The Executive Director and Head of School at The Liberty School leads the organization overall, acting as both the public face and the driving force behind its impact. Balancing strategic vision with hands-on management, this leader ensures that the organization remains financially stable, operationally excellent, and impactful at delivering a high-quality, rigorous, joyful educational program consistent with The Liberty School's vision and mission.

Reporting directly to the Board of Trustees, the Executive Director and Head of School is responsible for setting and implementing the organization's long-term strategy while managing day-to-day operations. This position oversees the full range of the school's program, spanning across academic program development, fundraising, financial management, staff leadership, and community engagement.

Key Responsibilities

1. Leadership and Management

• Vision and Strategy: Sustain momentum toward achieving the school's vision, developing strategies to deliver on the organization's mission and goals.
• Board Collaboration: Develop, maintain, and support a strong Board of Trustees. Work closely with the board to define and communicate the organization's vision and direction.
• Team Leadership: Recruit, hire, and manage a strong leadership team and staff. Foster a positive and inclusive culture and work environment.

2. Development and Community Relations

• Development: Devise and manage plans to attract support for and cultivate engagement with the school's mission and impact.
• Advocacy: Represent The Liberty School in local and national communities and advocate for its mission and programs.
• Partnerships: Build and maintain relationships with key stakeholders, community leaders, and current and prospective partners that could contribute to the school's impact.
• Community Engagement: Oversee the development and implementation of marketing, communications, and community-building strategies to enhance the organization's public image and outreach. Actively engage current and past families, student alumni, donors, foundations, and associations whose interests align with the school's mission.
• Fundraising: Orchestrate activities designed to attract donations and financial support for the school's mission, including individual contributions, grants, major gifts, and fundraising events.

3. Operational Oversight

• Educational Program Management: Maintain ongoing programmatic excellence, rigorous program evaluation, and consistent quality and outcomes.
• Operating Efficiency: Ensure the planning and execution of operational functions—such as IT, HR, and facilities—support the school's mission with appropriate overhead.
• Compliance and Policy Management: Ensure that the organization adheres to all legal, ethical, and regulatory requirements. Develop and implement policies to support smooth operations, impactful educational programs, and positive student experiences.

4. Financial Management

• Budgeting: Develop and manage the organization's budget. Manage ongoing financial stability and sustainability.
• Financial Reporting: Ensure accurate and timely financial reporting to the board and other stakeholders.

5. Admissions and Student Experience

• Planning and Process Oversight: Manage a clear and consistent process for admission to The Liberty School, including managing the applicant pool, managing process steps, and documenting admissions decisions.
• Prospective Student Cultivation: Implement marketing and communication plans with the goal of maintaining at-capacity enrollment and a waiting pool of qualified applicants.
• Communication: Provide prospective families with clear and timely information about the admissions process status.
• Financial Aid: Ensure scholarships and financial aid are awarded and communicated, in partnership with the school's Scholarship Committee.

Skills and Qualifications

• Leadership Skills: Ability to inspire and motivate staff, students, volunteers, donors, and the community. Proven experience in strategic planning and execution.
• Financial Acumen: Strong understanding of non-profit financial management. Experience with budgeting, financial reporting, and fundraising.
• Communication Skills: Excellent written and verbal communication skills. Able to effectively represent the organization to stakeholders and the public.
• Problem-solving Skills: Strong analytical and problem-solving abilities. Proven track record at making sound decisions under pressure.
• Interpersonal Skills: Ability to build and maintain strong relationships with the board, staff, students and their families, donors, and community partners. Strong negotiation and conflict-resolution skills.
• Commitment to Equity: A passion for inclusive and equitable access to education. Experience creating environments that support every individual to thrive.
• Experience: Requires 5-10 years of experience in general management, such as leading a small school, non-profit, or business. Experience with education or learning differences is a plus.