Crosby L. Sherman

Crosby L. Sherman
Crosby L. Sherman
Deputy Commissioner

Crosby L. Sherman, deputy commissioner of the Insurance Division, began his career at DFR in the 1980s, where he worked as an insurance examiner of property and casualty, life and captive insurance companies. He also oversaw domestic and captive examinations and played a key regulatory role during the initial stages of Vermont’s captive insurance market.

After DFR he worked in the private sector in various management capacities including his own property management company in Vermont. He also ran the insurance and restaurant divisions for Holt Enterprises in New York City and London and served as controller for Middlesex Mutual Assurance Co. in Connecticut.

He returned to his native Vermont in 2013 after serving 10 years in various positions for the New Jersey Department of Banking and Insurance culminating as chief of Captive Insurance.

Born in Brattleboro he moved with his family to St. Johnsbury at an early age, graduated from St. Johnsbury Academy and the University of Vermont. He served in the Vermont Air Force National Guard retiring with the rank of major.