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Community Charter School of Cambridge Community Charter School of Cambridge - Cambridge, Massachusetts Open in Google Maps Head of School 2027-28 Job Details Job ID: 5955137 Application Deadline: Dec 18, 2026 11:59 PM (UTC) Posted: Oct 08, 2026 12:00 AM (UTC) Starting Date: Jul 1, 2027 Job Description 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 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, the Department of Elementary and Secondary Education (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 to fulfill its fiduciary, strategic, and oversight responsibilities and seek Board input on major strategic, financial, legal, reputational, and organizational matters. Position Type: Full-time Salary: $150,000 to $200,000 Per Year Job Categories: Administration > Principal/Dean/Head of School Welcome to Community Charter School of Cambridge Community Charter School of Cambridge (CCSC) is a public charter school that serves students in grades 6-12. Focusing on post-secondary success for all students, CCSC combines high academic and behavioral standards with an environment of unconditional affection, acceptance, and belonging in which all students can thrive. Community Charter School of Cambridge (CCSC) is a public, tuition-free, college preparatory charter school. Located in the Kendall Square area near MIT, the school serves 360 students in grades 6-12. CCSC remains one of the highest ranking middle/high schools in the greater Boston area. The school has received an official state commendation and was runner-up for the prestigious Pozen Prize for Charter Schools. Job Requirements 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. Contact Information Board of Trustees , Board of Trustees 245 Bent Street Cambridge, Massachusetts 02141 Phone: 6173540047 Email: djillson@ccscambridge.org Map The content you submit, offer, contribute, attach, post, or display (each a “Submission”) will be viewed by other users of the service who may or may not be accurately representing who they are or who they represent. 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