitive advantage in an AI-saturated market. James shares real examples from his work with private equity firms, including how his team uses AI to identify acquisition targets—but always injects the human element when it's time to have a real conversation.

Sales and marketing alignment isn't a nice-to-have — it's the engine that drives predictable revenue. In this episode of the Thoughts on Selling podcast, I talk with Javier Lozano Jr., a fractional CMO and CRO who helps founder-led tech companies build the infrastructure where sales and marketing actually work together. Javier brings a rare perspective: he's lived on both sides of the revenue equation, and he's seen firsthand what happens when these teams are aligned on revenue goals versus when they're tossing leads over the fence and pointing fingers.

We get into some meaty territory — why customer success is really a marketing function (because those customer stories become your best sales enablement), how AI is already transforming the way smart teams analyze sales conversations and sharpen their messaging, and why the feedback loop between sales, marketing, and operations is a closed system that breaks when any piece gets out of sync. Javier shares a metric he calls HIRO pipel…

In this episode of Thoughts on Selling, Lee Levitt sits down with Drew Sechrist, CEO of Connect the Dots and an early Salesforce employee, to discuss the evolution of sales from the "No Software" era to the age of AI. Drew shares insights from his time working alongside Marc Benioff, emphasizing the critical role of "osmosis" in learning sales skills—a benefit he fears is being lost in today's remote-first work environment. He argues that while technology has made many aspects of sales easier, the loss of in-person mentorship and hallway conversations has made the profession harder for newcomers to master.

The conversation pivots to the future of selling in an AI-dominated world, where Drew asserts that "trust capital" is the only durable moat for sellers. As AI automates routine tasks, the human ability to build deep, high-stakes relationships becomes more valuable than ever. Drew explains how his company, Connect the Dots, is helping sellers leverage their "relationship capital" …

Episode Summary Is the "growth at all costs" era over? In this episode of Thoughts on Selling , Lee Levitt sits down with Amos Bar-Joseph , a third-time entrepreneur joining from Tel Aviv, to dismantle the broken "Unicorn Playbook." Amos describes himself as an "Anti-Capitalist Capitalist," rejecting the traditional VC model of raising massive rounds to hire bodies. Instead, he is building Swann , an Autonomous Business designed to scale with Artificial Intelligence , not headcount. We explore w...

In this episode of Thoughts on Selling, Lee Levitt sits down with ETA leader Garth Fasano to discuss the massive shift from traditional inside sales to "Agentic AI"—autonomous agents that think, adapt, and sell without fatigue. Garth explains why small businesses are adopting this technology faster than enterprises to solve the "consistency" problem, ensuring every prospect gets a "fully caffeinated" interaction even after 175 calls. We also explore the future of "Bot-to-Bot" commerce, where AI buyers negotiate with AI sellers, and how this shifts the sales function from simple execution to strategic business visibility.

Episode Summary In this episode of Thoughts on Selling , Lee Levitt geeks out with Maeve Ferguson , an ex-steeplechase jockey turned Big Four consultant and data expert. We dive deep into why the "Quiz Funnel" is dead and how Diagnostic Assessments are the new gold standard for generating high-quality leads. Maeve explains the "Delulu Factor"—how data exposes the gap between perception and reality—and how to leverage that gap to close deals. We also explore Agentic AI : agents that run continuou...