BREAKING: Head of School Judith Guild Announces Departure Plans

Mary Wang, Outgoing Editor-in-Chief • December 3, 2025

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Head of School Judith Guild recently announced her plan to retire at the end of the 2026-2027 academic year. Her leave will mark the end of her 36 years of service to the School.

According to Guild, she made the decision after 14 years of serving as Head of School and nearly four decades as a teacher and administrator.

Official Announcement Letters

From the Head of School

November 13, 2025

Dear Brimmer and May Community,

Throughout my years in education, I have learned that certain moments require us to pause, step back from our daily routines, and reflect. After much reflection and many conversations with members of my family, I have decided to retire as Head of School at the end of the 2026-2027 academic year. This decision comes after fourteen years of serving as your Head of School and thirty-six years as a teacher and administrator—a journey that has been the defining passion of my life as I worked hard to advance Brimmer's mission through the lens of the students' experience.

What began over four decades ago as a young teacher's calling has evolved into a lifelong passion that has shaped who I am as an educator, leader, and colleague. I am deeply humbled to have worked alongside exceptional people—individuals with great minds and even greater hearts.

The heart of Brimmer is its people, and I am deeply grateful to this community for partnering with me in service of our students. We are a school where people thrive, where growth and hard work yield transformation, and where love and joy sustain us all.

I have enjoyed working alongside our faculty who dedicate their lives with an unwavering commitment to serve young people. They possess not only an extraordinary love for learning but also the moral courage to guide students toward becoming their best and most authentic selves. They bring their whole hearts to their work, creating classrooms where curiosity flourishes and young minds are transformed. My administrative colleagues have enriched my life every single day, making it possible to embrace new challenges, dream bigger, and achieve goals I once thought beyond reach. Our staff members work with quiet dedication, finding genuine joy in watching children flourish and grow.

I have been honored to partner with families who trust us—who believe in their children and invest not just resources but also their time, energy, and faith in our shared mission. The Board of Trustees has tirelessly supported, guided, and championed both our school and my leadership. Their wisdom, courage, and strategic vision have been instrumental in every significant decision during my tenure.

Most of all, it has been my heart's desire to serve our students—at all ages and stages of growth. They have been the reason I wake up each morning with purpose and gratitude.

As I think about what the years ahead hold for our school, I do so with tremendous optimism. The role of Head of School at Brimmer will attract remarkable educators, and I am confident the school will continue to flourish under new leadership. Until my departure, there is still much to do, a building to open, and students to educate. I approach these remaining twenty months with great enthusiasm and an unwavering commitment to serve.

I look forward to watching Brimmer continue to grow and thrive, and I extend my heartfelt appreciation for your steadfast partnership through all these years.

With deep respect, gratitude, and love,

Judy Guild

Head of Sch

From the Chair of the Board of Trustees

November 13, 2025

Dear Members of the Brimmer and May School Community,

As you learned from Judy’s letter to the community, the 2026–2027 academic year will mark the close of her remarkable 36-year tenure as teacher and administrator at Brimmer and May School. As Head of School since 2012, Judy’s extraordinary leadership has touched every corner of Brimmer. Her steady vision, deep care for our students, and unwavering commitment to the School’s mission have shaped Brimmer in lasting and meaningful ways. We are profoundly grateful for all she has given to this community.

In reflecting on Judy’s tenure, I have been inspired by her approachable, student-centered leadership and her belief in the transformative power of education. I have seen this personally in the growth of my own children as well as in the flourishing of the School as a whole. Under her guidance, Brimmer has further advanced its academics; strengthened its creative arts, athletics, and extracurricular offerings; and deepened its sense of community and belonging. Judy has emphasized the importance of faculty and their critical role in making the educational experience at Brimmer what it is. She has prioritized supporting faculty, including investing in competitive compensation and professional growth that has made it possible for the School to attract and retain truly amazing teachers. Judy has paired this prioritization with elevating academic programming, as she expanded the Upper School Signature Diploma Programs, integrated STEAM into the PK-12 curriculum, and advanced the School’s global focus.

Judy’s leadership has enabled Brimmer to complete two strategic plans during her tenure that enhanced the student experience across all three divisions. She has raised more than $35 million during two successful capital campaigns, and the endowment has grown to five times where it was when she began. She has accomplished these goals all while leading significant campus improvements, including the construction of the Hastings Center, the upgrade of the Lower School Playground, the renovation of Cummings Hall, and the new Recreation & Wellness Center that we see progressing every day.

Judy has provided steady and compassionate leadership throughout her tenure as Head of School, particularly during extraordinary times. With the pandemic, she deftly balanced the dual priorities of maintaining the School’s academic programming while safeguarding the physical and mental health and safety of students, faculty, and staff.

