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Olivia Skelley has a diverse work experience. Olivia began their career in 2017 as a Campus Manager for University Tees. In 2018, they took on the role of Recruitment Director for Sigma Sigma Sigma National Sorority, as well as Digital Marketing Intern for B.GOOD. In 2019, they worked as a Marketing Intern for Acme Markets. From 2020 to the present, they have been employed by Grubhub, where they have held the roles of Account Executive II, Account Executive, and Inside Sales Executive. Olivia is currently employed by Gigpro as a Market Specialist.

Olivia Skelley attended Lynnfield High School from 2012 to 2016. Olivia then attended Saint Joseph's University from 2016 to 2020, studying Food Marketing. In 2018, they took a Study Abroad Semester at Florence University of the Arts, also studying Food Marketing.