In this episode of Thoughts on Selling, I sit down with Laura Keith, CEO of Hive Perform and Hive Learning — and self-proclaimed “Chief Entertainment Officer” of three kids. We dig into the psychology of selling, the human side of enablement, and how data, AI, and coaching are reshaping modern sales.

Laura’s journey from studying psychology to leading sales organizations is fascinating. She never planned to work in sales — but curiosity, empathy, and a deep understanding of human behavior naturally pulled her in. Those same traits now shape her leadership and the products she’s building at Hive Perform.

We talk about how sales has lost touch with its human side — too often focused on product features and process over people — and how AI might actually help bring humanity back into selling. As automation handles more of the science, the art becomes more valuable: listening deeply, reading motivation, and understanding buyer psychology.

A few big takeaways from our conversation:

• Sales is psychology. Understanding what makes buyers tick — their motivations, fears, and goals — is at the heart of effective selling.

• AI can’t replace empathy. The best sales reps will use AI as a tool but rely on human insight and curiosity to create connection.

• Coaching and practice drive performance. The highest-performing teams make time to practice and coach — not just inspect pipelines.

• Leaders must define “what good looks like.” Without clear frameworks, coaching and development can’t happen effectively.

• Data makes conversations objective. When performance data is visible, reps and leaders can focus on solving problems together, not defending opinions.

• Curiosity beats scripts. Great sellers ask one more question instead of firing back with a pre-rehearsed answer.

We wrap by talking about the future of sales enablement — one where data, AI, and human insight combine to make teams more adaptable, empathetic, and effective.

🎧 Give it a listen — and let me know what resonates most with you.

#SalesEnablement #SalesLeadership #AIinSales #PsychologyofSelling #ThoughtsOnSelling

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.

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 selling on product (easy but competitive), outcomes (about solving real business problems), and feelings (the hardest, but most powerful when done well).

• The heart of leadership. Why helping SDRs and junior salespeople grow into leaders is one of the most rewarding parts of a career.

• Hiring with discipline. Scorecards, structured onboarding, and clear expectations turn hiring from a gamble into a repeatable, measurable process.

• Culture in action. It’s not about slogans on the wall; it’s about building a place where individual motivations are recognized and supported.

• From landscaping to leadership. How lessons from selling plants, teaching swim lessons, and working in services carried forward into leading tech sales organizations.

David also shares his excitement about IP Co-Pilot — and how reducing the patent process from years to weeks can completely change the trajectory of companies large and small.

This one’s packed with stories, lessons, and practical ideas you can put into play immediately.

🎧 Tune in — and let me know which part resonates most with your sales journey.

#SalesLeadership #SalesEnablement #TeamBuilding #ThoughtsOnSelling