He co-founded Ives-Sillman, Inc. alongside partner Norman Seaton Ives, which published silkscreen prints and photographs in monographic art portfolios.
[2] Additionally he taught at Carnegie Institute of Technology (now known as Carnegie Mellon University) from 1963 to 1965; Rhode Island School of Design (RISD) from 1966 to 1985; and was a professor of art at University of Pennsylvania from 1985 to 1990.
[4] Sillman had many notable students including Bruce Helander,[5] Newton Harrison, Howardena Pindell,[6] as well as others.
Ives-Sillman, Inc. was founded in 1958 by Sillman and his co-worker and fellow professor at Yale University, Norman Seaton Ives.
[8] Other artist published included Walker Evans, Roy Lichtenstein, Piet Mondrian, Ad Reinhardt, Jean Dubuffet, Jacob Lawrence, and Romare Bearden.