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Bailey Armstrong started their work experience in 2010 at Walgreens as a Senior Certified Pharmacy Technician, where they worked until 2015. From 2015 to 2021, Bailey worked as a Senior Certified Pharmacy Technician at Sheldon's Express Pharmacy. In 2021, they joined RJ Young as a Customer Service Representative and later became an ITT Sales Coordinator. Currently, Bailey is working as a National Account Specialist at RJ Young.

Bailey Armstrong attended Western Kentucky University from 2010 to 2013. No specific degree or field of study was mentioned.