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Deb Day has extensive work experience in various roles and industries. Deb is the Founder, CEO, and Chief Strategist of Innovate by Day since 2010. Deb also held the position of Chair on the Program Advisory Committee for Centennial College's Interactive Media Management Program starting in 2017. Before that, they worked as a VP Director and VP at Canadian Accents from 2003 to 2010. Deb was the President of A Totally Mental Enterprise in 2009 and an Executive Producer at Just Comedy and Achilles Media in 2008. Additionally, they served as the President of Le Petit Chaperon Rouge from 2005 to 2008.

Deb Day has incomplete education information available. Deb attended Concordia University, where they pursued a Bachelor of Arts (B.A.) degree in Communication and Media Studies. However, the start and end years of their education are not provided. Additionally, Deb Day's education history includes enrollment at the Canadian Film Centre, but no degree or field of study details are given. Deb also attended Sacred Heart, but again, no specific degree or field of study information is available.