His first foray into the world of professional entertainment was as an Assistant Director on the set of "Frankenstein General Hospital," about a mad doctor who builds a new body from parts he confiscates from his job at a morgue. Following this dark tale, Grossman worked as a first assistant director on a number of TV movies, TV series and feature films, including "Where's Marlow," "Chinatown Connection," and "Vengeance Unlimited." In 1995 he took on his first ever director role, when he helmed two episodes of the series "Earth 2." The show was short lived, but Grossman's career as a television director was just taking off. He followed the episodes of "Earth 2" with three episodes of "Manhattan, AZ" and 11 episodes of "The Invisible Man," a spinoff of the highly successful movie starring Nicolas Cage. Grossman also directed a number of episodes of the HBO series Arli$$. He worked on the show from 1998 to 2002. In 2001 he began to take on work on a variety of network shows that were geared towards an adolescent audience. Many of the shows Grossman worked on had a focus on the supernatural, including "Angel," "Charmed," and "Buffy the Vampire Slayer," among others.