Raymond Maxwell holds an MA from the University of Wisconsin–Milwaukee, a BA from Western Washington University, and a Certificate in Nonprofit Management from the University of Washington. He has also studied at Sacred Heart University, Herzen University, and Harrison Middleton University, and was a recipient of two Fulbright scholarships, several National Endowment for the Humanities summer fellowships, as well as a Civic Education Project Fellow.

Raymond has taught and lectured at Ivane Javakhishvili State University, Yerevan State Brjussov Institute of Foreign Languages, John Cabot University, Hopkins-Nanjing Center for Chinese and American Studies, and numerous others across the world.