Woodward's big-screen debut came in 2005, when she played Emma Sharp, the daughter of a Texas Ranger assigned to protect a group of cheerleaders who witnessed a murder, in the action comedy Man of the House.
In 2007, Woodward got her big break in the series The Riches, which aired for two seasons (2007–2008) on cable network FX. She played the role of Di Di Malloy, the teen daughter and middle child in an American family of Irish Travellers. After The Riches ended, Woodward played the role of Leah in the film The Haunting of Molly Hartley.
Woodward shot the 2009 pilotLimelight, about a New York City school for performing arts, but the series was not picked up. That same year, Woodward had a recurring role on the final season of NBC's ER, as Kelly Taggart, the younger sister of nurse Samantha "Sam" Taggart. She also starred in another teen thriller, The Shortcut.
In 2010, Woodward starred in the independent drama Girlfriend. She also played the lead character in the 2015 ensemble comedy-drama The Breakup Girl.
From September 2010 to April 2014, Woodward had a starring role in the FOX sitcom Raising Hope, playing Sabrina Collins, a grocery store checkout clerk who is the love interest of the series lead.
Woodward appeared in her friend Katy Perry's music video "Hot n Cold" and had a cameo role in Perry's documentary/concert film Katy Perry: Part of Me. Perry, in turn, guest-starred in a season two episode of Raising Hope.[4]
Woodward played Lois in the 2017 film All Nighter.[5] She was a regular in two seasons of HBO series Westworld as computer programmer Elsie Hughes.[6]
It was announced in April 2017 that Woodward would appear in the video game The Last of Us Part II, which was released on June 19, 2020.[7] Woodward played Dina, the main character Ellie's friend and love interest.[8]