Gray was the general manager of the Michigan Unemployment Insurance Project, a nonprofit organization he established to marshal law students to provide representation to jobless workers who are denied unemployment insurance.
His primary areas of focus throughout his legal aid career have been public benefits litigation and advocacy and administrative law. Gray taught and helped establish a legal aid clinical program at the University of Namibia Law School as a Fulbright Scholar in 2008–2009. Before that, he was managing attorney at the Michigan Poverty Law Program, senior attorney at the Sargent Shriver National Center on Poverty Law, managing attorney at Legal Services of Southern Michigan, and staff attorney at Land of Lincoln Legal Assistance.