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Sydney Strauss has a diverse range of work experience, including roles in both education and event management. Sydney currently serves as a Head Teacher at Stephen Gaynor School, where they started in August 2021. Prior to this, they were a Co Teacher at the same school since September 2020. Sydney also worked as a Division Leader at Blue Rill Day Camp from June 2016 to August 2020. In addition, they have experience as an Assistant Teacher at Stephen Gaynor School from September 2018 to June 2020. Sydney has also held intern positions at Oak Grove Montessori School and Dorothy C. Goodwin Elementary School in 2018. Sydney has previous experience as an Events and Meetings Intern at KPMG in 2017. Before that, they served as the Director of External Chapter Events for Alpha Phi International Fraternity from August 2015 to December 2016. Sydney's earliest work experience includes being a Group Counselor at Blue Rill Day Camp from June 2011 to August 2015.

Sydney Strauss completed a Bachelor of Arts degree in Human Development and Family Studies from the University of Connecticut between 2014 and 2018. Currently, they are pursuing a Master of Science degree in Childhood General and Special Education at Bank Street College of Education, which is expected to be completed between 2020 and 2023. No specific field of study was provided for their master's degree.