Thoughts on Selling YouTube Video Library

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: - …

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: - …

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…

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 wal…

A brief trailer for the Ted McKenna podcast

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. Our conversation dives into the evolving dynamics of B2B sales, why buyers are more informed (and more hesitant) than ever, and what high-performing sellers do differently. We discuss: 👍 Data meets sales anthropology. Ted shares how deep analysis of 2.5 million sales calls revealed why more deals end in “no decision” — and what sellers can do about it. 👍 The JOLT Effect in practice. Why too much information overwhelms buyers, and how great sellers guide decisions rather than flood inboxes with decks. 👍 The Activator Advantage. A deep look at what makes “activators” so successful — consistent business development, building zipper relationships, and flowing value across networks. 👍 Fear of messing up.…

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 organizations can build learning plans to keep talent relevant and amplify what people already do well. Applied AI in Sales: from RFP prep to simulated buyer conversations, how sales teams can use AI for deliberate practice and better customer engagement. Systems Thinking & Change Management: why AI adoption fails without clear processes, data quality, and organizational alignment. Personal Branding in the AI Era: how individuals can leverage AI to publish, create, and stay visible in a world where r…

In this episode of the Thoughts on Selling podcast, I sit down with Kerry Curran — go-to-market strategist, agency veteran, and fierce advocate for customer-centric marketing and sales. Kerry brings a unique blend of analytical rigor and empathetic leadership to every conversation, and this one’s no different. We dig into what it really means to be customer-obsessed — and how that obsession shows up in everything from messaging to enablement to revenue alignment. Kerry shares insights from her time leading strategy at agency and consulting firms, and we talk about how B2B sellers can learn a lot from B2C when it comes to creating emotional resonance with buyers. Key takeaways from our conversation: The buyer is always human. Even in the most technical enterprise sale, people buy with emotion and justify with logic. Marketing and sales must align on customer understanding. ICP, messaging, and content strategy all depend on shared insight. Storytelling isn’t fluffy — it…

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. Keep them simple, transparent, and behavior-driving. A clear plan motivates, while a 65-page manual kills performance. Talk to customers — and closed-lost deals. Understand where you win, where you lose, and why. The gold is in the feedback loop. Assess the tech stack. Too many tools = administrivia. Too few = inefficiency. The goal: help reps spend more time selling. From there, we cover the importance of defining an ICP that’s not just a “total addressable market” (because “anyone between…

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 inside organizations shapes buying behavior, to the shifting role of brand and trust in an AI-driven world. Some key takeaways from our conversation: Sales + Marketing must share the same North Star. Vanity metrics and siloed KPIs create friction instead of customers. Account-based strategy works best when sales and marketing co-create it. Alignment starts with shared target accounts, shared narratives, and shared wins. AI is rewriting the buying journey. Buyers come to conversations armed …