The Hotchkiss School
Chief Financial & Operations Officer
DEERFIELD ASSOCIATES has been retained by The Hotchkiss School, located in Lakeville, Connecticut, to conduct a national search for a Chief Financial & Operations Officer.
Position Summary
Hotchkiss seeks a Chief Financial and Operations Officer (CFOO) who will serve as a strategic and operational leader, providing counsel to the Head of School and the Board of Trustees. The CFOO will ensure the efficient and effective stewardship of the School’s physical and financial resources, including operation of support services, oversight of risk management, and project management for the campus master planning and future capital project initiatives. The CFOO will report to the Head of School and serve as a member of the administrative leadership team. This opportunity is available July 1, 2026. Candidates may have the option to begin earlier to facilitate the transition.
The CFOO will ensure the continued excellence of the School’s financial and business operations. The new hire will also serve as a resource to the administrative leadership team and other campus groups. In these capacities, the CFOO will enable the School to realize its educational mission and ambitions. The CFOO will play a crucial role in developing the School’s advancement and capital campaign strategy.
The CFOO will have responsibility for nine direct reports and oversight of approximately 95 staff members. The CFOO will provide leadership and direction for the Finance, ITS, Facilities, and Child Care offices, as well as ancillary and support services. This leader will serve as the primary School liaison for the following committees of the Board of Trustees: Finance; Audit & Risk; Investment; and Buildings, Grounds & Environment.
Hotchkiss employs approximately 145 faculty FTEs and 163 staff FTEs and has an annual operating budget of $69 million and an endowment of $625 million. It sits on an 827-acre campus located in the scenic northwest corner of Connecticut. The scale of the School is comparable to that of a small liberal arts college. The School’s ability to fulfill its important and ambitious mission depends entirely on the sound and energetic management of its human, physical, and financial assets. For more background on Hotchkiss, please visit www.hotchkiss.org.
About The Hotchkiss School
The Hotchkiss School is an independent boarding school located in Lakeville, Connecticut. Founded in 1891, the school provides an education of academic distinction to 600 students in grades 9 through 12, including a small number of postgraduates. Students at Hotchkiss come from across the United States and around the world. Since its founding, Hotchkiss has aimed to provide a dynamic environment for teaching and learning as well as exceptional preparation for students’ future study and fulfilling adult lives. The School’s residential community—the network of relationships created by the School’s people, place, and opportunities—is its most effective means of providing a transformative educational experience, where students may grow and gain greater understanding of themselves and their responsibilities to others. Hotchkiss believes that a healthy and inclusive learning community nourishes students physically, emotionally, and intellectually; fosters joy in learning and living with others; and ensures that all students feel safe, seen, and supported. The School’s state-of-the-art facilities, combined with its surroundings, make Hotchkiss an extraordinary place to work, live, and learn.
The Hotchkiss School is defined by its commitment to fostering curious and engaged learners. As a top independent prep school, it provides an experience-based education. The School focuses on empowering students to become fully prepared for the future. Through small classes, a breadth of more than 200 courses, and teaching that cultivates academic curiosity, every student graduates ready to become a global citizen and a community leader. Hotchkiss’s student-centered community features a 95 percent boarding population living in 13 residence halls.
Hotchkiss’s financial condition is strong, positioning the School to continue to provide an exceptionally high-quality, residential secondary school experience. It is one of just a handful of independent schools that carries a AAA rating from S&P. The School exercises prudent financial discipline in managing its $69 million annual operating budget, including a rigorous planning process and a stipulated endowment-draw policy. Hotchkiss is currently nearing the completion of a multi-year, $250 million capital campaign. This fundraising initiative comprises both significant facilities-based and endowment-focused projects to support access and programs.
Key Relationships
Reports to
- Craig W. Bradley, Head of School
- Anne Bruder, Incoming Head of School (July 1, 2026)
Direct reports
- Director of Finance
- Senior Financial and Endowment Analyst
- Director of Facilities
- Director of Information Technology Services
- Director of the Children’s Center
- Golf Course Manager
- Executive Assistant to the CFOO
Other key relationships
The CFOO partners closely with School leaders, including the Associate Head of School, Assistant Head of School/Dean of Admission & Financial Aid, Chief Advancement Officer, Chief Communications Officer, Director of Human Resources, and the Dean of Summer Programs.
Other crucial constituencies include the Board of Trustees, faculty, staff, parents, students, and alumni.
Essential Responsibilities
- Develop and maintain highly collaborative relationships with the Head of School, Board of Trustees, senior administrative team, and School community. Consult and advise on the School’s financial, risk, and operational strategy.
- Develop, communicate, and lead the financial strategy across Hotchkiss, cultivating and fostering a collaborative environment with the senior administrative leadership team, faculty, and staff.
