Rear Adm. Shepherd is a native of Cleveland, and graduated from the University of Cincinnati in 1983, earning a Bachelor of Science degree in Business Administration, with a major in Marketing. He also earned a Master of Science degree in National Resource Strategy from the Industrial College of Armed Forces in 2006. Shepherd was commissioned an ensign in June 1984 and earned his naval flight officer wings July 1985.

Shepherd’s operational command tours include: Fleet Air Reconnaissance (VQ-3), the Navy’s largest aviation squadron. His major command was Strategic Communications Wing One and Task Force 124. He was the first black officer to command a "Take Charge and Move Out" (TACAMO) squadron and air wing.

His operational tours include: Patrol Special Projects Unit Two/VPU-2 (avionics division officer); Fleet Air Reconnaissance 3/VQ-3 (Naval Air Training and Operating Procedures Standardization (NATOPS), flight officer, and maintenance officer); and, CTF 70/75/CARGRU 5 (N6/IWC), Yokosuka, Japan, aboard USS Kitty Hawk (CV 63).

His shore tours include: Bureau of Naval Personnel/PERS-43 (Initial Assignment and VQ/Force Support detailer); Naval Training Support Unit/NTSU (NATOPS evaluator/instructor); U.S. Strategic Command (TACAMO/ABNCP current ops officer); Office of the Chief of Naval Operations (OPNAV)/N6F (executive assistant); OPNAV N00X (Strategic Alignment branch head); and, senior military assistant to the secretary of the Navy.

Shepherd’s decorations include: the Distinguished Service Medal, the Legion of Merit (2 awards), Defense Meritorious Service Medal, Navy and Marine Corp Meritorious Service Medal (2 awards), Navy and Marine Corps Commendation Medal (3 awards), Joint Achievement Medal, Navy and Marine Corps Achievement Medal (2 awards), Global War on Terrorism Service Medal, and other unit and service awards.

He is currently assigned to the Joint Staff as Director Manpower and Personnel/J1.