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The Chief Financial Officer (CFO) of Old Trail School serves as a strategic and forward-thinking partner to the Head of School, Board of Directors, and Leadership Team, stewarding the school’s financial health and operational strength while shaping mission-aligned, long-range financial strategy. In this highly collaborative and influential role, the CFO provides clear, data?informed guidance that supports institutional decision?making and ensures the school’s resources are deployed responsibly, sustainably, and in service of its educational mission. The CFO leads all aspects of financial planning, budgeting, forecasting, reporting, and compliance, ensuring accuracy, transparency, and alignment with best practices in independent school finance. This leadership extends to safeguarding the school’s long?term financial sustainability, strengthening internal controls and systems, and cultivating a culture of fiscal discipline and strategic resource management across the institution.

This position integrates strong technical acumen with collaborative leadership, clear communication, and a deep commitment to an inclusive school community. It represents an exceptional opportunity for a strategic, community?minded, and operationally skilled finance and operations leader—someone who builds robust systems, develops high?performing teams, and serves as a trusted partner to the Head of School, helping guide institutional decision?making with integrity, transparency, clarity, and long?range thinking. The successful candidate will demonstrate the ability to work effectively with all members of the Old Trail community, offering strategic insight paired with a cooperative, solutions?oriented approach. The ideal leader will bring both sophisticated financial expertise and strong operational leadership, along with the presence and relational skills to support a dynamic leadership team while fully engaging in the daily life of the school.

As a key member of the senior leadership team, the CFO will oversee budgeting and forecasting, financial reporting and compliance, investments, risk management, and supervision of the Business Office, Auxiliary Programs, Transportation and Logistics, Food Service, and HR staff. Beyond shaping financial strategy and managing all non?academic operations, the CFO will serve as a critical advisor and collaborator to the Head of School and a thought partner to leaders across the institution, including Enrollment Management and Development.

This is a highly visible, relationship?centered role within a community that values professionalism, transparency, collaboration, and integrity. The next CFO will be expected to engage with staff, families, the Board of Directors, and faculty with clarity and warmth, bringing sound judgment, operational agility, foresight, and a genuine appreciation for the school environment.

KEY RESPONSBILITIES:

Strategic Leadership, Collaboration, & Board Partnership 

• Serve as a principal strategic advisor to the Head of School, offering sophisticated financial analysis, scenario planning, and long?range modeling that inform institutional priorities, resource allocation, and mission?aligned decision?making. Provide clear, data?driven recommendations that help the Head of School navigate both opportunities and risks.
• Partner closely with the School Board of Directors and its Finance Committee to ensure strong governance, transparency, and fiduciary oversight. Prepare and present financial reports, multi?year forecasts, and strategic analyses that support informed Board deliberation and reinforce the school’s financial stewardship.
• Collaborate with the Foundation Board of Directors to guide endowment management, investment strategy, and long?term asset growth. Provide insight into spending policies, risk tolerance, and opportunities to strengthen the school’s financial foundation.
• Work in deep partnership with the Leadership Team to align financial strategy with programmatic goals, enrollment management, advancement priorities, and campus operations. Ensure that financial decisions support educational planning, institutional sustainability, and the school’s long?term strategic vision. Facilitate cross?departmental collaboration so that budgeting, staffing, and resource allocation reflect both mission and operational realities.

Fiscal Management and Accounting

• Lead the development, refinement, and implementation of the annual operating budget, working collaboratively with the Senior Leadership Team to ensure that financial planning reflects institutional priorities, programmatic needs, and long?term strategic goals. Maintain and continuously update multi?year financial projections that model various enrollment, revenue, and expense scenarios to support proactive decision?making.
• Provide clear, timely, and actionable financial reporting and analysis to the Head of School, Leadership Team, Finance Committee, and Board of Directors. Translate complex financial information into accessible insights that strengthen transparency, support governance, and enable leaders to make informed, mission?aligned decisions.
• Oversee the preparation of all financial statements and direct the full annual financial audit and 403(b) audit processes, ensuring accuracy, compliance with GAAP and regulatory requirements, and a high standard of internal controls. Serve as the primary liaison with external auditors, ensuring that audit findings are addressed promptly and that financial practices reflect best?in?class standards for independent schools.
• Direct tuition setting, financial aid modeling, and long?range enrollment?driven revenue planning, partnering closely with Enrollment Management and the Head of School to ensure that pricing strategy, affordability considerations, and financial aid policies support both access and long?term financial sustainability. Use data?informed analysis to forecast revenue trends and assess the financial implications of enrollment shifts.

Operational Oversight

• Provide strategic leadership and direct supervision of all Business Office functions, including accounting, payroll, purchasing, accounts receivable, and accounts payable. Ensure that financial operations are efficient, well?controlled, and aligned with best practices, while fostering a culture of accuracy, accountability, and customer service across all business functions.
• Oversee the school’s full portfolio of insurance coverage, liability policies, and risk?management practices, ensuring that the institution is adequately protected against operational, financial, and compliance?related risks. Partner with insurance advisors and brokers to evaluate coverage options, negotiate renewals, and secure policies that balance comprehensive protection with cost?effectiveness. Maintain and regularly update risk?management protocols to safeguard students, employees, and school assets.
• Provide leadership and oversight for auxiliary programs, transportation, and food service operations, ensuring that each function operates safely, efficiently, and in alignment with the school’s mission and community expectations. Collaborate closely with facilities leadership on capital planning, preventive maintenance, campus improvements, and long?term sustainability initiatives. Support transportation operations to ensure reliable, safe, and well?coordinated bus services. Oversee food service operations to maintain high standards of nutrition, compliance, and student experience.
• Negotiate vendor contracts, leading the full lifecycle of vendor contracting to ensure the school secures high?quality services, competitive pricing, and mission?aligned partnerships. This includes developing RFPs, evaluating proposals, conducting cost?benefit and risk analyses, negotiating terms that protect the school’s financial and operational interests, and ensuring compliance with legal, regulatory, and policy requirements. The CFO establishes performance expectations, monitors vendor accountability, and periodically rebids or renegotiates contracts to maintain value, transparency, and fiscal stewardship. This work spans facilities, technology, food service, transportation, insurance, and other major operational categories, with a focus on long?term sustainability and strategic alignment.

