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Cindy Bailey has a diverse work experience, starting their career at Toyota Motor Manufacturing Canada as an Environmental/Manufacturing Engineer from May 2004 to December 2009. Cindy then pursued an MBA at the Schulich School of Business - York University, graduating in June 2011. Following their graduation, they became a Business Strategy Consultant as part of the Global Leadership Program at Schulich School of Business. In August 2011, they joined CIBC as a Senior Manager in Corporate Environmental Management and later became the Director of Environmental Sustainability in October 2020. Lastly, they joined Purolator Inc. in July 2021, where they currently hold the position of Director and Head of Corporate Sustainability.

Cindy Bailey completed their education with an MBA in Sustainability from the Schulich School of Business - York University in 2011. Prior to that, they pursued a Bachelor of Applied Science (BASc) in Environmental Engineering with Honours Co-op from the University of Waterloo between 1999 and 2004. In addition to their academic qualifications, they obtained various certifications, including Workplace Mental Health Leadership from Queen's University in August 2022, the Emerging Leaders Program from the Global Risk Institute in June 2021, and ISO 14064-1:2018 Greenhouse Gas Inventories & Measuring Carbon Footprint from CSA Group in November 2020.