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Jason Shesky has held various roles throughout their work experience. Jason began their career in 2003 as the President of Truck Zone, where they served until 2019. In 2019, they transitioned to the role of Director at Truck Zone until 2020. In 2020, they moved on to become the Managing Director at Umbra Engineering Ltd. Currently, they hold the position of Vice President, Operations at Williams Engineering Canada Inc. starting in 2023.

Jason Shesky completed their education at the University of Alberta. Jason obtained a Master of Business Administration (MBA) degree in 1998. Prior to that, they earned a Bachelor of Science (B.Sc.) degree in Civil Engineering in 1994.