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Regan Hesse has a diverse work experience. In 2002, they worked as a Risk Analyst at Analytic Services Inc., where they supported the identification and assessment of potential terrorist targets and recommended security improvements for critical facilities. From 2005 to 2007, they served as a Homeland Security Analyst at Systems Planning and Analysis, Inc., identifying vulnerabilities and making recommendations for critical infrastructure facilities. Starting in 2007, they worked as a Budget Analyst at the Washington State Office of Financial Management, allocating and tracking administrative costs across state agency budgets. Their most recent role was Chief Financial Officer at the Military Department Washington, where they were responsible for directing program growth and development, revenue generation, and financial operations.

Regan Hesse completed their high school education at Decatur High School from 1994 to 1998, earning a High School Diploma. They went on to attend American University from 1998 to 2002, where they obtained a Bachelor of Science (BS) degree in Mathematics. In terms of additional certifications, Regan obtained a Prosci® Certified Change Practitioner certification from Prosci in May 2021. They have also earned an Emergency Medical Technician certification, although the institution and specific time of obtaining this certification are not provided.