Major Jackson began his career with the Hillsborough County Sheriff's Office in 2006 as a patrol deputy.
In 2009, Major Jackson transferred to the Special Investigations Division and was later promoted to the rank of Detective. In 2014, Major Jackson was promoted to the rank of Corporal and was assigned to District I Street Crimes. After one year, Major Jackson transferred back to the Special Investigations Division, where he supervised detectives in the Selective Operations Section. In 2017, Major Jackson was promoted to the rank of Sergeant and was assigned to Patrol District V. In 2020, Major Jackson was promoted to the rank of Lieutenant and was assigned to Patrol District I. In 2021, Major Jackson was promoted to the rank of Captain and remained in District I as the Deputy Division Commander. In 2022, he was promoted to the rank of Major and remains in District I as the District Commander.
Major Jackson is a native Floridian born and raised in Polk County. He received his Master's Degree in Business Administration from St. Leo University.