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Olivia Flannery has a diverse work experience. Olivia started their career as a Library Page at Penfield Public Library from February 2019 to August 2020. Olivia then worked at Penfield Country Club as a Kid's Club Attendant and Snack Bar Attendant from May 2021 to August 2021. Olivia served as a Front Line Worker at Bruegger's Bagels from August 2021 to April 2022. Later, they joined The Ohio State University as a Community Programs Assistant and Camp Recky Counselor from June 2022 to July 2022. Currently, they are employed as a Painting Instructor at Pinot's Palette starting from August 2022.

Olivia Flannery began their education at Penfield Senior High School from 2016 to 2020. Olivia then went on to attend The Ohio State University from 2020 to 2024, where they pursued a Bachelor of Science degree in Medical Radiologic Technology/Science - Radiation Therapist. During their time at Ohio State, Olivia also enrolled in the School of Health and Rehabilitation Sciences. In 2021, they briefly attended Monroe Community College, studying Physics. Additionally, Olivia has obtained certifications in BLS/CPR for Healthcare Providers from Central Ohio CPR and CPR/AED for Professional Rescuers with First Aid from the American Red Cross, both in June 2022.