In the early 1980's Roy was Associate Artistic Director for Carousel Theatre in Vancouver and Western Canada Theatre in Kamloops, B.C. He became the Artistic Director of Touchstone Theatre in 1984, directing many award-winning productions including Whale Riding Weather, Lion in the Streets, When We Were Singing, The Three Penny Opera, and The Number 14. Roy became Artistic Director for Victoria's premier company, The Belfry Theatre, in 1997. There, Roy directed over twenty-five plays including productions of Mary’s Wedding, Homechild, A Perfect Ganesh, and Picasso at the Lapin Agile. In November 2007, Roy began his tenure as Artistic & Executive Director of Montreal's flagship English language company, Centaur Theatre. For Centaur, Roy directed many innovative, challenging, acclaimed productions, several of which were huge box office successes of world premiere productions including The Saint Leonard Chronicles, Schwartz's: The Musical, Last Night at the Gayety and Triplex Nervosa. Roy has directed at the National Arts Centre, The Shaw Festival, Manitoba Theatre Centre, Prairie Theatre Exchange, Alberta Theatre Projects, Axis Theatre, The Arts Club Theatre Company, Carousel Theatre, The Kay Meek Centre, The Globe Theatre, Melbourne, The Kings Theatre, Glasgow, The National Theatre School, UBC, U Vic, and Studio 58.