CSM Shepherd entered military service at Fort Jackson, South Carolina, in April 1960, and attended Advanced Individual Training at Fort Knox, Kentucky. His subsequent military education included graduating from the Primary Leadership Development Course, Basic and Advanced Noncommissioned Officer Course, and the Sergeants Major Academy.

Command Sergeant Major Shepherd held a wide variety of key logistical command and staff positions during his distinguished career, to include: Command Sergeant Major, 260^th Quartermaster Battalion, 24^th Infantry Division, Hunter Army Airfield and in support of Operation Desert Storm; Command Sergeant Major, 262d Quartermaster Battalion, Fort Lee, Virginia; Sergeant Major, Area 2 and 25^th Transportation, Republic of Korea; Sergeant Major, Aviation/Transportation School, Fort Eustis, Virginia; First Sergeant, L Company, 262d Quartermaster Battalion, Fort Lee, Virginia; G-4, Division Food Service, 1^st Division, Germany; and NCOIC, Food Service Support, 5^th Brigade, Fort Dix, New Jersey.

His many awards and decorations include the Bronze Star Medal with “V” Device, Meritorious Service Medal (with three Oak Leaf Clusters), Army Commendation Medal (with three Oak Leaf Clusters), Vietnam Campaign Ribbon, Professional Development Ribbon (fourth award), and the Expert Infantry Badge.

In recognition of his unsurpassed service as a senior Quartermaster Noncommissioned Officer, Command Sergeant Major Shepherd was appointed Honorary Sergeant Major of the Quartermaster Regiment from March 1994 until October 1996.