Meet the Head of School

Matt Byrnes is in his eighth year as Head of School at Wooster School. Since arriving in Danbury he has facilitated Wooster’s continued evolution as a strongly relationship-based and learner-centered school community which is accessible to all members of our neighboring towns. Most notable among the many areas of emphasis under Matt’s tenure have been the development of the Deep Learning Initiative, the establishment and growth of the Bridge Program for students with language-based learning disabilities, and the adoption of the Altitude Learning platform, which has solidified our commitment to personalized learning and growth, and most recently the establishment of the Center for Equity and Justice. The design and implementation of the Variable Tuition Program has also further solidified Wooster’s commitment to serving students and families in the area regardless of financial circumstances. Matt, and his wife Madyn, an artist and designer, have also helped to conceptualize and manage the steady improvement of Wooster’s facilities and physical landscape since their arrival in 2013.

Throughout his career in public and independent schools, Matt has always been a learner and thought leader in the areas of school culture, leadership, change, and the science of thinking, learning, and wellness. Most recently, Matt was a presenter at the 2020 National Association of Independent Schools (NAIS) Annual Meeting and has written two essays for Independent School Magazine: Reflections on Confronting Unconscious Bias (2019), and Was Dewey Right? Are Schools a Reflection of Society? (2018). He also was invited to attend the Columbia University Klingenstein Center’s Heads of School Residency Program in January of 2018, which was a true honor and a genuinely transformative experience.

Currently, Matt serves as a Trustee on the Board of the Connecticut Association of Independent Schools (CAIS), and on the Board of The Heads Network, an organization committed to the advancement of women as leaders in independent schools. In 2020, Matt also became the Convener of the Fairchester Heads Association, which is made up of heads of school in Fairfield County, CT and Westchester County, NY.

Matt has been married for twenty-four years to his wife Madyn Gwynne and they have four children -- Kernochan ‘17, Cooper ‘19, Brooks, and Avery ‘24 -- and two dogs, Bean and Pepper.

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