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Jan Cirillo has worked in various roles since 2005. Jan began their career as a Marketing Services Assistant for ISP Sports in 2005. Jan then worked as a Teacher for Scotland County Schools and Chatham County Schools from 2005 to 2013. From 2013 to 2018, they were an Intervention Specialist for Chapel Hill-Carrboro City Schools. Most recently, they have been an Instructional Facilitator for The Hill Learning Center since 2018 and is currently an Implementation and Coaching Manager for 95 Percent Group LLC since 2023.

Jan Cirillo received a Masters of Education in Curriculum and Instruction from UNC Greensboro in 2007, and a Bachelor of Arts in Communication and Media Studies from UNC Wilmington in 2003.