[4] In 2010, Gross played Katie in Sharon Pollock's 1984 play Doc and directed Tennessee Williams' A Streetcar Named Desire (1947) for the Stella Adler Studio of Acting.

She performed in Williams' 1953 one-act play Talk to Me Like the Rain and Let Me Listen in 2012.

[4][1] Gross was cast in I Used to Be Darker (2013) after meeting its director, Matthew Porterfield, at the after show party for the New York City screening of his previous film, Putty Hill (2010).

[9][10][11] Also in 2014, Gross played the lead role in David Raboy's short film Beach Week.

[12] In 2017, Gross appeared in the Netflix drama Mindhunter, in which she played the role of Debbie Mitford, a post-graduate student at the University of Virginia and the girlfriend of one of the three leads.