Gary Osborne has 37 years of captive experience having worked in four different domiciles (Bermuda, Vermont, Hawaii and South Carolina). Gary has been involved in writing parts of the captive laws in South Carolina and Tennessee and was previously a faculty member of ICCIE. He joined Risk Partners as Vice President of Alternative Risk programs in 2018.
Gary’s career began on the audit staff of Deloitte Haskins and Sells, followed by a senior auditing role at Price Waterhouse. He then enjoyed progressive responsibilities while managing captive portfolios at Marsh & McLennan (Bermuda) and Johnson & Higgins (Vermont). He then moved to Sedgwick to establish a captive management operation in Hawaii. After Sedgwick outsourced captive management to USA Risk Group 1995, Gary held management positions there, including President from 1995-2018. He was responsible for all aspects of company operation including expanding the company through acquisitions, overseeing captive management, and financial operations.
Gary has often been featured in Captive Review, Risk Retention Reporter, Captive Insurance Times, and other publications. He has been active in industry trade associations, including Hawaii Captive Insurance Council, National Risk Retention Association, Tennessee Captive Insurance Association, South Carolina Captive Association, and the CICA task group for Captive Insurance Standards for Service Providers. Gary was recognized by the TCIA as the Jim Hinton Volunteer of the Year and by the Vermont Captive Insurance Association with its Industry Service Award. In 2019, he was inducted into the Captive Hall of Fame and named Captive Professional of the Year by Captive Review.