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Jamie Cass has a diverse range of work experience, starting in 2015 as an intern at Welfare Rights & Advocacy Service. In 2016, Jamie worked as a Direct Response Intern at Amnesty International USA, a Family Assistant for a private family, and interned for City Councilman Ivar Hyden. Jamie also became a District Leader for Election District 19 and later transitioned to the role of Assistant Head of Council District 4 at the City of New Rochelle in 2018. In 2019, Jamie interned at the Eileen Fisher Leadership Institute and later at Gurney's Resorts as a Marketing, Partnerships, and Programming Intern. In 2020, Jamie had brief roles as a Marketing Intern at LF Stores and as an Intern at 4 Artist Management (4AM). Lastly, Jamie worked as a Sales Floor Associate at Baybi Pop for a short period in 2020.

Jamie Cass's education history includes attending Hunter College, where they pursued a Bachelor's degree in Media Studies and had a minor in Human Rights. Their studies also included Political Science and Government. Additionally, Jamie attended New Rochelle High School, but no specific degree or field of study was mentioned for this institution.