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Jason Dille has a diverse work experience spanning several industries. Jason started their career as a Team Mascot for the Washington Wild Things in 2003 and continued in that role until 2008. Jason then transitioned to a Supervisor of Online Investment position at MARC USA from 2007 to 2009. In 2010, they returned to MARC USA as a Manager of Online Investment and later became an Associate Media Director, Interactive from 2012 to 2013. Concurrently, in 2017, they took on the role of President at the Media Association of Pittsburgh for a year. Currently, they are the Chief Media Officer at Chemistry, a position they have held since 2023. Jason had also previously served as the Executive Vice President, Media from 2019 onwards at the same company.

Jason Dille earned their Bachelor's degree in Advertising and Business Administration from West Virginia University, where they attended from 2000 to 2004.