The Hotchkiss School, located in Lakeville, Connecticut, is pleased to announce a search for a new Chief Financial & Operations Officer.  

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.

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.

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, Massachusetts. She will join Hotchkiss as Head of School on July 1, 2026.

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.

For a full search description of this high-profile opportunity, including required academic credentials, direct work experiences and skill sets visit: https://deerfieldassociates.com/the-hotchkiss-school-chief-financial-operations-officer/

 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 Hotchkiss School has retained the executive search firm of DEERFIELD ASSOCIATES

to conduct this national 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: jobs@deerfieldassociates.com

About The Hotchkiss School

Located in the scenic Berkshire-Taconic landscape in the quiet northwest corner of Connecticut, The Hotchkiss School is a community in which faculty and staff members build careers and grow as professionals. We seek to identify, recruit, and develop faculty and staff members who bring a diversity of experiences, perspectives, talents, and backgrounds. Collectively, we are dedicated to supporting the intellectual, social, and emotional growth of 620+ students who come from around the world. In the 2025-2026 school year, our student body includes 17% international students, 41% domestic students of color, and 34% of students receiving financial aid. Geographically diverse, our students represent 35 U.S.states, 32 countries, and span 5 continents. The School is eager to accept applications from individuals who are excited to support an inclusive and warm learning community for students from a wide array of backgrounds and experiences.

Connections working at The Hotchkiss School