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Winston Lee has extensive work experience in the gaming and technology industry. Winston began their career in 2000 as a Game Designer at Cryptologic and then held various roles at different companies, including Ockham's Razor Inc., BMO Financial Group, IP Devco Inc., Henderson Bas, Foote Cone and Belding, MapFusion Corp., and Cyberview Technology. In 2009, they joined Barcrest Games as a Senior Flash Game Developer before becoming the Technical Director at Push Gaming in 2011. Winston currently holds the position of Chief Operating Officer at Push Gaming. Throughout their career, Winston has displayed expertise in game development, application development, flash development, and team leadership.

Winston Lee attended the University of Toronto - University of St. Michael's College from 1996 to 2000, where they earned a Bachelor of Arts degree. Their areas of study were Economics and Computer Science.