The Windward School, Chief Financial Officer

The Windward School invites nominations and applications for the position of Chief Financial Officer (CFO). This is a compelling opportunity for an experienced financial and operational leader to join one of the nation’s most highly regarded independent schools serving students with language‑based learning disabilities at a moment of scale, complexity, and institutional maturity. 

The CFO is the school’s senior financial leader and a key member of the Executive Team, serving as a trusted strategic partner to the Head of School and working closely with the Board of Trustees and its Finance Committee, and Faculty and Staff. Reporting directly to the Head of School, the CFO provides leadership across financial strategy, business operations, facilities, risk management, and human resources, ensuring the school’s long‑term financial strength, operational effectiveness, and alignment with mission. 

This role offers meaningful visibility, influence, and partnership within a mission‑driven organization known for excellence, rigor, and impact—both within its campuses and across the broader educational landscape. 

About The Windward School 

Founded in 1926, The Windward School is a premier, coeducational, independent day school dedicated to educating students in grades 1–9 with dyslexia and other language‑based learning disabilities. Windward serves approximately 950 students across three campuses—two in White Plains, New York, and one in Manhattan—and employs more than 400 faculty and staff. 

Windward is widely recognized for its research‑based, multisensory instructional program and its proven success in preparing students to return to mainstream educational settings. The school’s mission is grounded in the belief that difference is power, and its work is guided by a growth mindset, a deep commitment to impact, and a strong sense of community. 

In addition to its core academic program, Windward extends its influence through the Windward Teacher Training Program and The Windward Institute, sharing its expertise with educators and schools nationwide. Together, these enterprises contribute to a sophisticated and multifaceted organizational and financial environment. 

The CFO Role at Windward 

The Chief Financial Officer serves as the school’s lead financial and business officer, overseeing all aspects of financial management and operational infrastructure across Windward’s three campuses and affiliated programs. 

The CFO balances strategic leadership with hands‑on operational oversight, ensuring disciplined financial practices, transparent reporting, strong internal controls, and effective systems that support the school’s mission and growth. Working in close partnership with the Head of School, senior administrators, and the Board, the CFO helps align resources with institutional priorities while supporting a complex, people‑centered organization. 

Primary Areas of Responsibility 

Financial Strategy and Governance 

• Partner with the Head of School and Board of Trustees to develop and advance annual budgets, long‑range financial planning, and capital initiatives. 
• Serve as a primary financial advisor to the Finance Committee and other Board committees as appropriate. 
• Provide clear financial analysis, modeling, and reporting to support informed institutional decision‑making. 

Financial Management, Controls, and Compliance 

• Oversee and supervise all financial operations, including accounting, budgeting, forecasting, cash management, investments, payroll, and benefits administration. 
• Ensure timely, accurate, and transparent financial reporting, supported by strong internal controls, sound policies, and fiscal discipline. 
• Lead the annual audit and regulatory compliance efforts, including Form 990 preparation, serving as the primary liaison to external auditors and ensuring compliance with all applicable federal, state, and local nonprofit requirements. 

Human Resources Leadership and Partnership 

• Supervise and partner closely with the Director of Human Resources, providing strategic and operational oversight of payroll, benefits administration, and employment practices. 
• Ensure compliance with federal, state, and local employment laws and regulations, supporting equitable, consistent, and legally sound personnel processes. 
• Align financial planning with staffing and compensation and benefits strategies in support of Windward’s mission, culture, and long‑term sustainability. 

Facilities, Risk, and Enterprise Oversight 

• Supervise and partner closely with the Director of the Physical Plant to provide oversight of facilities, plant operations, vendor management, and long‑term capital planning across multiple campuses. 
• Lead enterprise‑wide risk management, including liability, property, and asset insurance programs and safety policies. 
• Maintain productive relationships with external partners, including auditors, banks, legal counsel, insurers, and key vendors. 

Institutional Partnership and Business Office Leadership 

Lead, develop, and advance the business office team, set clear expectations, foster professional growth, and promote a collaborative, service‑oriented culture that supports the school’s mission. 

Partner with senior administrators on enrollment, tuition, and financial aid strategy, including service on the Financial Aid Committee and stewardship of mission‑aligned access and affordability. 

Actively support the school’s diversity, equity, inclusion, and belonging commitments through financial leadership and partnership. 

Serve as a visible institutional leader and ambassador, representing the school in regional, state, and national finance and independent school associations and managing key internal and external partnerships critical to the school’s long‑term success. 

What Makes This Opportunity Compelling 

1. A senior leadership role at a nationally recognized school with a powerful and deeply mission‑driven purpose. 
2. Direct partnership with the Head of School and Board, with meaningful influence on institutional strategy and sustainability. 
3. Stewardship of a complex, multi‑campus and multi‑program financial and operational enterprise, supported by a $70 million annual operating budget. 
4. An organization recognized for rigor, discipline, and excellence across finance, academics, and operations, reinforced by a $60 million combined endowment and board‑restricted investment portfolio. 
5. The opportunity to contribute to a school that changes students’ lives and shapes practice across the broader field of education. 

What Success Looks Like 

In the first several years, the successful CFO will: 

• Establish strong, trusted relationships with the Head of School and Executive Team, Board of Trustees, business operations team, and faculty and staff. 

• Strengthen financial planning, forecasting, and reporting to support confident, forward‑looking decisions. 

• Ensure operational systems and financial practices effectively support Windward’s scale and complexity. 

• Lead with clarity, integrity, and collaboration, earning confidence across the institution. 

• Help position Windward for long‑term financial resilience while advancing its mission and strategic priorities. 

Candidate Profile 

The ideal candidate will bring: 

• Significant senior‑level financial and operational leadership experience, ideally in an independent school, nonprofit, or mission‑driven organization. 

• Deep expertise in budgeting, financial planning, accounting, and nonprofit financial leadership. 

• Experience working closely with Boards and Board committees. 

• Knowledge of human resources administration, employment practices, facilities, and risk management. 

• Strong communication, relationship‑building, and leadership skills. 

• A leadership style grounded in professionalism, discretion, service, and alignment with Windward’s mission and values. 

• A bachelor’s degree in accounting or finance is required; CPA, MBA, or similar credentials are preferred. 

 

The Search Process 

The Windward School has engaged NBOA Advisory Services to lead the search for its Chief Financial Officer. This search is being conducted in close partnership with Head of School Jamie Williamson and his CFO Search Committee.    

The salary range for this position is $300,000 – $325,000, commensurate with experience and qualifications. Additionally, The Windward School provides a comprehensive benefits program that supports employees’ personal well‑being and professional growth throughout their careers.   

All inquiries, nominations, and questions should be directed in confidence to: James Palmieri, CEO and Search Lead     

jpalmieri@nboaadvisoryservices.com         

Interested candidates are invited to submit a resume and letter of interest ASAP through the application link on this page. Applications will be reviewed on a rolling basis, and the position will remain open until filled. The desired start date is July 2026 or as soon as possible thereafter.  

Please do not contact the school directly. Interested candidates should apply using the form on this page at their earliest convenience. 

Equal Opportunity Statement 

The Windward School is an equal opportunity employer and provides equal employment opportunities without regard to race, color, national and ethnic origin, citizenship, age, sex (including pregnancy and gender identity), religion, disability, marital status, sexual orientation, military service, genetic information, or any other category protected by applicable federal, state, or local law to all employees and applicants for employment.