Freire Charter School Wilmington, Head of School

Edgility Search•Wilmington, DE

12d•$140,000 - $170,000

About The Position

The Head of School serves as the instructional, cultural, and operational leader of Freire Charter School Wilmington. This is an opportunity for a hands-on, student-centered school leader to lead a rigorous and demanding school while preserving the heart and humanity of a small, mission-driven community. Believes deeply in educational equity, college access, and the transformative power of public education Brings an entrepreneurial mindset – energized by building systems, solving problems, and turning vision into action Leads with both empathy and resolve, balancing care for people with clear expectations and accountability Thrives in a high-autonomy, “scrappy” environment that requires initiative, adaptability, and follow-through Is highly visible with students, present and trusted with staff, and relentlessly focused on results Effectively challenges and supports teachers and staff through a culture of continuous improvement The Head of School will be responsible for FCSW’s enrollment strategy, clarifying vision, strengthening academics, rebuilding trust, and translating good ideas into consistent practice. Success will require balancing strong relationships with firm expectations, and innovation with follow-through.

Requirements

An experienced school-based leader (Principal or Head of School preferred) with a strong foundation as a classroom teacher – ideally at the secondary level – and a deep understanding of the daily realities faced by educators and students.
A mission-aligned, equity-driven leader who believes in Freire’s commitment to student voice, social justice, and college access, and can translate values into daily practice.
An entrepreneurial leader who can design and execute creative strategies to drive student recruitment, enrollment growth, and long-term retention.
A strong instructional leader with demonstrated success improving academic outcomes, particularly for students entering significantly below grade level.
An effective people manager and culture builder who can balance warmth with accountability, avoid micromanagement, and develop leadership in others.
A clear, consistent communicator who values transparency, listens actively, and follows through on commitments.
An experienced change manager with the resilience, courage, and emotional steadiness to lead through complexity, resistance, and ambiguity.
Organized, detail-oriented, and operationally strong, with experience managing budgets, systems, and competing priorities.

Nice To Haves

Ideally familiar with the Delaware and/or Wilmington education landscape (preferred but not required).

Responsibilities

Lead and execute a comprehensive student enrollment and retention strategy, with the goal of significantly increasing and sustaining student enrollment;
Serve as the public face of the school to prospective families, current families, community partners, and the broader Wilmington and Delaware education and civic landscape;
Build trust with families through consistent, transparent, and culturally responsive communication;
Effectively recruit students by strengthening outreach, admissions processes, and the school’s value proposition;
Cultivate strategic partnerships that expand student opportunity, enhance the school’s reputation, and support enrollment growth.
Lead the design and execution of a rigorous, coherent, and truly college-preparatory academic program, with a particular focus on improving Math and ELA outcomes
Strengthen curriculum alignment, support effective instruction, and ensure students build foundational skills while progressing toward grade-level expectations
Partner closely with Freire Network academic leaders and resources to leverage shared expertise, tools, and best practices in service of student achievement
Provide meaningful opportunities for students to excel, thrive, and see themselves as capable scholars.
Establish a consistent, joyful, and accountable school culture that prioritizes safety, belonging, and high expectations for behavior and effort;
Strengthen discipline systems, reinforce norms (including dress code and attendance), and increase student engagement through electives, athletics, and enrichment.
Recruit, develop, retain, and support high-quality teachers and staff;
Improve teacher and leader retention by clarifying roles, strengthening feedback and evaluation systems, building leadership capacity;
Foster a culture of trust, collaboration, and professional growth.
Bring structure, clarity, and coherence to school operations, decision-making, and internal communication;
Design and implement clear systems, processes, and accountability measures across teams;
Manage the school’s budget responsibly, ensuring financial sustainability and alignment to strategic priorities;
Oversee facilities and operations to ensure a safe, efficient, and well-maintained learning environment;
Support fundraising and advancement efforts in partnership with the Board and Network;
Partner effectively with the Freire Network central office to leverage shared services, expertise, and infrastructure.