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Stephen Dwyer has an extensive work experience in various roles and companies. Stephen started their career as an Associate at Chadbourne & Parke LLP in 1994, and then moved on to work as an Associate at De Forest & Duer from 1995 to 1998. Following this, they joined Piliero Mazza & Pargament as an Associate from 1998 to 2001. Stephen then served as the Deputy General Counsel at NEW Corp in 2001. In 2002, Stephen joined the American Staffing Association as the Senior Vice President, Chief Legal and Operating Officer. Stephen held this position until the present time. From 2010 to 2013, they also served as the Past President and Member of the Board of Directors at the Washington Metropolitan Area Corporate Counsel Association (WMACCA).

Stephen Dwyer attended Bucknell University from 1986 to 1990, though the specific degree and field of study are unknown. From 1991 to 1994, they attended Boston College Law School and obtained a JD degree.