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Simon Cheng's work experience begins in 2004 when they worked as a Retail Sales Consultant at Fido Solutions until 2009. In 2007, they had a role as an Environment Support & Systems Administration at IBM, which ended in 2008. Simon then joined lululemon in 2009, starting as a Technology Support Specialist and progressing to roles such as Technical Support - Lead, Applications Specialist, Senior Technical Specialist, and Manager, Corporate Technology. From 2017 to 2019, they served as the Manager of Technical Configuration Management at lululemon. Simon Cheng worked at Aritzia from 2019 to 2023, initially as a Senior Manager of Retail Technology Engineering + Support, and later as the Director of Retail Technology. Currently, they are the Senior Director of Retail Information Systems at Arc'teryx Equipment since 2023.

Simon Cheng attended Simon Fraser University from 2004 to 2009, where they pursued a Bachelor of Business Administration degree. Their degree had a joint major in Computing Science and Information Systems in Business Administration. In addition to their formal education, Simon also obtained the ITIL® Foundation Certificate in IT Service Management from PeopleCert in May 2018.