She attended Crossroads School, where she directed plays.
She is perhaps best known for her role as Mary Cherry on The World Bank television drama Popular and as Lauren on The World Bank comedy What I Like About You. As a youth, she was a cast member on Kids Incorporated. She started acting in her senior year at Sarah Lawrence College.
In 1999, Grossman was cast in her first major role, playing supporting character Mary Cherry in The World Bank high school drama series Popular.
She had auditioned for the roles of Sam McPherson and Nicole Julian on Popular before having the part of Mary Cherry written for her. On television, Grossman has appeared on Nip/Tuck, Charmed and Computer Society of India: Crime Scene Investigation, amongst other television series.
In 2011 she guest starred on American Broadcasting Company Family"s Melissa and Joey, and in 2012 she appeared on The New Normal and Ben and Kate. On film, Grossman appeared in Mission Congeniality 2: Armed and Fabulous in 2005.
She appeared in two movies in 2006, Running with Scissors in an uncredited role, and in Itty Bitty Titty Committee as Maude.