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Karlyn Simpson has a diverse work experience, beginning in 2014 as an intern for Mechanica. In 2015, they held internships with American Woolen Company, LaxPlus as an Assistant Coach, and Wells Media Group, Inc. as a Remote Database Intern. In 2016, they were an Intern for GO Media CT and an Account Management Intern for MMB. In 2017, they worked at Hill Holliday as an Assistant Account Executive and Account Coordinator. In 2018, they were a Yoga Instructor and Studio Experience Team Member for CorePower Yoga. Finally, in 2019, they worked at Questus as an Account Supervisor, Senior Account Manager, and Account Manager, where they managed the development and launch of social media campaigns, resulting in $48.5M in global revenue and an 88% increase in hotel brand portfolio.

Karlyn Simpson has been involved in furthering their education since 2009, when they obtained their High School Diploma from The Williston Northampton School. Karlyn then attended Trinity College-Hartford and graduated in 2017 with a Bachelor of Arts in Public Policy and Law. During their time at Trinity College-Hartford, they also attended Trinity College Rome Campus in 2015. In 2019, Karlyn Simpson completed the Institute of Advanced Advertising Studies Program at the American Association of Advertising Agencies. Additionally, Karlyn Simpson has obtained two certifications: a Make the Move from Individual Contributor to Manager certification from LinkedIn in 2021 and a 200 HR Yoga Alliance Certified certification from CorePower Yoga in 2018.