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Winston Mok has a diverse work experience spanning various roles and industries. Starting in 2001, they worked at BlackBerry, first as an Engineering Associate in Manufacturing, then as a Manager in Test Integration, and later as a Team Lead in Software Development & Integration. In 2008, they co-founded Simply Good Technologies, where they served as the CEO and co-founder for seven years. During their time at Simply Good Technologies, Winston focused on developing Offer Management Solutions to simplify promotion distribution and redemption. In 2012, they participated in the Techstars startup program as a co-founder. Winston served as the CEO of Level One Analytics from 2013 to 2015, leading the company in providing actionable analytics to brick and mortar businesses. Notable clients included Canadian Tire, Hudson Bay Company, Sears, Indigo, and General Motors. From 2015 to 2021, they worked at Google as a Senior Product Manager. Currently, Winston is the Founder and Product Lead at Woosh Air, a position they have held since March 2020.

Winston Mok has not specified the start or end years for their education at the University of Waterloo. Winston pursued a degree in Engineering with a focus on Computer & Mechatronics. Additionally, they obtained a Project Management Professional (PMP) certification from PMI. Hence, their education background consists of a degree in Engineering and a PMP certification.