Derek, a Chicago native, is a product of that city's improv scene. As a child he was trained under the Piven Theatre Workshop and Interlochen Arts Camp. He attended Indiana University where he co-founded improv troupe Full Frontal Comedy while taking classes at Second City and iO (formerly Improv Olympic.) Derek has been a mainstay of the L.A. improv community - performing and teaching for over 15 years. He still performs at i.O. West with Opening Night: The Improvised Musical! in over 650 performances.

In 2008 after touring with Second City at Sea, Derek landed the series "The Hills: According to Me" for MTV (where he played over 20 roles) and then in 2009 the Comedy Central series, "Sercret Girlfriend" playing the role of Phil and acting as a consulting writer.

2012 saw Derek joining TBS' hour-long comedy "Wedding Band" Derek plays Barry the band's drummer - an instrument he had never played before.