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 serves as Captive Director for the Oklahoma Insurance Department, a role he began in 2022 under Insurance Commissioner Glen Mulready. He previously led the Bureau of Captive and Financial Insurance Products at the Delaware Insurance Department, where he grew the state's captive program from 38 companies to one of the largest captive domiciles in the world. He holds the Associate in Captive Insurance designation, the highest professional credential in the field, held by fewer than 650 people worldwide, and Captive Review magazine has repeatedly named him to its global "Power 50" list of the most influential figures in captive insurance. Steven is active in regulatory matters before the National Association of Insurance Commissioners, including chairing the subgroup that redrafted the purchasing group provisions in the Risk Retention and Risk Purchasing Group Handbook. He first joined the Oklahoma Insurance Department in 1995 and served more than thirty years in the U.S. Army Reserve, retiring as a lieutenant colonel.
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.