About — Darrin De Stasio

27 years.
Every quota hit.
One rule.

Darrin De Stasio is not a sales consultant who studied the profession from the outside. He lived it — for 27 years, at the highest level, inside some of the most competitive sales environments in enterprise technology. He built teams that hit quota. He mentored people who had never been told the truth about what it actually takes. And then he wrote it all down.

"I believe there comes a point when success stops being about what we achieve ourselves and starts being about how many people we help along the way."

Built from doing it,
not studying it.

"The things that separate the top five percent from everyone else are not complicated. They are just not written down clearly enough for the people who need them most."

I started in sales because I believed in the profession — not the version with the aggressive closer and the manipulative tactics, but the real version. The one where you understand a buyer's world well enough to show them something they had not seen yet. Where you earn trust before you ask for a decision. Where being genuinely useful is the strategy.

Twenty-seven years later, I still believe that. And I have the results to show it is not naive — it is the only approach that actually works at scale, over time, across markets and conditions.

I have worked at Oracle, IBM, Demandware, Bronto/NetSuite, MicroStrategy, and Alteryx — and I am currently part of the team at Horizon-Five. I have been an individual contributor, a manager, and a Vice President. I have built teams from scratch and inherited ones that needed to be rebuilt. I have hit quota in up markets and down markets, with strong products and with ones that needed to be sold harder.

Along the way I have mentored dozens of sales professionals — people who needed someone to believe in them, show them what great looks like, and tell them the truth. Every one of those conversations taught me something. And eventually I realized I needed to write it down.

Sell the Hole, Not the Drill is the result of that. Not a theory — a career.

The part of the career
that matters most.

Over the past 20 years, Darrin has mentored dozens of sales professionals — people at every stage of the career, from new reps who had never made a cold call to seasoned sellers who knew something was off but could not name it.

The conversations he is most proud of are not the big deals he closed. They are the ones where something clicked for someone who needed it — where a rep left the call and went into their next conversation differently.

That is why the book exists. Because there are more people who need those conversations than Darrin can reach one at a time. The book is the attempt to scale the mentoring — to put into writing the things that have made the biggest difference for the people he has worked with directly.

If you are in sales and you are struggling — or you are building a career and you want to talk it through — Darrin reads every message and responds personally.

27 years.
Every quota hit.
One rule.

Built from doing it,
not studying it.

The philosophy behind everything.

The part of the career
that matters most.

The results speak for themselves.

Ready to change outcomes?

27 years.Every quota hit.One rule.

Built from doing it,not studying it.

The philosophy behind everything.

The part of the careerthat matters most.

The results speak for themselves.

Ready to change outcomes?

27 years.
Every quota hit.
One rule.

Built from doing it,
not studying it.

The part of the career
that matters most.