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Maddysun W. has a diverse work experience in the retail industry. Starting in 2016, they worked as a Cashier at Sears for eight months. They then moved on to JCPenney and served as a Sales Floor Associate for seven months. In 2018, Maddysun joined rue21 as a Sales Floor Associate and later became an Assistant Store Manager. At Victoria's Secret Pink, they held the role of a Beauty Supervisor, responsible for driving results and coaching direct reports. They also worked at Aeropostale as an Assistant Manager, collaborating with the Store Manager to achieve sales goals. Currently, Maddysun holds the position of Customer Experience Lead at Victoria's Secret & Co., where they are involved in enhancing customer satisfaction.

Maddysun W. obtained a High School Diploma in General Studies from Limestone Community High School in the years 2014 to 2018. Maddysun then pursued an Associate's degree in Cosmetology, Barber/Styling, and Nail Instructor from Tricoci University of Beauty Culture from 2020 to 2021. Currently, they are enrolled at DeVry University since 2022, working towards a Bachelor of Science degree in Entrepreneurial and Small Business Operations. It is unclear if they attended Illinois Central College or obtained any degree from there.