The conversation delves into the challenges of managing multiple stakeholders in enterprise sales, with a focus on the transition from a restaurant franchise to a sales career. It explores the lessons learned from the restaurant business and ad sales, comparing ad tech sales with SaaS sales. The discussion also covers the sales process and challenges in selling True Rating, including the ROI pitch and objections. Additionally, it highlights the data-driven play and the approach to handling objections in the sales process. The conversation covers the importance of balancing storytelling and data in sales pitches, as well as the challenges and strategies for stakeholder management and alignment in complex deals. Takeaways Managing multiple stakeholders in enterprise sales Transition from restaurant franchise to sales career Storytelling vs. Data Stakeholder Management Chapters 00:00 Introduction to Managing Multiple Stakeholders in Enterprise Sales 05:43 Comparison of Ad Tech Sales and SaaS Sales 13:39 ROI Pitch and Objections in Sales Process 18:50 Data-Driven Play and Handling Objections

The conversation delves into the innovative use of AI in sales coaching, highlighting the challenges, benefits, and tactical approaches. It explores the impact of AI on sales coaching and the potential pitfalls to avoid. The role of AI in exposing coaching practices is also discussed, providing valuable insights for sales leaders and professionals. Takeaways Sales coaching with AI Differentiating coaching, training, and feedback Chapters 00:00 Transition into Sales and Coaching 06:36 Custom GPT for Sales Coaching 15:05 Impact of AI on Sales Coaching 23:41 Mistakes to Avoid in Implementing AI in Sales Coaching

"I Just Want to Play More Golf" — Why ROI Isn't Always the Right AI Pitch What happens when you pitch a lawyer on billing 30% more hours and they say they'd rather leave early to hit the golf course? You learn that ROI isn't always the story that closes deals. James Lawler is the Managing Director of TriCoStar, an AI-powered time recording and email management platform built specifically for law firms. His company has been in legal tech for 38 years—his dad started it in the late 80s with a device called a Psion that most of us have never heard of. Today, James is doing founder-led sales into one of the most change-resistant industries out there. In this episode, we dig into what it actually takes to sell AI to buyers who are skeptical by profession. Turns out, the biggest objection isn't whether AI works—it's whether it'll catch them checking football scores. We cover: → Why privacy concerns beat performance skepticism in conservative industries → How James uses Copilot live during sales calls to translate technical answers into plain language → The difference between selling "bill more hours" vs. "get your evenings back"—same product, completely different pitch → What happens to the legal profession if firms automate paralegal work (and why apprenticeship-style contracts might make a comeback) → How to keep deals warm without filling inboxes with boilerplate when you're running founder-led sales If you're selling into traditional industries or trying to figure out how AI fits into your own sales motion, this one's worth your time. 🎧 Follow Selling AI on Apple Podcasts, Spotify, and YouTube.

Molly Sestak has spent years building sales enablement programs from scratch—and now she's using AI to do in 5 minutes what used to take hours. In this episode, we dig into how custom GPTs can create truly personalized onboarding plans for new reps (not just role-specific templates), and why the combination of RevOps and Enablement is becoming a powerhouse pairing. Molly shares her vision for the future of sales teams: leaner on the selling side, more robust on the operational side, with reps acting as conductors orchestrating AI-powered workflows. If you're in enablement trying to figure out where to start with AI, this one's for you.

The Selling AI Podcast focuses on generating revenue with AI tools and simplifying decisions for buyers, as well as adapting sales strategies to navigate the AI shift in real time.