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Olivia Fleming has a diverse range of work experience in the banking industry. Olivia began their career in 2005 at American Savings Bank, where they worked in various roles including Bank Teller, Corporate Trainer, Personal Banking Officer, Assistant Branch Manager, Cash Management Specialist, and eventually became a VP, Cash Management Sales Officer. In 2021, they joined Central Pacific Bank as a VP, Institutional Deposit and Cash Management Officer, where they stayed until 2022. Olivia is currently working at First Hawaiian Bank as a VP, Treasury Management Solutions Officer, starting in 2023.

Olivia Fleming attended Punahou School, where they earned a High School Diploma. Olivia then pursued higher education at the University of Hawaii at Manoa, where they earned a Bachelor's degree in Liberal Arts and Sciences with a focus on Applied Linguistics.