Hopkins School

Chief Financial Officer

Reports to: Head of School

School History and Mission

In 1660, Edward Hopkins, the second governor of the Connecticut Colony, established the nation’s first charitable trust to found Hopkins Grammar School on the New Haven Green. The school was dedicated to preparing “hopeful youths. . . for the public service of the country in future times.”

More than three centuries later, Hopkins School continues to fulfill its original mission. Now the third oldest independent school in the country, Hopkins is a day school for 715 boys and girls in grades 7–12 located on a hill-top campus in New Haven. A community of civility and learning, the school employs a distinguished faculty who work with curious, talented, and diverse students to:

Develop in young people the habits of mind of scholars as the foundation for a lifelong love of learning.
Foster the courage to live and think as distinct individuals who embrace their responsibilities in the larger world.
Expose every student to the deep satisfaction that derives from service to others.
Enlarge the educational experience to include the creative joy and aesthetic sensibility of the artist, and the vitality and competitive spirit of the athlete.
Provide, through the School’s advisers, the wisdom and goodwill necessary to guide young people to confident self-reliance.
Nurture the development of character essential to leading a rich and purposeful life.

Remaining true to its founding purpose, Hopkins is committed to academic excellence. Students have access to extensive programmatic offerings, including 190 courses in the major academic disciplines, 60 athletic teams playing in 20 sports, 20+ drama and music performances per year, and over 100 student clubs and activities. Over the past five years, 20% of Hopkins graduates have matriculated to Ivy League institutions, 36% to the nation’s 30 most selective schools (those with acceptance rates below 10%), and 70% to the U.S. News and World Report’s top 100 colleges and universities.

Position Summary, Key Partners, and Priorities

Current Chief Financial & Operating Officer David Baxter will retire on June 30, 2027 after 20 years at Hopkins. During his tenure, Hopkins’ total assets have grown from $116M to $368M, and the school’s investments have increased from $65M to $235M. Across two decades, Baxter helped transform the physical campus, overseeing more than $73M of capital projects, including academic buildings, athletic facilities, residential housing, and security infrastructure. He also led Hopkins in securing the school’s first stand-alone bond rating (AA- from S&P) and the issuance of four bonds through CHEFA. Baxter and his team in the Business Office delivered clean financial audits every year.

Hopkins’ next Chief Financial Officer will continue this legacy as a senior leader, systems thinker, and strategic partner to the Head of School and Committee of Trustees. The CFO oversees the complex financial operation of the school, including a $40 million operating budget, a 108-acre campus with 25 buildings and 265,000 square feet under roof, $20 million in debt, and 181 regular employees.

Combining financial acumen, analytical capability, and a data-oriented mindset with exceptional interpersonal skills, the CFO uses strong controls and processes to ensure long-term sustainability and alignment with the school’s mission, values, and strategic priorities. As a collaborative change leader, the CFO fosters cross-departmental coordination and models a culture of service that directly supports the student, family, and employee experience.

The CFO works closely with Head of School Matt Glendinning (M.A., M.Ed., Ph.D.), now in his fifth year at Hopkins after serving as Head for 13 years at Moses Brown School in Rhode Island. During Glendinning’s tenure, Hopkins has developed a forward-looking strategic plan, its implementation fueled by more than $65M in fundraising. Priorities include:

Adapting Hopkins’ model of academic excellence to the demands of the 21st century (including a new slate of advanced courses to replace APs; a new daily schedule; and a strong emphasis on real-world, experiential learning).
Serving as a strong civic partner for the communities and organizations of New Haven (including a new public service internship program and use of campus to support local nonprofits).
Supporting the people of Hopkins through wellness programs, competitive compensation, equity initiatives, and affordability programs.
Providing state-of-the-art facilities to support Hopkins’ mission, including a new performing arts center (2025), pool (2027), and a 32,000 sq. ft. LEED-certified STEM and innovation center (opening 2028).

Officers of the Committee of Trustees include:

President Gwen Evans ’84, who spent more than 20 years at Credit Suisse, where she served as Managing Director in the Investment Banking division.
Vice President Mark H. Lynch ’62 HGS, Senior Counsel & Co-Chair of Covington and Burling LLP’s Pharmaceutical Litigation and Government Investigations Group.
Secretary Lisa Takoudes, who served as Hopkins Parent Association President during the 2020–2021 school year and is the parent of three Hopkins alumni (‘20, ‘22, ‘25).
Treasurer Josh Samuelson ’91 and parent ’22 and ’26, Co-Founder and Co-CEO of Mycor Capital, with more than 20 years of experience in investing, strategy, and operations management.

