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John Flaherty has a diverse work experience in various industries. Their most recent position is Senior Director of Business Development at Harold Brothers Mechanical Contractors, Inc. Prior to that, they worked as a Real Estate Agent at Olde Towne Real Estate. John also held multiple roles at Boston College High School, including Head Ice Hockey Coach, Director of Major Gifts, Director of Leadership Gifts, Director of Alumni Programs, and Assistant Director of Admissions. Before working at the high school, they had a long tenure as a Coach from 1992 to 2010. John also has experience as a Vice President at Sovereign Bank and as a Probation Officer at the Massachusetts Trial Court. John started their career as a Legal Assistant at Murray & Murray, where they prepared and managed social security disability claims.

John Flaherty attended Boston College High School in 1988 and received their high school diploma. After completing high school, they enrolled at Boston College in the same year and graduated in 1992 with a Bachelor of Arts degree in Political Science. Subsequently, they attended Boston University School of Law from 1992 to 1995 as a Juris Doctor Candidate.