Willy comes to Willwork from an accomplished career in secondary teaching and sports coaching. At Oliver Ames High School in North Easton, MA, he taught history and coached for 39 years. He also served a stint during this period as a negotiator for the teachers' union. Willy was so successful as a basketball coach that in 2001 he was elected to the Massachusetts Basketball Coaches Association Hall of Fame.

Willy holds a bachelor's degree in liberal arts from Stonehill College and a master's in education degree from Bridgewater State College.