Director of Finance and Operations

On behalf of Educators Collaborative, we are assisting Fayerweather Street School in its search for a Director of Finance and Operations (DFO). This is a meaningful opportunity for a thoughtful, mission-driven finance and operations leader to join a highly regarded progressive independent school known for its strong sense of community, student-centered educational philosophy, and commitment to joyful, experiential learning.

About the Role

The Director of Finance and Operations will play a vital role in supporting the school’s financial sustainability, operational effectiveness, and long-term strategic priorities while serving as a trusted strategic partner to the Head of School, the Board, and the broader school community. The Head of School seeks a collaborative, strategically minded leader who brings strong financial acumen, operational insight, sound judgment, and relational intelligence to lead effectively within a highly engaged, progressive school community.

Responsibilities

• Serve as a key strategic partner to the Head of School and an essential member of the school’s leadership team.
• Oversee the school’s financial health and operational functions to ensure resources, systems, and structures effectively support its educational mission and long-term sustainability.
• Demonstrate approachable leadership grounded in authenticity, accessibility, trust, and genuine human connection within a deeply relational community.
• Navigate complex community dynamics with professionalism, empathy, and good humor while maintaining healthy professional boundaries.
• Lead financial and operational initiatives, including budgeting, forecasting, financial analysis, and strategic planning.
• Supervise and manage staff, fostering a collaborative and solutions-oriented work environment.
• Communicate financial information clearly to non-financial audiences.
• Support enrollment management, long-term financial planning, operational sustainability, and organizational growth.

Requirements

• Bachelor’s degree required; advanced degree preferred.
• Senior-level experience in finance and operations leadership.
• Experience in independent schools, nonprofit organizations, or similarly mission-driven environments preferred.
• Expertise in budgeting, forecasting, financial analysis, and strategic planning.
• Knowledge of human resources, risk management, and operational systems.
• Strong organizational leadership and supervisory experience.
• Excellent written and verbal communication skills.
• Demonstrated commitment to equity, inclusion, and belonging.
• Experience with tuition management systems (FACTS preferred) and financial aid administration is a plus.
• Background in admissions/registrar administration or enrollment management is a plus.
• Experience in progressive, student-centered, or mission-driven educational settings is a plus.

Skills

• Strong financial and operational leadership experience.
• Sound decision-making and organizational judgment.
• Proactive and solutions-oriented mindset.
• Excellent judgment and emotional intelligence.
• Collaborative and approachable leadership style.
• Genuine warmth, authenticity, and relatability.
• Ability to work effectively across differences in identity, background, and perspective.
• Commitment to self-awareness and ongoing learning about identity and positionality.

Benefits

This is a full-time, salaried, benefits-eligible position.

Pay

Based on qualifications and prior experience, this position offers an anticipated salary range of approximately $150,000–$175,000 annually.

About Fayerweather Street School

Fayerweather Street School (FSS) is a co-educational independent day school enrolling approximately 200 students in Pre-Kindergarten through 8th grade. Located in the Fresh Pond neighborhood in Cambridge, Fayerweather offers a progressive, hands-on experiential learning environment where the pace of childhood is respected, and where children develop a love of learning, know how they learn best, and have voice and agency in their school community. The school helps young people develop the knowledge, skills, and awareness to flourish in a complex, diverse, and increasingly interdependent world. Fayerweather is committed to building a diverse, welcoming, and equitable community in which compassion, humor, and respect are woven throughout the curriculum and spirit of the day.