In 2008, Sampson appeared in two episodes of the ABC Family series Greek and followed that up with an episode of CSI: Crime Scene Investigation in 2010. In July 2013, Sampson booked the recurring role of Jesse in the fifth season of The CW series, The Vampire Diaries. In January 2014, Sampson was cast in the role of Dean Iverson in the Fox miniseries, Gracepoint. In early 2015, Sampson shot the pilot for a potential ABC series called The Kingmakers but the series wasn't picked up. In July 2015, Sampson booked the recurring role of Caleb Hapstall in season 2 of ABC's prime time legal drama, How to Get Away with Murder, produced by Shonda Rhimes. Sampson has also started his own production company called Sampson Studios.
