Pilots to Partners

Matt Gambino

Pilots to Partners

Winning strategies for converting pilots into sales

Watch The Replay
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Stop finding "Veruca Salts." Start building a process to find your "Rudys."

Most edtech companies make it all too easy to start a pilot. We flood the zone with free access, hoping for the best. The result? A misalignment of expectations. The teacher just wants a free tool, and we're left chasing them for a discovery meeting.

This process is broken. It devalues your product and attracts the wrong users—the "Veruca Salts" who have no skin in the game. You need a new playbook.

In this training, I show you how to abandon the all too easy approach and build a pilot process that expects heavy lifting. You'll learn how to create a high-value experience that filters for your "Rudys"—the curious, motivated teachers who will work to become true partners.

This training is for...

  • Sales Leaders who need to fix their "pilot-to-paid" conversion rates.
  • Account Executives tired of chasing low-engagement pilots that go nowhere.
  • Customer Success Managers responsible for onboarding and converting free users to paid accounts.

Key frameworks and takeaways

This session provides my "Three E's" framework for designing a pilot program that converts. You will learn:

  • 1. Build EXPERIENCES: How to replace your static request form with a questionnaire that gathers high-gain data and makes the application itself a valuable brand experience.
  • 2. Set EXPECTATIONS: How to get admin buy-in for compliance and record-keeping, so the superintendent is in the loop from day one.
  • 3. Encourage EXPERIMENTS: How to require skin in the game by having pilots test a thorny concept using a "mini pilot."
  • How to Reframe Onboarding: A simple language shift to stop requiring a kickoff call and start rewarding them with a meeting they qualified for.

Feedback from industry leaders.

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"Matt is the go-to professional for elevating sales strategy in education. His trainings are engaging and results-driven. In my twenty years in the business, he's the best I've worked with."

John Kline

Head of Sales, SAM Labs
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"I asked my team to rate Matt's training. The lowest rating was 4.5, and one of my most experienced reps said, '5.5! I’m going to start using this Monday!'"

Allison Duquette

CRO, CampusLogic
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"We're already seeing an impact... He's authentic, he's brilliant, and I would recommend him to anyone who seeks to take their sales skills to the next level."

Tamara Bousquet

EVP Sales, Carnegie Learning

About your trainer.

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As a leading sales trainer for the education technology industry, Matt Gambino partners with edtech sales and marketing leaders to build high-performing teams and scalable sales processes. Rooted in decades of direct experience, his strategies help organizations from startups to market leaders shorten sales cycles and drive revenue. Matt's practical, no-nonsense workshops provide the specific frameworks and language your team needs to win in today's complex edtech market.