- Develop sophisticated planning for Hotchkiss’s short- and long-term financial health; ensure adequate controls; and lead strategic financial planning for the School’s multi-year annual operating budgets, capital budgets, and forecasting.
- Oversee and support the full range of financial and accounting functions, including financial planning, reporting and analysis, accounting services, budget planning, cash control, treasury management, accounts payable and receivable, payroll, strategic sourcing, procurement, contracts, cashier, and tax reporting.
- Work effectively with all levels of a socially and culturally rich and diverse independent school, ultimately serving as a role model to promote a positive and productive work climate.
- Serve as a critical business thinker, capable of providing positive and proactive solutions to business issues.
- Oversee the management of the physical plant, including new construction and major renovation projects in collaboration with the Director of Facilities.
- Collaborate with the Investment Committee of the Board of Trustees on issues relating to the management of the School’s endowment, debt, and bond issues.
- Ensure enterprise risk management protocols are proactively assessed and updated schoolwide. Serve as the School’s liaison with outside legal counsel and local town officials.
- Represent the School to financial partners, outsourced service providers, financial institutions, auditors, insurance brokers, and other relevant providers.
- Provide professional leadership to maintain strong teams in finance, facilities, ITS, security, and child care; support and develop employees, including through performance management and coaching.
Skills and Work Experiences
Senior Finance Experience:
- 15 years total experience in financial leadership roles with strong analytical skills and a deep knowledge of accounting and finance, legal and risk management, payroll, and facilities.
- Knowledge and experience in setting up and monitoring effective financial controls and providing financial modeling and forecasting skills.
Leadership/Management Experience:
Experience leading and managing a team, including hiring, performance management, training, and professional development. Prior experience overseeing construction projects is preferred.
Strategic Planning:
A strong business orientation, including setting short- and long-term priorities and charting an informed, sustainable, and ambitious future, matched with the ability to communicate effectively to the Head of School and other School leaders the short- and long-term financial implications of decisions.
Mission Orientation:
Experience working in, or exposure to, a school setting and/or non-profit organization is desirable but not required.
Technical and Analytical Acumen:
Strong technological capability and exceptional analytical skills, including expertise with enterprise-wide financial systems.
Academic Credentials:
Strong academic credentials, a Bachelor’s degree in a related field, including a CPA and/or a related graduate degree in finance, is strongly preferred. An MBA would be an asset.
Critical Leadership Capabilities
Strategic Financial Management
- Adopts a long-term perspective about the School’s finances while remaining cognizant of short-term needs; brings a sophisticated understanding of the financial levers and risks.
- Provides accurate, comprehensive, and transparent financial information to the senior administrative team and Board members to inform priority setting. Helps guide multi-year decision-making and long-term implications of capital investments.
- Seeks innovative approaches to support the School’s strategic objectives.
Operational Leadership
- Provides discipline and focus on efficiency, effectiveness, and continuous improvement of operational processes.
- Supports major capital, technology, and deferred maintenance projects on campus, planning the scope and financing necessary for them.
- Manages and builds good rapport with a staff that is highly valued within the organization. Prioritizes the professional development of all members of the team.
Collaborative Partner
- Demonstrates a consultative demeanor to build rapport and establish credibility with all constituents. Possesses a deftness of style that solicits input, listens well, and incorporates feedback while making timely decisions. Provides counsel and maintains close relationships within the institution and community.
- Engages faculty and staff in discussions around the financial objectives and challenges of the School, conveying a strong appreciation for the School’s mission and the need to make informed decisions regarding competing priorities.
- Enjoys working with diverse teams and takes initiative to build and deepen partnerships with a broad range of constituents at the School.
- Appropriately delegates projects to members of the CFOO team with a clear set of agreed-upon objectives.
- Able to work in a fast-paced environment and manage multiple priorities.
Head of School Craig W. Bradley
Since his appointment as Head of School in 2016, Craig Bradley has focused on building a stronger, more pluralistic Hotchkiss community. The student body and the faculty have become demonstrably more diverse while student admission to Hotchkiss has become increasingly selective.
- In recent years, Hotchkiss has admitted 12 to 14 percent of applicants, down from 21 percent in 2016.
- In 2016, 29 percent of students received need-based financial aid; in the current year, 37 percent of Hotchkiss students and families received financial aid.
- The School has become increasingly competitive vis-à-vis its peers in terms of faculty compensation.
- The School is on track to complete a $250 million capital campaign, its first campaign in more than 30 years, to support financial aid and the renewal of vital community spaces. These include: a new dining hall and renovation facilities, including the oldest dorms on campus, Walker Auditorium, the fitness center within the Mars Athletic Center (MAC), Edsel Ford Memorial Library, and the art wing.
- New academic programs have been established in partnership with Yale, Harvard, Cornell, Princeton, and Stanford Universities.
- Hotchkiss’s renowned music program has become ever more impressive, including the establishment of the Hotchkiss Philharmonic in 2018.
