Williamson began his scouting career as the Assistant Recruiting Coordinator at the University of Pittsburgh. During his three years at Pitt, he helped bring in such players as Larry Fitzgerald, Joe Flacco and Darrelle Revis. Williamson then moved on to become the Director of Football Operations at the University of Akron. After a short stint there, he became a pro and college scout for the Cleveland Browns. Williamson then spent 10 seasons working for ESPN as an NFL analyst, working in very many capacities during that time. Since then, Williamson worked for many media outlets, hosts the Locked the NFL Podcast and has finally found a home with ClaytonFootball.