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Hilary McCain has a long and varied work experience. In 2008, they began their career as a Restructuring Intern at Ernst & Young. Hilary then moved on to become a Strategy Analyst at Maple Leaf Foods Inc in 2009. In 2010, they were a Summer Associate at The Boston Consulting Group, and then became an Associate in 2011. In 2014, they took on the role of Corporate Strategy Manager at Chobani. In 2015, they were a Summer Associate at Baird Capital. In 2016, they became President of Riverview Capital Ltd., a company looking to acquire a business from an owner-operator. Most recently, in 2018, they founded and became CEO of Sweet Reason Beverage Co., a hemp CBD-infused sparkling water company. Sweet Reason was acquired by Cann in September 2022, and Hilary McCain is currently the SVP Emerging Products at Cann.

Hilary McCain attended Harvard Business School from 2014 to 2016, where they earned a Master of Business Administration (MBA). Hilary also participated in an International Exchange at Esade. Additionally, they attended Ivey Business School at Western University and earned an Honors of Business Administration in Business Administration and Management.