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James Lettieri has a diverse work experience, starting in 2012 as a Maintenance Worker at Point O' Woods Maintenance, where they learned how to establish valuable workplace relationships and maintained facilities. In 2013, they worked as a Cashier at Italianos Pizzeria, acquiring valuable communication skills and experience in high-pressure situations. From 2014 to 2015, they served as an Office Clerk at Frenkel Lambert Weiss Weisman & Gordon, handling valuable legal forms and observing a professional workplace setting. In 2015, they volunteered as a Manager for the University of Rhode Island Men's Basketball Team, managing equipment and gaining insight into the operations of college sports. In 2016, James worked as an Advertising Clerk at Good 5 Cent Cigar and served as the Vice President of Communications for Sigma Phi Epsilon.

James Lettieri completed their Associate's degree in Liberal Arts and Sciences/Liberal Studies from Farmingdale State College from 2013 to 2015. James then pursued a degree in Public Relations with a focus on Communication and Media Studies at the University of Rhode Island from 2015 to 2017.