Rupert was in account management at Boase Massimi Pollitt/DDB and McCann Erickson in London before he moved to Canada in 1967. He eventually became Chairman and CEO at DMB&B Canada – a position he held for 16 years. In 1983, Rupert founded NABS Canada, and in 1993 he founded the CASSIES (Effectiveness Awards). More recently, Rupert has spearheaded the Marketing Communications Education Trust (MCET) of which he is Chairman and Trustee, in an effort to raise the $2 million necessary to establish a Chair and Degree in Brand Communication at Wilfrid Laurier University. He was President & CEO of the Institute of Communications and Advertising (1996 – 2006) during which time he conceived and contributed to two books; "Excellence in Brand Communication" and “Vulcans, Earthlings and Marketing ROI”, published winter 2006/2007.
In 2007 Rupert was inducted into the Marketing Hall of Legends. He is included in Canadian Who's Who, where he lists his interests as wine, opera, ice hockey and his lake-side farm in Muskoka. He is married, with a daughter and granddaughter.