Jesse Cassaday
Group Head, Enterprise Growth @Staples Canada
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WORK HISTORY
Group Head, Enterprise Growth @Staples Canada
Toronto, ON, CA
Responsible for strategy, planning and execution of Staples Canada’s Services business and three-year growth plan. Focused on driving revenue and customer acquisition growth by identifying, developing, and implementing innovative business strategies that capitalize on emerging market opportunities. Enterprise Growth plays a pivotal role in supporting Staples Canada’s strategic direction, fostering innovation, and ensuring we remain agile in an ever-evolving market landscape.
EDUCATION
University of Toronto - Rotman School of Management
Master of Business Administration (MBA), Business Administration and Management, General
York University
Certificate, Online Advertising and Internet Marketing
ABOUT JESSE CASSADAY
Enterprise growth leader with 15+ years of experience driving revenue, partnerships, and strategic transformation across retail, media, sports, and non-profit sectors. Currently leading the Services business and three-year growth plan at Staples Canada, with a mandate to deliver transformational revenue growth, customer acquisition, and innovative B2B service models. Recognized as a dynamic and empathetic leader who develops top-performing talent, I combine strategic vision with disciplined execution, advancing growth through effective partnerships, operational excellence, and a collaborative approach that builds long-term value.
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