DARRIN DeSTASIO

Sales & Leadership Development

Better Leaders.
Smarter Sellers.
Stronger Deals.

Practical sales and leadership academies built to improve how reps execute, how managers coach, and how teams advance real deals.

The Standard: Better Leaders. Smarter Sellers. Stronger Deals.

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What We Offer

Two Academies. One Standard.

Comprehensive programs for reps and frontline managers, built to improve behavior and performance long after the lesson ends.

Sales Academy

A practical 10-part program that gives reps the mindset, frameworks, and tools to run stronger conversations, create more value, and win more deals.

Included: 185-page Field Guide Companion with 28 practical tools and templates.

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Leadership Academy

A 6-course, 23-lesson program for frontline managers to coach effectively, build high-performing teams, and create accountability that drives real results.

Included: 185-page Field Guide Companion with 28 practical tools and templates.

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FOCUSED, IN-PERSON DEVELOPMENT

One-Day Intensives

Need a more targeted engagement? Bring practical, interactive sales or leadership development to your next Sales Kickoff, in-person QBR, or team development day.

Designed to stand alone or serve as a first experience with the principles behind the academies.

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Darrin DeStasio in a pinstripe suit

Meet Darrin

Built on experience. Designed for execution.

Drawing on 25 years in sales across Oracle, IBM, Demandware, Alteryx, and beyond, Darrin brings firsthand experience to the lessons, workshops, and coaching conversations that matter.

  • Qualified for President's Club in 72% of eligible years
  • Built from the principles in Sell the Hole, Not the Drill
  • Designed for real-world execution—not theory
Learn About Darrin
Darrin DeStasio in a pinstripe suit against a stone wall

Darrin DeStasio · Founder & Lead Instructor

The Book

Sell the Hole,
Not the Drill

A blunt, practical guide to what top sales performers do differently. No fluff. Just principles, frameworks, and behaviors that help sellers think differently, prepare differently, and show up differently.

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Sell the Hole, Not the Drill book cover

Watch

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

A short video on the mission behind the book and how it connects to the academies, intensives, and speaking sessions.

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Darrin DeStasio
Or watch directly on YouTube ↗

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.

James Dwyer

Chief Revenue Officer

“

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

Ready to elevate how your team sells?

Let's discuss how the academies, intensives, or speaking can help your organization.

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