Captive Town Hall: Risk Ownership & Captive Insurance Strategy
Moderated by Jason Willeford, with panelists Chad Dillingham, Blake Kerr, and Steven Kinion
August 25, 2026 | 9:00 to 10:30 a.m.
The Lively | Oklahoma City
Chad Dillingham
Vice Chairman, Dillingham Insurance
Chad serves as Co-Chairman and Senior Business Insurance Consultant at Dillingham Insurance, providing strategic guidance on the firm's long-term growth. With deep experience across business and insurance, he is focused on keeping the firm entrepreneurial and closely attuned to client coverage and service needs. He was appointed by Governor Kevin J. Stitt as Commissioner of the Oklahoma Department of Wildlife Conservation for District 8, and his career reflects a blend of business acumen, community service, and a longstanding connection to Oklahoma's heritage.
Blake Kerr, CPA
Partner and CFO, Helio Risk
Blake has been a public accountant for fifteen years and currently serves as Partner and Chief Financial Officer of Helio Risk, a captive insurance consulting, design, and management firm headquartered in Oklahoma City with offices in Chicago, Dallas, Florida, and Vermont. He began his career as an analyst with the Oklahoma Insurance Department and has since built deep expertise in captive accounting and tax management for high-net-worth individuals and family offices. Blake and the Helio Risk team focus on helping businesses develop their own risk financing capacity through the captive model.
Steven Kinion
Captive Director, Oklahoma Insurance Department
Steven Kinion serves as the chief captive insurance regulator for the Oklahoma Insurance Department, a role he assumed in October 2022. Under his leadership, Oklahoma ranks as the 13th largest U.S. captive insurance domicile with more than 70 domiciled captive insurers. In August 2024, Captive Review named Oklahoma U.S. Captive Domicile of the Year for domiciles with annual premium under $5 billion.
From 2009 to 2022, Steven directed the Delaware Insurance Department Bureau of Captive and Financial Insurance Products. During his tenure, Delaware grew to become the third largest U.S. captive domicile and the fifth largest in the world, with captive insurers generating more than $5.4 billion in annual premium and holding $49.5 billion in assets. Captive Review named Delaware U.S. Domicile of the Year in 2013. From 2014 to 2019 and 2021 to 2026, Captive Review named Steven among the 50 most influential figures in the global captive insurance industry.
A Cleveland, Oklahoma native, Steven earned his bachelor's degree from Northeastern State University and a JD/MBA from the University of Tulsa. He retired as a lieutenant colonel from the U.S. Army Reserve after more than thirty years of service.
Jason Willeford
President/CEO, Dillingham Insurance
Jason serves as President/CEO of Dillingham Insurance, leading the firm's strategic direction through trust and a focus on helping every employee and client reach their full potential. Under his leadership, Dillingham Insurance has been recognized as the 2025 Marsh Berry Max Performer, the 2022 IIAO Agency of the Year, and the 2021 Marsh Berry National Firm of the Year, and consistently ranks in the top one percent of all U.S. insurance agencies. A Duncan, Oklahoma native, he attended Columbia University before completing his degree at the University of Oklahoma, where he met his wife, Becky. They live in Norman with their four children.