Episode Details

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