After serving as an assistant at Wagner College, the United States Merchant Marine Academy, and Boston University, Masella became the first head coach of the Fairfield University football team. He left prior to their first game to return to Boston University, thus was the only coach at Fairfield who never coached a game. Masella coached BU to a 2–20 over two seasons before the university dropped football.
After BU, Masella was an assistant at the University of Connecticut, Louisiana Tech University, and UMass before becoming the head coach at Central Connecticut State University. Masella left Central Connecticut State to become head coach at Fordham. In 2007, his second season at Fordham, he led the Rams to an 8–4 record, the Patriot League championship, and a spot in the NCAA FCS playoffs.
