Shepherd is a litigator who focuses on the defense of complex commercial disputes, including toxic torts, business torts, business and contract disputes, commercial lease and real estate matters, municipal liability, civil rights litigation, labor and employment matters, and personal injury claims. Shepherd serves as national pathology counsel for a major U.S. automaker, managing expert retention for a major U.S. automaker’s asbestos cases and trying mesothelioma cases throughout the United States. As a former deputy commonwealth's attorney for the city of Virginia Beach, Shepherd uses his expertise in Fourth, Fifth and Sixth Amendment issues to defend police officers in wrongful death/excessive force civil rights actions.

Shepherd has tried more than 75 jury trials and hundreds of bench trials. He has appeared in federal and state courts throughout the United States and has argued appeals before the Supreme Court of Virginia.