Director of Finance and Business Operations

About Stratton Mountain School

Stratton Mountain School (SMS) is an independent boarding and day school in Southern Vermont serving approximately 150 students with a dedicated team of approximately 60 employees. SMS combines a rigorous academic experience with competitive winter sports training in a close-knit school community.

SMS seeks an experienced, forward-thinking Director of Finance and Business Operations to lead the school’s financial management and business office. Serving as the school’s chief financial officer and a member of the Senior Leadership Team, this individual will report directly to the Head of School and supervise a business office team of three to four employees.

The Opportunity

This position offers the opportunity to shape the financial systems, practices, and planning that support SMS’s long-term success. The Director will combine strategic financial leadership with active oversight of daily business operations, ensuring that the school’s financial information is accurate, its resources are responsibly managed, and its leadership can make well-informed decisions.

The successful candidate will translate financial information into clear recommendations for the Head of School and Board of Trustees. They will anticipate challenges, evaluate opportunities, and provide practical guidance on cash flow, budgeting, staffing, enrollment, and capital investment.

We seek a leader who is comfortable both presenting a multiyear financial plan and working directly in QuickBooks, reviewing reconciliations, or resolving a payroll question.

Key Responsibilities:

Financial Strategy and Planning

• Serve as the primary financial adviser to the Head of School and a resource to the Board of Trustees and its finance committee.
• Lead the annual operating and capital budgeting processes in collaboration with school leadership and department heads.
• Develop and maintain multiyear financial projections that connect enrollment, net tuition revenue, staffing, compensation, fundraising, debt, and facilities needs.
• Maintain a rolling cash flow forecast that reflects the school’s seasonal revenue and spending patterns, identifies potential shortfalls early, and recommends appropriate action.
• Evaluate financial scenarios and explain the implications of proposed programs, staffing changes, tuition adjustments, and major expenditures.
• Provide timely financial dashboards and written reports that explain performance against budget, emerging risks, and decisions requiring leadership attention.

Accounting and Business Office Leadership

• Oversee all accounting and financial operations, including the general ledger, accounts payable and receivable, tuition billing and collections, payroll, banking, and reconciliations.
• Maintain accurate financial records in QuickBooks and ensure consistent accounting practices across departments and programs.
• Establish a reliable monthly close process and produce timely financial statements, budget-to-actual reports, and updated forecasts.
• Lead, develop, and evaluate a team of three to four employees, with clear responsibilities, deadlines, cross-training, and service expectations.
• Strengthen documented procedures, approval processes, segregation of duties, and internal controls appropriate to the school’s size.
• Oversee banking transactions, wire transfers, payment approvals, positive pay submissions, and secure retention of supporting records.
• Work with families on billing questions, payment arrangements, and outstanding balances with professionalism, discretion, and consistent application of school policies.
• Improve financial workflows and the use of technology to increase accuracy, efficiency, and visibility.

Audit, Financial Stewardship, and Risk Management

• Coordinate the annual independent financial audit, prepare supporting schedules, and address auditor recommendations.
• Oversee required financial and tax reporting in collaboration with external accounting and professional advisers.
• Manage banking relationships and monitor debt obligations, financing arrangements, and applicable reporting requirements.
• Coordinate with investment advisers and board leadership on endowment reporting, approved distributions, and cash management.
• Partner with the advancement office to reconcile gifts and pledges, track restricted funds, and ensure expenditures align with donor requirements.
• Manage the school’s insurance portfolio, renewal process, coverage reviews, and claims coordination.
• Oversee workers’ compensation claims and annual audits, coordinating appropriately with employees, insurers, and providers.
• Safeguard confidential financial, employee, donor, and family information.

Payroll, Benefits, and Human Resources Administration

• Ensure accurate and timely biweekly payroll, including review of payroll changes, deductions, and supporting documentation.
• Oversee employee benefits administration, including annual renewals, enrollment, qualifying life events, and termination of coverage.
• Partner with the Head of School on personnel administration, compensation planning, and consistent implementation of employment policies.
• Oversee onboarding and offboarding, including employment paperwork, background checks, payroll setup, exit interviews, and coordination of technology access.
• Maintain accurate personnel records and coordinate employment verifications and related documentation.
• Work with external advisers to support applicable employment, payroll, and benefits requirements.

Purchasing and Administrative Operations

• Establish clear purchasing practices and review expenditures for budget alignment, appropriate authorization, and value.
• Manage business office vendor relationships, contracts, and renewals, including telecommunications and related administrative services.
• Oversee coordination of employee programs, including resort passes, through appropriate delegation and reliable tracking.
• Collaborate with academic, athletic, residential, admissions, advancement, and facilities leaders to support effective resource planning.
• Contribute actively to the Senior Leadership Team and the broader life of the school.

Qualifications

• Bachelor’s degree in accounting, finance, business administration, or a related field, or an equivalent combination of relevant education and substantial experience.
• At least five years of progressively responsible financial management experience, including responsibility for budgets, financial reporting, forecasting, and staff supervision.
• Strong working knowledge of accounting principles, internal controls, audit preparation, payroll, and financial management practices.
• Demonstrated proficiency with QuickBooks and advanced spreadsheet skills, including financial modeling and scenario analysis.
• Experience managing cash flow and translating complex financial information into clear, actionable recommendations.
• Demonstrated ability to lead a small team while remaining directly engaged in daily operations.
• Sound judgment, strong organizational skills, attention to detail, and the ability to manage competing deadlines.
• Excellent communication skills and the ability to build productive relationships with colleagues, families, trustees, and external partners.
• High standards of integrity, discretion, accountability, and service.

Preferred Experience

• Financial leadership in an independent school, nonprofit organization, or similarly complex organization.
• Familiarity with nonprofit accounting, donor restrictions, endowment reporting, and tuition-dependent revenue models.
• Experience presenting financial information to boards or finance committees.
• Experience overseeing employee benefits, insurance, and HR administration.
• CPA, MBA, or another relevant advanced credential preferred.

What Success Looks Like

The Director will establish a dependable financial reporting and forecasting rhythm, strengthen business office practices, and give school leadership a clear understanding of both current financial performance and future obligations. Success means accurate reporting, proactive cash management, a capable and accountable team, and practical recommendations that support the school’s educational mission and long-term financial health.

Compensation and Work Expectations

The annual salary range is 125,000–140,000, depending on experience and qualifications. This is a full-time, year-round position based on campus in Stratton, Vermont. Participation in occasional evening or weekend board meetings and school commitments is expected.

How to Apply

Please apply through Indeed with a résumé and cover letter describing your relevant financial leadership experience and interest in Stratton Mountain School. Please include examples of your work in forecasting, improving financial processes, and supporting executive or board decision-making.

Pay: $125,000.00 - $140,000.00 per year

Benefits:

• 403(b)
• Dental insurance
• Health insurance
• Health savings account
• Paid time off
• Vision insurance

Work Location: In person