Prestigiacomo began his career in Corrections in 1980 as a Correctional Officer at the Kentucky State Reformatory (KSR). In 1982 he was promoted to Lieutenant and assigned to Internal Affairs. In 1986 Prestigiacomo left the Department of Corrections to work for a private law firm. He returned to Corrections in 1996 as an Officer at Green River Correctional Complex (GRCC) and in 1999, was promoted to Production Supervisor at the Kentucky Correctional Industries furniture plant at GRCC.
In 2001 Prestigiacomo transferred to the Luther Luckett Correctional Complex in LaGrange as a Correctional Sergeant. A year later he was promoted to Lieutenant and assigned to Internal Affairs. In 2004 he was promoted to Administrative Specialist III at KSR and assumed the duties of Accreditation Manager, Public Information Officer and Litigation Coordinator. In 2005 Prestigiacomo was given the duty of coordinating the smoking cessation programs for inmates and staff. As a result the Reformatory became the first tobacco-free prison in the state. In June 2006 he was promoted again, this time to the position of Unit Administrator at the Reformatory.
An 21-year veteran of the Department, Prestigiacomo is a 2004 and 2010 Achievement Award recipient for DOC. He is a member of the American Correctional Association, Correctional Accreditation Managers Association, Kentucky Council on Crime & Delinquency and the Correctional Peace Officers Foundation. He has attended the University of Kentucky and University of Louisville.