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Derek Underwood has a diverse work experience. Derek started their career as a Research and Planning Economist at the FL Department of Revenue in 2011, and later became an Economic Analyst within the same department. In 2017, Derek joined the Florida Legislature, Office of Economic and Demographic Research (EDR) as an Economist. In 2019, they transitioned to the State Board of Administration of Florida and worked as a Senior Quantitative Data Analyst, followed by a role as a Senior Investment Analyst. In 2023, Derek became the Director of Total Fund Analytics and Reporting at the State Board of Administration of Florida.

Derek Underwood pursued a Master of Science degree in Applied Economics from Florida State University from 2009 to 2010.