Gary Osborne

Gary Osborne is President of USA Risk Group. In this role he is responsible for developing innovative alternative and traditional risk strategies and programs for clients and prospects of USA Risk Group (USARG). Gary is also responsible for oversight of the captive and alternative market divisions of USA Risk Group. Gary has been working in the alternative market for nineteen years, having held positions in Bermuda , Hawaii and Vermont . He has been involved in the establishment of numerous single parent captives, association captives, risk retention groups and traditional group insurance programs. He has spoken at the CPCU annual meeting, RIMS , the American Society of Association Executives conference, the Hawaii , Vermont , IBC and South Carolina Captive Conferences, and has previously served on the membership committee for the NRRA, and as treasurer of the Hawaii Captive Insurance Council. He currently serves as the Chairman of the Legislative Committee of the Vermont Captive Insurance Association.

Gary joined USA Risk Group in October 1995 as head of the company’s Hawaii operations and relocated back to Vermont in November 1996, where he was promoted to Senior Vice President of USA Risk Group. Gary was promoted to President of USA Risk Group in July 2004. From February 1994 to October, 1995, Gary was Vice President of Sedgwick Management Services (U.S.) Limited in Hawaii . During this time, Gary was responsible for the Hawaiian domiciled captives of Sedgwick Management Services (U.S.) Limited.

In October 1985, Gary joined Price Waterhouse in Bermuda and worked on the audits of a number of captive insurance companies. He moved to Marsh & McLennan (Bermuda) in June 1987 as an Account Manager and relocated to Vermont in December 1989 where he accepted a position with Johnson & Higgins Services as an Account Manager. He was promoted to Assistant Vice President and Senior Account Manager in March 1991. As an Account Manager, he was responsible for providing accounting and reporting services for a variety of captive and other non-traditional insurance companies.



  • B.A., University of Glasgow

Professional Designations

  • ARM
  • Member, Scottish Institute of Chartered Accountants