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Greg Osborn has a diverse work experience, beginning in 2008 with the Philadelphia Flyers as a Sales Associate and Marketing Intern. In 2010, they took a Secondary Education Teacher role with the Bristol Township School District. In 2012, they began working with CURE Auto Insurance (Citizens United Reciprocal Exchange) as a Claims Trainee, eventually progressing to a PIP Supervisor, Business Analyst, Claims Operations Assistant Manager, Claims Director/Operations Manager, and AVP, Claims Operations.

Greg Osborn received their Bachelor of Arts in History from Millersville University of Pennsylvania from 2004 to 2008. Greg then went on to pursue a Master of Science in Sport Management from West Virginia University from 2008 to 2009. Finally, they obtained a Master of Arts in Secondary Education and Teaching from Saint Joseph's University from 2010 to 2011.