Shepherd was a member of the inaugural men's basketball team in 2007-2008 along with head coach Pete Hamilton. He played for four years and was a two-year captain. The WildCats reached the OCAC Championship game in his senior year.
Since graduating in 2011, Shepherd has coached at the high school level. For the past four seasons, he has been the head varsity boys' basketball coach at Jefferson Forest High School. This past season, Shepherd coached his squad to a 25-5 record which was the best in program history. His team made its third state tournament appearance this year, its first back-to-back state tournament appearance, and its first ever semifinal appearance.
Shepherd was named the Region 4D Coach of the Year. In back-to-back seasons, Shepherd had a player voted District and Region Player of the Year as well as first team All-State. That same player committed to play at Division I VMI.
Shepherd has also been an assistant coach at William Byrd and Craig County High School.
Shepherd earned a Bachelor of Arts Degree in Health and Physical Education from Randolph in 2011.
