 After graduating from Clare College, Cambridge, with a double first-class honours in Social and Political Sciences and an M.Phil from the Cambridge Institute of Criminology, Diamond was elected as the National Chair of Labour Students from May 1998 - April 1999.While attending Cambridge University, Diamond was Chair of the Cambridge University Labour Club during the 1997 general election.Following a brief stint at Finsbury Financial Communications and the Institute for Public Policy Research, Diamond was appointed as Director of the Labour Party organization and magazine Progress.