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Tim Whitehead has a diverse work experience spanning various industries. Tim began their career as a Head Basketball Coach at 3D Basketball in 2009 before taking on roles as an Assistant Coach at The University of British Columbia and Langara College. Tim also worked as a Customer Relations representative at Apple Inc., Investor Relations at Rose Country Management Inc., and as a Purchasing Analyst at lululemon athletica. In 2011, they joined BCLC as a Product Specialist, eventually being promoted to Senior Product Manager, Sportsbook. Tim then moved to Churchill Downs Incorporated as a Senior Product Manager, Sportsbook before taking on the role of Director of Product, Sportsbook at Rush Street Interactive. Currently, Tim is the Head of Sportsbook for Rush Street Interactive, overseeing operations and managing multiple teams.

Tim Whitehead obtained a Bachelor of Human Kinetics degree with a focus on Sport Psychology from The University of British Columbia in the years 2004 to 2009. Tim then pursued a Master of Human Kinetics degree with a specialization in Sports Marketing & Sports Psychology from the same university during the period of 2009 to 2011. Additionally, Whitehead completed the Emerging Leaders program in Leadership Development at the British Columbia Lottery Corporation from 2014 to 2015. Tim also received Level 3 Theory & Technical Certification in basketball from the National Coaching Certification Program in 2009. Whitehead attended Southridge School, but no specific degree or field of study is indicated. In February 2019, they earned a Professional Scrum Product Owner certification from Scrum.org.