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

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