How to Sell Software by Asking Better Questions | Dillan Dove (JewelLink)

In this episode, I sit down with Dillan Dove, VP of Sales at JewelLink, to talk about building a sales motion from the ground up, coaching reps hard, and turning industry knowledge into a real software sales advantage. Dillan shares how he went from selling and leading teams at Podium to helping build JewelLink’s go-to-market motion in the jewelry industry, including why the early playbook is less about pitching every feature and more about asking better questions, finding real pain, and knowing when a customer is or is not a fit.We also get into sales leadership, rep development, and what separates average reps from top performers. Dillan breaks down his direct coaching style, why honest feedback only works when people know you actually care, and how one tough conversation helped turn a top rep into a much higher performer. He also shares lessons from Podium that he now applies as a VP, including why sales leaders should understand onboarding, implementation, product, and the full customer experience — not just quota and pipeline. TOPICS WE COVER How Dillan is building the early sales playbook at JewelLink, and why the foundation is asking meaningful questions instead of dumping product features  Why industry knowledge only matters if it helps you understand customer pain and connect the product to a real business problem  How consulting with JewelLink before joining full-time helped Dillan step into a bigger leadership role and think more like a VP  What brutal but caring sales coaching looks like, including how honest feedback can unlock a rep’s next level  Why stalled deals usually come back to weak discovery, unclear pain, and reps pitching every tool instead of the one that matters most  The biggest lessons Dillan took from Podium, including why sales leaders should study onboarding, implementation, and the full customer journey ABOUT THE GUESTDillan Dove is the VP of Sales at JewelLink, a software company helping jewelry stores improve sales training and performance. Before joining JewelLink, Dillan was Director of Sales at Podium.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about JewelLink: https://www.jewellink.com/