HEAD of SCHOOL 2027-28 (Full Time)

Community Charter School of Cambridge; Boston (MA); On-site; USD 150,000 - 200,000; Full time

Job summary

Community Charter School of Cambridge (CCSC) seeks a Head of School to become the chief executive officer, reporting to the Board of Trustees. You will guide strategy, academics, culture, operations, and external relations in a unionized charter context, while navigating enrollment trends for long-term sustainability.

The ideal candidate brings significant senior leadership experience, expertise in enrollment strategy, and a proven record of improving student outcomes in urban, multilingual

Qualifications

• Senior leadership experience in a school, charter organization, district, nonprofit, or similar mission-driven entity.
• Experience leading enrollment growth or sustainability initiatives.
• Track record of strengthening organizational performance and student outcomes.
• Experience with budgets, financial statements, and risk management.
• Familiarity with unionized environments and collective bargaining a plus.
• Strong strategic planning and execution capabilities.
• Proven ability to recruit, develop, and retain leaders and staff.
• Experience working in urban, multilingual, and diverse communities.

Responsibilities

• Translate mission, vision, and values into strategic priorities and measurable goals.
• Lead strategy, academics, culture, operations, and external relations.
• Oversee enrollment growth and sustainability to support long-term viability.
• Ensure compliance with laws, charter conditions, and renewal processes.
• Provide financial oversight and risk management for facilities and operations.
• Collaborate with the Board and development staff on fundraising strategy.
• Represent management in union relations and labor matters.
• Partner with Board to fulfill fiduciary and governance responsibilities.

Skills

Senior leadership

Enrollment strategy

Budgets & finance

Unionized environment

Strategic planning

Stakeholder relations

Staff development

Job description

The Community Charter School of Cambridge (CCSC), grades 6-12, with students from Cambridge, Chelsea, Everett, Revere, and other Massachusetts cities and towns, seeks to hire a Head of School beginning July 1, 2027.

Founded in 2005 with a commitment to ensuring all students have access to an education that couples high expectations with high levels of individualized support, CCSC is consistently recognized as an exemplar in the community, across the state, and nationally. We are a student and family centered community whose vision, mission and values are represented in the image on the right.

ROLE SUMMARY

The Head of School (HoS) is the chief executive officer of CCSC, accountable to the Board of Trustees for advancing the school’s mission, vision, and values and navigating broader trends in declining school enrollments to ensure long-term sustainability. The HoS leads strategy, academics, culture, operations, Board and external relations in a unionized, charter public school context.

KEY RESPONSIBILITIES

The following items represent overarching areas of responsibility; please consult this full job description for more details on each area:

• Mission, Vision, Values and Strategy: Translate CCSC’s mission, vision, and values into clear priorities, measurable goals, and actionable strategies to secure organizational sustainability through consistent growth in enrollment.
• Academic Program and Student Outcomes: Collaborate with other leaders to set academic priorities, monitor progress, ensure accountability for student success across the organization, and adjust programs accordingly.
• People Leadership and Organizational Effectiveness: Nurture and maintain a strong, positive, mission-aligned culture that promotes trust, employee accountability, inclusive leadership practice, and collective responsibility.
• External Relations, Development, and Advocacy: Serve as the face of CCSC in building and sustaining strong relationships with the school community, DESE, elected officials, current and potential donors, and the public. Partner with the Board and development staff on leading fundraising strategy.
• Union and Compliance: Represent management in CCSC’s relationship with the union; ensure compliance with laws, charter conditions, and accountability measures; and successfully lead CCSC through charter renewal cycles.
• Financial and Operational Oversight: Provide leadership for financial health and risk management. Ensure all facilities and operational systems are safe, efficient, and aligned with strategic priorities.
• Board Partnership and Governance: As an ex officio member of the Board of Trustees, provide timely information necessary for the Board to fulfill its fiduciary, strategic, and oversight responsibilities and seek Board input on major strategic, financial, legal, reputational, and organizational matters.

REQUIRED QUALIFICATIONS AND EXPERIENCE

The successful candidate will bring:

• A deep commitment to CCSC’s mission and to preparing students from diverse backgrounds for college, career, and civic success;
• Significant senior leadership experience in a school, charter organization, district, nonprofit, or similarly complex mission-driven organization;
• Experience leading enrollment strategy or sustainable organizational growth initiatives;
• A record of strengthening organizational performance and leading initiatives improving student outcomes;
• Experience working in the communities served by CCSC or in a comparable urban, multilingual, and diverse educational environment;
• Experience leading strategic planning and translating strategy into measurable execution;
• Demonstrated ability to recruit, develop, manage, and retain talented leaders and staff;
• Experience managing budgets, financial statements, resource allocation, and organizational risk;
• Experience navigating complex stakeholder environments, including Boards, public agencies, families, community partners, and employee organizations;
• Experience with collective bargaining, labor relations, or other unionized environments;
• Strong knowledge of—or the ability to quickly develop expertise in—Massachusetts charter-school law, DESE requirements, and charter accountability processes;
• Outstanding written, verbal, and interpersonal communication skills; and
• The judgment, integrity, resilience, and follow-through required to lead through ambiguity and competing priorities.

PREFERRED QUALIFICATIONS

• Experience as a Head of School, superintendent, principal, chief executive, chief academic officer, or senior charter-school leader;
• Experience leading a unionized school or education organization;
• Experience with charter renewal, authorizer relations, or state accountability processes;
• Experience improving outcomes for students with disabilities and multilingual learners;
• Experience with fundraising, donor cultivation, or public-private partnerships; and
• School leadership experience including program development and instructional coaching.

REPORTING RELATIONSHIPS

The Head of School reports to a 12-member Board of strong charter advocates, representing the public, private, and non-profit sectors. Direct reports currently include the Principal, Director of Curriculum & Instruction, Director of Student Support, Director of College & Career Counseling, Director of Operations and Technology, Director of Human Capital, Director of Communications & Development, and Head of Finance & Accounting.

COMPENSATION

The salary for the Head of School role ranges from $150,000 to $200,000 depending on experience, plus a comprehensive benefits and time off package.