Head of School

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.

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.

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
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  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.

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,…