Massey began his career in the music industry in 1982 as an artist manager, firstly representing the British new wave group, Wang Chung – who signed with Geffen and enjoyed five US Top 40 singles.
[3] In addition to artist representation, Massey also ran a small independent label and music publishing company called Big World Records.
He also founded and became President of Daylight Records, a Sony imprint and home to such artists as Anastacia, Delta Goodrem, Good Charlotte, The Jonas Brothers, Phantom Planet and Cyndi Lauper.
[5] During his time at Mercury Records, the label released albums by Neon Trees, The Wanted, The Gaslight Anthem, Duffy, Portishead, Parachute, Jessie James, and Taio Cruz.
[6][7] Recent additions to the Island roster include Avicii, American Authors, Bishop Briggs, Nick Jonas, Tove Lo, Shawn Mendes, Elton John, Mike Posner, and Keke Palmer among others.
During Massey's tenure at Island, the label has relaunched the 4th & Broadway imprint to focus on dance music, which includes signings Kiesza, Sam Feldt, and Ansolo.