About Old Trail School

Old Trail School is an independent, coeducational day school in Northeast Ohio, serving 440 students from toddlers through grade 8. Founded in 1920, Old Trail offers a holistic and hands-on approach to education, taking learning beyond the classroom and into the wide-open spaces of its picturesque 62-acre campus, nestled in Cuyahoga Valley National Park. Guided by its Core Values of Respect, Responsibility, Goodness and Service, Old Trail is dedicated to an inclusive environment where all students are known, heard and valued. As the nation's only independent school located in a national park, Old Trail and its community have daily access to abundant resources, unparalleled experiences and a beautiful setting to call home.

Job Summary

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.

Job Qualifications

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.

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 the school's vision, strengthening operational excellence, and fostering 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.

Old Trail School

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