The majority of Howe's career was in property management before joining John Madejski in 1995 when he took over as chief executive of Reading F.C. Howe has led the redevelopment of both the club's stadium and its business management, and now Reading F.C. is widely regarded[who?] as one of the best managed clubs in the Football League. Howe is also a non-executive director of a number of other businesses in which John Madejski has invested including the BenhamGoodhead Print Group, Sackville Properties and the Ark Group. He is also a non-executive director of the Clearview Traffic Group.