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Madison Staley began their work experience as a Cashier at Walgreens in September 2015 and worked there until January 2017. From August 2016 to March 2017, they worked as a Caregiver at SeekingSitters. In March 2017, they joined Cimarrone Golf Club as a Server/Bartender and worked until February 2018. From February 2018 to May 2020, Madison served as a Server at Chili's. Madison then interned at Day of Difference, a non-profit organization, from March 2019 to May 2020, where they worked as an IT Project Manager and Web Developer. Madison's next role was at Fortegra, where they worked from June 2020 to July 2022. At Fortegra, they completed a Leadership Development Program as an IT Project Manager/Business Analyst. Madison then worked as a Real Estate Agent at CENTURY 21 Lighthouse Realty from March 2022 to May 2022. Currently, Madison holds the position of Assistant Vice President, Project Manager I at Eastern Bank since July 2022.

Madison Staley attended the University of North Florida from 2016 to 2020, where they earned a Bachelor of Science (BS) degree in Computer Information Systems. In February 2022, they obtained a certification as a Florida Real Estate Sales Associate from the Florida Real Estate Institute, Inc.