Thoughts on Selling YouTube Video Library

On this episode of Thoughts on Selling, I sit down with Jackie Retig, a passionate sales enablement leader and COO at EnableWorks. Jackie recently made the leap into entrepreneurship after years in the tech space, and she brings a grounded, practical perspective to what it really takes to build consistent, scalable sales teams. We get into why enablement is more than just onboarding and training—it's about creating the conditions for consistency, repeatability, and predictability in your sales org. Jackie and I talk about the transformation that comes from good enablement, how to help reps lean in and grow, and why the founder-led sales playbook doesn’t scale. We also dive into: Why enablement is finally being seen as a force multiplier by CROs and VPs of Sales How tribal knowledge is great—but institutional knowledge wins What makes discovery truly impactful (hint: it’s not about checking boxes) Why AI is an assist—not a substitute—for great selling The power of deliberate pra…

For this episode, I had the pleasure of chatting with David Kirkdorffer — marketing veteran, recording artist, hat enthusiast, and self-proclaimed connective tissue between sales and marketing. We talked all about how sales and marketing can actually get along, the evolution of enablement, and what happens when buyers (and AI) start running the show. 🔑 Key Takeaways from Our Conversation: Sales and marketing should be allies David and I have both seen our fair share of friction between the two functions, but alignment starts with empathy. He shared how marketing should serve sales like a customer — and how simplifying CRMs, decluttering processes, and building real relationships makes a huge difference. We're not in a sales-led world anymore The buyer journey has changed — again. Buyers want to self-educate. They're forming shortlists before they ever talk to a rep, and in many cases, the first vendor they speak to is the one they buy from. So your content better be out there, and …

In this episode, I had a great conversation with Tim Bradley, founder of Pennant—a video marketing firm that’s laser-focused on helping companies improve conversion rates in the middle of the funnel. Tim’s all about storytelling, yes—but with a clear eye on how that story supports sales performance. We talked a lot about the line between marketing and sales enablement, and how the best content—especially video—can serve both when it’s done right. Video as a Sales Tool: Tim broke down his “video marketing trifecta”: Anthem (why you exist), Explainer (what you do), and Endorsement (proof you work). These aren’t just for brand awareness—they’re tools for sales teams to build trust and clarity with buyers throughout the journey. Marketing vs. Enablement: We got into the distinction—and overlap—between traditional marketing assets and true sales enablement content. Great video doesn’t just influence customers; it reinforces key messages for reps too. When reps know the story and underst…

In this episode of Thoughts on Selling, I sit down with sales coach and former VP of Sales, Shane Jamison, to talk about the real work behind sustainable sales—coaching to the numbers, managing pipeline pressure without compromising relationships, and becoming the guide your customer needs. We dive into what it means to stay authentic when management wants pull-ins, how to balance urgency with trust, and why pressuring a customer to act early can create more harm than good. Shane shares lessons from his time building and leading teams, and how his passion for coaching emerged from a love of helping people do more than just hit quota—helping them discover where they thrive. 👉 Key Takeaways: Align deal timing to customer priorities, not fiscal quarter deadlines. Pressure testing a deal timeline isn’t pushy—it’s collaborative. Discounts rarely drive true urgency in B2B—clarity does. Coaching is about surfacing what reps already know and helping them apply it with confidence. Sometimes th…

In this episode of the Thoughts on Selling podcast, I welcome Steven Ethridge, an accomplished sales trainer, coach, and expert in Neuro-Linguistic Programming (NLP). Our conversation dives into the pivotal roles that mindset and intentional communication play in driving meaningful sales outcomes. Steven shares his structured two-part methodology: Sales Mindset Self-Mastery and his NLP-based Five-Step Sales Process. He highlights how a salesperson's internal belief system shapes external performance and how aligning communication with a buyer's motivations fosters authentic connections and improved results. Key discussion points: 👉 Mindset as a foundation. Steven explains how reshaping internal narratives and removing limiting beliefs can dramatically enhance sales performance. 👉 Building rapport effectively. We discuss the importance of observing and mirroring both verbal and non-verbal cues to establish deep, authentic rapport. 👉 Tailoring communication. Steven emphasizes the nee…

Welcome back to Thoughts on Selling. This one’s a little different — and a little deeper. I had the chance to sit down with fellow ultrarunner, entrepreneur, and coach Troy Meadows to talk about something foundational: your why — personally, professionally, and organizationally. Just like an ultramarathon, building something meaningful in sales (or life) demands more than tactics. You need a reason to keep going when it gets hard. And believe me, it will get hard. 🏃‍♂️ Key Takeaways Your “why” is your North Star: Whether you're selling software or running 100 miles, the why behind your effort determines how you show up when it gets tough. Good sales isn’t about features — it’s about values: If your customer’s why and your company’s values align, magic happens. Think 20-year partnerships, not transactional closes. Hire for values, not just skills: High performers who aren’t aligned to the mission will quietly (or loudly) tank your culture and your customer experience. …

Dustin Beaudoin joins the Thoughts on Selling podcast to discuss the intersection of AI and sales strategy, the critical importance of in-depth preparation, and how these elements are shaping the future of sales. Here’s a deeper dive into our conversation: Dustin's Background and Sales Philosophy Dustin Beaudoin, with his extensive background in enterprise SaaS sales, brings a unique perspective to the sales process, particularly through the lens of strategic enterprise sales. His journey through the ranks of sales has made him a staunch advocate for leveraging AI to enhance sales effectiveness. He shares insights on how he has developed a passion for integrating AI into sales to make strategic engagements more impactful. His approach revolves around smart utilization of technology to augment the human elements of sales. Deep Preparation in Sales Dustin emphasizes that successful sales strategies heavily rely on meticulous preparation. This involves understanding not just the ov…

I sit down with my good friend and former Oracle teammate Jane Scott for a deep dive into customer success. Jane and I worked together for years on the key account team supporting Xerox, and she was the glue that held it all together — truly the most important person in the room. We covered a lot in this conversation: from the foundational elements of long-term account management, to the evolving role of customer success in today’s SaaS world. Jane brings a wealth of experience and a refreshingly candid perspective on what it takes to really support customers. Here are a few key points we dug into: Why consistency and historical knowledge matter — and how Jane’s 12 years on a single account gave her unmatched influence and insight. How customer success is about enabling outcomes, not just solving problems. The importance of aligning to the customer’s business rhythm and strategic objectives. Why some SaaS companies may not need a dedicated CS team — but the function must still b…

Welcome back to another episode of the "Thoughts on Selling" podcast. In this episode, we delve into the nuanced world of sales negotiations with Ron Hubsher, a seasoned expert in the field. Here’s a detailed breakdown of our conversation and the key insights we uncovered. Introduction to Sales Negotiations: Ron introduces himself as an engineer turned sales professional who applies engineering principles to sales, advocating for a systematic approach to sales akin to a manufacturing process. This ensures consistent, quality outcomes through qualified opportunities and repeatable best practices. The Underappreciated Art of Negotiation Training: Ron observes that while many sales professionals have undergone various forms of sales training, few have deeply explored negotiation training. He highlights the complexity of negotiations, comparing it to different branches of mathematics, where skills range from basic arithmetic to complex calculus. He stresses that negotiations in sales…

Lee and Todd dive into the evolving nature of sales, the importance of coaching over managing, and why the best salespeople are often ex-athletes, musicians, or gamers. They also explore how reps can leverage relationships and first-party data to improve efficiency in an increasingly difficult outbound sales environment.