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Jessica Jennings has a diverse work experience. Jessica currently works at Lutheran Community Services Northwest as a DOJ Accredited Legal Representative and previously held the position of Immigration Specialist. Prior to that, they worked at Automation Solutions as an Inside Sales representative, where they handled customer communication, project management tasks, and problem-solving. Jessica also has experience as a Small Business Owner at El Spot Comayagua, a Consultant at Stoneage Farmacy, and a Bilingual Teller at Wells Fargo. Jessica has also worked as a Teacher's Aide at PORTLAND MEET PORTLAND, assisting with a citizenship preparation course for refugees, and as a Waitress at Cruise in Country Diner, where they excelled in both front and back of house roles.

Jessica Jennings completed their Master's degree in Political Science and Government at the University of Illinois Springfield from 2019 to 2020. Before that, they earned a Bachelor of Arts (B.A.) in International Development, with a focus in Latin America, from Portland State University between 2015 and 2017. Prior to their undergraduate studies, Jessica attended Portland Community College from 2012 to 2015, where they obtained an Oregon Transfer Associate of Arts degree. Before entering college, Jessica received their High School Diploma from the American School of Correspondence in 2011. Jessica completed their secondary education at Glencoe High School from 2008 to 2011.