David Baxter leaves Hopkins in superb financial shape after 20 years of consistent and expert management. His successor will inherit well developed processes, an unparalleled assemblage of pertinent longitudinal data, and a highly effective team. Top priorities for the next CFO include bolstering long-term financial sustainability, completing the strategic plan, optimizing school operations, and cultivating a positive, vibrant, and inclusive workplace culture.

Essential Duties and Responsibilities

This is a full-time, year-round leadership role in a professional school environment. Evening and weekend work, as well as occasional travel, are required. The primary, recurring responsibilities of the role are described below. Duties may change at any time based on school needs.

Strategic Leadership & Systems Change

Lead Hopkins School’s financial strategy, cultivating strong relationships across the school community and building consensus around critical financial and organizational priorities.
Help develop policies, practices, and goals that proactively advance Hopkins’ strategic plan, strengthen school operations, and enhance the experience of families and employees.
Provide consultation and guidance to strengthen campus operations, helping to coordinate and streamline workflows across finance, facilities, dining, security, transportation, and technology.
Stay current with emerging industry trends, challenges, and best practices to anticipate opportunities, develop innovative solutions, and advance the school’s strategic priorities.

Financial Management, Reporting, and Institutional Analysis

Organize, direct, and evaluate the school’s fiscal functions, business operations, and financial performance.
Keep leadership and trustees informed of the financial condition of the school through longitudinal data tracking, institutional analysis, and presentation of timely financial statements, dashboards, forecasts, and scenario modeling.
Maintain appropriate internal controls and financial procedures in accordance with GAAP and other applicable standards.
Oversee the annual independent audit and preparation of all required financial work papers, tax filings, and compliance reports.

Budgeting, Forecasting, and Tuition Strategy

Lead the annual operating and capital budget process in partnership with the Head of School, budget managers, and trustees.
Develop recommendations regarding tuition, financial aid, compensation, benefit design, and other major budget drivers.
Maintain multi-year financial forecasts and dynamic scenario models to support data-driven, strategic decision-making.

Investments, Banking, and Debt

Oversee liquidity needs and cash flow management.
Manage all banking, borrowing, and debt relationships and support refinancing or restructuring activity as needed.
In partnership with the Finance and Investment Committee and the School’s Outsourced Chief Investment Officer (Morgan Stanley), steward the school’s investment manager relationship and monitor invested assets, endowment-related activity, spending draws, and compliance with Board policy.

Capital Planning, Compliance, and Risk Management

Partner with school leadership and trustees to anticipate, plan, and execute major facility improvements, campus construction, and renovation projects, serving as the school’s owner’s representative as needed.
Lead institutional compliance and risk management efforts, coordinating with the school’s general counsel on the full range of legal and regulatory matters and maintaining appropriate insurance coverage, including property, liability, workers’ compensation, and directors’ and officers’ insurance. Represent Hopkins in peer school risk consortia.
Oversee and serve as signatory for contracting with outside vendors and service providers, prioritizing sustainable and equitable vendor partnerships.

Human Resources, Culture, and Employee Support

Oversee human resources, HR systems, and talent development across the school, ensuring compliance with employment laws and fostering a supportive, service-oriented work culture.
Supervise payroll, benefits administration, compensation, and personnel records.
In partnership with Human Resources, supervise all non-teaching staff, providing professional growth opportunities and establishing clear performance goals.

Student Billing, Financial Aid, and Enrollment Alignment

Oversee student billing, accounts receivable, tuition collection, and family account management.
Partner with admission and financial aid leadership to reach budgeted enrollment goals and ensure financial aid resources and distribution align with institutional objectives.
Monitor demographic and financial trends in partnership with the Director of Admissions, Director of Financial Aid, and Head of School.

Board and Committee Support

Present regularly to the Committee of Trustees and relevant Board committees on financial, investment, legal, and facilities matters.
Serve as a principal staff liaison to the Board’s Finance & Investment, Audit, and Buildings & Grounds committees.
Provide high-quality materials, scenario modeling, and data analytics to support fiduciary oversight and strategic decisions.

