Jesse Olsen

Chief OPerating officer

Chief Operating Officer Jesse Olsen, CPCU, ARM, has been working in the fields of risk finance and captive consulting since 2006 and brings a distinctively client-focused element to the COO role.

Prior to joining Helio, Jesse was Managing Director and a senior consultant at Strategic Risk Solutions, the world’s largest independent captive management and consulting firm. There he was responsible for conducting feasibility studies, forming new captives, providing strategic consulting to existing captives, and guiding captive business plan expansions. He had previously led the Specialty Risk Services practice for Lockton Companies’ Texas Series, overseeing captive consulting & analytics, risk control, and claims teams throughout the state. Jesse started in the insurance industry in Lockton’s Kansas City headquarters, consulting nationally and internationally on risk finance matters. Jesse started off his professional career in the Fixed Income division of Lehman Brothers and was based in New York City.

Jesse is a past committee member and presenter for numerous captive conferences throughout the United States such as the Western Region Captive Insurance Conference and Vermont Captive Insurance Association annual conference. He has been recruited to speak at a wide array of risk management gatherings such as the Chicagoland Risk Forum. Commercial insurance carriers and brokers routinely ask him to speak or serve on panels for their various client events.Jesse is passionate about education and serves on the board of local high school St. Athanasius & St. Catherine Academy. He utilizes his strategic planning and execution skills in service of his local parish vision casting team. A lifelong baseball fan, Jesse also manages his boys’ baseball teams.

Jesse completed the entire coursework and testing for the Chartered Property Casualty Underwriter designation from The Institutes in less than a year. Prior to that, he earned the Associate in Risk Management designation. He holds a Bachelor of the Arts from Yale University with a double major in Economics and Political Science.

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