Grimes began his career with the Department of Corrections in 2007 as a correctional officer at RCC. Later that same year, Grimes was promoted to classification treatment officer in the Assessment Center at RCC. In 2011, Grimes was promoted to unit administrator in the assessment center. In this role, he was responsible for coordinating the intake of inmates that were transported in from jails. He also classified male inmates entering the prison system and scheduled their transfers to other state facilities. 

In 2017, Grimes was promoted to program administrator for the Classification Branch at Central Office. He returned to the assessment center at RCC in 2019.

During his career, he has been a firearms instructor, member of the Corrections Emergency Response Team (CERT), and a member of the Hostage Negotiation Team. 

A graduate of Eastern Kentucky University, Grimes has a bachelor's degree in police administration as well as a master's degree in criminal justice. He is a 2014 graduate of the Commissioner's Executive Leadership Program. 

Grimes has been recognized with numerous awards during his career including the Deputy Commissioner's Award in 2009 and 2013. He was also awarded the 2012 RCC Programs Employee of the Year and the 2016 RCC Non-Security Supervisor of the Year.​​