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Cailey Asher has a diverse work experience spanning different industries and roles. In 2007, they worked as a Client Development Manager at RM Auctions. From 2008 to 2010, they served as a Business Analyst at Rudson Valuation Group Inc. Starting in 2010, Cailey joined Vision Critical as a Director of Business Development, where they worked until 2016. During their time at Maru/Blue, they held two positions: Director of Strategy and Development, Market Communities from April 2016 to September 2018, and Vice President of Strategy and Development from May 2018 to September 2018. In 2018, they became the Senior Vice President of Strategy and Development at Angus Reid Global. Lastly, from July 2019 to April 2020, they worked as the Vice President of Strategy & Partnerships at Rival Technologies.

Cailey Asher attended Wilfrid Laurier University from 2002 to 2006, where they pursued a degree in Business. Cailey'sfield of study during this time was also Business. In 2006, they briefly attended HKUST Business School, though the degree name and field of study for this program are not provided.