Human Resources Leadership

• Support and strengthen core HR functions, including compensation modeling, benefits administration, and the development and interpretation of employment policies. Ensure that compensation structures are equitable, competitive, and aligned with the school’s financial strategy and market conditions, while maintaining compliance with all applicable laws and regulations.
• Provide strategic oversight of HR operations, including talent acquisition, workforce planning, and hiring processes. Partner with school leaders to design recruitment strategies that attract, hire, and retain high?quality faculty and staff who embody the school’s mission and values. Ensure that hiring practices are consistent, legally compliant, and grounded in best practices for independent schools.
• Lead the development, implementation, and ongoing maintenance of the school’s salary scale, ensuring it reflects internal equity, market competitiveness, and long?term financial sustainability. Oversee the preparation and issuance of all faculty and staff employment contracts, ensuring accuracy, clarity, and alignment with school policies and compensation frameworks.
• Oversee employee relations with a focus on fostering a fair, supportive, and inclusive workplace culture. Provide guidance to supervisors and staff on conflict resolution, performance concerns, and workplace expectations. Lead or support internal investigations as needed, ensuring that processes are handled with discretion, consistency, and adherence to legal and ethical standards. Promote practices that strengthen communication, accountability, and employee well?being across the school.

Systems, Controls & Process Improvement

• Maintain and continuously strengthen the school’s internal control environment, ensuring that financial practices, approval workflows, and documentation standards meet or exceed best?practice expectations. Promote audit readiness throughout the year by establishing disciplined processes, monitoring compliance, and fostering a culture of accuracy, accountability, and transparency across all financial operations.
• Lead enterprise?wide initiatives to enhance financial data security, implementing rigorous protections, protocols, and monitoring systems to safeguard all sensitive information managed by the Business Office and external vendors. Partner with IT, legal advisors, and third?party providers to ensure that data governance, privacy standards, and cybersecurity measures remain current, robust, and aligned with evolving regulatory requirements.
• Evaluate, modernize, and optimize financial systems, technology platforms, and operational workflows to improve efficiency, accuracy, and data integrity. Identify opportunities to streamline processes, reduce manual work, and strengthen reporting capabilities. Lead system upgrades, vendor evaluations, and implementation projects that enhance the school’s financial infrastructure and support long?term scalability.
• Lead or support cross?functional initiatives that advance operational excellence and responsible resource stewardship, collaborating with academic, administrative, and operational leaders to improve processes, strengthen interdepartmental coordination, and ensure that systems and procedures effectively support the school’s mission. Champion continuous improvement practices that enhance service delivery, reduce risk, and increase institutional effectiveness.

The Chief Financial Officer plays a pivotal role in ensuring Old Trail School’s long?term strength, stability, and capacity to deliver an exceptional educational experience. This leader will join a dedicated, mission?driven community that values collaboration, integrity, and thoughtful stewardship. Guided by a commitment to students, families, and faculty, the CFO will help shape the school’s future by aligning resources with vision, strengthening operational excellence, and supporting a culture where every member of the community can thrive. This is an opportunity to make a lasting impact on a school poised for continued growth and innovation. The candidate should be a role model for the school’s core values of Respect, Responsibility, Goodness, and Service.

QUALIFICATIONS:

Experience & Education 

• Bachelor’s degree in finance, accounting, business administration, or a related field required; CPA or MBA preferred.
• 5+ years of progressive financial leadership experience, with independent school or mission?driven nonprofit experience, strongly preferred.
• Proven ability to manage teams, lead cross?departmental initiatives, and support organizational change.
• Deep knowledge of nonprofit or independent school finance, including GAAP, budgeting, and audit practices.
• Strong analytical and quantitative skills, including financial modeling and data?driven decision?making.
• Advanced proficiency in Excel, financial analysis, and cross?platform technology, with a solid understanding of accounting policies, procedures, and financial software. Direct experience with payroll systems, financial platforms, and technology?driven process improvements required.
• Exceptional collaborator who builds trust and strong working relationships with the Head of School, Board, faculty, staff, and families.
• Clear, confident communicator who can translate complex financial concepts into accessible, actionable insights.
• Strategic thinker able to balance mission, people, and financial discipline in decision?making.
• High emotional intelligence, sound judgment, and unwavering discretion in handling sensitive information.
• Committed to diversity, equity, inclusion, and fostering a positive, community?centered culture of belonging.
• Proven ability to lead through change, bringing steadiness, clarity, and a solution-oriented mindset during periods of transition or uncertainty.
• Skilled at developing and mentoring teams, cultivating a culture of accountability, professional growth, and shared purpose.
• Demonstrates a proactive, forward?looking approach to identifying risks, anticipating challenges, and positioning the school for long?term success.
• Values transparency and open communication, ensuring stakeholders are informed, engaged, and aligned around key decisions.
• Brings a collaborative, institution?wide perspective, recognizing how financial and operational decisions impact teaching, learning, and community experience.

About Old Trail School

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