​Caudill began her career in 1998 as a correctional officer at the Kentucky State Reformatory, and then transferred to Roederer Correctional Complex (RCC).  In April 2000 she was promoted to classification and treatment officer for the Assessment Center at RCC. In October 2000, Caudill transferred to the Division of Probation and Parole and served as an officer in multiple counties. In September 2005 she went back to RCC managing the minimum-security unit and the 200-bed substance abuse program. In May 2006 she was promoted to unit administrator I at RCC and in September 2007, was promoted to unit administrator II, where she served as the grievance coordinator for the institution and managed the inmate education program. In April 2012 she promoted to program administrator for the Assessment Center at RCC.

In 2015, Caudill was promoted to deputy warden at Blackburn. During her time there, she has overseen programs/operations and security.

Caudill was one of the original master trainers for the department's case management tool and served as an institutional trainer for the offender management system. In November 2014 she earned her certification as an auditor for the Prison Rape Elimination Act (PREA) and she is also certified as an Incident Command Center Section Chief.

An active member of the Kentucky Council on Crime and Delinquency (KCCD), Caudill served as president from 2016-17 and has served on the state board as the membership chair/assistant to the treasurer.

A 1998 graduate of Murray State University, Caudill is also a 2012 graduate of the Commissioner's Executive Leadership Program.​