The Executive Sessions: Ryan Westerman, President at AndDone

2025-10-21

The Executive Sessions: Ryan Westerman, President at AndDone Executive Sessions are all about humanizing the C-suite, and this one does just that. Jason sits down with Ryan Westerman, President at AndDone, to talk about his path from physics major to payments innovator, the lessons that shaped his leadership, and how AndDone is changing the way agents get paid. What starts as a career story unfolds into an honest look at communication, responsibility, and the human side of leading a growing company. Key Topics: Ryan’s journey from physics and public a...

Executive Sessions are all about humanizing the C-suite, and this one does just that. Jason sits down with Ryan Westerman, President at AndDone, to talk about his path from physics major to payments innovator, the lessons that shaped his leadership, and how AndDone is changing the way agents get paid. What starts as a career story unfolds into an honest look at communication, responsibility, and the human side of leading a growing company.

Key Topics:

Ryan’s journey from physics and public administration to leading a fintech company in insurance
How a Pepsi bottling job sparked his entry into payment facilitation and technology innovation
The birth of AndDone and its mission to simplify premium collection for agents
Why Ryan believes technology and business models must evolve together
Lessons from early mentors on communication, clarity, and explaining ideas that inspire buy-in
The human side of executive leadership and carrying the weight of others’ livelihoods
What’s next for payments, AI, and data in the insurance ecosystem