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Tim Bailey has held various roles across multiple companies since 1993. Tim began their career as the General Manager of Nasco Canada in 1993. In 2000, they became a Sales Representative for Remax Twin City Realty Inc. Brokerage. In 2003, they worked as an Account Manager for Great Northern Insulation Inc. In 2004, they were an Administrator/Vice President for Stonecroft Homes/Schout Communities. Since 2009, they have been the Chief Strategy Officer (CSO) Avid Ratings & HomeKeep and Division President-Canada for Avid Ratings, a customer experience technology company for the homebuilding industry.

Tim Bailey completed a B.Sc. in Chemistry/Biology at Wilfrid Laurier University from 1987 to 1990. Prior to that, they attended Waterloo Oxford District Secondary School from 1982 to 1987.