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Bailey Rosales has extensive work experience in various roles and industries. Starting in 2014, they worked as a Radio Personality at EIU Odyssey - Online Radio Station until May 2015. In October 2015, they became a Server at Marty's Bar and Grill, concluding their role in May 2017. From February to May 2016, Bailey was part of the Media Team for the EIU Baseball Team. In 2018, they held multiple positions simultaneously. They worked as a Server and a Social Media Coordinator at Four Corners from August 2018 to June 2020. Additionally, from December 2018 to September 2019, they were a Pharmacy Technician at Meijer Pharmacy and a Customer Service Supervisor at Burlington Stores, Inc. Lastly, Bailey served as a Customer Success Manager at Yelp from April 2021 to March 2022 and is currently working as a Customer Success Manager at Cision starting from April 2022.

Bailey Rosales attended Eastern Illinois University from 2013 to 2017, where they earned a Bachelor of Arts (B.A.) degree in Mass Communication/Media Studies. In addition to their degree, Bailey Rosales has obtained several certifications. They obtained the Certified Customer Success Manager (CCSM) Level 1 certification from SuccessHACKER in September 2022 and the Certified Customer Success Manager (CCSM) Level 2 certification in March 2023. They also obtained CPR certification in December 2013, although the institution where they obtained this certification is not specified.