She played Jessica Hamby in the HBO drama series True Blood (2008–2014), which earned her a nomination for a Screen Actors Guild Award.

In 2008, Woll landed her breakout role as Bill Compton's vampire progeny, Jessica Hamby, in the HBO fantasy drama series True Blood.

At the 16th Screen Actors Guild Awards which took place the year following, she and her co-stars were nominated for Outstanding Performance by an Ensemble in a Drama Series.

[10] In 2009, she made a guest appearance in an episode of Law & Order: Special Victims Unit, portraying a young woman who is found alive after being reported missing by her boyfriend.

[12] In 2011, she starred in the supernatural thriller Little Murder,[13][14] the sports drama Seven Days in Utopia,[15] the action film Catch .44,[16] and the comedy-drama Someday This Pain Will Be Useful to You.

[21] She has portrayed Karen Page in the Marvel Cinematic Universe,[22][23] specifically as the female lead in Daredevil (2015-2018) and as a recurring actor in The Punisher (2017-2019) and The Defenders (2017).

[31][32] In 2022, she performed as Katherine in director Shana Cooper's stage production of The Taming of the Shrew at the Old Globe in San Diego.

[42][43][44][45] Woll starred in the second season of Force Grey: Lost City of Omu (2017), a Dungeons & Dragons (D&D) web series which focused on the Tomb of Annihilation storyline,[46][47][48] and appeared as a guest player in Critical Role's second campaign.

[40][49] Greg Tito, in the book Welcome to Dragon Talk (2022), noted that Woll for a long time was "reluctant to do anything publicly with" Dungeons & Dragons, however, "Force Grey cracked the protective shell she had separating the game from her acting career, and she fully embraced her skills as a storyteller and a Dungeon Master".

[51][52][53] Tito called the show "really magical" and thought it created "something special" with "a brilliant execution blending imagination and TV production".

[58] In 2023, Woll was the author of the D&D adventure module Heroes' Feast: Saving the Children's Menu released digitally on D&D Beyond.