​Chisholm began his career as a correctional officer in 2004 at the Kentucky State Reformatory (KSR) where he promoted through the ranks. In 2014 he joined the security team at RCC and was promoted to his most recent position of major. His previous roles include supervising offender housing units as part of the unit management concept and as a captain, managing shifts of up to 180 security staff. He has served as assistant commander of CERT and as the regional CERT commander for RCC, KSR, Luther Luckett Correctional Complex, and Kentucky Correctional Institution for Women.

A graduate of the 2015 Commissioner's Executive Leadership Program, Chisholm is also a recipient of the 2014 Achievement Award for RCC. He has served as a train the trainer and instructor in several areas including cell entry, room clearing, less than lethal weapons, Tasers, firearms, and pepper ball.