Oldfields School, Head of School

Mission and Philosophy
Oldfields School’s mission is to embrace each girl’s authentic self, educate through collaboration, empower the individual voice, and inspire confidence and continual growth, leading to a life of purpose.

The school’s motto, Fortezza, Umilitade, e Largo Core— Courage, Humility, and Largeness of Heart — encapsulates the core values that define the Oldfields experience. These principles are the foundation of our school community, ensuring that every student is genuinely known, heard, and supported.

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.

We are proud to offer a comprehensive and generous benefits package designed to support the Head of School’s well-being, family life, and professional success. Health, Dental, and Vision Insurance: Strong coverage to ensure excellent care for you and your family. Retirement Plan: A school-supported retirement program to help you plan confidently for the future. Housing: A fully provided, newly renovated three-story home on campus, offering comfort, convenience, and a beautiful space to call home. Professional Development: Opportunities for continued leadership growth and national networking, supported as needs and priorities arise. Tuition Remission: Full tuition remission for school-aged children of the Head of School. Work-Life Balance: Generous vacation and leave benefits, aligned with the rhythms of the school year. Community Perks: Access to on-campus workout facilities, a gym, and the school’s equestrian program, along with daily meals and opportunities to engage in the life of a vibrant, close-knit community. This package reflects the school’s deep commitment to attracting and supporting outstanding leadership. We want our Head of School not only to succeed in their role, but also to thrive personally and as part of our community.

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

Opportunity Statement

www.oldfieldsschool.org