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

Qualifications

• Bachelor’s in Finance, Accounting, or related field (MBA/CPA preferred)
• 7–15+ years of senior financial leadership experience
• Independent school experience preferred
• Demonstrated success in financial planning, business operations, and Board partnership

About Chartwell School

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