Tony Caldwell

Tony Caldwell joined the board in 2018.  In addition to Chairman of the Board, Caldwell serves as Chair of the Governance and Strategic Planning committees and as a member of the Board Loan and ALCO Committees. He is a distinguished serial entrepreneur and visionary leader, renowned for transforming OAA into one of the largest regional insurance distributors in the U.S., achieving over $700 million in sales. Under his stewardship, OAA has flourished as the top-ranked Strategic Master Agency of SIAA, fostering 185 successful insurance agency partnerships nationwide. Recognized for outstanding growth, OAA has been celebrated as one of Oklahoma City's fastest-growing businesses and a perennial "Best Place to Work" in Oklahoma.

Beyond insurance, Tony serves as Chairman of the Board for Prism Bank, a community bank with branches across Oklahoma. As a thought leader in the business and insurance sectors, Tony shares his expertise through his blog "Growth Agent Insight" and the popular podcast "UnCaptive Agent: The Future of Insurance". He is the author of several influential books, including the Amazon Best Seller "UnCaptive Agent" and "COVIDProof Your Agency", addressing cutting-edge strategies for entrepreneurial growth in the insurance industry.

Tony's dedication to community service is profound, demonstrated through his leadership roles in various organizations, including the Independent Insurance Agents of Oklahoma, where he served as Chairman and board member. His civic contributions have extended to the Oklahoma House of Representatives and numerous nonprofit organizations dedicated to social welfare and youth empowerment.

Tony earned his BA in Government from Centenary College of Louisiana and pursued theological studies at Southwestern Baptist Theological Seminary. An avid outdoorsman and instrument-rated commercial pilot, Tony enjoys spending time with his family—wife Sharon and their two sons.