The clock atop the School Building chimed twelve times as Director of Spiritual Life Bobby Fisher closed the Installation of the thirteenth head of school, Heather Willis Daly. “Heather, through your leadership, relationships, and life unfolding here at Pomfret, may you be rooted in this principle of loving fellowship…” he said as the bell tolled. The unplanned moment felt symbolic of a new era on the Hilltop. A new leader has arrived, and the community is eager to begin this next chapter in the School’s history.

More than five hundred students, faculty, staff, trustees, alumni, and friends gathered for this historic occasion. Daly now joins the ranks of Pomfret’s visionary and accomplished leaders — and is the first woman to hold the role of head of school. .

Board of Trustees Chair Daryle Bost ’89 welcomed guests to the ceremony that honored Daly’s leadership and vision and marked an important chapter in the history of the School. As the chair of the Head of School Search Committee, Bost helped lead the process that ultimately brought her to Pomfret. “Heather embodies all of the qualities I value in a school leader: a deep respect for education, a commitment to students, an inclusive and collaborative spirit, and the courage to lead with conviction,” he said. “I stand before you on this day with gratitude in my heart for everything that has led us to this moment, and a deep and abiding hope for the future of this remarkable institution. May this new chapter be filled with wisdom, joy, and the enduring spirit that is Pomfret — and may we all commit to supporting Heather in this journey.”

A graduate of Wellesley College and the University of Illinois Urbana-Champaign, Daly has spent three decades living and working in independent schools. Before coming to Pomfret, she was the associate head at Laurel School in Shaker Heights, Ohio.

At Laurel, Daly worked closely with Ann Klotz, who spoke at the Installation. Klotz shared anecdotes and warm praise from colleagues and students: “Heather is steady and clear-headed. She lifts others as she leads, stays calm under pressure, and celebrates her colleagues and community generously.” She added that Daly’s rare combination of strategic vision and personal warmth makes students, parents, and colleagues feel seen, heard, and valued. She leads with integrity, grace, and care. “She is the real deal, and her preparation for this new chapter has been thoughtful and thorough.”

As part of a long-term succession plan, Daly spent the past year working closely with Board Chair Daryle Bost ’89, former Head of School Tim Richards, and members of Pomfret’s senior leadership team to ensure a smooth transition. Since arriving on the Hilltop in July, she has collaborated with faculty, staff, student leaders, and trustees to deepen her understanding of Pomfret School. “I look forward to our work together as we build upon the foundation of so many individuals who have made Pomfret what it is today, from William Peck to Tim Richards.

To better understand Pomfret's history, Daly has been reading The Spirit that is Pomfret. In its foreword, then-Board President Barclay Robinson, Jr. wrote, “Like every teacher and student, every headmaster has made, and left his mark on Pomfret School. (Inevitably, with time, we shall say her mark.)” Reflecting on those words, Daly said, "While it's still too early to know what my mark will be, I am filled with pride to know that the time Robinson alluded to is here. Thank you for entrusting me with the honor and responsibility of leading Pomfret in this next chapter. With the help of so many of you who are gathered here today — students, faculty, staff, trustees, and alumni, I’m excited to imagine the possibilities of what’s to come.

Daly has reflected deeply on what it means to be Pomfret’s first female head of school. “I'm proud to count myself as one of the thirteen individuals who have led Pomfret School,” she said. “I am proud to be the first woman, and I hope that someday, there will be others who come after me.”

Growing up in a family of all girls, Daly had parents who believed in her talents and abilities in a world that didn’t always send that message to girls and women. At Wellesley College, she was surrounded by extraordinary women and a legacy of ambitious alumnae.

“It's my hope that in serving in this role, students and adults of all genders at Pomfret see a woman leader with authenticity, humor, and integrity. I hope to enable others to grow in their ambitions in the same way that I’ve been given those opportunities throughout my career.” 

With the School Building bell still echoing across the Hilltop, Pomfret has officially entered a new era. Daly’s Installation was not only a celebration of a new leader, but also a reaffirmation of Pomfret’s values. As the School begins this chapter under her guidance, there is a shared sense of possibility and promise. Just as those before her left their mark, so too will Daly — shaping Pomfret’s future with clarity, compassion, and conviction.

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