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 & Operations Officer (CFOO) who will be 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, operation of support services, oversight of risk management for the School, and project management for the campus master planning and future multi-building capital project initiatives. The CFOO reports to the Head of School and serves as a member of the administrative leadership team. This opportunity is available July 1, 2025.

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 groups on campus. In these roles, the CFOO enables the School to deliver on its educational mission and ambitions. At Hotchkiss, the CFOO plays a critical role in its development and execution of the advancement/capital campaign strategy.

The CFOO has responsibility for nine direct reports and oversight of approximately ninety-five (95) staff members. The CFOO provides leadership and direction for the Finance, ITS, Facilities, Safety & Security, and Child Care teams as well as ancillary and support services. They will serve as the primary School liaison for the Board of Trustees’ committees of Finance, Audit & Risk, Investment, and Buildings, Grounds and Environment.

A School with approximately 145 faculty FTEs, 163 staff FTEs, an annual operating budget of $61 million, an endowment of $600 million, and an 827-acre campus located in the scenic northwest corner of Connecticut, the scale of the enterprise is comparable to 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

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, The Hotchkiss School has aimed to provide a dynamic environment for teaching and learning, as well as exceptional preparation for 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. The Hotchkiss School 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 feel safe, seen, and supported. The School’s state-of-the-art facilities, combined with these surroundings, make Hotchkiss an extraordinary place to work, live and learn.

Hotchkiss’s financial condition is strong and positions 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 respect of its $61 million annual operating budget, including a rigorous planning process and a stipulated endowment draw policy. Hotchkiss is currently in a large, multi-year capital campaign to raise $250 million. This fund-raising initiative consists of both significant facilities-based and endowment-focused projects in support of access and programs.

The Hotchkiss School is defined by our commitment to fostering excellent, wholly developed learners. As a top independent prep school, we provide an experience-based education. We focus on empowering students to become fully prepared for the future beyond. Through small class sizes, 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. Our student-centered community, with 96% residing in 13 residence halls, fosters academic readiness and empowers future leaders.

Key Relationships

Reports to

Craig W. Bradley, Head of School

Direct reports

Controller
Senior Financial Analyst (2)
Director of Facilities
Director of Information Technology Services
Director of Safety and Security
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, Faculty, Staff, Parents, Students and Alumni.

Essential Responsibilities

Develop and maintain a highly collaborative relationship with the Head of School and Board of Trustees and consult and advise on financial, risk and operational strategy for the School.
Develop sophisticated planning for the short- and long-term financial health of Hotchkiss; ensure adequate controls, lead the strategic financial planning for the School’s multi-year plan, 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.
The ability to 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.
Develop, communicate, and lead the financial strategy across Hotchkiss, cultivating and fostering an on-going collaborative environment with the senior administrative leadership team, faculty, and staff.
Collaborate with the School’s Investment Committee 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 and primary contact 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 the professional leadership necessary to maintain strong finance, facilities, ITS, security, and child care teams; support and develop employees, including 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, including an MBA and/or a related graduate degree in finance is strongly preferred. CPA strongly preferred.

Critical Leadership Capabilities

Strategic Financial Management

Adopts a long-term perspective about the School’s finances while also 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 and 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 and serving as project manager for facilities projects.
Manages and builds good rapport with a staff that is highly valued within the organization.

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, yet can make decisions.
Provides counsel and maintains close relationships within the institution and community.
Engages faculty and staff in discussion around the financial objectives and challenges of the School, conveying a strong appreciation of the School’s mission and the need to make informed decisions around 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 their team members and with a clear set of agreed-upon objectives.

Head of School Craig W. Bradley

Since his appointment as Head of School in 2016, Craig Bradley has focused on building a stronger, more diverse and pluralistic Hotchkiss community. The student body and the faculty have become demonstrably more diverse while student admission to Hotchkiss has become even more selective. In recent years, Hotchkiss has admitted between 12 -14% of applicants, down from 21% in 2016. In 2016, 29% of students received need-based financial aid; in the current year, 37% of Hotchkiss students and families received financial aid. The School has become even more 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 over 30 years, to support financial aid and the renewal of vital community spaces, including a new dining hall and the renovation of the oldest dorms on campus, the auditorium, the fitness center, the library, and the art wing. New academic programs have been established in partnership with Yale, Harvard, and Stanford Universities, and others are currently in the planning stages. Hotchkiss’s renowned music program has become ever more impressive, including the establishment of the Hotchkiss Philharmonic in 2018. Bradley has built a strong and effective senior administration, a team that works well together.

The Academic Experience at Hotchkiss

The Hotchkiss School is committed to cultivating curiosity, excellence and creativity.

Our 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, our independent high school 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 — whether they’re discussing environmental issues, examining global trends, or analyzing literature.

As a top college preparatory and boarding high school in Connecticut, our seven areas of study offer a comprehensive educational experience. These core disciplines include:

Within each of these areas is a developed curriculum offering each Hotchkiss student the chance to gain subject mastery. Every learner will gain a holistic education that speaks to the whole being, from the classic academics to individual expression and creativity.

Hotchkiss students develop clarity of thought, confidence and facility in expressing ideas, and artistic and aesthetic sensitivity. Our graduates leave Hotchkiss with a commitment to public service and environmental stewardship, informed by a greater understanding of themselves and their role in a global society.

The Arts at Hotchkiss

All Hotchkiss students have opportunities to study music, studio art, theatre, photography, film, related media, and dance, whether as a serious discipline or a new found interest.

Learn more about the Arts Academic Programs

Hotchkiss Athletics

At The Hotchkiss School, athletics are an important part of our identity and school spirit. We are proud of our Bearcats and their award-winning athletic skills. More than anything, we are proud to be a Connecticut private high school with an athletic community that focuses on perseverance, team spirit, and personal integrity.

Our expansive athletics programs run year-round, with options for students to participate and grow alongside their teammates. With 94% of students participating in a team sport, athletics are truly part of the Hotchkiss experience. You’ll find students cheering each other on during matches, competing in off-season intramural teams, and challenging themselves beyond what they thought possible.

School Benefits for Employees

The Hotchkiss School offers an exciting and supportive work environment. The Chief Financial & Operations Officer position includes a competitive salary and benefit package which 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.

DEI Commitment

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. It is not intended to be construed as an exhaustive list of all functions, responsibilities, skills, and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

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 send a resume, a letter of interest (outlining your career aspirations, applicable work experiences and personal interest in the opportunity), and a list of 5 references including contact information (which 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: [email protected]