From 2012 until its ending in 2014, she appeared in Aaron Sorkin's HBO series "The Newsroom" as Maggie Jordan. Pill appeared in "Cooties" starring Elijah Wood. In "Zoom", Pill played Emma, an aspiring comic book artist. She had a part in "Hail, Caesar!" as Eddie Mannix's wife. Pill is attached to star in Sook-Yin Lee's Canadian indie "Octavio is Dead", a role that will chase her late father's ghost in Mexico City. Pill starred in ' as Eva Glatt, Glatt's love interest in first movie "Goon", now married to Glatt. Pill was part of the cast of "The Family" as Willa Warren. In 2016, Pill co-starred with Jessica Chastain in the EuropaCorp thriller "Miss Sloane". In 2017, she joined ', starring as Ivy Mayfair-Richards, one of the main characters of the storyline. In 2018 she played former Vice President Dick Cheney's daughter Mary in the Oscar-nominated film "Vice".