Dean has a degree in TV production from the NZ Broadcasting School. Since 2003 he has written several plays, beginning with Head of the House, winner of the NZ Young Playwrights Competition and Chapman Tripp Theatre Award nominee for Outstanding New Playwright. He has since written Brain Power, The Henchman (Young and Hungry 2007), FootBallistic, Hypnotastic and co-wrote 2009 STAB commission Live at Six, which was remounted at Downstage in 2012 and later toured to several NZ arts festivals.
In 2010 Dean wrote and performed in Giggles Live – a theatre spin-off of a TV show for which he had been post-production director. Other writing projects have included a feature film called Maintain, co-writing the award-winning radio show Out of Bounds Sounds, and writing and directing several short films - many of which were award-winners including 2013's 48HOURS Wellington City winner and Grand National Champion The Sleeping Plot, which also won Dean the Wellington and National Best Director awards.
Dean co-wrote and directed the feature film How To Meet Girls From a Distance, which premiered in the 2012 NZ Film Festival before screening internationally.
In 2014 he wrote and directed Conversations with my Penis which has since been translated into French and produced in Canada.
He produced and directed the film version of Arthur Meek's On the Conditions and Possibilities of Hillary Clinton Taking Me as Her Young Lover (2016).