In this episode of Front Cover: A Rough Notes Podcast on the Agency Intelligence Podcast Network, Jason Cass sits down with Jackson Rollo, President at Rollo Insurance, the agency featured on the October 2025 front cover of Rough Notes Magazine.
Key Topics:
The honor of being featured on the Rough Notes Magazine front cover
Carrying forward a family agency legacy while creating new impact
Jackson’s journey from aspiring attorney to agency president
The “God, Family, Country” framework shaping their culture
Why investing in a Director of Culture transformed their agency
Building unity through quarterly leadership book studies
Lessons from Good to Great and embracing healthy debate
Scaling from 60 to 275 employees while preserving culture
AI as a tool for growth, not replacement, in the insurance industry
Balancing rapid expansion with staying true to core values
Reach out to:
Jackson Rollo
Jason Cass
Visit Website:
Rollo Insurance
Rough Notes Magazine
Produced by PodSquad.fm
