Therese Cunningham, CPA

Therese Cunningham, CPA, is a seasoned financial and operational executive with 30 years of leadership experience in a strong mission‑driven nonprofit institution. Across a distinguished three‑decade career at Middlesex School, Therese served as Controller, Director of Finance, and Chief Financial Officer, shaping the organization’s financial infrastructure, operational continuity, long‑term sustainability, and collaboratively turning institutional strategies into operational plans.

Therese has led every dimension of nonprofit financial management, overseeing a $35 million operating budget, stewarding a $225 million endowment, obtaining private and public debt financing, and managing complex multi‑year financial models that guided strategic and capital decision‑making. She directed audits, supervised tax compliance, redesigned the general ledger, and modernized accounting systems to improve reporting accuracy, transparency, and regulatory compliance.

Her operational leadership extends deeply into HR, payroll, benefits design, risk management, insurance, contract review, and vendor oversight. She has guided major institutional transitions, including restructuring retirement plans, implementing new payroll systems, developing comprehensive benefits frameworks, and digitizing decades of financial, student, and alumni records.

Therese has also played a pivotal role in supporting governance as the school’s liaison to trustee committees for Finance, Audit, Investment, and Gift Acceptance, as well as collaborating closely with the Buildings & Grounds Committee. She managed financing and cash flow strategies for more than $100 million in construction projects.

Beyond the numbers, Therese remained deeply committed to the human element of Middlesex. Whether serving as a student advisor or as a dorm parent for over 20 years, or when collaborating with Trustees and colleagues, she consistently worked to bring relentless dedication to the underlying mission of Middlesex School while also exemplifying an exceptional work ethic, and an unyielding commitment to integrity, empathy, and fiscal health.

With a professional foundation at Coopers & Lybrand, Therese brings rigorous audit discipline and analytical strength to her consulting engagements. As a Fractional CFO/COO, she supports nonprofits seeking stability, modernization, and mission‑aligned financial strategy and operational support.