After a career in the field of civil engineering, Caudill joined the Department of Corrections in 2009 in Offender Information Services. In 2010 he was promoted to classification and treatment officer at Blackburn Correctional Complex in Fayette County. He was responsible for conducting orientations for incoming inmates as well as classifying offenders and recommending programs. Cuadill was also the first programs staff member at the prison to be on the K-9 special response team.
In 2011, he transferred to the Division of Probation and Parole as an officer for District 9 in Fayette County. He supervised an offender caseload, prepared pre-sentence investigation reports, and served as the fire/safety officer for the district. In addition, he was a 'Thinking for Change' facilitator, a re-entry officer, and assisted with PORTAL for district 9.
In 2014, Caudill was promoted to the department's Victim Service Branch. As a victim advocate, he responded to daily contacts from victims and traveled the state to conduct training on Kentucky DOC's automated victim notification services. He also assisted with reviewing grants for the state Justice and Public Safety Cabinet.
In January 2015, Caudill was promoted to Public Information Officer in the department's Communications Office. He served as liaison between the department and the news media, prepared press releases and served as the open records coordinator for Central Office. He also helped prepare responses to critical incidents for the commissioner and was assigned special projects by the commissioner.
Caudill is a 2000 graduate of University of Kentucky, where he earned his bachelor's degree in integrated strategic communications. He is a member of the 2014 Commissioner's Executive Leadership Program and has served as a project coach for the program. He is a member of the Southern States Correctional Association (SSCA) and the Kentucky Council on Crime and Delinquency (KCCD) and has served on the KCCD board of directors.