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Secrets of Rockstar CFOs

Inside Oakbridge Insurance's Rise: A CFO's Perspective with Matt James

Secrets of Rockstar CFOs · 2025-09-02 · 38 min

Episode notes

Building a thriving company in today's complex financial landscape requires a delicate balance between data-driven decisions and people-centered relationships. This episode dives into that challenge as we hear from Matt James , CFO and Chief Acquisition Officer of Oakbridge Insurance , a rapidly growing agency that has risen to the top 50 US brokerages in just a few years. Matt discusses Oakbridge's impressive trajectory since its launch in 2021, emphasizing their unique approach of blending "small-town values" with corporate efficiency, and how he navigates the dual role of financial leader and M&A strategist. We explore his career path, from history major to finance executive, and how he utilizes a differentiated mindset to drive growth while maintaining a strong company culture. Join us to learn about Matt's experience with mentors, managing rapid growth during the COVID era, and his insights on the evolving role of the CFO.

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