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Stephen Constantino has a diverse work experience in various companies. Stephen started their career in 1989 as a Senior Accountant at Boyle Leasing Technologies Inc. Stephen then moved up the ranks and served as an Accounting Manager, Controller, and eventually Director of Human Resources at the same company. In 1999, Stephen joined MicroFinancial Inc, where they held roles as Director of Human Resources, Vice President of Human Resources, and Vice President of Human Resources & Administrative Services. In 2015, they joined SJC HR & Benefits as a Senior Consultant. Stephen also worked as a Consultant at EyeGate Pharmaceuticals, Inc. from 2016 to 2018. Currently, they are working at Granite City Electric Supply Co., Inc, where they started as the Human Resources Director in 2018 and was later promoted to Vice President of Human Resources.

Stephen Constantino attended UMass Boston where they studied at the School of Management with concentrations in Accounting and Finance. Stephen also obtained a Real Estate Salesperson License from the MA Academy of Real Estate. In addition, they hold a certification called SPHR, however, no information is provided regarding the institution or the year it was obtained.