President – USA Risk Group, Inc.
President – USA Risk Group (Bermuda), Ltd.
President – USA Risk Group of the Virgin Islands
President – Cyberisk Holdings, Inc.
Gary Osborne is President of USA Risk Group, operating from our Greenville, South Carolina office. 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 twenty years, having held positions in Bermuda, Hawaii, Vermont and South Carolina. He has been involved in the establishment of numerous single parent captives, association captives, risk retention groups and traditional group insurance programs. He is a frequent industry speaker and has spoken at the CPCU Annual Meeting, RIMS, the American Society of Association Executives’ Conference, the Casualty Actuarial Society Conference, IBC Conference, Self Insurance Institute of America Conference, as well as captive industry conferences in Hawaii, Vermont, South Carolina, Arizona, Tennessee and Cayman. In addition, he is a regular contributor to industry publications and has been published and quoted in Captive Review, Captive Times, Business Insurance, Risk and Insurance, National Underwriter and the Risk Retention Reporter. Captive Review recently ranked Gary as number 4 in the “Power 50” for the alternative risk industry.
Gary has served as treasurer of the Hawaii Captive Insurance Council, as Chairman of the Legislative Committee and member of the Finance and Conference Committees for the Vermont Captive Insurance Association, as a director of the National Risk Retention Association where he currently participates on the Legislative Committee, as a faculty member for the International Center for Captive Insurance Education and as a founding member of the Tennessee 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.
A native of Glasgow, Scotland, Gary attended the University of Glasgow, receiving his Bachelor of Accounting in 1982. He qualified as a Member of the Scottish Institute of Chartered Accountants in 1985 and received the Association of Risk Management designation in 1996.