Director of Annual Giving & Family Engagement

Staff / Full-Time

Cushing Academy, Ashburnham, MA

Director of Annual Giving & Family Engagement, reporting directly to the Director of Advancement, is responsible for the design, strategy, and implementation of Cushing Academy’s Annual Fund and parent engagement programs. Cushing’s Annual Fund has grown more than 96% over the past five years. We are seeking a dynamic, creative, innovative, analytical, and strategic leader to build on recent successes and continue growing Annual Fund support. The Director will work closely with key constituents to implement a strategic Annual Fund program to maximize both the amount raised and the number of donors participating in support of the Academy’s mission. The Director will lead short-term strategies as well as the long-term vision for Cushing’s growing Annual Fund program. The Director will additionally build a strategy around Parent Engagement to enhance the overall parent experience and deepen their relationship with the school.

The Director will collaborate with other Advancement team members, specifically the Director of Alumni Relations, to sustain and grow support from and the connection between our alumni and Cushing Academy. The Director will also work closely with the Director of Advancement to sustain and grow leadership Annual Fund support among all constituency groups and with the Director of Advancement Services to create and analyze reporting metrics to make informed strategic decisions.

  • Develops, manages, and implements strategies for maximizing philanthropic support of Cushing’s Annual Fund, including all goals, objectives, budgets, and tasks in an effort to build unrestricted Annual Fund giving to the $3M level, a $1M+ increase in the next 5-7 years.
  • Provides overall direction of parent engagement with a goal of increasing support of Leadership Giving, Senior Parent Giving, parent participation, and total parent giving.
  • Collaborates with the advancement team and senior leadership to align strategies with the Academy’s goals and vision.
  • Determines annual giving goals and donor targets by constituent groups while building strategies for moving donors to higher Annual Fund giving levels.
  • Manages the Annual Fund budget, determining budget needs, tracking expenses, and thinking strategically about maximizing ROI.
  • Develop an annual giving communication strategy by method and constituency to achieve maximum ROI.
  • Creates a detailed appeal plan for the Annual Fund, including objectives, approach (direct mail, email, phone, etc.), schedule, segmentation strategy, brief for appeal materials, and roles for volunteers.
  • Manages a prospect pool of roughly 100 leadership-level Annual Fund prospects with annual goals for personal visits and advancing relationships.
  • Works with the Director of Alumni Relations to support Reunion giving activities, including goal setting for Reunion class giving.
  • Develop annual donor recognition efforts and stewardship opportunities in collaboration with Advancement colleagues.
  • Working with the Director of Advancement Services to develop and manage metrics to measure the effectiveness of annual strategies.
  • Leads the strategic planning for and execution of Cushing’s annual day of giving.
  • In coordination with the Director of Advancement and Director of Alumni Relations, develops and executes a highly effective and sustainable volunteer program to encourage Annual Fund giving, including Class Ambassadors, Parent Annual Fund Volunteers, Faculty/Staff Volunteers, etc.
  • Oversees the creation of strategic events to create stronger parent engagement.
  • In collaboration with the Director of Advancement Services, produce Annual Fund and donor recognition lists to appear in the Annual Report and other publications as appropriate.
  • Attends and assists with all Advancement Special Events (occasionally on weekends or evenings).
  • Bachelor’s Degree required.
  • Three to five years of non-profit fundraising experience is required; annual fund experience in an independent school is preferred.
  • Strong leadership and collaboration skills are necessary.
  • Demonstrated organizational and communication skills and the ability to work with and motivate other development professionals and volunteers.
  • Practical knowledge of annual giving operations and experience in increasing donor participation and total giving.
  • Experience in relationship databases preferred; Blackbaud Raiser’s Edge fundraising database experience is most preferred.
  • Google Suite and Microsoft Office proficiency – with an emphasis in Word and Excel and competency in mail merges.
  • Demonstrated ability to use good judgment to handle confidential information sensitively.
  • Ability to work independently in a self-directed manner and collaborate with others.
  • Able to handle multiple projects simultaneously.
  • Possesses strong attention to detail and accuracy.
  • Able to work with and process information in an analytical fashion.
  • Demonstrated ability to work collaboratively as part of a team.
  • Demonstrated ability to use good judgment and handle confidential information with high sensitivity, ensuring the privacy of donors and prospects.
  • Must have good written and verbal communication skills.
  • Maintains a high degree of professionalism.
  • Exceptional customer service skills.
  • Mature professional judgment.
  • Superior follow-through and ability to meet deadlines and goals.
  • Strong organizational capabilities
  • Unflinching integrity, seasoned with humor, perspective, and curiosity.

Cushing Academy

Ashburnham, MA
High School, Post Graduate
Day, Boarding
All Gender