​Kessinger began his career with the Kentucky Department of Corrections in 1998 at Luther Luckett Correctional Complex (LLCC). He left DOC in 2001 and returned to the agency in 2005 at the Kentucky State Reformatory (KSR). He became a member of the Corrections Emergency Response Team (CERT) in 1999 and served with them through 2012. He has held the positions of correctional officer, sergeant, lieutenant, captain, unit administrator, and fire and safety administrator. Kessinger has overseen both general population and special management units for security and programs.

A graduate from the University of the Cumberlands, Kessinger earned degrees in both criminal justice and ministry. He also has earned the certification of Occupational Health and Safety Specialist from Eastern Kentucky University and recently received his trainer certification in emergency management from Texas A&M University.