Heather Willis Daly is Pomfret’s thirteenth head of school and is the first female head in the School’s history. She has an MS in management from the University of Illinois Urbana-Champaign, and a BA in English and history from Wellesley College.

Heather began her independent school career at Santa Catalina School in California as an assistant director of admission and resident faculty member. Over the course of the next thirteen years, she held additional leadership roles on campus, including director of admission and director of financial aid. From there, Heather began her decade-long tenure at Hawken School in Ohio, culminating in her role as assistant head of school for enrollment management. During her time at Hawken, she worked alongside colleagues to implement significant curricular changes and innovations, putting Hawken at the forefront in national conversations in education related to service and experiential learning, community partnerships, development of signature academic programs, and creation of the Mastery Transcript Consortium. In 2018, Heather became dean of admission and financial aid at St. Andrew’s School in Delaware, increasing application numbers by 40 percent, achieving all-time high selectivity and enrollment figures, and helping to create an orientation program for new students and families of color. Most recently, Heather served as associate head at Laurel School, working with the leaders of a broad array of school programs and overseeing implementation of Laurel’s strategic plan.

Heather has presented at numerous conferences on topics related to enrollment, financial aid, and leadership practices in schools offering experiential education. She was a founding faculty member of the Enrollment Management Association's Admission Director Institute, preparing admission officers to step into leadership roles in schools' enrollment offices. She also served as the chair of the NAIS Financial Aid Advisory Task Force, advising school leaders on developing sound financial aid policies and best practices regarding financial accessibility.

Heather is married to Brendan Daly, who is a science teacher at Pomfret. They have three children who are all currently in college, as well as two dogs who live with them on the Hilltop.