How to scale a family owned insurance agency.

How to scale a family owned insurance agency.

July 16, 2026 · 59 min · Episode 340

About this episode

Jackson Rollo discusses how his family-owned insurance agency achieved significant growth through community focus and innovative strategies.

In this weeks episde here in Insurance Town I got to interview my friend Jackson Rollo. In this episode Jackson, president of Rollo Insurance Group, shares how a second-generation family agency achieved remarkable growth by embracing unorthodox strategies rooted in community focus, technological innovation, and strong culture. Discover how intentional investment in people and purpose can transform an agency into a leading industry force. Main Topics Covered: The evolution and rapid growth of Rollo Insurance over the past five years, doubling its offices despite a 26-year history The agency’s dedication to community involvement, including volunteer programs that foster local relationships Reinventing agency culture: Building trust, loyalty, and unconventional hiring practices The importance of niching versus community focus, with insights into their local-market strategies in Arkansas How adopting technology and AI enhances human creativity and service, not replaces it Balancing profit, purpose, and team development within a family-owned business The mindset shifts necessary for agency owners to move from producer to leader Timestamps: 00:00 - Welcome & overview of Jackson…

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