This impressive record is a testament to the fact that Judy never asks more of others than she is willing to give herself. Her tireless work ethic and personal commitment to Brimmer's mission consistently set the standard for her team and the entire community. By consistently modeling the values of hard work, vision, and dedication, Judy ensures that the entire community understands what it means to truly embody Brimmer's spirit.

Please join me in expressing our deep gratitude to Judy for her extraordinary service and her enduring impact on the Brimmer community. We look forward to celebrating her many accomplishments and contributions over the next year and a half. Judy’s legacy will

continue to inspire our students, faculty, and families for generations to come. In announcing her departure now, she has given the community ample runway to conduct a full and thorough search, and we look forward to benefitting from her continued leadership for the next year and a half.

The Board of Trustees is beginning a comprehensive search to identify Brimmer’s next Head of School and has engaged the globally recognized firm Carney, Sandoe & Associates. Our goal is to find a leader who will build upon the strong foundation Judy has established and carry forward Brimmer’s mission with the same sense of purpose, warmth, and innovation that has defined her leadership. We will continue to keep the community updated as we move forward with the search and will be reaching out to all constituencies as we gather thoughts and insights about the qualities that can make the next Head of School a success at Brimmer.

With heartfelt appreciation and great optimism for the future,

Chris Chou P '29, '33

Chair, Board of Trustees

Brimmer and May School

Guild explains that she would like to leave opportunities for a younger person to take over the School.

“It feels to me like it should be somebody else’s chance to take the School to the next level,” Guild said, “ I am very aware of the fact that when you’re 68 years old, maybe it’s just time.”

Guild called for an all-faculty meeting where she announced her plan to depart, shortly before sending out the message to other members of the community.

In the announcement email to the School on November 13, Guild expresses her love for the School and its community members.

“The heart of Brimmer is its people, and I am deeply grateful to this community for partnering with me in service of our students,” Guild said.

Guild’s connection to the School stretches back many years.

She first arrived in 1984 as an English teacher, establishing a trusted presence in the Upper School. In 1991, she stepped away to welcome her son and to complete her master’s degree in American and British Literature at Harvard, expecting to move on from the School.

In 1996, however, the School called Guild back to help with a series of projects that over time evolved into a full-time role and deepened her dedication to the community.

Guild’s responsibilities continued to expand as she took on administrative positions. Ultimately, she made the decision to stay at the School as Head of School due to her love for K-12 education, and the opportunity she has to maintain close relationships with each student and their families at a smaller school.

During her years as Head of School, Guild helped expand the School’s academics, athletics, creative arts, and extracurriculars through further developing the Signature Diploma Programs and integrating STEAM into the School’s curriculum.

She mentored teachers and administrators, ensuring that each faculty member prioritizes the interests of students.

“Training and mentoring new administrators is a really important thing I do, so that all the people you’re working with directly remember to put students first and to hear what students are saying,” Guid said.

In addition, Guild’s leadership allowed the School to complete two strategic plans during her time as Head of School, raising more than $35 million during two successful capital campaigns.

Meanwhile, she led notable improvements for various buildings on campus–the construction of the Hastings Center, the renovation of Cummings Hall, and the new Recreation & Wellness Center set to open next year.

In a community-wide letter, Chair of the Board of Trustees Chris Chou expresses gratitude for Guild’s leadership over the years.

“Her steady vision, deep care for our students, and unwavering commitment to the School’s mission have shaped Brimmer in lasting and meaningful ways,” Chou said in his letter to the community.

Guild will continue her leadership for the next year and a half. In making this announcement, she said, she hopes to give the community ample time to conduct a comprehensive search for the next Head of School—and to ensure the leadership transition runs smoothly.

Looking forward, Guild expresses her optimism for the future of the School.

“The role of Head of School at Brimmer will attract remarkable educators, and I am confident that the School will continue to flourish under new leadership.”

She also outlines her plans post-retirement, emphasizing her desire to help and to learn.

“I would love to help anyone in a school that might need my help,” Guild said.

While she will stay working and involved with education, Guild also looks forward to having slower-paced days and more time with her husband and children.

“My son lives in Ohio with my grandson,” Guild said. “I think I want to be able to go whenever I want, because I’ve never been able to do that.”

Guild will stay on through the 2026-2027 academic year as the School conducts its search for the next Head of School.

About the Contributor

Mary Wang, Outgoing Editor-in-Chief

Mary is thrilled to return to The Gator for another year as Editor-in-Chief! This is her 6th semester in the newsroom, and she is excited to continue writing news, op-ed, and arts pieces. Outside of journalism, she enjoys acting, public speaking, and cooking.