Chief Advancement Officer

October 2023 | Cheshire, CT
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Cheshire Academy seeks a creative and strategic Chief Advancement Officer to lead and grow an ambitious Advancement program.

About Cheshire Academy

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

About Philanthropy at Cheshire Academy

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.

About the Position

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.

Key Responsibilities

Planning and Leadership

• Plan, develop, and implement a multi-year strategic plan of action for increasing engagement and support for the school
• Serve as an Ambassador for CA by helping to share the Administration’s vision
• Support the Head of School for all Advancement activities and serve as liaison to the Board of Trustees and Board Advancement Committee, reporting office goals and progress on the following areas: annual fund; special interest fundraising; stewardship; alumni and parent relations; and data integrity
• Serve as a member of CA’s Leadership team
• Collaborate with CA’s marketing and admission teams on donor communications, welcoming and engaging new families and overall support of CA’s constituent relations

Fundraising, Campaigns and Events

• Manage a portfolio of top principal, major gift and planned giving prospects using effective and timely engagement and communication skills to determine what motivates each donor
• Set strategy and solicit support for CA
• Plan and execute advancement travel with and without the Head of School and other CA natural partners and key players to cultivate, solicit, and steward donors and prospects
• Lead and manage all aspects of the $15M Capital Campaign

Team Management

• Manage the Senior Director of Advancement Operations and work with that role in the following ways:
  • Set inspiring but attainable fundraising goals for the Advancement team
  • Design the structure, process, and performance metrics to hold the Advancement team accountable
  • Develop a pipeline of capital and annual fund prospects for strategic fundraising opportunities
  • Oversee and manage the office budget
  • Develop a robust pipeline of prospective Trustee candidates
• Promote inter-departmental collaborations as a connector across campus

Key Qualifications

• 8+ years of fundraising experience, preferably in an educational setting
• Knowledge of the principles and best practices in fundraising and constituent engagement and a demonstrated track record of success in soliciting and closing charitable gifts at the 6+-figure level
• Experience with event planning and oversight
• Track record of identification, qualification, solicitation, and stewardship of new donors and increasing support from existing donors
• Strong technical and analytical skills, including expertise in fundraising databases and the ability to analyze and use data to set goals and track progress
• Experience leveraging social media
• Experience with campaign planning and implementation
• Experience staffing a Board of Trustees
• Personal and professional commitment to diversity, equity, and inclusion and interest in creating an inclusive experience for all Cheshire Academy constituents

• The highest degree of professionalism, demonstrating leadership and gravitas to reflect the brand of CA
• Persistence and patience
• Persuasive written and verbal skills
• Strong attention to detail
• A results-oriented nature and the ability to work well with people at all levels of an organization, warmly developing relationships with diverse constituencies while simultaneously employing keen judgment
• A passion for being a part of Cheshire’s community and a commitment to the mission, programs, and future aspirations of the school.
• Effective leadership and management of high-performance teams plus mentoring skills and a collaborative administrative style based on authenticity and trust.
• Ability to travel locally and , throughout the US, and internationally (specifically to Asia) approximately 25 – 40% including overnight travel for meetings 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: cheshire@developmentguild.com 


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.

Tracy Marshall

Senior Vice President, Principal

Development Guild DDI