 Massie turned professional in 2009 when he signed with the Harrisburg City Islanders in the USL Second Division.He made his professional debut on 18 April 2009 in Harrisburg's opening day 2-2 tie with the Richmond Kickers, and went on to make 13 appearances for the team before being released at the end of the season.Having been unable to secure a professional contract elsewhere, Massie signed to play with USL Premier Development League expansion franchise GPS Portland Phoenix in 2010; the Phoenix are owned by the same parent company that ran the Cape Cod Crusaders.