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Tim Leahy has a diverse work experience spanning various organizations. Tim began their career at United Way of Dutchess County as the Director of Allocations & Agency Relations from February 1995 to November 1997. Tim then worked at The Salvation Army as the Director of Development, Mass Bay from November 1997 to August 1999. Tim joined Community Servings in August 1999 and held two roles simultaneously: Chief Development Officer and Director of Development & Communications. Tim remained at Community Servings until February 2009. In 2007, Tim became a Men's Event Planning Committee Member at Fenway Community Health, a position they held until April 2013. From September 2009 to June 2015, Tim served as a Board Member and Treasurer at AIDS Support Group of Cape Cod.

Tim Leahy attended UMass Boston from 1987 to 1991, where they earned a Bachelor of Arts (B.A.) degree in English & Economics. Prior to that, they attended James Madison University from 1980 to 1981, although it is not specified whether they obtained a degree or studied a specific field at that institution.