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Wooster School

Chief Financial Officer

Deerfield Associates Executive Search, Inc. has been retained by Wooster School, located in Danbury, Connecticut, to conduct a national search for a Chief Financial Officer.

Wooster School

Wooster School, founded in 1926 by Rev. Dr. Aaron C. Coburn is located in Danbury, Connecticut. The Head of School is Matt Byrnes. The religious affiliation is Episcopalian heritage, although Wooster serves students from many faiths and religious traditions. The School is located on a scenic 127-acre campus with 15 buildings. Wooster School is primarily a day school though there are some boarders who live with host families in the area. The annual operating budget is $10.4 million dollars. Enrollment is comprised of 366 boys and girls in grades K – 12. Lower School (K-5): 60, Middle School (6-8): 101, Upper School (9-12): 205. Twenty (20) Connecticut towns and twenty-two (22) New York State towns are represented. Number of full-time faculty: 54; number of full-time faculty with advanced degrees: (95%). In Lower School (K through Grade 5), the individual class size ranges from 8-16, with an average of 11 students per class. In Middle and Upper School, a faculty member typically teaches 4-5 sections per day, and the class size ranges from 4-18 students, with an average of 12 students per class.

For more background on Wooster School please visit,

At Wooster School, our learning environment is built on the bedrock of relationships because we know that people learn best when they feel physically, intellectually and emotionally safe. Through our small class groupings (5 – 15 students) students learn to develop relationships with teachers and fellow students that allow them to best develop their own intellectual and emotional intelligence. While developing “academic skills” like reading, writing, and computation is an important part of our mission, our ultimate goal is to produce independent thinkers who can use those skills to observe, analyze, understand, collaborate and create in multiple contexts. We don’t just want to create “academic rigor” for our students, but rather want students who build skills and pursue intellectual rigor through our academic programs. We also recognize that if we aspire to produce independent, successful, young adults who have an emerging sense of purpose, we need to teach our students at all levels how to use their developing skills and dispositions in the service of the communities within which they live and work. An emphasis on the whole life of the Wooster school community, and the roles and responsibilities of students as community members has been intrinsic to our culture since our founding in 1926.

The Responsibilities

Wooster School seeks a strategically-oriented and experienced financial and business leader to fill the key position of Chief Financial Officer. This opportunity is available in July 2019. The CFO will work closely with the Head of School in support of the school’s mission and strategic plan. The CFO is responsible for the organization, management and implementation of comprehensive business, financial, facilities and investment initiatives for the school. The new CFO will be a key member of the senior leadership team that oversees the day-to-day operation of the school as well as the “big picture” issues and ambitious plans that outline the school’s future.

The ideal candidate for this high-profile position is a strategic thinker who has exceptional leadership and critical thinking skills. Our goal is to recruit a seasoned professional who will build on the significant accomplishments of the outgoing CFO (who is retiring in July 2019) and determine what policies, technologies and programs need to be adapted to respond to the needs of the school and its strategic priorities. The candidate will be proficient with accounting systems and in effective data management and analysis to support innovation and efficiency across the organization. The candidate of choice will have demonstrated leadership in implementing change, the ability to foster a high level of teamwork and customer service while embracing technological advancement.

The CFO manages and leads two members of the Business Office, including the Bursar and the Controller, the Physical Plant staff, the Director of Technology and a contracted food service vendor. Wooster seeks a CFO who is thoughtful, even-tempered, and a team player. The candidate we seek will instinctively understand the interdependence of all aspects of an educational institution and the overriding need to best serve the Wooster community: its students, teachers, and staff which comprise the Wooster community. The candidate of choice must demonstrate the curiosity to question existing processes and constantly seek better ways to serve the school’s constituencies and mission with innovative tools and methodologies.

The School is most interested in candidates who demonstrate the skills, knowledge, and abilities to undertake the following:

  • Ensure and promote the integrity of all school functions by manifesting the highest levels of personal honesty, compassion, and care for the Wooster community.
  • Oversee the development, administration, and reporting of the operating and long-term budgets to the Head of School, the School’s Board of Trustees; the Business Committee; auditors; lenders; donors; and various School administrative offices.
  • Oversee School operations for personnel, maintenance, and food service.
  • Lead the negotiation and implementation, as well as administer all employee benefit programs including health insurance; retirement; worker’s compensation; life insurance; and other related plans.
  • Build and/or maintain the School’s short- and long-term strategic financial models.
  • Serve as chief staff liaison to the Business, Audit, and Investment Committee of the Board of Trustees, working closely with committee chairs and organizing agendas and meeting materials.
  • Oversee the administration of the School’s endowment; execute endowment and investment policy; implement investment decisions of the Investment Committee ensuring effective endowment allocations, performance, and reporting.
  • Collaborate with the School’s counsel and insurance agents regarding all legal and risk management matters.
  • Ensure that the School is in compliance with all local, state, and federal reporting requirements.
  • Oversee the physical plant, grounds, and construction functions; help plan and direct all replacements and renewals of the physical plant.
  • Publicly represent the School in a positive and proactive way, collaborating with other School administrators, the Head of School and Board.
  • Maintain and nurture the School’s key strategic relationship with the Savings Bank of Danbury.
  • Provide sound and consistent employment policies, adequate staffing levels, compensation, and appropriate benefits programs for all facets of School operations.
  • Collaborate with the Head of School and other senior administrators on providing leadership regarding employee hiring, termination, compensation, and management.
  • Oversee the annual financial and 403b plan audits and filings of tax returns.
  • Provide transparent financial reporting and planning that builds trust among administrators, faculty, staff, students, alumni, parents, and trustees.


