Gilpin began his career in corrections in 1974 as a Correctional Officer at Kentucky State Reformatory. He worked there until 1980 when he was promoted to lieutenant and moved to Luther Luckett Correctional Complex. From 1983 to 1991 Gilpin served at Kentucky Correctional Institution for Women and Eastern Kentucky Correctional Complex (EKCC) as a captain. In 1991 he was promoted to Correctional Unit Administrator and remained at EKCC until he retired in January 1997. After retirement, Gilpin returned to work for Corrections Corporation of America where he served as Assistant Warden at Lee Adjustment Center (LAC) from 1997 to 2000. In 2000 he was promoted to Warden and remained at LAC. In 2003 Gilpin moved to the Marion County Jail in Indianapolis where he served as Warden until he retired again in March 2006.
While serving for the Kentucky Department of Corrections, Gilpin was a recipient of the Commissioner’s Outstanding Employee Award.