​Jesse Stack began his career with DOC in 2004 as a correctional officer at the Kentucky State Reformatory (KSR). In 2005 he was promoted to classification and treatment officer and in 2007 was again promoted to corrections unit administrator. 

In 2009 Stack transferred to Luther Luckett Correctional Complex (LLCC), where he initially worked in the pre-release office. In 2010, Stack was promoted to corrections unit administrator II where he managed an honor dorm, the substance abuse program and inmate orientation. Stack also served as the public information officer for LLCC and as an instructor for the “I-LEAD" regional leadership program. 

In 2014 he promoted to deputy warden at LLCC and oversaw programs, operations, and security. In 2018, he became the deputy warden in charge of security at KSR and then acting warden in 2022 for four months, handling all responsibilities and job duties of the warden position. 

A 2003 graduate of Eastern Kentucky University, Stack is also a graduate of the Commissioner's Executive Leadership Program.