Since earning a Bachelor's degree in Pharmacology from the University of Leeds, England and a Master's degree in Business Administration from the University of Manchester, Rupert Duchesne served as co-owner of LCB Consultants of London, England, when the international firm Mercer Management Consultants bought his company in 1994 and appointed Rupert a Vice-President.

In 1996, Rupert joined Air Canada as Vice-President, Marketing, and was promoted to Senior Vice-President, International in 1999. During that year, he was appointed Chief Integration Executive, overseeing the integration of Canadian Airlines with Air Canada. Rupert was appointed President of Aeroplan in August 2000.