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Courtney Files has held a variety of roles in the sports and entertainment industry since 2003. In 2021, they began their current role as Business Development Manager at VBO Tickets. From 2016 to 2021, they were Operations & Dispatch Manager at Universal Limousine and Transportation Co. Inc., where they managed the Operations Department, organized schedules, approved timecards, and updated standard operating procedures. From 2007 to 2016, they were Senior Project Management Consultant at ABI Inc., providing senior level consulting and project management services to sports and entertainment venues. From 2004 to 2007, they were Manager of Event Operations & Guest Services at the Kansas City Royals, where they assisted with the planning, coordination, and physical presence at all games and events held at Kauffman Stadium. Courtney also developed and implemented an Employee Incentive Program. From 2003 to 2004, they were Special Events Assistant at WIN for KC / Kansas City Sports Commission & Foundation.

Courtney Files obtained a Master's degree in Sports Administration & Exercise Science from the University of Central Missouri in 2004. Courtney also obtained two Bachelor's degrees from the University of Central Missouri in 2002, one in Parks, Recreation and Leisure Studies and the other in Tourism and Travel Services Management.