Every talk Darrin delivers is built from 27 years of actually doing it — at Oracle, IBM, Demandware, Alteryx, and beyond. No theory. No frameworks invented in a conference room. Just what works, and why, delivered in a way your team can use the next morning.
From a forty-five minute keynote to a full training day — and one-on-one mentoring for reps who need real-time help. Every engagement is customized to your team, your industry, and what you are trying to solve.
The definitive talk for any sales team that wants to understand why the top performers consistently win — and what everyone else is getting wrong. Darrin covers the mindset shifts, the buyer psychology, and the practical habits that separate the reps who make President's Club from the ones who always seem to fall just short. This is the talk built from the book — and it hits differently live.
A complete training day built around the principles in Sell the Hole, Not the Drill — working through mindset, discovery, demos, objections, negotiation, follow-up, and closing in a format that is interactive, practical, and immediately applicable. Every participant leaves with tools they can use in their very next conversation. This is not a day of slides and lectures. It is a day of real work.
Buyers have been conditioned to tune out anything that feels like a pitch. This talk covers how the best reps flip the dynamic — from presenting to educating, from pushing to guiding — and why that shift is the single biggest unlock for sustained sales performance. Practical, immediately applicable, and built for teams who want to change how they show up in every conversation.
Most reps work hard. The ones who make President's Club work smart — with a system. This talk breaks down the exact math from quota to weekly activity targets, the daily rhythm that top performers follow, and why persistence without a system is just noise. Includes a live math exercise where every rep leaves knowing exactly what their weekly number needs to be.
Deals rarely die because of product gaps. They die because the buyer never fully trusted the person across the table. This talk covers how trust is built — and how it is lost — and what the best reps do in every single interaction to make sure the buyer feels understood rather than managed. One of the most powerful conversations a sales team can have.
Sometimes you do not need a training day — you need a conversation. A live one-on-one session with Darrin built around your specific situation: a deal that is stalling, a prospect you cannot read, a negotiation you are walking into tomorrow, or a career move you are trying to figure out. Darrin has had hundreds of these conversations over 27 years. This is the one that could change everything for you.
Darrin speaks at a wide range of events — from large-scale sales kickoffs to intimate team training days. Every engagement is customized to your audience and goals.
Set the tone for the year with a keynote that gives your team a framework they will come back to all year long. Perfect for SKOs of any size.
Bring a mid-year energy reset with practical content that connects directly to the metrics your team is being measured on right now.
A keynote that works for a mixed audience of reps, managers, and revenue leaders — everyone leaves with something actionable.
Give new reps the foundation they need from day one — the mindset, the habits, and the framework that separates the people who last from the ones who do not.
A session for managers and leaders on how to coach the behaviors that actually drive performance — not just the numbers on a dashboard.
A high-level conversation for senior leaders about building a sales culture where the best people stay, grow, and win consistently.
Whether you are planning a sales kickoff, a QBR, or a full training day — reach out and let's have a conversation about what your team needs and what that looks like.
Darrin responds to every inquiry personally.
This was the most practical sales training I've ever attended. No fluff — just real things I could use the next day. In our team survey, this session was the highest rated, and many asked how we could book more time with Darrin.
I became acquainted with Darrin 25+ years ago as we both cut our teeth in the depths of the IBM sales discipline. What always stood out to me about Darrin is his relentless focus to unearth the real pain the prospect is experiencing and then carefully illustrate how he can help diminish such pain. Darrin embraces every challenge like it's a new Rubik's cube, using persistent and varying techniques to drive at solutions that previously seemed elusive. He possesses a perfect blend of determination and consultative value that transforms hesitant prospects into long-term strategic partners. If you are looking for force multiplication in your life's work, I strongly urge you to find a way to get to know Darrin.
Throughout my career, I've worked alongside many successful sales professionals, each with their own style and approach. What has always set Darrin DeStasio apart is his disciplined, customer-centric methodology. Darrin's focus on thoughtful outreach, customer success, and strategic expansion has consistently driven exceptional results. During our time together as Vice Presidents at Oracle, Darrin was someone I regularly turned to for advice, fresh ideas, and guidance on developing high-performing sales teams. When we later worked together at Alteryx, I had the opportunity to see his approach in action once again as he became one of the top-performing account executives in the company. His success was never based on shortcuts, built on preparation, hard work, and an unwavering commitment to helping customers achieve their goals. As a leader, Darrin generously shared his expertise, helping build sales programs and teaching prospecting techniques that benefited teams across the organization. The principles he shares in this book are grounded in real-world success and years of proven results. If you apply Darrin's methods, you will significantly increase your chances of success in sales and leadership alike.
Darrin was one of the most influential mentors in my early sales career. When we worked together at Alteryx, he taught me that great sales isn't about pitching features, it's about understanding what matters to each person you're speaking with and communicating value in a way that resonates. He invested countless hours helping me refine my approach, develop executive-level conversations, and build the confidence to run my own sales cycles. Beyond the skills he taught me, Darrin consistently advocated for my growth and opened doors that accelerated my career. The success I've achieved since, including earning Presidents Club alongside him, is due in no small part to his guidance, mentorship, and friendship.
Reach out to check availability, discuss your event, and talk through what the right format looks like for your team. Darrin responds to every inquiry personally.
Helping sales professionals win. Helping kids eat.
One book at a time.