In November 2008 he took the plunge and moved to Toronto where he found himself immersed in improv and dance workshops, and had the amazing experience of taking the 2010 ITC Improv Summer Intensive. He has also trained with The National Theatre Of The World, Second City, PROJECTproject, and Ghost Jail Theatre of Toronto; as well as Matt Hovde of Second City Chicago; Bill Arnett, Aaron Merke, Jet Eveleth, and Paul Brittain of iO Theatre; Taz Vanrassel of Vancouver's The Sunday Service; and Austin, Texas superstars, Parallelogramophonograph.

Oliver has been a member of Ghost Jail Theatre, Improv At Global Village, The Mistress' Boyfriend at the 2011 Toronto Fringe Festival, the ITC sketch team Kobayashi Maru, and Incubator team Panzer. He is currently a part of the ITC Harold team Red Scare, and performs with the cast of Bye Bye Liver: The Toronto Drinking Play every Saturday night.