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Richard Macy has a diverse work experience spanning several companies and roles. Richard has held executive positions such as President and CEO at USAble Life, where they have been working since 2012. Prior to this, they served as CIO and COO at Pension Benefit Guaranty Corporation (PBGC) from 2006 to 2012. Richard also worked at ADP, where they were a Vice President, and at EmployeeLife.com as an Executive Vice President. Richard co-founded WTR Data Services, a benefit administration software provider, which was later purchased by ADP. Richard Macy's expertise lies in leadership, operations, technology solutions, and risk management.

Richard Macy attended St. Albans School (D.C.) from 1974 to 1980. Richard then enrolled at Wesleyan University and obtained a Bachelor of Arts (BA) degree in Math/Computer Science, completing their studies from 1980 to 1984. Later, from 1986 to 1987, Richard went to Columbia Business School, where they earned a Master of Business Administration (MBA) degree with a focus on Production/Operations Management.