Chief Financial Officer (CFO)

Upland Country Day School — Kennett Square, PA

Upland Country Day School, a Pre-K through Grade 9 independent school of roughly 200 students in Kennett Square, PA, seeks a Chief Financial Officer to join its leadership team. This is a full-time, twelve-month position reporting directly to the Head of School.

Upland is entering its first full year under new leadership, with a clear set of priorities around enrollment, program growth, fundraising, and community building. The CFO will be a close strategic partner to the Head of School in that work, not simply the steward of the school's books. We are looking for a leader who can bring financial discipline and long-term thinking to a small, tight-knit school community, and who is energized by the idea of helping shape Upland's next chapter.

The CFO oversees the school's financial management, business office operations, human resources, facilities, technology infrastructure, and legal and compliance matters. This is a leadership team position with direct engagement with the Board of Trustees, particularly the Finance and Buildings and Grounds Committees.

The ideal candidate is:

● A strategic partner who brings clear, actionable financial insight to the Head of School and Board, and who helps translate strategic priorities, including enrollment growth and fundraising, into sound financial planning.

● A trusted operator who runs a tight, accurate business office: budgeting, accounts payable and receivable, payroll, benefits, and audit.

● A collaborative colleague who works well across a small administrative team, including close partnership with the Director of Advancement on gift accounting, campaign reporting, and endowment stewardship; with Admissions on structuring tuition assistance around a defined, available pool rather than an open-ended commitment; and with the Grounds crew on maintenance budgeting and a model for addressing short-term repairs.

● A steady hand on risk, comfortable navigating employment law, contracts, insurance, and compliance matters as they arise in a school setting.

● Comfortable with modern systems, including budgeting and financial software, HR/payroll platforms, and the judgment to know where technology can create efficiency in a small office.

Budgeting and Finance:

● Maintain accurate, continuous records of the school's cash position and overall financial health.

● Prepare monthly operating statements for the Head of School and Board of Trustees, and monthly expenditure reports by budget center.

● Lead the annual budgeting process on a timeline that supports Board approval of tuition each winter.

● Oversee the annual independent audit.

● Manage purchasing, banking, investments, payroll, and benefits administration.

● Support enrollment-linked financial modeling, including tuition setting and financial aid budgeting, in partnership with the Head of School and Admissions.

● Serve as staff liaison to the Finance Committee of the Board.

● Manage institutional risk and insurance coverage.

● Oversee vendor contracts and performance.

Human Resources:

● Own HR policy, employee files, and compliance with applicable employment law.

● Advise the Head of School on compensation and benefits decisions.

● Support hiring, onboarding, and performance management processes across the school.

Facilities and Technology:

● Partner with the Director of Facilities on building maintenance, capital planning, and the equipment replacement budget, including oversight of the ice rink and the lease arrangement with CCSC.

● Partner with the Director of Technology on the school's technology plan and capital and operating technology budgets.

● Serve as staff liaison to the Buildings and Grounds Committee of the Board.

Legal and Compliance:

● Manage day-to-day legal matters affecting the school, including contracts and regulatory compliance, engaging outside counsel as needed.

● Ensure the school's policies and practices meet current legal requirements across HR, finance, and operations.

We welcome candidates from independent schools as well as strong financial leaders from the corporate or nonprofit sector, particularly those drawn to mission-driven work. What matters most is a track record of sound financial leadership, sound judgment, and the ability to build trust quickly with a small, close community. Candidates without prior school experience should expect a genuine onboarding runway to learn school-specific systems and rhythms.

● Bachelor's degree required; CPA or equivalent financial credential strongly preferred.

● A minimum of five years of progressively responsible financial leadership experience.

● Experience in HR, facilities, or compliance functions is a plus, though not required at the level a school business office demands; a willingness to grow into the full scope of the role matters more than having done all of it before.

● Strong written and verbal communication skills, and the judgment to communicate clearly with a Board of Trustees, including handling sensitive and confidential matters with discretion.

● Comfort with Quickbooks, Google Suite, and Microsoft Office; NAIS DASL experience a plus but not required.

[Salary range to be finalized] Full-time position with a competitive benefits package including medical and dental insurance, tuition remission, professional development support, and an employer-matched retirement plan.

Benefits:

403(b)
Dental insurance
Employee discount
Health insurance
Life insurance
Paid time off
Professional development assistance
Tuition reimbursement
Vision insurance

Education:

Bachelor's (Required)

Experience:

Financial services: 5 years (Preferred)

License/Certification:

CPA (Preferred)

Work Location: In person

Upland Country Day School

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