In 2008, Woll landed her breakout role as Bill Compton's vampire progeny, Jessica Hamby, in the HBO fantasy drama series True Blood. She originally joined as a recurring character in the first season, but was promoted to a regular cast member for the second season onwards. In 2009, she and her True Blood co-stars won the Satellite Award for Best Cast – Television Series at the 14th annual ceremony. Woll maintained the role of Jessica until the series' ending in 2014. 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.