S2E10: Ron Masi, Orchestrating a 7-Figure Deal to Perfection
Ron Masi - Linkedin
Ron spent 10 years selling ink on paper before moving into SaaS in 2015. He built his enterprise game the hard way — through coaches, mentors, and a lot of swing-and-miss — until he had a system for running deals at a level most AEs never reach.
This episode is about a deal he's never forgotten. Not because of the size, but because of the execution. Every piece moved on purpose. The research, the internal alignment, the mind maps, the 90-minute demo that didn't show a single feature — it all came together and they walked out knowing they'd won.
What you'll take away:
How to build a deal dossier that actually changes how you sell, how to run an internal team across a complex opportunity without being in every room, and what it looks like when a demo stops being a demo and becomes a story.
On research:
"We highlighted every page of the CEO's book. We knew everything about them first."
On internal selling:
"Some people want to run really fast with you. Some people want to go slow. You have to think about how you're going to set this up."
On not connecting the dots for the customer:
"Never let the customer have to connect the dots. You need to connect them as much as possible."
On the demo:
"We didn't show the platform. We told them a story. We maybe clicked on four things. Maybe."
On the win:
"There was no possible way the people coming next were going to do that."
On the feeling:
"It's like an energy you don't even understand. Like if you played sports and you're in the zone — the basket was as big as the ocean."
People Mentioned:
- Jamal Reimer — Mega deal coach, mentor to Ron
- Brian Burns — Sales coach, introduced Ron to mind mapping & "map to money"
- Dennis Sorensen — Mentor, taught Ron how to unpack annual reports & 10-Ks
- Mind mapping — Core tool Ron used to organize deal strategy and move pieces as the deal evolved
