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Cheshire Academy
Cheshire, CT, United States
30+ days ago
Cheshire Academy
Cheshire, Connecticut, United States
30+ days ago


FUNCTION:  Reporting to the Chief Advancement Officer, the Director of Annual Giving will design, implement and manage all aspects of a comprehensive Annual Giving program that includes setting goals and developing strategies to build and engage Cheshire Academy’s donor base. The Director will oversee leadership annual giving, reunion giving, direct mail, phone-a-thons, and class-based initiatives, as well as other targeted constituent appeals and programs. The Director is a key member of a team responsible for growing participation percentages, moving donors to higher levels of giving and building a deeper culture of giving at the Academy.  The successful candidate will have a demonstrated track record as an annual giving professional with expertise in relationship management, and strong analytical, written and oral communication skills.


  • Create and manage a comprehensive fundraising plan and multi-dimensional appeal schedule for the Annual Fund that uses a variety of mediums.
  • Establish and monitor goals on a monthly basis, applying course correction when needed.
  • Working closely with marketing and communications, develop and manage constituent mailings and special fundraising appeals.
  • Identify strategies to acquire new donors, renew donors at increased amounts, and reacquire lapsed donors of all constituencies.
  • Prepare and analyze Annual Giving reports; collaborate with Advancement Services Manager to maximize use of the Raiser’s Edge database and enhance data integrity.
  • Collaborate with Director of Donor Relations to develop stewardship programs for new and renewed donors, loyal contributors, and leadership annual fund donors.
  • Collaborate with the director of alumni relations to recruit class agent and reunion class committee volunteers; create volunteer/solicitor training program, materials and communications.
  • Implement Give Campus platform to support micro-campaigns and volunteer management.
  • Manage the Advancement Student Intern afternoon program (3-5 interns/semester; 1-3 in the summer), Senior Class Gift Program, Thank-o-grams and various other strategies for educating students about philanthropy.
  • Participate fully in the life of the School. 


  • Special event coverage, including some weekend and evening work is expected;
  • Other duties as deemed necessary by the Chief Advancement Officer.


Bachelor's degree and minimum of three years of progressively successful experience working within an Annual Giving program with revenues in excess of $1,000,000, preferably in education.


  • Familiarity with and appreciation for the mission, purpose and environment of a boarding school
  • A strong sense of fundraising ethics and practice.
  • Ability to cultivate and build superior relationships with donors.
  • Ability to interact with all levels of the school community – the Head of School, faculty and staff, the Board of Trustees, alumni, parents and friends.
  • Experience with database segmentation and a keen understanding and ability to market to different audiences.
  • Excellent oral and written communication skills; able to write clear and compelling messages to inspire giving.
  • Experience with online fundraising
  • Experience with CRM systems, preferably Raiser’s Edge.
  • Strong analytical skills with the ability to quickly and regularly adjust strategy based on giving trends
  • Must be an independent and strategic thinker capable of understanding the full scope of projects and managing several tasks simultaneously.
  • An open and collaborative style, creative ability, positive outlook, and sense of humor.

Compensation will be commensurate with experience and qualifications. Offer will be contingent upon successful completion of a background check.  Interested applicants should send a letter of interest, resume, and three professional references to Kristin Welage, Director of Human Resources at


Employment Diversity Statement

Cheshire Academy is an internationally minded college-preparatory school with a diverse student body representing over 31 different countries. We are fully committed to hiring and retaining faculty and staff that reflect the diversity of our student body. Candidates should demonstrate dedication to promoting diversity, equity, inclusion, and social justice within our community. We encourage candidates from historically underrepresented groups to apply.

Nondiscrimination Policy

Cheshire Academy, as an equal opportunity employer, complies with all applicable federal and state laws regarding nondiscrimination. Cheshire Academy is committed to a policy of equal opportunity for all persons and does not discriminate based on race, color, national origin, age, marital status, sex, sexual orientation, gender identity, gender expression, disability, religion, height, weight, or veteran status in employment, educational programs and activities, and admissions.

Job Information

  • Job ID: 64392977
  • Location:
    Cheshire, Connecticut, United States
  • Company Name For Job: Cheshire Academy
  • Position Title: Director of Annual Giving
  • Job Function: Development/Advancement
  • Job Type: Full-Time
  • Job Duration: Indefinite
  • Min Education: BA/BS/Undergraduate
  • Min Experience: 2-3 Years
  • Required Travel: 10-25%

Please refer to the company's website or job descriptions to learn more about them.

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