Stamford, Connecticut
St. Thomas, U.S. Virgin Islands
Posted: 08-Jun-26
Location: Cambridge, Massachusetts
Type: Full Time
Salary: $150,000 - $175,000
Preferred Education:
Please review the full position description linked here
On behalf of Educators Collaborative, Carol Santos is pleased to assist Fayerweather Street School in its search for a Director of Finance and Operations (DFO). This search offers 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.
The next 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.
Financial Leadership in a Relational Community
The Director of Finance and Operations will serve as a key strategic partner to the Head of School and an essential member of the school’s leadership team. Responsible for overseeing the school’s financial health and operational functions, the DFO will help ensure that Fayerweather’s resources, systems, and structures effectively support its educational mission and long-term sustainability.
Fayerweather is a deeply relational community where leadership is grounded in authenticity, accessibility, trust, and genuine human connection. Students experience adults as partners in learning—approachable, invested, and fully present—while also recognizing them as trusted adults and institutional leaders. This relational culture extends throughout the broader community and shapes how leadership is practiced across the school.
The successful candidate will understand that approachable leadership and clear authority are not contradictory, but mutually reinforcing within a progressive school environment. The next DFO must possess the emotional intelligence, judgment, and communication skills to navigate a highly engaged, values-driven community in which individuals often hold multiple roles and relationships within the institution.
Fayerweather presents a compelling opportunity for a leader who enjoys both strategic thinking and hands-on operational problem-solving and who can build trust across constituencies while helping the school navigate enrollment pressures, long-term financial planning, operational sustainability, and organizational growth. This role will be especially compelling to a leader who values mission-driven work, authentic relationships, and the opportunity to contribute meaningfully within a deeply engaged school community.
Leadership Profile
The successful candidate will demonstrate:
Financial and Operational Leadership
- Strong financial and operational leadership experience
- Expertise in budgeting, forecasting, financial analysis, and strategic planning
- Sound decision-making and organizational judgment
- Strong supervisory and people-management skills
- A proactive and solutions-oriented mindset
Relational and Community Leadership
- Excellent judgment and emotional intelligence
- A collaborative and approachable leadership style
- Genuine warmth, authenticity, and relatability
- Strong written and verbal communication skills
- The ability to explain financial information clearly to non-financial audiences
- The ability to navigate complex community dynamics with professionalism, empathy, and good humor
- The ability to establish healthy professional boundaries while maintaining authentic relationships and presence
Cultural Fluency and Equity
- Cultural fluency, including awareness of identity and the socioeconomic, racial, gender, and other social dynamics that shape it, is essential to how we teach and lead.
- The ability to work effectively across differences in identity, background, and perspective
- A commitment to self-awareness and ongoing learning about how your own identity and positionality shape your understanding of and relation to the people around you.
The ideal candidate will be someone genuinely energized by mission-driven work and who finds meaning in building relationships and systems that serve a community’s values. This is a role for someone who understands that authentic human connection and clear leadership reinforce one another.
Qualifications
Qualified candidates will demonstrate many of the following experiences and attributes:
- 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
- Experience communicating financial information to diverse audiences
- 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 a plus
- Experience in progressive, student-centered, or mission-driven educational settings a plus
How to Apply
Fayerweather Street School is committed to fostering a diverse, equitable, inclusive, and welcoming community and encourages applications from candidates whose experiences and perspectives will contribute to and strengthen that commitment.
This is a full-time, salaried, benefits-eligible position. Based on qualifications and prior experience, this position offers an anticipated salary range of approximately $150,000–$175,000 annually.
Fayerweather Street School is an equal opportunity employer and does not discriminate based on race, color, religion, national or ethnic origin, ancestry, sex, disabilities, sexual orientation, gender identity and expression, family composition, or any other status protected by applicable law.
Applications will be reviewed as they are received. Candidates interested in this position are asked to submit the following materials in a single merged PDF document, in the order listed:
- EC Candidate Summary Sheet (you’ll be asked to make a copy upon opening)
- Letter of interest addressed to the Head of School
- Current résumé
- A list of five or more professional references with contact information, including phone numbers and email addresses
- Disclosure Form (you’ll be asked to make a copy upon opening)
Please send applications and inquiries to:
Carol Santos, Partner, Educators Collaborative
csantos@educatorscollaborative.com
Please review the full position description linked here
