Pressman was born in Los Angeles in 1955 and obtained an undergraduate degree in political science from the University of California at Berkeley.

[1] He has two adult children and lived in San Francisco with his wife, writer and former book publishing executive Liz Perle,[1][2] who died in August 2015.

Pressman began his filmmaking career by producing short videos for the American Conservatory Theater in San Francisco, California.

In 2013, he directed and produced the documentary film 50 Children: The Rescue Mission of Mr. and Mrs. Kraus, which premiered on HBO and tells the story of Gilbert and Eleanor Kraus, a Jewish couple from Philadelphia who traveled to Nazi Germany in 1939 and, with the help of the B'rith Sholom fraternal organization, saved Jewish children in Vienna from likely death in the Holocaust by finding them new homes in Philadelphia.

In 2020, Pressman directed and produced the documentary film Holy Silence, which tells the story of the Vatican's actions, and inactions, during the Holocaust and in the years leading up to it.