[7] In 2006, Wein co-wrote and directed Unlocked, a short psychological drama starring Olivia Thirlby executive produced by Stephen Daldry.

[7] Wein's debut feature-length film was Sex Positive, a documentary about gay hustler and AIDS activist Richard Berkowitz.

[citation needed] Wein's first feature-length narrative film was Breaking Upwards (2009),[8] starring Zoe Lister-Jones, Julie White, Peter Friedman, Olivia Thirlby and Andrea Martin.

[13] Distributed by Fox Searchlight Pictures, Lola Versus opened in theaters during the summer of 2012; It stars Greta Gerwig, Zoe Lister-Jones, Bill Pullman, Hamish Linklater, Debra Winger, Joel Kinnaman, and Ebon Moss-Bachrach.

Wein's feature Blueprint (2017), developed with, co-written by and starring Jerod Haynes, chronicles the crisis of a young African American living in South Side of Chicago whose best friend is killed in a police shooting.

Wein executive produced Band Aid, written and directed by Zoe Lister-Jones, which premiered at the 2017 Sundance Film Festival.

[19] Wein co-directed, co-produced, co-wrote, and co-DP'd the film How It Ends, which premiered at the 2021 Sundance Film Festival and stars Zoe Lister-Jones, Cailee Spaeny, Nick Kroll, Olivia Wilde, Helen Hunt, Lamorne Morris, Fred Armisen, Bradley Whitford, Charlie Day, and Whitney Cummings.