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Olivia Truby has a comprehensive work experience history. Olivia started their career as an intern at ESPN Madison and later interned at Badger Sports Properties and Cramer-Krasselt. Olivia then became a New Student Leader at the Center for the First-Year Experience. Olivia also worked as a Circulation Desk Assistant at the University of Wisconsin-Madison Law Library. Additionally, they served as the President and Secretary of the UW-Madison Sports Business Club, where they organized events and coordinated trips. Olivia joined the Big Ten Conference as a Bob Hammel Communications Intern before moving on to the Miami Dolphins & Sun Life Stadium as a Communications Coordinator for the Dolphins Cancer Challenge. Their most recent work experience has been with the United States Olympic & Paralympic Committee, where they held various roles such as Associate Director of Olympic Communications and Manager of Media Relations. Overall, Olivia Truby has gained valuable experience in sports communication and event coordination throughout their career.

Olivia Truby pursued their Bachelor of Art degree in Journalism and Mass Communication at the University of Wisconsin-Madison from 2009 to 2013.