Cheshire Academy seeks a creative and strategic Chief Advancement Officer to lead and grow an ambitious Advancement program.
Cheshire Academy (CA) is an inclusive boarding and day school for students in grades 9-12 and postgraduates, with a target enrollment of approximately 375 students who currently hail from 14 states and 27 countries. Founded in 1794, the historic 104-acre campus is located in the safe, walkable town of Cheshire, Connecticut, named by Money Magazine among the best places to live in the U.S., and is just two hours from Boston and from New York City.
With small class sizes and a nurturing faculty, CA takes a personal and tailored approach to teaching. Cheshire is not a “one path fits all” school, but instead focuses on the unique strengths and individual needs of each student with the goal of helping each find their passion. CA is proud of their unique place of offering challenging course work and the formal academic support to ensure student success.
CA allows students to partake in diverse academic and extracurricular offerings. Many students choose to enroll in the renown International Baccalaureate® Diploma Programme. The IB is for students who think globally, want to take ownership of their learning, and seek to become more determined, mature learners. As a comprehensive, nuanced alternative to Advanced Placement (AP) courses, the IB offers students a chance to earn college credits while broadening their academic experience beyond constrictive exam-based approaches.
Cheshire’s unique Art Major program offers an honors-level, yearlong course that prepares students who are considering majoring or minoring in art in college and may aspire to a career as an artist. Students, guided by faculty who are professional artists, develop a portfolio of work in their own personal workspace, utilizing resources such as a digital art lab, ceramics studio, and printmaking equipment.
CA has a rich athletics program with more than 15 athletic championships in the last 10 years. CA alumni have gone on to play at top universities, and on the professional level have competed in the LPGA, NFL, NBA, and the Olympics.
For more information, please visit cheshireacademy.org
Cheshire Academy is supported each year with gifts from alumni, current families, families of alumni, and friends. Gifts to CA totaled more than $1.2M in FY22 and giving is on target to surpass that total for FY23. The incoming Chief Advancement Officer (CAO) will partner with the Head of School and Board of Trustees in leading the $15 million capital campaign to support campus improvements. Cheshire Academy’s 230-year-old campus is undergoing critical renovations to upgrade athletic facilities and playing surfaces to provide more playing space and increase equity in playing time for boys’ and girls’ teams. CA, which has a strong track record of athletic excellence, has already completed construction of a new all-purpose turf field, as well as brand new tennis courts, and they are in the process of renovating their athletics field house. To date, more than $2.5M has been raised for the campaign which is expected to be completed by the end of the 2028-2029 academic year.
The new CAO will also be charged with increasing annual fund participation from alumni, and with partnering with new Alumni Association Leadership to increase overall engagement from CA’s more than 5,000 alumni.
Reporting to the Head of School, the new Chief Advancement Officer will provide the strategic vision for all aspects of the school’s fundraising and engagement activities, with the goal of significantly increasing philanthropic support from across CA’s larger community, including alumni, families, faculty and staff, and families of alumni. This position will lead a team of six and will serve on the schools’ leadership team.
The CAO will be actively engaged in the school’s anti-racist work and will speak with knowledge and promise about the school’s commitment to fostering inclusivity and belonging in a diverse and equitable learning and working environment.
Planning and Leadership
Fundraising, Campaigns and Events
If you are interested in being considered for this search, please use the form below or email your cover letter and resume in confidence to: firstname.lastname@example.org
The salary range for this position is $170,000 – $200,000. The successful candidate’s starting salary and benefits are competitive and will be determined commensurate with experience, competencies, and skillset.
Cheshire Academy provides equal employment opportunities to all applicants and employees without regard to race, color, religion, gender, sexual orientation, gender expression, age, alienage or citizenship status, creed, genetic predisposition or carrier status, national origin, disability condition, marital status, or any other protected characteristic as established by law.
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