In this episode of Thoughts on Selling, I sit down with Jeff Kirchick — sales leader, author, and big believer in authenticity. We dig into how authenticity plays out in sales, what AI can and can’t replace, and why building trust matters more than ever.

Jeff shares his journey from English major and aspiring screenwriter to startup sales leader, selling seven-figure deals to Fortune 500s. We talk about his book, the hard truths he learned writing it, and why he believes authenticity is the ultimate differentiator in a world where AI can generate scripts, emails, and playbooks.

We get into some fun and unexpected territory too — from Dennis Rodman and Larry David as surprising role models for authenticity, to the cultural differences between selling in Boston, Japan, and Boulder. The through-line? Real relationships, built on curiosity, honesty, and non-attachment to outcomes, are what drive sustainable success in sales.

A few key takeaways:

• Authenticity builds trust. Buyers can tell when you’re real — and they reward it.

• AI can’t replace relationships. Tools help, but risk management and shared experience still come from humans.

• Deliberate practice matters. Salespeople need to rehearse pivots and build confidence outside scripts.

• Non-attachment to outcomes frees you. Curiosity and care create openings, even if they don’t lead to immediate deals.

• Great leaders go first. Vulnerability and empathy from the top invite teams to bring their full selves.

This conversation is packed with stories, insights, and practical wisdom for anyone looking to level up as a sales leader or seller.

🎧 Give it a listen, and let me know what lands with you.