Captain Ogletree joined Monroe County Sheriff's Office in 1990 as a detention officer. After working the jail he transferred into the Uniform Patrol Divsion. From there he transferred to the Criminal Investigations Division, specializing in the Narcotics Unit and serving as the S.E.R.T. Commander. In 2018, Lieutenant Ogletree was promoted to Captain of Support Services.

Captain Ogletree is a 2007 graduate of the FBI National Academy.