Derek Sifton has had a long and successful career with various companies. Derek started in 1985 as the President of Million Air Toronto. In 1989, they became the Vice-President of Armadale Company Limited. In 1990, they took on the role of Vice-President at Highland Chevrolet Cadillac Limited. In 1999, they became the Vice-President of Canadian Flight Academy, a position they held until 2016.
Derek Sifton attended St. Andrew's College from 1979 to 1985, where they obtained their high school degree. Derek went on to pursue a Bachelor's degree in Psychology at the University of Virginia from 1985 to 1989.
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