Captain Bennett has been employed with the Denton County Sheriff's Office since March of 1999. Captain Bennett was promoted through the detention ranks and, in 2021, was promoted to the position of Captain and assigned to the support division. During his tenure with the Sheriff's Office, Captain Bennett has been assigned to Main Jail, Pre-Trial, and Quartermaster positions.
Captain Bennett was chosen to attend the Denton County Sheriff's Academy in 2008. While in the academy, Captain Bennett was selected by his peers to serve as class president. In addition, Captain Bennett was class valedictorian and a top shooter.
Captain Bennett holds a Master Jailer's license and an Advanced Peace Officer's License and is a member of the Texas Jailers Association.