  • Bachelor’s degree required; advanced degree preferred.
  • 8+years of financial and business leadership experience.
  • Wooster is a self-help school and the ability to work as a “Player-Manager” who is willing to step into any situation to benefit the school and its students and provide leadership by demonstrating that no task is beneath the office of CFO, is essential.
  • Experience on senior administrative teams and working with nonprofit
  • Independent school experience a plus.
  • Demonstrated experience in leading and implementing technology-based solutions to improve data management for operational and strategic planning purposes, as well as to drive this institution forward on its path of sustainability.
  • Demonstrated experience in the development of analysis for strategic decision-making, such as key cost drivers, competitive analysis, market analysis, organizational strengths, and weaknesses, etc.
  • Demonstrated ability to take complex subjects, distill them, and then communicate appropriate topics to various audiences.

Personal Qualities

  • High energy – brings a sense of urgency to the organization
  • Strategic thinker who sees the larger picture
  • Ability to understand and embrace Wooster’s mission
  • Ability to balance and prioritize the needs of the School
  • Ability to manage and mentor staff
  • Process-oriented
  • Superb people skills; compassionate
  • A strong team player
  • Fair, but demanding; a willingness to say “no”
  • Committed to diversity and inclusion practices
  • Excellent communications skills
  • A high level of integrity and an extraordinary work ethic.
  • A sense of humor
  • Strong desire to be part of a dynamic school community

Strength to Strength Plan 2015-16

Dear Community Members,

I am excited to share with you our Strength to Strength Plan for 2015-16. As many of you will remember from last Spring, Strength to Strength is designed to document our roadmap for continually improving learning experiences at Wooster and to communicate personnel transitions from year to year. By focusing on the goals we outlined a year ago, we’ve generated excellent momentum over the past twelve months, extending the strong foundation of learning at Wooster. As you will see in pages accompanying this letter, we have every intention of continuing this momentum through the Summer and into the Fall.

As we all know, and as I often emphasize, Wooster’s traditions are a great source of strength, and are integral to our future as a vibrant community of learners. Much of our work this year, and into the next, is focused on designing ways to build on the strength of our legacy — self-help, the jobs program, service to the community, experiential learning, and sustainability — by becoming more intentional about the experiences that we create for our students. The backbone of learning at Wooster is of course our curriculum, which we continue to strengthen, refine, and connect across our three divisions. Based upon our focus group work with community members this year, we will also continue to improve the physical spaces in which learning occurs and community is fostered; as always, our eye will be on efficiency, effectiveness, comfort, and appropriate technology while maintaining the essential elements of our beautiful surroundings. As we improve our programs and environments, it is also imperative that we support our accomplished faculty in their efforts to improve; to that end, you will see that we are taking steps to ensure that all of our teachers can become the model learners that we want to have working side-by-side with our students.

None of this would be possible without your support, and that of Wooster families past and present. Your continued contributions of time, resources, hard work and good will are essential to the success of our partnership to grow smart, humane, purposeful and self-aware young people. When I think about how our support has expanded in terms of community participation, it really has been a banner year—capped by the paddle raise at the Parents’ Association Gala, which ensured funds for the three Summer projects described below.

All of our institutional decision-making revolves around the question “What is best for our students?” That’s at the core of our commitment to make the experience at Wooster personal, meaningful and visible every day. I think that you will see that focus and that commitment reflected throughout our plans for next year, and into the future.

Matt Byrnes, Head of School
P ’17, ’19, ’22, ’24

Matt Byrnes

Head of School

Wooster School’s Benefits

Wooster School offers a dynamic and supportive work environment, competitive salaries and a generous benefits package including a retirement plan, paid vacations, and medical insurance.

Wooster School is an Equal Opportunity Employer.

Contact Information

To explore this superb career opportunity on a highly confidential basis please send a letter of interest and a resume (both as Microsoft Word documents) to:

Doug Cooney, Executive Search Consultant, Deerfield Associates Executive Search, Inc.
572 Washington Street, Suite 15, Wellesley, MA 02482
Telephone: 781.237.2800

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