"Most salespeople are selling the wrong thing. Here is the shift that changes everything."
There is a gap between what most salespeople are taught and what actually works. The reps who consistently make President's Club are not the ones with the best territory or the most natural talent. They think differently, prepare differently, and show up differently — in every single conversation.
Read the BookWhether you want to read, learn, or train your entire team — there is a path for you.
31 chapters. No fluff. A blunt, practical guide built from 27 years of doing it at Oracle, IBM, Demandware, Alteryx, and beyond. Available now on Amazon.
Get the BookKeynotes and talks for sales kickoffs, QBRs, revenue summits, and leadership events. Not motivational speeches — real, practical content your team can use the next day.
View TalksA full day with your team working through mindset, discovery, demos, objections, negotiation, and closing. Interactive, practical, and immediately applicable.
Book a DayDarrin is the kind of sales leader who elevates everyone around him. He combines strategic vision, operational discipline, and genuine care for people in a way that drives both exceptional business results and lasting relationships. Throughout his career, he has consistently built high-performing teams, developed future leaders, and created cultures centered on accountability, growth, and impact, all while always keeping his customers and partners first.
I could write an entire chapter of this book just about Darrin's leadership, his positive influence on my life, and how he taught me how to show up for those around me. I am the leader I am today because of the discipline, persistence, and team first mindset Darrin instilled in me. This book will change how you approach your days, weeks, quarters, and year in sales.
A true solution-focused leader who I had the privilege to work with, Darrin always kept the customer at the center of every conversation — zeroing in on the problems worth solving rather than the technology being sold. His ability to understand and articulate customer challenges before ever pitching a product set him apart as both a trusted advisor and a results-driven professional. He had a rare gift for persistence — always bringing new value to every interaction — and conducted himself with the integrity, discipline, and intelligence that made customers genuinely trust him. Beyond his professional brilliance, he is simply a great friend and mentor — Sell the Hole, Not the Drill is the embodiment of everything he stands for.
Darrin DeStasio taught me that great sales isn't about pitching products — it's about deeply understanding customer pain and building solutions around it. He drilled into our team the discipline of multithreading, never letting a deal rest on a single relationship, and always being more prepared than the competition. His coaching changed how I approach every deal, and those lessons have compounded throughout my entire career. Darrin doesn't just make salespeople better — he makes them think like business leaders.
Get the book on Amazon, or reach out to book Darrin for your next sales kickoff, QBR, or training day.
Helping sales professionals win. Helping kids eat.
One book at a time.