- Bradley has built a strong, effective, and collaborative senior administrative team.
A native of Winchester, MA, Bradley received his undergraduate degree from Dartmouth and studied in England, France, and Scotland. He received his master’s degree from the University of Edinburgh.
Incoming Head of School Dr. Anne Bruder
A dedicated teacher and academic leader, Dr. Anne Bruder is currently completing her final year as dean of academic affairs at Deerfield Academy in Deerfield, MA. She will join Hotchkiss as Head of School on July 1, 2026.
During her time at Deerfield, Anne has built structures for pedagogical partnership and joyful experimentation, advanced curricular alignment, and guided the institution through its reaccreditation process. Prior to Deerfield, Anne spent 11 years at Berea College in Kentucky, a tuition-free liberal arts college serving low-income students. There, she served as a professor of literature and writing, as well as chair of the English Department, and built a highly successful bridge program for incoming first-year students. Early in her career, she spent two years at Hotchkiss teaching English, coaching lacrosse and soccer, and living in a dorm.
At the heart of Anne’s work is a vision of school as a place of growth and transformation where young people prepare not merely for college or a career but for lives of deep meaning.
Anne earned her B.A. in religion at Middlebury College. She later attended the University of North Carolina at Chapel Hill, where she completed a master’s and Ph.D. in English, followed by a post-doctoral fellowship at Bryn Mawr College. She grew up in Traverse City, Michigan.
The Academic Experience at Hotchkiss
The Hotchkiss School is committed to cultivating curiosity, excellence, and creativity.
Hotchkiss students learn how to take risks, fail, persist, and succeed. The average class size is 12, and the learning environment is interactive and inclusive. In every class, students share their opinions. They speak up. They disagree. They learn from their teachers and from one another.
With more than 200 courses in seven departments and small class sizes, the School’s academic program offers a breadth and depth of study most students will not experience until college. Guided by thoughtful, engaged instructors, Hotchkiss students push themselves intellectually and form deep bonds with their classmates. As a top college preparatory and boarding high school in Connecticut, the seven areas of study offer a comprehensive educational experience. These core disciplines are:
- Classical and Modern Languages
- English
- Humanities and Social Sciences (H&SS)
- Mathematics and Computer Science
- Science
- Visual and Performing Arts
- Human Development
Within each of these areas is a developed curriculum that offers each Hotchkiss student the opportunity to gain subject mastery. Hotchkiss students develop clarity of thought, confidence and facility in expressing ideas, and artistic and aesthetic sensitivity. The School strives to inspire in students a commitment to public service and environmental stewardship.
The Arts
This is a rigorous and required academic program at Hotchkiss. It offers breadth, depth, and access to practicing artists across disciplines. All students have opportunities to study music, studio art, theatre, photography, and film and related media, whether as a serious area of focus or a newfound interest.
Hotchkiss Athletics
Athletics are an important part of the School’s identity and a significant source of school spirit. 94 percent of students participate in a team sport. The community takes pride in its athletes and their accomplishments, enthusiastically cheering on teams at all levels of competition. Above all, Hotchkiss focuses on nurturing an athletic community that prioritizes perseverance, team spirit, and personal integrity.
School Benefits for Employees
The Hotchkiss School offers an exciting and supportive work environment. The CFOO position features a competitive salary and benefit package that includes School-provided housing (taxable benefit), health, dental and vision plans, a strong 403(b) retirement savings plan with match, tuition remission, and paid vacation.
Pluralism and Community
The Hotchkiss School is an equal opportunity employer and is committed to basing judgments concerning the employment of individuals upon their qualifications and abilities. The School is firmly committed to equal employment and advancement opportunities for all employees and applicants in all phases of the employment process (including recruitment, hiring, assignment, terms and conditions of employment, compensation, benefits, training, promotion, transfer, discipline, and termination).
In accordance with applicable law, the School does not discriminate against any individual based on age, ancestry, color, genetic information, learning disability, marital status, past or present history of mental disability, national origin, physical disability, race, religious creed, sex, pregnancy, sexual orientation, gender identity or expression, veteran status, or any other protected characteristic.
The essential functions and basic skills have been included in this job description. This document is not intended to be construed as an exhaustive list of all functions, responsibilities, skills, and abilities required for the position. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.
For the candidate of choice, a thorough background check, including a criminal background check, is required as a condition of employment.
Contact Information
The Hotchkiss School has retained the executive search firm of DEERFIELD ASSOCIATES to conduct this search. Nominations and recommendations of top tier talent are encouraged, with referrals sent to our search consultant.
To explore this career opportunity on a confidential basis, interested candidates should submit a résumé, a letter of interest (outlining career aspirations, applicable work experiences, and personal interest in the opportunity), and a list of five references, including contact information. (References will only be contacted if mutual interest is determined.) Please send materials 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
