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Jason Willeford

CEO and Partner

Meet Our Team - Professional and Welcoming Group at a Conference Table Faces the Camera, Team Leader Sitting on the Table with Arms Folded

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Jason serves as President/CEO of Dillingham Insurance. He leads the strategic direction of the firm through trust and empowerment and is passionate to see every employee and client reach their best and highest potential. Under Jason’s direction, Dillingham Insurance has been recognized as the 2025 Marsh Berry Max Performer, the 2022 IIAO Agency of the Year, the 2021 Marsh Berry National Firm of the Year and consistently ranks in the top 1% of all U.S. insurance agencies.

Jason also serves on the board of directors for Watermark Bank, Search Ministries, The Oklahoma Board of Pharmacy and the Young Presidents Organization.

Jason was born and raised in Duncan, Ok and attended Columbia University in New York City before finishing at The University of Oklahoma where he and his wife Becky met. Becky and Jason live in Norman with their four children, Ben, Jones, Annie and Tom.

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