In November 2008 he took the plunge and moved to Toronto where he found himself immersed in the city's vibrant improv community, 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, Jane Spidell, 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; Christian Capozzoli of UCB and New York's Magnet 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, Bye Bye Liver: The Toronto Drinking Play, the ITC sketch team Kobayashi Maru, Incubator teams Panzer, The Watchers, and Mom Jeans, and Harold team Red Scare. He is currently a part of the ITC Harold team Delorean, the fast-paced ideaprov of OUI!, and can be found regularly doing Comedy At The Swan at Black Swan Tavern on the Danforth.