From 2001 to 2002 and 2012-2013, Healey served as the Republican National Committeewoman for the state of Massachusetts. Healey currently serves on the boards of public companies, universities, cultural organizations and the Forward Party. She was the inaugural president of the Milken Institute's Center for Advancing the American Dream in Washington, DC, 2019-2022. She served as a special advisor for Mitt Romney's Presidential Campaign in 2012. She then served as the president of Babson College for six years, retiring in 2019. She left the Republican Party on January 7, 2021 and joined the Forward Party in June 2023.