The Challenge: Scaling a Team Without a Repeatable Process

Janet Pittock, an experienced edtech sales leader, was leading a newer team at Legends of Learning that was full of potential but lacked a "predictable, repeatable sales process."

This created challenges across the entire funnel. The company couldn't accurately forecast, and reps were struggling to scale their prospecting, run consultative discovery meetings, gain access to decision-makers, and deliver high-energy, compelling demos. Janet needed to install a complete operating system for her team to build their skills and drive results.

The Solution: A Hybrid "Full-Process" Enablement Program

I designed a custom, hybrid engagement model for the Legends team, built for maximum adoption and rapid skill-building. It combined:

• Virtual "Bite-Sized" Workshops: A series of virtual, "road-test" style sessions focused on core skills. We'd introduce a concept (like my prospecting framework), have the team apply it in the field (with specific "homework"), and then review the results together.
• An On-site "Demo Day": We complemented the virtual sessions with a full-day, in-person workshop focused entirely on mastering compelling, high-energy product demonstrations and running real-world role-play scenarios.

This hybrid approach allowed us to install a new, full-funnel sales process—from prospecting to discovery to demo—in a way that stuck.

The Outcome: Team-Wide Transformation and a Saved Renewal

The impact was immediate and came from all directions.

• Executive-Level Proof: Janet forwarded me a message from one of her top salespeople: "Gambino’s training is simply transforming me as a salesperson. Simply put: it works!"
• Immediate Prospecting Results: Just days after our first prospecting session, Janet shared that one rep, Aryah, "sent out 10 emails following your structure... and by Wednesday he had a district coordinator meeting set up."
• Cultural Adoption: The new language became part of the team's DNA. Janet shared a Slack message from another rep, Joselyn, who suggested, "Or maybe we can 'Gambino' it and have more success :)"
• Bottom-Line Impact: The real proof came from Account Executive Sean Reidy: "I recently had a partner who wasn't planning to renew, but after using Matt's techniques, they changed their mind. His training has boosted my confidence."

We didn't just build a process; we built a high-performance culture and, in the process, saved a key customer.