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Madeline Kaupa has a diverse work experience. Madeline began their career as a Camp Counselor at Camp Wakeshma in 2015. In the same year, they also worked as a Hostess for BOLD Dining and Catering. In 2017, they worked as a Beverage Cart at The Moors Golf Club. In 2019, they interned in Human Resources at Michigan State University. In 2021, they worked as a Universal Banker at PNC, where they managed the customer experience by identifying opportunities to improve the customer's financial wellbeing. Currently, they are a People Ops Coordinator at Campspot.

Madeline Kaupa completed their Bachelor's degree in Human Resources Management from Michigan State University in 2021. Prior to that, they attended Mattawan High School.