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Darrin De Stasio
Sell the Hole, Not the Drill — book cover by Darrin De Stasio
"This book will be the golden ticket to president's club."
"But now other people are going to get access to all the little nuggets of insight I gathered from you over the years. Ok, fine. Let it rip."
"Every time we chat I learn something — can't wait to have it all written down."
"Anyone who's worked with Darrin knows the impact he has on people professionally and personally."
"You've been my boss, my colleague, a trusted partner, my mentor, and most importantly, my friend over the last 16 years."
"This book will be the golden ticket to president's club."
"But now other people are going to get access to all the little nuggets of insight I gathered from you over the years. Ok, fine. Let it rip."
"Every time we chat I learn something — can't wait to have it all written down."
"Anyone who's worked with Darrin knows the impact he has on people professionally and personally."
"You've been my boss, my colleague, a trusted partner, my mentor, and most importantly, my friend over the last 16 years."
Previous Employers
IBM
Demandware
Oracle
MicroStrategy
Bronto
Alteryx
Watch

Why Darrin wrote the book — and what it will do for you.

Video Coming Soon
Recording in progress — 90-second overview

"Most salespeople are selling the wrong thing. Here is the shift that changes everything."

"Stop selling and start educating. People who are educated, buy."
— Sell the Hole, Not the Drill
The Real Problem

Most reps are busy. The best reps are effective.

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 Book
What Darrin Offers

Three ways to get better at sales.

Whether you want to read, learn, or train your entire team — there is a path for you.

01
The Book

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 Book
02
Speaking

Keynotes 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 Talks
03
Training Days

A full day with your team working through mindset, discovery, demos, objections, negotiation, and closing. Interactive, practical, and immediately applicable.

Book a Day
What People Say

Real feedback from real teams.

"

Darrin 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.

James Dwyer  ·  Chief Revenue Officer
Technology Company
"

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.

Dustin Hampton  ·  Senior Group Vice President
Technology Company
"

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.

Fred Haubold  ·  VP of Sales
SaaS Company
"

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.

Jared Philcox  ·  Senior Account Executive
Enterprise Software

Ready to change how your team sells?

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.