National Captive Management and Risk Consulting Firm Hires Captive Insurance Expert Jesse Olsen

Oklahoma City (December, 5 2023)

Media Contact

Heather McClure


Helio, a captive management and risk consulting services company with offices in Dallas, Tulsa, Oklahoma City, and Kansas City, has announced the key industry hire of Jesse Olsen, CPCU, ARM, as Chief Operating Officer.

“Jesse comes to Helio with 18 years of experience in captive and risk finance. His primary focus will be to design and implement business strategies, processes, and systems. In overseeing operations, he will guide client services, analyze expansion activities, and manage relationships with industry partners,” said Blake Kerr, Helio’s Chief Executive Officer.

Olsen was most recently at Strategic Risk Solutions. There he led feasibility studies, formed captives, and developed and delivered captive strategic planning services. Prior to SRS, Olsen rose to Practice Leader of Lockton Texas’ Specialty Risk Services, overseeing teams delivering captive consulting, data analytics, and risk and claims control. Olsen began his career in investment banking after graduating with a double major in Economics and Political Science from Yale University.

Heather McClure, Helio’s General Counsel & Chief Risk Officer said, “We are thrilled to have Jesse join Helio. We crossed paths many times on the speaking and teaching circuit over the years. It is clear to me Jesse shares a similar vision for delivering best-in-class service and consulting to current and prospective captive owners.”

“The hiring of a Chief Operating Officer of Jesse’s caliber is consistent with Helio’s vision to provide clients true experts within the industry. Jesse will build on the phenomenal success we’ve had over the past year, and his expertise will move us even more quickly into sustainable growth,” said Kyle Sweet, Helio’s Chief Strategy Officer.

“As I begin this fantastic new role, I have many reasons to be thankful,” Olsen reflected. “Foremost are relationships with colleagues who provide extraordinary opportunities to learn. There is incredible momentum as captive utilization and related risk financing strategies continue to disrupt conventional paradigms of how to manage risk.”

Jesse can be reached at


About Helio

Helio’s partners have decades of experience and relationships within the risk and insurance industry, enabling innovative financing and management solutions.

Chief Executive Officer Blake Kerr, CPA, brings extensive experience in accounting, financial operations, consulting, and syndicating capital to Helio Risk. Kerr’s thought leadership in captive tax and risk financing allows Helio to provide innovative solutions in a uniquely comprehensive manner.

General Counsel & Chief Risk Officer Heather McClure, JD, LLM, has managed risk inside law firms and large healthcare systems, overseeing risk financing and management, insurance procurement, captive operations, and claims for over 25 years. McClure, a frequent speaker and educator, has previously been elected by peers as U.S. Captive Risk Manager of the Year and voted to the industry’s Power 50 list. McClure is an executive officer of the board of the Captive Insurance Companies Association, the largest non-domicile industry association for captives in the world.

Chief Strategy Officer Kyle Sweet, JD, has decades of experience as a complex claim litigator, entrepreneur, and captive owner for several businesses he owns and operates. Kyle advises clients on risk and safety issues across the United States and has experienced first-hand how captives transform managing and financing risk, improving safety, and increasing financial returns.