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Anne E. Swayze has over 40 years of work experience in various educational institutions. Anne E. currently serves as the Head of School at The Greenwood School since June 2019. Prior to that, they were the Assistant Head of School starting from June 2018. In 1986, they joined Proctor Academy as the Assistant Head of School/Dean of Students. From 2016 to 2018, they worked at North Country School as the Director of School and Assistant Head of School. Anne's career in education started in 1980 at Oldfields School, where they held multiple roles including Athletic Director, Teacher, and Dorm Parent until 1985.

Anne E. Swayze began their education at Indiana University Bloomington in 1977, where they pursued a Bachelor of Science degree. Anne E. focused on the field of study in Physical Education/Leadership and Exercise Physiology. Anne E. successfully completed their undergraduate studies in this program in 1980. Afterwards, in 1985, they enrolled at the University of Colorado to pursue a Master of Education degree in Education Leadership. Anne completed their studies and earned their MEd in 1986.