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Gabby McKessey has extensive work experience in various roles and industries. Gabby started their career as a Scanner/Filer at The B.A.C.K. Center from 2014 to 2016. In 2016, they worked as an Admissions Specialist at Busch Gardens Tampa for a few months. From 2017 to 2018, they gained experience as a Sales Associate at Forever 21. Gabby then worked as a Barista at Felicitous from 2018 to 2018 and at Buddy Brew Coffee from 2018 to 2020, where they also took on a role as a Marketing Intern from 2018 to 2019. In 2019, they had an internship as a Social Media and Studio/Productions Intern at SPARK. In 2020, Gabby worked as a Graphic Designer at The Tampa Club, where they focused on designing various materials for the club and its members. Additionally, from 2020 to 2021, they were a Barista at Commune + Co. Gabby then transitioned into the marketing field, working as a Marketing Coordinator at Diamond View - Creative Video Agency from 2021 to 2022. Currently, they hold the position of Senior Marketing Coordinator at Vu Technologies, starting in 2022.

Gabby Mckessey pursued their education between the years 2016 and 2019 at the University of South Florida. During this time, they obtained a combined Bachelors and Masters degree in Business Advertising.