The professor put him in touch with TSR, and soon after, Sutherland was working for them. Sutherland worked with the "D&D" game's co-inventor, Gary Gygax, as part of a team of illustrators, including Erol Otus, Darlene Pekul, David Trampier, and others. Sutherland also worked as TSR's artistic director, but preferred working on his own illustrations. He worked at TSR until 1997 when the company was in the process of being purchased by Wizards of the Coast and he was not offered further employment.