Supervisory Responsibilities

The CFO directly leads a team of six that includes:

Director of Human Resources
Finance and Accounting Manager
Finance and Accounting Associate
Student Billing and Accounts Receivable Coordinator
Accounts Payable Coordinator
HR and Payroll Administrator

In addition, the CFO partners closely with, but does not directly oversee, the following positions and functions to ensure aligned operational excellence:

Assistant Head of School (event logistics, routine facilities maintenance, transportation).
Director of Community Safety (campus security, emergency planning).
Director of Technology (academic and administrative technology systems, institutional data infrastructure, cyber-security).
Director of Advancement (philanthropy, alumni relations).
Director of Communications and Marketing (school store).

Required Skills and Work Experience

10+ years of progressive financial leadership experience, with deep expertise in accounting, finance, legal and risk management, payroll, and administrative operations.
Exceptional analytical capabilities and a proven track record of implementing effective financial controls, developing sophisticated forecasting models, and guiding long-range financial planning.
Proven track record as a collaborative leader and systems thinker who can break down operational silos and build strong, service-oriented teams.
Demonstrated commitment to inclusion in organizational leadership, financial planning, and talent management.
Prior involvement in the planning, execution, and financial oversight of major construction or facilities projects is preferred.
Demonstrated understanding of GAAP, audit processes, internal controls, debt management, and long-range financial planning.
Strong business orientation focused on efficiency, continuous improvement, and modernizing operational processes and tech infrastructure.
Experience in independent schools, higher education, or complex non-profit organizations strongly preferred.
Advanced technological proficiency, including experience with enterprise financial systems and data visualization tools.
Exceptional written and verbal communication skills.
Bachelor’s degree in a related field required. A graduate degree in finance, an MBA, and/or CPA is strongly preferred.

Personal Attributes

The successful candidate will have a demonstrated track record of strategic financial leadership and an ability to apply critical, creative thinking to the complex operations of a nonprofit school. Hopkins’ next CFO will be a person of impeccable integrity, sound judgment, and an extraordinary work ethic. They will be a collaborative team player who models empathy, listens actively, solicits feedback, and builds trust across all constituent groups. The CFO will possess superior communication skills, patience, versatility, and a deep dedication to Hopkins’ educational mission in a dynamic, fast-paced environment.

Starting Date, Compensation, and Benefits

Job Classification: Full-time, 12-month, Exempt

The new CFO will assume duties coinciding with the new fiscal year on July 1, 2027.

Base Compensation: $250,000 – $300,000 (commensurate with experience, qualifications, and benchmarked against peer institutions).

Hopkins offers a highly competitive package of employee benefits, including:

Health Insurance (Anthem BCBS): School pays 100% of the PPO HDHP 3500/7000 premium and 75% of the deductible. Dental: School pays 90% of the core plan premium.
403(b) (TIAA): School contributes between 7% and 12% of base salary depending on experience.
FMLA: Up to 12 weeks of paid, job-protected leave.
Tuition Remission: 100% for all admitted children.
Vacation: Four weeks in summer, one week at Thanksgiving, two weeks in December, one week in March, plus various single-day holidays.
Life Insurance: School pays 100% of premium; benefit = annual salary (up to $350,000).

Hopkins School believes that all persons are entitled to equal employment opportunity, and it prohibits discrimination because of race, color, creed, sex, religion, national origin, age, gender, gender identity, genetic information, physical or mental disability, veteran status, marital or civil union status, sexual orientation and other legally protected classes or classifications.

Employment Background Check

For the candidate of choice, a thorough background check including a criminal background check is required as a condition of employment.

Contact Information and Search Timeline

To explore this career opportunity on a confidential basis, please send your resume and letter of interest, and list of five (5) references (who will only be contacted if mutual interest is determined), to:

Doug Cooney, Executive Search Consultant, DEERFIELD ASSOCIATES Executive Search, Inc.
572 Washington Street, Suite 15, Wellesley, MA 02482 Telephone: 781-237-2800.
Email: jobs@deerfieldassociates.com

Promising candidates will be interviewed by Deerfield Associates and the Head of School between November 1 and January 1, 2027. Further interviews and on-campus visits will take place in January and February, with the new hire anticipated by March 1, 2027.