After four decades of extraordinary service to Oldfields School, Ansley Smithwick has announced her retirement. During her 40 years at Oldfields, Ansley has served in numerous roles with devotion and distinction, culminating in her tenure as Head of School. Her steady leadership, her deep commitment to the Oldfields community, and her tireless dedication to students have shaped the School in lasting and meaningful ways.

The Board of Trustees is profoundly grateful for Ansley’s commitment and stewardship. As we celebrate her legacy, the Board is equally committed to ensuring a smooth and thoughtful transition in leadership. Our search for the next Head of School will be guided by the same values that define Oldfields: academic excellence, close-knit community, and the belief that each student’s potential is best nurtured in an environment of care and challenge.

The Board is engaging in a deliberate process to identify a highly-qualified and inspiring leader who will continue to advance the School’s mission and prepare Oldfields for a bright future. Should the search require additional time, the Board will appoint an interim Head of School for the 2026–27 academic year to provide continuity and strong leadership during this important transition.

We recognize that the choice of a Head of School is one of the most significant responsibilities entrusted to the Board, and we will approach this search with the greatest care. We invite our community—alumnae, parents, faculty, staff, and friends—to stay engaged and informed. All updates regarding the search process will be shared on this page.

Head of School Search Updates

Overview
Oldfields School presents an unique opportunity for its new leader to engage in and advance the School’s mission, signature programs, and its aspirational vision to redefine a girls’ boarding and day school education in today’s ever-changing world, balancing innovation with the rich, time honored traditions of the School. Visitors to the School will experience something different about Oldfields School—its unpretentious nature and strong community spirit. Faculty, students, parents, and alumnae talk about the authentic relationships between students and faculty. It is not unusual to hear about the teachers who go out of their way to support and engage a student’s interest.

Oldfields lives its student-centered philosophy in and out of the classroom, as adults and students create a true family-like community. Oldfields is committed to teachable moments as it expands the boundaries of the traditional academic classroom to include arts, athletics, character development, community and residential life, riding, and rich traditions carried through its long history. Students are part of an active learning community dedicated to engaging in self-discovery and to developing independent and collaborative learning experiences. Students are expected to acquire the skills and attitudes to support lifelong learning. At Oldfields, the faculty and staff put the School’s mission, motto, and values into practice by providing a diverse, innovative, and deeply personalized educational experience.

IDEAL CANDIDATE ATTRIBUTES AND EXPERIENCES 

The next Head of School will be an experienced, mission-driven leader who brings clarity of vision, strong execution, and a deep commitment to the Oldfields ethos. The ideal candidate should demonstrate:

• A proven ability to lead a student-centered academic program and recruit, retain, and support exceptional faculty and staff;

• Financial leadership equivalent to a CFO: including budgeting, cash flow management, long-term forecasting,and oversight of all business operations;

• Independent school administrative experience;

• Hands-on experience with boarding school culture;

• Marketing and Communications experience;

• Fundraising experience and the ability to build strong philanthropic partnerships

• Experience in admissions and enrollment growth strategies;

• Excellent organizational, interpersonal, and follow-through skills;

• Strong written and verbal communication skills tailored to a range of audiences.

  Interested Candidates for the position of Interim and/or Permanent Head of School, please download the full Opportunity Statement.