Wolford took over color analyst duties for the world champion Colts in the 2007 season, working alongside longtime Colts voice Bob Lamey. He replaces Ted Marchibroda, who remains on the crew in another role. Wolford was also co-host of The Bob and Will Show, working alongside Bob Valvano on WQKC, an all-sports station in Louisville, until that station changed formats in November 2008.
In 2013, Wolford became the head football coach at his alma mater of St. Xavier High, replacing the retiring Mike Glaser. He remains in this post as of the 2015 season.