Holloway began his career as a deputy jailer in Rowan County in 1989. He came to work for the Department of Corrections later that same year as one of the first Correctional Officers hired at EKCC and was promoted to sergeant a year later.
In 1991 Holloway was promoted again, this time to the position of Correctional Lieutenant. He served in this role until 1998 when he was promoted to Captain. He was promoted to Senior Captain in October 2002, and in that role supervises 276 uniform security staff on three shifts.
Holloway is a member of EKCC’s Corrections Emergency Response Team (CERT) and for two years served as the squad commander. He is one of the prison’s Firearms Instructor and he also served as interim deputy warden for security at EKCC from 2003 to 2005 and as a state monitor at the private prisons.