Following her graduation from Boalt Hall, the law school of the University of California at Berkeley, Dorothy Robinson spent three years at Hughes Hubbard in New York before being handpicked in 1978 by Jose Cabranes (now a federal appeals court judge) to assist him following his appointment to the newly-created position of Yale's General Counsel. Robinson rose through the ranks of Yale's legal department to herself gain the top position in 1987. During her tenure at Yale, she has handled numerous nationally-reported disputes, including a federal investigation into universities' ability to standardize financial aid evaluations, and the 2000 "Yale Four" case brought by orthodox Jewish students challenging Yale's on-campus living policy, as well as negotiated groundbreaking research collaborations between Yale University and leading universities China. Robinson serves as an active liaison between Yale and Washington, D.C. in an ongoing quest to explain and explore appropriate limits on governmental regulation of education. She writes a regular column on legal issues for the Association of Governing Boards' magazine Trusteeship.

In 1987, Yale elevated its general counsel to one of six officer positions, making Robinson only the second female officer in Yale's history. In 1996, Yale President Richard Levin named Robinson a Vice President of the University as well.