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Jonathan Poole has a diverse work experience spanning several industries. Jonathan began their career in the US Navy, serving in various roles including Navigator, Main Propulsion Officer, and Electrical Officer from 2014 to 2018. Following their military service, Jonathan worked at the Military Sealift Command as part of the Commander's Action Group from 2018 to 2020. In 2020, they transitioned to the Maine Department of Economic and Community Development, where they served as a Business and Investment Capital Manager until 2022. From 2022 to 2023, Jonathan worked at Qualtrics as a Principal Customer Success Consultant for the Public Sector. Currently, they are the Director of Strategic Growth at the Finance Authority of Maine.

Jonathan Poole attended the United States Naval Academy from 2009 to 2013, where they received a Bachelor of Science degree in Applied Mathematics. Jonathan then pursued further education at University College Cork from 2013 to 2014, obtaining a Master of Business Studies in International Public Policy and Diplomacy. Prior to their time at the Naval Academy, Jonathan briefly attended Trinity College-Hartford in 2008-2009 but did not complete a degree or field of study there.