Episode Library

Episode SummaryIs your sales pitch a rehearsed monologue or a collaborative improv scene? In this episode of Thoughts on Selling, Lee Levitt sits down with Kevin Hubschmann, former enterprise rep turned comedian and founder of Laugh.Events.

We dig into the fascinating parallels between stand-up comedy and enterprise sales. Kevin shares his story of balancing daytime sales calls with nighttime open mics, realizing that skills like Presence, Timing, and Curiosity are missing from modern playbooks...

Episode SummaryIs sales a science or a performance art? In this episode of Thoughts on Selling, Lee Levitt sits down with Jake Isham, a filmmaker, creative director, and founder of Creative Minds Agency.

Jake’s story is pure art-meets-entrepreneurship. He started as an actor, moved behind the camera to direct, and eventually became what he calls an "accidental marketer." We dig deep into the intersection of Storytelling and Revenue—exploring how the best salespeople are actually performers. Not...

Episode SummaryIs sales a business process or a psychological one? In this episode of Thoughts on Selling, Lee Levitt sits down with Laura Keith, CEO of Hive Perform and Hive Learning (and self-proclaimed "Chief Entertainment Officer" to three kids).

Laura’s journey is fascinating: she never planned to work in sales. She studied psychology. But she quickly realized that the traits required to understand the human mind—Curiosity, Empathy, and Motivation—are the exact same traits required to clos...

Episode SummaryIn a world where AI can write your emails, generate your scripts, and predict your forecast, is there anything left for the human seller? Lee sits down with Jeff Kirchick—sales leader, author, and unapologetic advocate for authenticity—to answer that question.

Jeff’s journey is unconventional: from an English major and aspiring screenwriter to a startup sales leader closing seven-figure deals with Fortune 500s. We dig into why Authenticity is no longer just a "nice to have"—it is...

In this episode of Thoughts on Selling, I sit down with David Donlan, VP of Sales at IP Co-Pilot, longtime tech sales leader, and passionate mentor for the next generation of sales professionals.

David and I cover a wide range of topics — from his early days upselling azaleas with fertilizer at age 15 to shaping sales teams at HubSpot, and now building a company that helps innovators protect and accelerate patents.

A few highlights from our conversation:

Three ways to sell. David breaks down ...

In this episode of Thoughts on Selling, I sit down with Ted McKenna — researcher, author, and co-creator of some of the most influential sales frameworks of the past two decades. Ted has been behind The Challenger Sale, The JOLT Effect, and most recently, The Activator Advantage.

We dive into the evolving dynamics of B2B sales, why buyers are more informed (and more hesitant) than ever, and what high-performing sellers do differently.

Some highlights from our discussion:

Data meets sales anth...

In this episode of Thoughts on Selling, I sit down with AI strategist and workforce transformation expert Ben Tasker. Ben has spent over a decade helping organizations harness AI not just as a shiny tool, but as a way to amplify human abilities through upskilling, reskilling, and smarter systems thinking.

We dive into:

The “AI Between Times”: why we’re in a transition period where adoption is fast, mistakes will happen, and systems thinking is essential.

Upskilling & Reskilling: how organizat...

In this episode of Thoughts on Selling, I sit down with Mike Baron — longtime sales leader, mentor, and operator who has lived the startup, PE, and enterprise trenches. Our conversation is part playbook, part reality check, and packed with practical wisdom for anyone leading or enabling sales teams.

We dive right into a “what if” scenario: if Mike were CRO and I were head of sales enablement at a security startup, what would we do first? Mike breaks it down with clarity:

Start with comp plans....

In this episode, I sit down with Matt Wilkinson — life sciences marketer turned AI strategy partner, Visiting Fellow at Cranfield School of Management, and board member at the Association of Key Account Management. Matt brings a sharp lens to the challenges of sales and marketing alignment, the rise of AI in B2B, and what it really takes to create customers in today’s environment.

We cover a wide range of topics, from why account-based approaches are so powerful when done right, to how culture ...

Tracy Linne, an experienced sales leader and strategist, joins me for a powerful conversation on the intersection of leadership, clarity, and sales performance for this episode of the Thoughts on Selling podcast.

Tracy emphasizes the role of leaders in shaping not just strategy but belief within teams. Our discussion covers the importance of creating clarity in complex environments, the necessity of building trust as the foundation for growth, and why adaptability is a hallmark of modern sales ...