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Jennifer Healy began their work experience in 1991 as a Management Training Program participant and Branch Manager at Fleet Bank. Jennifer then worked as a Senior Banking Consultant at KPMG from 1995 to 1999. After that, they joined Smith Barney Citigroup as a Financial Consultant, specializing in financial planning and investment advice, until 2001. From 2001 to 2003, they served as the Sales and Marketing Director at NWS Corporation, where they sold telecommunication services to various clients. Jennifer then worked as a Managing Director at CCR LLP from 2003 to 2009. Following that, Jennifer joined Northeastern Banking Services Group as the Managing Director, overseeing projects for financial institutions. Currently, they are employed at COCC, where they started as a Conversion Project Management and Executive Client Services role in 2015. Jennifer then worked as a Conversion Manager - Core and Ancillary Banking Systems before assuming their current position as the Director of Financial Management & Business Intelligence in April 2021.

Jennifer Healy has a Masters in Business from the University of Massachusetts and Western New England University. Prior to that, they attended the University of Massachusetts Amherst from 1986 to 1989, studying Business Administration and Management. Jennifer also attended Longmeadow High School from 1982 to 1986.