Shepherd was commissioned as an
ensign in the
United States Navy in June 1984 and earned his
Naval Flight Officer wings in July 1985. Shepherd's operational command tours include
Fleet Air Reconnaissance Squadron 3 (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 (VPU) 2 (Avionics Division Officer), VQ-3 (Naval Air Training and Operating Procedures (NATOPS), flight officer and maintenance officer), and Commander Task Force 70/75/
Carrier Strike Group 5 (N6/IWC), Yokosuka, Japan, aboard . 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), and Office of the Chief of Naval Operations (OPNAV)/N6F (executive assistant), OPNAV N00X (strategic alignment branch head), senior military assistant to the secretary of the Navy, and director, Manpower and Personnel, J1,
Joint Staff. Shepherd retired from the United States Navy with 32 years of service in August 2016. == Post-military career ==