Director of Annual Giving
  • Advancement
  • Fundraising

The Cambridge School of Weston, Weston, MA

Accredited by NEASC

The Cambridge School of Weston (CSW) seeks a Director of Annual Giving, who will be actively involved in the Development Office for the purpose of cultivation, solicitation, and stewardship of The Cambridge School of Weston’s various constituencies. The role will develop and oversee strategic tactics to build and sustain a $1 million Annual Fund program. The Director of Annual Giving will have an assigned portfolio of prospects and will be comfortable soliciting gifts from donors in the range of $1,000-$50,000 to advance the fundraising and community support building mission of the Development Office. The candidate will be highly organized and embody a self-motivating and strong work ethic. They will be familiar with current trends in philanthropy and fundraising best practices in independent schools. They will play a frontline client relations role to engage, recognize, and inspire CSW donors.

The Director of Annual Giving leads and implements a comprehensive annual giving program, including a leadership giving program that effectively drives growth in both dollars and donors to The Cambridge School of Weston. The Director of Annual Giving will collaborate with colleagues to develop individual strategies and systems to identify, qualify, cultivate, secure, and then steward all levels of annual unrestricted gifts, focusing on major donor gifts ranging from $1,000 to $50,000, as well as restricted major gifts. They will execute and expand upon a strategic annual schedule of stewardship, cultivation, and solicitation activities for  new parents, current parents, alumni/ae, donor society members, and prospects. They will develop appropriate volunteer structures and then recruit, manage, and work closely with members of the committees.

The Director joins a department of five professionals and administrative staff and collaborates with colleagues in Development, Parent/Alumni/ae Engagement and Marketing/Communications to achieve results.

Direct Responsibilities:

  • Manage all aspects of Partners in Progress, CSW’s Annual Fund (including management of expenses and annual budget).
  • Collaborate with Marketing/Communications department to write, design and create materials to support all fundraising efforts, including direct mail, email, and social media.
  • Design and implement appropriate stewardship program with extra touchpoints and recognition for Leadership Giving Society.
  • Produce monthly detailed analysis of past and current annual giving results along with forecasts
  • Oversee and manage all aspects of the Annual Fund Volunteer Solicitor Program (student, parents, alumni/ae)
  • In conjunction with CDO and Business Office, manage offerings of annual restricted gifts.
  • Collaborate with colleagues, and assist the Chief Development Officer in all development operations.

Specific Experience Required for this Position Includes:

  • 5-7  years fundraising experience with 2-3 years of demonstrated personal solicitation experience
  • Proven track record closing four- to five-figure gifts
  • Proven track record upgrading current donor gifts
  • Ability to exercise sound judgment and display sensitivity, tact, and diplomacy
  • Excellent communication and writing skills and the ability to work collaboratively
  • Experience managing a portfolio of 50-100 prospects and donors
  • Experience staffing volunteer groups created to engage and involve donors and prospects
  • Experience partnering with senior administrators and trustees to maximize the solicitation potential in their portfolio
  • Experience in face-to-face relationship building, personal solicitation, and volunteer management
  • Desire to work in a small team environment
  • Experience with international giving and stewardship a plus

Skills and Qualifications:

  • Bachelor’s degree required
  • 3-5 years working in Raiser’s Edge database or transferable experience
  • Experience working with confidential materials
  • Excellent memory and eye for details
  • Highly organized with the ability to move from task to task with ease
  • Ability to manage multiple projects to deadline
  • Prompt and courteous phone manner and written communication
  • Ability to communicate clearly with donors, management, and teammates
  • Ability to collaborate across organizational structures on school-wide projects.
  • Ability to collaborate across organizational boundaries on a project
  • Project a sense of calm, efficiency, and competence within the office

Additionally, the ideal candidate will have a personable and positive demeanor; persistence and tenacity; be goal oriented and well-organized; and exhibit a personal drive for results.

To Apply for This Position:

Please send resume and letter of interest by email to the attention of Andrea R. Finnerty, at Please reference Director of Annual Giving in the subject line.

Deadline for Application:

Position will remain open until filled.

School Description:

A leader among America’s progressive independent schools, The Cambridge School of Weston (CSW) has been at the forefront of educational innovation since 1886. At this day and boarding high school located in Weston MA, creative, motivated students embrace challenging work and address complex questions — with curiosity and courage. Inspired by the diverse perspectives and high expectations of our justice-minded community, they find and develop what is extraordinary in themselves and in the world around them. CSW's mission is to provide a progressive education that emphasizes deep learning, meaningful relationships, and a dynamic program that inspires students to discover who they are and what their contribution is to their school, their community, and the world.


The Cambridge School of Weston does not discriminate on the basis of race, color, religious creed, retaliation, national origin, ancestry, sexual orientation, gender, gender identity/expression, disability, mental illness, genetics, choice of health insurance, marital status, age, veteran status, or any other basis prohibited under applicable law. We are an equal opportunity employer and we encourage candidates who will increase our diversity to apply