Head of Finance, Payroll & Operations

The Country School is seeking a strategic, collaborative, and experienced Director of Finance & Operations to serve as a key member of the senior leadership team. Reporting directly to the Head of School, this individual provides leadership across finance, operations, human resources, facilities, and risk management while helping ensure the long-term sustainability and mission alignment of the school.

The Director of Finance & Operations oversees the school’s financial strategy and daily business operations, leads operational planning and systems improvement initiatives, and partners closely with school leadership on budgeting, enrollment forecasting, compensation planning, and strategic decision-making. This role also works collaboratively with admissions, advancement, communications, and academic leadership to support the overall health and success of the school community. Additionally, the Director of Finance & Operations collaborates closely with the Board of Trustees Finance Committee Chair.

The ideal candidate is a thoughtful and solutions-oriented leader who communicates effectively with varied audiences, builds strong relationships across the community, and brings sound judgment, integrity, and operational excellence to the role. Finance, Strategy, Planning & Operations

Provide strategic leadership and oversight for the school’s financial operations and long-range financial sustainability.

Lead the development, administration, and monitoring of the annual operating budget and multi-year financial planning process.

Prepare and present financial reports, forecasts, and cash flow analyses for the Head of School, Board of Trustees, and Finance Committee.

implement investment decisions of the investment committee; and coordinate with investment managers, ensuring effective endowment allocations, performance, and reporting.

Lead the annual financial audit process and ensure timely completion of all tax filings and regulatory reporting requirements.

Ensure compliance with all applicable federal, state, and local financial and reporting requirements.

Oversee the school’s human resources function, including employee benefits administration, compensation practices, policy development, compliance, and employee relations in partnership with school leadership.

Collaborate with the Head of School and senior administrators on hiring, onboarding, performance management, organizational planning, and employment matters.

Operations & Facilities

Provide strategic oversight of campus operations, facilities planning, maintenance, safety initiatives, and vendor management.

Lead the Business Office functions, including accounting, payroll, budgeting, financial modeling, risk management, and operational reporting.

Partner with the Director of Facilities & Technology to oversee the physical plant, campus infrastructure, capital improvement projects, and long-term maintenance planning.

Oversee the administration of all insurance programs including property, casualty, medical, workers’ compensation, and D&O.

Community Participation

Serve on the school’s senior administrative team and lead or participate in several other committees.

Prepare committee materials, present financial and operational updates, and partner closely with committee chairs and trustees.

Collaborate effectively with admissions, development, communications, main office, and academic leadership to support institutional goals.

Represent the school professionally and positively within the broader community and maintain collaborative relationships with local organizations, partners, and public agencies.

Demonstrate a commitment to fostering an inclusive and welcoming community and participate in ongoing professional development related to diversity, equity, inclusion, and belonging.

Bachelor’s degree required, MBA or CPA preferred.

Experience leading financial planning, budgeting, operational strategy, and organizational management initiatives.

however, candidates new to schools with strong financial and operational leadership experience are encouraged to apply.

Experience in human resources management, employee benefits, payroll, administration, and employment compliance.

Demonstrated ability to communicate complex financial and operational information clearly to diverse audiences.

Demonstrated experience in the development of analytical tools for strategic decision-making such as key cost drivers, competitive analysis, market analysis, organizational strengths and weaknesses.

Knowledge of business and not-for-profit accounting policies, procedures, practices, and software programs.

Strategic thinker with strong business and financial acumen.

Strong organizational skills with the ability to manage multiple priorities and deadlines.

Sound judgment, discretion, and integrity in handling confidential and sensitive matters.

Ability to navigate complex organizational dynamics with professionalism and emotional intelligence.

Collaborative leadership style with a commitment to building strong relationships across the school community.

Commitment to equity, inclusion, and belonging practices.

The Country School Diversity Statement

The Country School believes that seeking and valuing diversity of ideas, experiences, and identities, developing meaningful connections, and fostering a sense of belonging are vital to each student’s education and growth. A diverse, inclusive, and equitable school community is critical for preparing students for a role in a complex, pluralistic, and interconnected society. We actively see and value the differences of our school community, among them ability/disability, age, ethnicity, faith traditions, family composition, gender identity and expression, learning styles, race, sexuality, and socio-economic status.

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