Assistant Superintendent of Teaching & Learning

Dr. Anna Mahon brings a wealth of experience and a distinguished career in education to the Westport Public Schools. She served as the Assistant Superintendent of Schools for Curriculum, Instruction, and Human Resources with the Brookfield Public Schools from 2022-2025. Prior to that role, Dr. Mahon had a long and accomplished tenure at Amity Regional High School in Woodbridge, Connecticut. She began as an English teacher in 2000, advanced to English Department Chairperson in 2007, was promoted to Associate Principal in 2010, and later served as Principal from 2015 to 2022. Dr. Mahon has also taught high school English in Darien and Stamford. Her nearly three decades in education, spanning various leadership roles across multiple districts, will be an invaluable asset to Westport Public Schools.

In addition to her extensive school and district-level experience, Dr. Mahon is widely recognized as a leader in education throughout Connecticut and New England. She recently completed a term as a Commission Member with the New England Association of Schools and Colleges (NEASC) and is currently chairing a site visit for the organization. She has also served on the National Merit Scholarship Corporation Advisory Board and the Executive Board for the Connecticut Interscholastic Athletic Conference (CIAC) Board of Control. Additionally, Dr. Mahon is an Adjunct Professor in the Doctoral Program in Educational Leadership at the University of Bridgeport, further demonstrating her commitment to advancing the field of education.

Dr. Mahon holds a Bachelor of Arts degree in English and Psychology from the University of Vermont. Motivated by a passion for teaching, she earned a Master of Arts in Teaching, Secondary English, from Boston University. She continued her studies with a Sixth Year Degree in Educational Leadership from Southern Connecticut State University and a Doctor of Education in Educational Leadership and International Educational Studies from the University of Bridgeport.

Beyond her contributions to education, Dr. Mahon is also a former Olympic athlete. She competed as a member of the United States Track and Field Team in the women's 4-kilogram hammer throw at the 2004 Athens Olympics. Her passion for athletics extended beyond competition, as she later served as an assistant coach for Yale University's Men's and Women's Track and Field teams from 2004 to 2012. Her experiences as both an elite athlete and coach have further shaped her leadership skills and dedication to excellence.