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Peconic Community School

Head of School

Peconic Community School, Southold, New York, United States

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Peconic Community School (PCS) is a vibrant, progressive, and deeply human-centered learning environment located on the North Fork of Long Island, a bucolic seaside region approximately two hours east of New York City. Rooted in

project-based ,

place-based , and

social-emotional

learning, PCS serves children from early childhood through middle school with a mission to nurture creativity, compassion, critical thinking, and community. We believe that education should be joyful, purposeful, and deeply connected to making the world around us a better place.

The Board of Trustees has launched a search for a new Head of School. The Board and community will look to the new Head to provide strategic vision and leadership. Priorities include:

Continuing to foster the robust academic and curricular programming – and the infrastructure that supports it – to help maintain excellence and uphold PCS's educational philosophy.

Grow the school's reach and reputation, successfully executing fundraising for the annual fund and capital campaign.

Advancing improvements and renovations to the school campus and facilities to help use "place" as another key way to realize our mission.

Serve as a key advocate and leader in the schools continued efforts in areas of diversity, equity and inclusion.

About the Role We are seeking a

dynamic, experienced, visionary and collaborative leader

with a deep belief in child-centered schools and a passion for sustaining and growing a thriving learning community. This is a full-time, year-round leadership role reporting to the Board of Trustees, with lead responsibility for all educational, operational, and strategic dimensions of the school. The Head of School works closely with a small leadership team and directly supervises all staff.

Fast Facts:

Students enrolled: 98

Faculty and staff: 27

Annual operating budget: $2.9M

Grades served: 2 years through Grade 8

Community Partners: 100+

The Ideal Candidate We are looking for an experienced educator and leader who:

Believes deeply in progressive education , especially child-centered, project-based and place-based learning

Has

child development expertise

and

classroom experience

in a progressive or project-based school setting

Understands that

happy teachers make happy students

and is committed to supporting and empowering staff

Is a

compassionate, skilled communicator

—with students, staff, and especially with parents as true partners

A skilled

problem solver , adept at navigating conflict and troubleshooting

Values

emotional intelligence

and fosters a culture of inclusion, equity, and kindness

Is

comfortable wearing many hats

in a small school setting, moving fluidly between instructional leadership, operations, development, HR, marketing, and finances

Leads with humility, curiosity, and integrity— with trust in a collaborative team

Thrives in a role that balances

big-picture visioning

with

hands-on day-to-day leadership

Key Responsibilities Educational Leadership

Uphold and evolve PCS’s educational philosophy in alignment with progressive, project-based, and place-based pedagogy

Work closely with trustees and other key constituents on the school’s strategic direction and campus improvement plans

Support faculty in designing and delivering meaningful, inquiry-based learning experiences. Empower faculty and staff through delegation of responsibilities while retaining ultimate accountability.

Foster a culture of reflective practice, innovation, and professional growth

Recruiting and retaining outstanding faculty and staff as well as student population

Serve as a key advocate and leader in the schools continued efforts in areas of diversity, equity and inclusion.

Collaborate closely with other directors, including the Director of Teaching and Learning, Program Director and Director of Admissions

Community & Culture

Maintain a warm, inclusive, and emotionally intelligent school culture for children, families, and staff

Foster an environment for culturally responsive sustaining practices and pedagogy

Lead with empathy and clarity, modeling open communication and deep respect for each community member

Act as a trusted liaison with parents, building strong partnerships through active listening, collaboration, and transparency

Support and expand the various programs PCS runs for the community at large

Fundraising & Outreach

Serve as an ambassador for PCS’s mission within the local community and to independent schools regionally and beyond.

Partner with the Board and development team to lead strategic fundraising initiatives and campaigns

Cultivate, solicit, and steward relationships with donors, foundations, and community partners

Strengthen partnerships with local nonprofits and businesses to advance shared goals

Oversee and support community events and outreach efforts that raise awareness and engagement

Administrative & Operational Oversight

Oversee day-to-day school operations, including scheduling, compliance, health/safety, and HR

Work closely with the Board of Trustees on budgeting, finances, and strategic planning

Lead and support marketing and enrollment initiatives to share PCS’s story and expand its reach

Steward relationships with donors and lead fundraising efforts to ensure long-term sustainability

Student Support

Provide leadership in promoting a safe, inclusive, and supportive school climate that fosters student growth and well‑being.

Assist in the management of student behavioral concerns, working closely with staff, students, and families to ensure consistent and developmentally appropriate approaches.

Collaborate with counselors, learning specialists, and faculty to proactively identify and address academic, social‑emotional, and behavioral needs.

Attend and contribute to child study meetings, ensuring appropriate interventions, accommodations, and next steps are implemented and followed up.

Maintain open, empathetic, and proactive communication with parents/guardians regarding student concerns, progress, and plans for support.

Support teachers in developing and implementing effective classroom management strategies and differentiated instruction to meet diverse student needs.

Stay informed about students with IEPs, 504 Plans, and other support documents; ensure school-wide awareness and implementation of accommodations as appropriate

Qualifications

At least 5 years of teaching and leadership experience in progressive and/or child-centered education

Deep understanding of child development and inquiry-based pedagogy

Demonstrated success in organizational leadership, communication, and team management

Experience that includes: an ability to lead organizations through continuous improvement ; experience with fiscal management ; successful track record of recruiting and maintaining faculty, staff and student body

Strong organizational and communication skills; adept at managing multiple priorities

Proven ability to foster strong relationships with families, staff, and the wider community

Experience with school operations, including budgeting, HR, fundraising, and compliance

Master’s degree in education, school leadership/administration, non‑profit administration, or a related field preferred

Why Join Peconic Community School? Peconic Community School is a close-knit, joyful learning community on the North Fork of Long Island, where children are known, seen, and celebrated. The Head of School will be supported by a dedicated team of progressive educators and a highly engaged and supportive Board of Trustees. This is an exciting opportunity to build on a strong foundation and help shape the future of a beloved and mission-driven school with strong governance.

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