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Jacqueline Bailey worked as a Head Teacher at Children's Academy from October 2013 until now. Prior to that, they held multiple roles as a Child Watch Assistant, Pre-School Camp Counselor, and School Aged Child Care Assistant at Bay View YMCA Family Branch from May 2012 to August 2013.

Jacqueline Bailey earned a Bachelor of Education (B.Ed.) degree in Elementary and Special Education from St. Bonaventure University between 2009 and 2013. Later, they pursued a Master of Education (M.Ed.) degree in Early Childhood Special Education with an extension in Applied Behavior Analysis at Queens College from 2014 to 2016.