In 2009, Cummings was appointed deputy assistant secretary for the Office of Vocational & Adult Education.
Cummings worked for the Goodwill Hinckley School in Fairfield, Maine as president and executive director.
[1][2] On September 2, 2014, University of Maine System Chancellor James H. Page announced Cummings' appointment as interim president of the University of Maine at Augusta, succeeding Allyson Hughes Handley, Ed.D.
[3] On May 21, 2015, Page announced Cummings would become the 13th president of the University of Southern Maine, effective July 1, 2015.
[4] On October 5, 2021, Cummings announced he would be stepping down as president on June 30, 2022.