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Cassi Weatherington has a diverse work experience spanning over a decade. Cassi started as an Administrative Assistant at the New York State Assembly in 2008 and later worked as a Lobbyist for A Better Way Foundation from 2010 to 2012. In 2011, they joined Learn It Systems as a Program Specialist, and then moved to Nutmeg State Financial Credit Union in 2012, where they held various roles including Personal Banker, Assistant Branch Manager, and Contact Center Manager. Starting in 2016, Cassi worked as an IT Service Manager at CharlesIT for a year. In 2018, they joined Webster Bank as an Assistant Vice President, Banking Center Manager, and later became a Vice President Banking Center Manager in 2021.

Cassi Weatherington earned a Bachelor of Science (BS) degree in Political Science and Government from Syracuse University in the years 2005 to 2009.