Crouch began his career with the Department of Corrections in 2000 as a correctional officer at the Kentucky State Reformatory. In 2001, he transferred to Roederer Correctional Complex as a drill instructor for the Boot Camp Program. He went on to promote through the ranks from correctional sergeant all the way to major in 2018 at EKCC. 

During his tenure with the Department of Corrections, Crouch has served as internal affairs captain, administrative captain, PREA compliance manager, CERT member, HNT member, and critical incident manager across various institutions.

Crouch has consistently displayed leadership abilities and was named Supervisor of the 2nd Quarter 2014.