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Jessica Stolfi began their work experience in 2016 as a Sales Associate at Lilly Pulitzer, where they worked until 2020. In 2022, they joined Lolly List as a Marketing Specialist and later transitioned to the role of Web Content Coordinator at OUTFRONT Media.

Jessica Stolfi completed their Bachelor of Arts degree in Communications at Loyola University Maryland from 2018 to 2022. Prior to that, they attended Canterbury School from 2014 to 2018, although no specific degree or field of study information was available for this period.