Sterritt began his career at Boston After Dark (now the Boston Phoenix), where he was Chief Editor. He then moved to The Christian Science Monitor, where he worked as the newspaper's Film Critic and Special Correspondent. During his tenure at the Monitor, Dr. Sterritt held a number of additional appointments. From 1978-1980 he was the Film Critic for All Things Considered, on National Public Radio. From 1969 to 1973, he was the Boston Theater Critic for Variety, and sat on the selection committee for the New York Film Festival from 1988 to 1992. Between 1994 and 2002 he was Senior Critic at the National Critics Institute of the Eugene O'Neill Theater Center, and he served as the video critic for Islands magazine from 2000-2003. From 2005-2007 he was Programming Associate at the Makor/Steinhardt Center of the 92nd Street Y. He is a member of the National Editorial Advisory Group of Tikkun, sits on the Editorial Board of Quarterly Review of Film and Video, is a Contributing Writer to MovieMaker magazine, and the Chief Book Critic for Film Quarterly.Sterritt has also held a number of significant academic appointments. From 1999-2005 he was the Co-Chair, with William Luhr, of the Columbia University Seminar on Cinema and Interdisciplinary Interpretation. He is currently on the Film Studies Faculty at Columbia University's Graduate Film Division, and Adjunct Faculty at the Maryland Institute College of Art in the Department of Language, Literature and Culture and the Department of Art History. He is also Distinguished Visiting Faculty in the Goldring Arts Journalism Program at the S.I. Newhouse School of Public Communications at Syracuse University, and Professor Emeritus of Theater and Film at Long Island University, where he taught from 1993 to 2005, obtaining tenure in 1998.

Sterritt is the partner of psychoanalyst, author and cultural critic Mikita Brottman.