She has held senior editorial positions at such magazines as Canadian Business, Quest and Toronto Life and has been active in the magazine industry as a volunteer board member of industry organizations, a judge, a consultant and a leader of professional development programs. Cunningham served as a member of the 1993-94 Tasse-O'Callaghan federal task force on magazines and is a freelance book and magazine editor. In 1999 she won the National Magazine Awards' Lifetime Achievement award. Her 2001 master's thesis, entitled "Culture Wars: How Canada Lost the Battle to Protect Its Magazines," explored the federal government's failed attempts to construct cultural measures to foster Canadian magazines.