The Pomfret Board of Trustees has selected Heather Willis Daly as Pomfret School’s thirteenth head of school, effective July 1, 2025. Following a rigorous global search that yielded a number of highly qualified school leaders, the Board unanimously and enthusiastically endorsed the recommendation of the Head of School Search Committee. Heather is the first female head in Pomfret’s history. 

A graduate of Wellesley College with a master’s degree in management from the University of Illinois, Heather has spent nearly thirty years living and working in independent schools. Heather began her career in admissions and has been highly successful as both an educator and an administrator. 

In her current role as an associate head at Laurel School in Shaker Heights, Ohio, Heather oversees admissions, marketing and communications, athletics, college counseling, health and safety, food service, signature programming, summer programs, and sustainability. She is also the driving force behind Laurel’s new strategic plan. In addition, Heather is the 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.

“Today’s announcement ensures that Pomfret will remain one of the best small independent schools in the country for many years to come,” says Board Chair Justin Klein ’65. “We are confident that Heather’s formidable leadership experience will directly empower Pomfret students to pursue lives of purpose and meaning as the School continues to inspire the next generation of change makers and problem solvers.”

Prior to Laurel School, Heather 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. In addition, Heather worked closely with the St. Andrew’s Advancement Office to guide and support financial aid donor appeals, scholar selections, and stewardship efforts. In the midst of the pandemic, the school turned to Heather to redesign its recruitment process, marketing materials, and comprehensive yield plan. 

Before St. Andrew’s, Heather spent a decade at Hawken School in Ohio. During her time there, she implemented significant curricular changes and innovations alongside colleagues, helping to put Hawken at the forefront of a national conversation related to service and experiential learning, community partnerships, signature academic programs, and the creation of the Mastery Transcript Consortium (MTC). In addition, she grew Hawken’s student of color population from 18 percent to 30 percent, boosted overall enrollment by 173 students, and realized eight consecutive years of record enrollment growth.

The Search Process

This announcement follows a thoughtful, thorough, and rigorous search process. In January 2024, the Board of Trustees announced the formation of the Head of School Search Committee. The committee — led by the Vice Board Chair Daryle Bost ’89, and composed of seven other trustees, four faculty members, and one staff member — was ably supported by RG175, an executive search firm consisting of former heads of school with deep experience in national independent school leadership searches.

The committee was charged with identifying an accomplished and diverse group of candidates. Working in partnership with RG175, the committee initiated a global search, which drew interest from a large number of highly qualified school leaders. Throughout the search process, the committee was guided by the priorities of the Pomfret community. 

“In Heather Daly, Pomfret has found a leader who typifies the characteristics our students, faculty, staff, alumni, and parents value in a leader,” says Bost. “According to her references, Heather is, quite simply, a superstar. The committee was immediately excited by her excellent communication skills. It is abundantly clear that she is truly respected by faculty. She is a savvy, authentic, and gracious leader who constantly keeps the big picture in mind. She prioritizes integrity and collaboration. She exemplifies Pomfret’s brand, institutional growth, and Griffin spirit.”

Looking Ahead

As part of a long-term succession plan, Head of School Tim Richards will work hand-in-hand with Heather and the Board of Trustees to ensure a smooth transition. She will officially begin her new role as head of school on July 1. 

In accepting the position, Heather said, “I am deeply honored to have the opportunity to serve as Pomfret’s next head of school, and I am excited to lead such a vibrant and innovative boarding community. Pomfret’s mission to empower students to pursue lives of purpose and meaning resonates with me deeply, and I am inspired by how this mission is woven into the fabric of everyday life on the Hilltop. The warmth, connection, and genuine sense of belonging I experienced during my visit with students, faculty, and staff affirmed my desire to join this remarkable community. I am truly grateful to Daryle Bost, Justin Klein, the search committee, and the Board of Trustees for entrusting me with the privilege of leading Pomfret into its next chapter, building on the legacy of Tim Richards and those who came before him.”

Heather is married to Brendan Daly, who is an independent school science teacher. Together, they have three children: a son at Rose-Hulman Institute of Technology, a daughter at the University of Richmond, and a daughter at St. Andrew’s School in Delaware.

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