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Jenna Isleib has a diverse work experience that spans various industries. In 2014, they worked as an Arts & Crafts Director at Durham Parks Recreation Ctr and also as an Administrative Assistant at Torrison Stone & Garden. In 2016, they took on the role of a Hostess at Chucks Steakhouse. From 2017 to 2021, they worked as a Marketing Intern at RLI Electric, LLC and as a Student Administrative Assistant at the Office of Undergraduate Admissions, University of Connecticut. In 2020, they completed a Financial Advising Internship at Connecticut Wealth Management, LLC, and in 2021, they joined the same company as a Financial Analyst. Prior to that, they gained experience as a Marketing and Advertising Intern at Mintz + Hoke. Throughout their career, they have demonstrated strong skills in financial planning, marketing, administration, and customer service.

Jenna Isleib attended Coginchaug Regional High School from 2013 to 2017, where they obtained a diploma. After completing high school, they enrolled at the University of Connecticut in 2017. Jenna pursued a Bachelor's degree in Communication and Media Studies and successfully graduated in 2021. In addition to their formal education, Jenna Isleib obtained the Series 65 License from FINRA in February 2022. Jenna also obtained certification in Personal Relations and Social Engagement from the University of Connecticut, but the specific month and year of completion are not provided.