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Jonathan Gross has a long history of professional experience, beginning in 2013 when they worked as a Law Clerk at the Law Offices of Scott D. Gross. In 2015, they were an intern at the New Jersey Institute of Technology in the Sports Management program. In 2016, they were an Event Management Intern at the Lincoln Center for the Performing Arts and was also on the Jill Behrman 5K Steering Committee at Indiana University Bloomington. In 2017, they were a Summer Intern at Optimum Sports. In 2018, they worked as a Coordinator for Diageo Brands at MKTG. In 2019, they were a Partnership Sales Associate at FANCHEST, where they built strategic relationships with professional sports teams and leagues, college athletic departments, corporate brands and charitable foundations. Jonathan was also the exclusive merchandise gifting provider at Super Bowls 51-54. In 2020, they began working at StackCommerce, where they held roles as Senior Account Manager, Account Manager, and Account Associate in Publisher Partnerships.

Jonathan Gross attended Indiana University Bloomington from 2014 to 2018, where they studied Sport Marketing and Management. Jonathan also completed the SMWW basketball GM and scouting program.