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In September of 2024, Heather Willis Daly received a call that would change her life. Pomfret trustee Daryle Bost ’89, the chair of Pomfret’s Head of School Search Committee, was calling to share that she had just been selected as Pomfret’s thirteenth head of school.

Twelve months later, Daly rose from her chair and stood to address the more than five hundred Pomfret students, faculty, staff, trustees, alumni, and friends who had gathered on the Clark Memorial Chapel Lawn to witness her installation.

I'm proud to count myself as one of the thirteen individuals who have led Pomfret School,” she said. “And I am proud to be the first woman. Thank you for entrusting me with the honor and responsibility of leading Pomfret in this next chapter.”

Daly was selected following a nationwide search process led by Board Chair Daryle Bost ’89 that yielded a number of highly qualified school leaders. The search committee was ably supported by RG175, an executive search firm consisting of former heads of school with deep experience in national independent school leadership searches. 

Upon her arrival on July 1, 2025, still surrounded by half-open boxes, Daly wrote a letter to her new community: “As I pen this message from my office in the School Building, I am reminded of all the amazing heads who came before me: William Peck, William “Bull” Olmsted, Jay Milnor, Brad Hastings ’68, and, of course, Tim Richards, to name just a few. Pomfret’s mission to empower students to pursue lives of purpose and meaning resonates with me deeply.”

Growing up in Wassaic, New York, in the Hudson Valley, the eldest of four sisters, Daly was rarely seen without a stack of books in her arms. But despite her love of reading, she struggled in school — until one fateful week in the eighth grade. 

As she tells it, a bout of strep throat had forced her to slow down and study. That small moment of focus unlocked something larger: confidence in her own ability to succeed. She found her calling in boarding school admissions, driven by a belief in the transformative power of education and the importance of inclusive, kind communities.

In her inaugural chapel talk, Daly told students, “Everyone at Pomfret has a story, a journey full of twists and turns in their lives, that has ultimately brought them to this chapel today.”

A graduate of Wellesley College and the University of Illinois Urbana-Champaign, Daly has spent most of that journey 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 Head of School Ann Klotz, who spoke at the Installation. “Heather is steady and clear-headed. She lifts others as she leads, stays calm under pressure, and celebrates her colleagues and community generously.” Klotz 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.”

Prior to Laurel, Daly was the dean of admissions and financial aid at St. Andrew’s School in Delaware. There, she increased applications by 40 percent, achieving all-time high selectivity rates. Before St. Andrew’s, Daly spent a decade at Hawken School, where she helped put Hawken at the forefront of a national conversation related to competency-based learning and the Mastery Transcript Consortium. 

Notably, she is the former chair of the National Association of Independent Schools (NAIS) Financial Aid Advisory Task Force, which advises school leaders on developing sound financial aid policies and best practices, something Daly is especially passionate about.

As part of the School’s long-term succession plan, Daly spent all of last year working closely with Board Chair Daryle Bost ’89, former Head of School Tim Richards, and members of Pomfret’s senior leadership team to prepare for this year. “Heather embodies all of the qualities I value in a school leader,” Bost says. “She has a deep respect for education, a commitment to students, an inclusive and collaborative spirit, and the courage to lead with conviction.”

Heather is married to Brendan Daly, who teaches science at Pomfret. Together, they have three children: a son at Rose-Hulman Institute of Technology, a daughter at the University of Richmond, and a daughter at Davidson.
 

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