[10] In 2008, Wolk landed his first starring television role in Hallmark Hall of Fame's drama film Front of the Class, as Brad Cohen.

In 2010, Wolk was cast as the lead in the Fox drama series Lone Star, as Robert "Bob" Allen, a Texas con man married to the daughter of one of his targets while simultaneously maintaining a relationship in another town.

Wolk played the recurring role of Grant in three episodes of the ABC comedy series Happy Endings, beginning with the first installment on February 8, 2012.

[17] In 2013, Wolk joined the sixth-season cast of the AMC period drama series Mad Men, playing mysterious junior account man Bob Benson.

In the 2013–14 television season, Wolk was part of the cast of the CBS sitcom The Crazy Ones, starring Robin Williams and Sarah Michelle Gellar.

In November 2014, Wolk was cast as the lead in the CBS drama thriller series Zoo, based on the novel by James Patterson and Michael Ledwidge.

[21] He also starred as Philip in the independent comedy film This Is Happening, which focuses on an estranged brother and sister who go on a road trip to find their runaway grandmother.