Visionary Head of School & Strategy Leader

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

Benefits offered by this job

Comprehensive benefits

Time off package

Job summary

Community Charter School of Cambridge is seeking a Head of School to serve as the chief executive officer, reporting to the Board of Trustees and guiding mission, vision, and values. You will navigate enrollment trends, lead strategy across academics, culture, and operations, and partner with the Board on governance and external relations.

The role requires deep commitment to students from diverse backgrounds, strong leadership in a charter environment, and the ability to manage budgets, labor

Qualifications

• Senior leadership experience in schools, charter organizations, districts, nonprofits, or complex mission-driven organizations.
• Experience leading enrollment strategy or sustainable growth initiatives.
• Track record of improving student outcomes and organizational performance.
• Experience working in diverse urban multilingual educational environments.
• Experience translating strategy into measurable execution.
• Ability to recruit, develop, manage, and retain leaders and staff.
• Experience with budgeting, financial statements, resource allocation, and risk management.
• Familiarity with unionized environments and collective bargaining.

Responsibilities

• Translate CCSC’s mission and values into priorities, goals, and actionable strategies to secure sustainability and growth.
• Lead strategy across academics, culture, operations, external relations, and governance.
• Represent CCSC in union relations, compliance, and charter renewal processes.
• Oversee financial health, facilities, and operations in alignment with strategic priorities.
• Collaborate with the Board and leadership to ensure timely information and fiduciary oversight.

Skills

Senior leadership experience

Enrollment strategy

Budget management

Staff recruitment and development

Union and labor relations

Massachusetts charter-school law

Communication skills

Job description

Community Charter School of Cambridge is seeking a Head of School to serve as the chief executive officer, reporting to the Board of Trustees and guiding mission, vision, and values. You will navigate enrollment trends, lead strategy across academics, culture, and operations, and partner with the Board on governance and external relations.

The role requires deep commitment to students from diverse backgrounds, strong leadership in a charter environment, and the ability to manage budgets, labor