Position Summary 

The CFOO is 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 following prior operating deficits. Core operational teams are in place; the CFOO provides strategic oversight, integration, and accountability across functions. 

Reporting Structure 

• 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

Chartwell School provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. 

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

About Chartwell

For 40 years, Chartwell School has been educating students, who have been diagnosed with a specific language-based learning disability, in a way that provides them with the academic skills necessary to be successful in future educational endeavors. We believe that all of our students are capable learners who can discover new pathways to learn skills and apply knowledge. Chartwell offers a full academic program, with well-structured, multi-sensory teaching in all classes.  Our fully accredited curriculum includes all areas of reading and language instruction, mathematics, social studies, science, health and fitness, the arts, technology, and a wide array of enrichment activities.  Students build academic skills one layer at a time.  Each layer integrates higher-order thinking, creativity, perseverance, and practical problem-solving.  Chartwell teaches students to overcome academic challenges and helps them grow in self-reliance, character, and respect for the effort and abilities of others.

Mission

Chartwell empowers students with dyslexia and associated learning differences to unlock their full potential. We provide a college preparatory, strength-based program that gives students the skills, strategies, tools, and mindset needed to become successful lifelong learners. We share our expertise through partnerships and outreach initiatives to transform education. 

Vision 

Chartwell aspires to show the world that young people with language-based learning differences and diverse learning styles and profiles can be among the most creative, productive, and valuable members of any community. We further aim to inspire others to get to know, understand and value these students from very young ages and to help them realize their full potential. We seek to see them develop into confident young people and adults, committed to lifelong learning and equipped with the knowledge, skills and social and emotional competencies to achieve their goals.

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

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 

About Chartwell School

The mission of Chartwell School is to diagnostically educate students with specific learning variations, including dyslexia, in a way that provides them with the academic skills, confidence, creativity and perseverance necessary to meet the challenges of mainstream education and lifelong learning. Our students have average or better intelligence but may have struggled in traditional classrooms due to dyslexia or other learning disabilities and academic challenges. We provide co-ed students ages 5-18 with the skills, knowledge, and tools they need to succeed. A Chartwell education includes: small class sizes, a 1:5 teacher-to-student ratio, attention to learning styles, emphasis on social skills and character building, multi-sensory learning, integrated technology, enrichment activities, sports, and a healthful, green campus.

Connections working at Chartwell School