Director of the Canterbury Annual Fund

Posted on 03/01/2023

Canterbury School

New Milford, CT

The Opportunity: 

Canterbury School seeks a Director of the Canterbury Annual Fund with broad annual giving experience to join a dynamic team at an exciting time in the life of the school. Reporting to the Director of Development, this full-time, in-person position will play a prominent role in securing philanthropic support for Canterbury’s strategic priorities and mission.

About You: 

You like to scale and create new donor program initiatives that connect the importance of historical data to meaningful content. You are comfortable working with donors and volunteers and use your strong communication and diplomacy skills to build and sustain these relationships resulting in successful solicitations. You enjoy collaborating to enhance your ideas and execute them well. As a results-oriented professional, you have proven yourself as someone who can take on increased responsibility, collaborate with others, and tackle competing priorities with integrity and sound judgment. You demonstrate concern for others, share your ideas confidently and respectfully, and approach your work with cheerful persistence. You understand the importance of best practices in annual giving fundraising and will embrace change and creative solutions to meet the unique needs of the Canterbury community.


The ideal candidate will be an experienced fundraising professional and project manager with a primary focus on the Canterbury Annual Fund. This position is focused on engaging and soliciting gifts from small and mid-level donors, qualifying donors up to higher giving levels, managing broad mass-market donor outreach, and assisting in stewarding donors to maintain donor retention.

While parent giving is vital to the short and long-term growth of Canterbury, The Director of the Annual Fund will also create, manage, and scale alumni, grandparent, and other constituent giving.

The Director of Canterbury Annual Giving works with the Advancement team to develop strategies and implements tactics that increase the donor base and grow philanthropic support for Canterbury.

  • Executes initiatives to encourage new donors to support Canterbury and existing donors to renew or increase.
  • Develops and implements strategy for direct mail and electronic fundraising, donorlevel communications, and cultivation efforts, including events and donor stewardship.
  • Collaborates successfully with the Advancement team and outside vendors on appeal writing, donor communications, and direct mail production.
  • Manages a detailed Canterbury Fund direct marketing activities schedule and ensures the appropriate review of copy and mailing list selection.
  • Develops a data-centric approach for solicitation impact, including unique key performance indicators per appeal type.
  • Leads the efforts around Saints Giving Day, Giving Tuesday, and Alumni Reunion Giving.
  • In partnership with the advancement team, ensures data integrity by using best practices to review gift entries and gift acknowledgments for accuracy.

Candidate Requirements: 

The Advancement Team enthusiastically accepts other duties, as well as learning opportunities, as needed and assigned. Attendance at select night and weekend Advancement events is required as a team member. Qualifications: Bachelor’s degree required and a minimum of four years demonstrated success in annual giving, specifically with operating in or managing donor-centric programs. Experience in an educational setting is preferred.


The compensation package is competitive and commensurate with qualifications and experience.

Canterbury School Mission and Values: 

Founded in 1915 and guided by Catholic heritage, Canterbury is a college preparatory, coeducational boarding, and day school for students in grades 9-12. The School prides itself on creating a community based on its Five Values—Honesty, Respect, Compassion, Spirituality, and Self Reliance—in which students and faculty forge lasting bonds and every student experience a broad and challenging program in a small school setting. The School’s educational environment fosters academic rigor, athletic development, artistic enrichment, spiritual growth, and strives to ensure a superior experience that prepares students for leading colleges and universities and for life.

With its rigorous and humane approach to students, both in and out of the classroom, Canterbury’s program inculcates vital intellectual and ethical habits of mind. The School sees all students as individuals, encourages them as necessary, challenges them as appropriate, and inspires them to become moral leaders in a complex, secular world.

Applicant Review:

Confidential applications and nominations will be accepted until the position is filled. For best consideration, applications and nominations should be provided by April 1, 2023.

How to Apply: 

Shaff Fundraising Group is assisting the Canterbury School with the search for their next Director of the Annual Fund. Initial screening of applications will begin immediately and continue until an appointment is made. Individuals who wish to nominate a candidate should submit a nomination letter, including the nominee’s contact information. Application materials should include a letter addressing how the candidate’s experiences match the position requirements, a curriculum vitae or resume, and three references. References will not be contacted without the candidate’s permission. Submission of materials as PDF attachments is strongly encouraged.

Confidential inquiries, nominations, and application materials should be directed to the following:

Brittany Shaff, Founder and CEO Shaff Fundraising Group

Email: [email protected]

For more information about the Canterbury School, please visit

Canterbury School, in the treatment of employees and applicants for employment, is committed to a policy of equal opportunity and non-discrimination. To learn more about Canterbury’s efforts to maintain a diverse and inclusive community, please visit our website at Finally, Canterbury complies with all federal and state guidelines regarding COVID-19 prevention, including the Connecticut state mandate that all employees of K-12 schools be fully vaccinated against the COVID-19 virus. This mandate is subject to medical and religious exemptions.