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Jaime Simpson has worked in a variety of roles since 2018. Starting as a Retail Sales Associate at Michael Kors in 2018, they then moved to the Boys and Girls Club of Collier County as a Youth Development Specialist in 2019. In 2020, they held two roles, a Medical Sales Representative at Lincare, and a Management Trainee Intern at Enterprise Rent-A-Car. In 2021, they were a Sales Support Representative at Paychex, and is currently a Sales Development Representative at SUMMUS.

Jaime Simpson attended Florida Gulf Coast University from 2016 to 2020 and obtained a Bachelor's degree in Health Science and Professional Selling, as well as a Bachelor's of Science in Health Science/Professional Selling.