In June 1997, Skipper became senior vice president and general manager of ESPN the Magazine. Since October 2005, he has served as executive vice president of content.
Skipper attended Lexington High School in Lexington, North Carolina. He then attended UNC-Chapel Hill and earned a bachelor's degree in English literature. After receiving his master's degree in the same field from Columbia University, he went to work for Rolling Stone, starting as a secretary but moving up. He also worked for Us and Spin before becoming senior vice president of Disney Publishing Group.