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Jay Tillman has a diverse work experience in the education sector. Jay started as a Career Services Advisor at Career Education Corporation from June 2006 to April 2008. Jay then worked as a Classroom Teacher at Chicago Public Schools from August 2008 to June 2012. Following that, they served as a Secondary Gifted and Talented Teacher at Leander Independent School District from August 2012 to June 2017. Jay also worked as an Instructional Coach at Manor ISD from June 2017 to June 2018 before becoming an Assistant Principal-Dean of Academics at Del Valle ISD from June 2018 to October 2018. Jay then worked independently as an Independent Education Consultant from October 2018 to June 2020. Jay later held the position of Director, Instructional Leadership and Program-St. Louis at Teach For America from August 2020 to June 2022. Currently, they are the Director of School Support at Achievement Network (ANet) since July 2019.

Jay Tillman attended Elmhurst University from 2002 to 2006, where they earned a Bachelor of Arts (B.A.) degree in Music Business. In 2008, they enrolled at National Louis University and completed a Master of Arts (M.A.) degree in Education from 2008 to 2010. Later, in 2015 to 2016, Jay participated in the Principal Licensure Certification Program at Angelo State University, focusing on Educational Leadership and Administration, General.