Thoughts on Selling YouTube Video Library

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 …

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 leadership. Key insights include: 👉 Sales as an energy exchange. Leaders must embody the inspiration they want their teams to deliver. 👉 The power of simplicity. Clear direction removes friction and accelerates execution. 👉 Trust as a multiplier. High-trust environments drive accountability, creativity, and resilience. 👉 Leadership by example. The behaviors modeled by leaders set the cultural tone. This episode is particularly relevant for sales executives, revenue leaders, and anyon…

In this episode of Thoughts on Selling, I get to sit down with the incredible Kaivona Parker—the Unboring Sales Specialist—and let me tell you, she lives up to the name. We talk about what it really means to sell without the mask on. Kaivona shares her journey from breaking into tech sales to becoming a voice for underrepresented sellers, and how she’s using enablement to create safe spaces where people can bring their whole selves to work. We swap stories on improv, authenticity, faith, motherhood, and the mental game of sales—and how all of it ties back to showing up real in every conversation. 💡 My Favorite Takeaways Authenticity wins every time—but you have to give yourself permission to show it. Sales is improv—every objection is just an offer. Storytelling beats scripts—the right story can make the sale without ever talking specs. Great leaders create space for others to be themselves. Your reps’ story matters—start onboarding there, not in the LMS. 🔥 Why This Conversation Stuc…

In this episode of the Thoughts on Selling podcast, I sit down with Dre Baldwin — entrepreneur, keynote speaker, and former pro basketball player — to talk about the intersection of mindset, sales, and performance. Dre brings an intense, no-nonsense perspective to the world of business and selling, grounded in his experience hustling his way from overlooked high school athlete to a nine-year pro basketball career overseas. And he applies the same discipline, strategy, and mindset to his work now as a content creator, coach, and sales leader. We talk about: Why confidence is a decision, not a feeling How discipline beats motivation (every time) The parallels between cold outreach and showing up to practice How to handle rejection, objections, and ghosting without taking it personally What salespeople can learn from athletes about preparation and mental conditioning Dre also breaks down why many reps overthink instead of act, and why clarity + execution = momentum. He calls out …

On this episode of Thoughts On Selling, I’m joined by the fabulous Stacy Bishop, and wow, we cover some ground. From Midwest values and fintech sales to improv comedy and why your brain should zip it sometimes—we’re bringing the laughs and the lessons. If you’ve ever wondered whether you’re selling—or just waiting to talk—or struggled with how to pivot in a sales call without face-planting, this one’s for you. Here’s a taste of what we dig into: 🎯 Authenticity over ego Stacy shares how growing up in the Midwest shaped her career in banking and fintech sales—and how being real beats trying to be someone else. I confess to the times I tried on other people’s “sales personas” like ill-fitting suits. (Spoiler: It didn’t work.) We talk about dropping the mask and just being you—even when you’re the only woman in the boardroom. 🎭 Improv wisdom for sellers Why every statement in a conversation is an offer, not an objection. The magic of “Yes, and…” How I learned from improv (and my dog…

For this episode I’m joined by Vance Morris—a guy whose journey goes from rock bands to Disney to running premium home services, and now helping businesses “Disney-fy” their customer experience. And let me tell you, the parallels to sales are everywhere. If you’re in sales and think “customer experience” doesn’t apply to you—this episode will change your mind. ✅ Systems Create Freedom… and Room for Delight At Disney, every detail is scripted and systematized so cast members can focus on the magic. It’s the same in sales: if you’ve got your basics dialed in—your research, your process, your CRM—you’re free to actually connect with buyers and deliver value instead of scrambling. ✅ First and Last Touches Make or Break You Disney obsesses over the first impression (parking, music, greetings) and the final moment (fireworks). As salespeople, our first touch is the brand experience. Whether it’s an email, call, or meeting, buyers decide quickly whether they trust us—or not. And how we en…

This episode was an absolute blast. I’m joined by Guy Rubin, CEO of Ebsta, who brings not just revenue intelligence expertise—but also a love of physics, football (the British kind), and skiing—to the conversation. We talk about the problem that’s plagued sales teams for decades: data that’s incomplete, inaccurate, or invisible. Guy shares how Ebsta evolved from solving Salesforce data issues into building a revenue intelligence platform that helps companies truly understand what’s driving wins—and where deals stall. Some of the big takeaways from our chat: ✅ Your CRM isn’t the whole truth. Email, calendars, and "hidden” stakeholder interactions hold critical data about deals. Mining that signals where opportunities are real—and where they’re just wishful thinking. ✅ Sales is the last department to get truly data-driven. Imagine marketing running on gut feel—it’s unthinkable. Sales orgs need to catch up. ✅ B and C players can level up. Guy makes a strong case that coaching and da…

In this episode of Thoughts on Selling, I sit down with Borja Cuan, co-founder of Four15 Digital, to talk all things demand gen, agency life, and what it takes to deliver results—not just leads. Borja's been in the digital marketing game since the late '90s, and his perspective on execution, transparency, and the importance of asking the right questions is both refreshing and, frankly, necessary in today’s B2B landscape. We dig into the realities of running a growth agency in a high-pressure environment, including the need to go deep with clients—not just generate leads and toss them over the fence. Borja shares how they push for real alignment and results, why communication is everything, and how referrals and transparency build trust in an industry plagued by skepticism. We also talk about the importance of recognizing client pressure, being honest about what’s working (and what’s not), and how to keep your team focused on delivering high-quality outcomes every single time. Oh, a…