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Chelsea Riccio has a diverse work experience spanning several roles and companies. From 2007 to 2008, they worked as a Substitute Teacher in the East Hartford School District. In 2010, they joined Education, Inc., where they held various positions including Behavioral Health Teacher, Team Leader, Associate Manager, Manager, and Regional Director of Teaching Operations. During their time at Education, Inc., they were responsible for strategic growth, launching new sites, and overseeing hiring and performance tactics. In 2018, they moved to LearnWell as the Regional Director for New England & Western US. Chelsea later became the Senior Director of Operations and eventually the VP of Teaching Operations. Overall, Chelsea has a strong background in education and operations management.

Chelsea Riccio attended Emmanuel College (Boston) and obtained a Bachelor's Degree in History and Secondary Education. In addition, they obtained a Certified Internet Recruiter (CIR) certification from AIRS in August 2012. No specific start and end years were provided for their education at Emmanuel College, suggesting that the duration of their studies is unknown.