Derek was a drama major at Cawthra Park High School in Mississauga ON., a school specializing in visual and performing arts. He studied theater at University of Windsor and Humber College. He has performed on various Toronto stages over the last decade, most notably as Father Flynn in John Patrick Shanley's Doubt: A Parable, as Victor in Noel Coward's Private Lives, as Louie in Neil Simon's Lost in Yonkers, as Comte de Guiche in Edmond Rostand's Cyrano de Bergerac, as Jean-François Millet/Daisy Tillou in Mark Twain's Is He Dead, as Stuart in Christopher Durang's Beyond Therapy, and as Don Carlos Homenides De Histangua in Georges Feydeau's A Flea in Her Ear.

He most recently completed filming his first role in a major motion picture as Psych Patient in David Ayer's Suicide Squad, to be released in the summer of 2016.

He has also starred in web series Bike Cop: Begins (2013) and American Pussy (2015) as well as the TV series Reign (2013).