| Chartwell School is in search of a senior leader and strategic partner to the Head of School and Board, responsible for the school’s financial sustainability, operational effectiveness, and long-term stability. This role leads the school’s financial stabilization efforts, including identifying structural vs. temporary deficits, aligning resources to mission priorities, and implementing a multi-year path to sustainability. The CFOO oversees finance, operations, facilities, technology, human resources, and risk management, ensuring disciplined, transparent, and data-informed decision-making across the organization. Institutional Context Chartwell School is a nonprofit nonpublic school serving students with dyslexia and language-based learning differences. The school is in a period of leadership transition and continued financial stabilization. Core operational teams are in place; the CFOO provides strategic oversight, integration, and accountability across functions. - Reports to: Head of School
- Partners: Board of Trustees, Finance & Audit Committees
- Oversees: Finance, HR, Facilities, IT, and Operations
Core Responsibilities Financial Strategy & Management - Lead a 3–5 year financial sustainability plan
- Diagnose and address structural financial drivers
- Develop scenario-based models (enrollment, tuition, staffing, fundraising)
- Oversee budgeting, forecasting, cash flow, and financial reporting
- Ensure strong internal controls and financial discipline
Board Partnership & Governance - Serve as primary financial liaison to the Board and committees
- Deliver clear, actionable financial reporting and analysis
- Support scenario planning, risk assessment, and decision-making
- Manage key financial cycles (tuition-setting, budget approval)
Operations & Infrastructure - Oversee Facilities, IT, and operational systems
- Lead cross-functional improvements to increase efficiency and cost control
- Provide oversight of capital projects, deferred maintenance, and vendors
- Ensure technology and data systems support institutional needs
Human Resources Oversight - Provide executive oversight of HR strategy and compliance
- Support HR leadership in employee relations and performance systems
Compliance, Risk & Stewardship - Ensure compliance with GAAP, nonprofit regulations, and accreditation requirements
- Lead audit, 990/5500 filings, and financial reporting integrity
- Oversee risk management, insurance, and fiduciary responsibilities (including 403(b))
Advancement & Revenue Alignment - Partner with Admissions and Advancement on enrollment modeling and financial aid strategy
- Align fundraising and restricted funds with financial priorities
- Support development of diversified revenue streams
Leadership & Culture - Build and lead a high-performing finance and operations team
- Foster a culture of accountability, transparency, and financial discipline
Year One Priorities - Establish accurate, timely financial reporting and cash flow visibility
- Conduct operational assessment (HR, IT, Facilities) to identify risks and gaps
- Strengthen systems, controls, and processes
Leadership Profile - Strategic, analytical, and solutions-oriented
- Comfortable navigating complex financial models with clarity and candor
- Strong communicator with both financial and non-financial stakeholders
- Systems thinker with the ability to translate strategy into execution
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