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Bill Whitehead has a diverse work experience that spans several companies and roles. Bill started their career in 1999 as an Art Director at Apex Publishing Ltd. Bill then joined The Co-operators as a Senior Designer in 2006 before becoming a Partner at Billion Ideas, a role they still hold. In 2007, they transitioned to Blue North Strategies, where they initially served as a Design Lead before becoming Design Lead and Studio Manager. In 2017, Bill took on the role of Partner at Heartwood Farm & Cidery, a small-batch craft cidery focused on regenerative farming practices.

Bill Whitehead's education history includes attending the University of Guelph, although specific details about the degree and field of study are not provided. In addition to their university education, they have obtained certifications in "Planning a Career in User Experience," "UX Design: 1 Overview," and "UX Design: 2 Analyzing User Data" from LinkedIn in the year 2021.