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Crosby Janda Bugenhagen has a long and varied work experience. Crosby began their career in 2003 as a Graduate Assistant Athletic Trainer at the University of Louisville Athletics, where they were responsible for the prevention, recognition, treatment and rehabilitation of all athletes on the Women's soccer and Tennis teams. In 2004, they moved to KORT - Kentucky Orthopedic Rehab Team, where they split their time between the outpatient physical therapy clinic in J-Town and as the outreach Athletic Trainer at the Christian Academy of Louisville. Crosby was also responsible for maintaining a corporate relationship with Chevron Texaco providing ergonomic services to the corporate office employees. In 2006, they joined ATI Physical Therapy as an Athletic Trainer, where they were responsible for the prevention, recognition, treatment and rehabilitation of the hockey players, as well as maintaining medical records, communicating with treating physicians, other teams in a trade situation, and scouts from various professional teams with regards to the health of the athletes. In 2011, they joined Ascension Wisconsin/ Midwest Orthopedic Sports Medicine as an Athletic Training Supervisor, Concussion Care Network, and Continuing Education Coordinator. Crosby worked as a supervisor of athletic training for the Milwaukee market and was the lead athletic trainer for the Concussion Care Network of Waukesha and Milwaukee counties. In 2012, they joined Groves WorkReady as a Provider, where they provided industrial ergonomics and early injury intervention to contracted companies in Southern WI. In 2014, they worked as the Operations Director for Paul Bugenhagen Jr for Waukesha County Circuit Court Judge, Branch 10, where they were responsible for scheduling, writing and editing press releases and radio commercials, and assisting and managing the candidate during events. Finally, in 2021, they joined SportGait, Inc. as the Director of Operations and Operations Manager.

Crosby Janda Bugenhagen obtained a Bachelor's Degree in Kinesiology and Exercise Science/Athletic Training from the University of Wisconsin-Milwaukee in 2003. Crosby also obtained a Bachelor of Science in Kinesiology and Athletic Training from the same university between 1999 and 2002. In 2005, they completed a Master's Degree in Sport and Fitness Administration/Management from the University of Louisville. Additionally, they obtained certifications in ITAT in 2015, ATC in 2003, CWcHP, and LAT.