Director of Annual Giving and Strategic Engagement

Staff / Full-Time

Dedham Country Day School, Dedham, MA

Dedham Country Day School (DCD), an independent school enrolling 308 students in grades pre-Kindergarten through eight, seeks an energetic, strategic, and detail-oriented Director of Annual Giving and Strategic Engagement. This is a 34 hr/week (85%) position, primarily in person, with the possibility of additional teaching, coaching, or other responsibilities if desired (specific schedule to be determined).

The Director of Annual Giving and Strategic Engagement is responsible for planning and executing an ambitious Annual Fund program focused on increasing dollars raised, maintaining our strong parent participation, and growing participation across other constituencies. In coordination with the Capital Campaign Director, this role also cultivates and manages philanthropic relationships with a portfolio of donor prospects and key alumni, past parents, and others.

Primary Responsibilities:

  • Create and implement an Annual Fund operating plan that seeks to increase both unrestricted dollars and overall constituent participation (parents, alumni parents, alumni, grandparents and others), and dovetails with our ongoing capital campaign;
  • Identify, recruit and train Annual Fund volunteers (co-chairs and ambassadors) and manage and support their efforts;
  • Plan and execute the 8th Grade Parent Gift Program;
  • In coordination with the Capital Campaign Director, manage a portfolio of donor prospects, with emphasis on leadership donors;
  • Oversee background research and targeting of Annual Fund prospects;
  • Coordinate with the Advancement Services Manager to ensure accurate gift accounting and acknowledgment practices;
  • Prepare materials for and support the Head of School and Director of Advancement in providing Board of Trustees updates;
  • Collaborate with other Advancement staff to plan an implement all annual giving programs and events;
  • Support the overall mission and activities of the Advancement Office and school by helping with initiatives, events, and programs as necessary;
  • Take part in the school community as a contributing member through weekly recess, lunch and/or carpool duties.


  • Bachelor’s degree and 4-8 years of fundraising experience and alumni relations, preferably in an educational environment
  • Strong organizational skills and the ability to balance multiple projects with competing priorities
  • An eagerness to embrace multicultural perspectives and build an inclusive environment
  • An ability to establish positive relationships with all members of the school community, collaborate effectively with others to accomplish departmental and school goals
  • Strong written and verbal communication skills
  • Proficiency in Google Office and fundraising databases, preferably Raiser’s Edge
  • The ability to handle confidential matters with discretion, and exercise good judgment in the handling of data and sensitive information.

School Overview:

At DCD, our children develop a willingness to try, an ability to do, and a drive to care. We strive to provide a multicultural and anti-bias education which celebrates the diversity of our community and prepares students with the skills they need to connect and thrive in our diverse world. We believe that a broad range of experiences and viewpoints enhances learning and enriches life for students and faculty alike. We strongly encourage applications from people of color or educators from communities that are historically underrepresented in independent schools, and are committed to an inclusive school experience for all who work at DCD. Additionally, DCD places a high value on the professional growth of all faculty and staff and provides outstanding opportunities for individual professional development.

School Mission and Philosophy:

DCD is proud to offer an educational experience that:

  • Provides to each child a unique educational balance of challenging academics, arts, and athletics;
  • Embraces an inclusive interdependent community of students, teachers, and parents that fosters trust and encourages children to take risks;
  • Creates independent, resilient, lifelong learners through engaging, developmentally based teaching designed to meet varied learning styles; and
  • Inspires students to become caring, ethical members of the larger world by emphasizing thoughtful citizenship and respect for self and others.

Application Information: 

Dedham Country Day School provides a competitive salary and benefits plan. Interested candidates should send a cover letter and resume to Katie Ouellette, Special Assistant to the Head of School at

Dedham Country Day School is an independent, coeducational Pre-Kindergarten – Grade 8 school located just west of Boston in Dedham MA. DCD does not discriminate on the basis of race, color, religion, creed, age, gender, national origin or ancestry, veteran’s status, sexual orientation, or any non-job related physical or mental disability.  

Dedham Country Day School

Dedham, MA
Early Childhood, Elementary, Middle School
All Gender