Jackson began his active duty naval service in 1995 at Naval Medical Center Portsmouth, where he completed his internship in Transitional Medicine. After completing his internship at a Transitional residency program in 1996, he went on to become the honor graduate of the Navy’s Undersea Medical Officer Program in Groton, Connecticut. Qualified in Submarine and Hyperbaric Medicine, his subsequent operational assignments included: instructor at the Naval Diving and Salvage Training Center in Panama City, Florida; det. officer in charge and diving medical officer at Explosive Ordnance Disposal Mobile Unit 8 in Sigonella, Italy; and diving safety officer at the Naval Safety Center in Norfolk.