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Dillingham Insurance

Management

Jason Willeford

CEO and Partner

About

Family-owned, forward-thinking strategic insurance and benefits partner founded in 1927 and headquartered in Enid, OK. As a fourth-generation agency with nearly a century of experience, Dillingham Insurance provides comprehensive business insurance, personal insurance, employee benefits, HR consulting, and risk management solutions. Serving clients of all sizes across Oklahoma and multiple states through tailored strategies, strong domestic and international carrier relationships, and a client-focused approach with over 80 team members and 3000+ clients served.

Why we like Dillingham Insurance

Dillingham Insurance earns its place among top Employee Benefits Brokers in Enid through nearly a century of family-owned expertise dating to 1927 and a fourth-generation commitment to client partnership. The firm delivers comprehensive group health, dental, vision, life, disability, EAP, and HR consulting solutions via an integrated ELEVATE process that customizes strategies to protect people and strengthen businesses. With a large professional team, multi-state reach, and preferred access to leading carriers, it supports employers of all sizes across diverse industries with thoughtful risk management and benefits design. Its blend of deep Oklahoma heritage, innovative consulting, and proven longevity clearly separates it as a capable, forward-thinking local leader.

View Our Review of Evans National Group

Pros & Cons

Pros

  • Nearly 100 years of continuous operation as a fourth-generation family-owned agency headquartered in Enid with deep local roots and multi-state licensing
  • Full suite of employee benefits including group health, dental, vision, life, disability, EAP, voluntary coverages, and integrated HR consulting services

Cons

  • Standard Monday-Friday 8:00 AM to 5:00 PM office hours may require appointments for non-standard scheduling needs
  • As a multi-office regional firm with broad service scope, highly specialized ultra-local boutique preferences may find the scale less intimate than smaller single-location agencies

Review Scores

Facebook4.9

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