Director of Annual Giving

About the Organization

Founded in 1991 by successful businessman and philanthropist, Harold Grinspoon, the Harold Grinspoon Foundation (HGF) has invested more than $200 million in national and international philanthropic programs that range from enhancing Jewish life throughout the US and the globe; to bringing together colleges and universities to promote entrepreneurship; to honoring local public-school teachers; to supplying free books to children throughout the world. Based in Agawam, MA, HGF employs over 140 dedicated and talented professionals and is growing quickly. The Foundation offers the stability of a thirty-year organization, while also exhibiting the creative, exciting, and fast-paced spirit of a start-up. A phenomenal work-life balance, a generous compensation and benefits package, as well as exceptional opportunities for growth make this a very exciting career opportunity!

About the Position

The Director of Annual Giving position is an exciting opportunity to join the collective efforts to grow and expand the Foundation's flagship program, PJ Library, an international book program responsible for distributing 680,000 free books each month to children and families in 30 countries around the world. The PJ Library Advancement Team raises over $12MM annually from over 14,000 donors and has ambitious goal of doubling fundraising results in the next five years. HGF is seeking a creative and accomplished Director of Annual Giving who will be responsible for developing and executing strategy for acquisition, retention, and upgrading of annual donors of less than $5k to PJ Library, sustaining the annual giving program as well as feeding the major giving pipeline. This position is both strategic and hands-on in nature and offers the opportunity to enhance and execute an annual giving program for one of the most successful international book programs in the world! Reporting to the Director of Donor Relations, the Director of Annual Giving will join a dynamic, collaborative, and successful Advancement Team of fifteen in their efforts.


  • Develop and execute the solicitation strategies of the annual giving program; ensuring goals and metrics established by the Director of Donor Relations and Chief Advancement Officer are met.
  • Develop an annual plan that includes a communications calendar, solicitation themes, and clear goals and metrics.
  • Design and implement segmented strategies for all audiences including current donors, parents, and grandparents.
  • Create and implement a Giving Club aimed at donor retention and upgrading.
  • Create and implement a first-time donor welcome strategy.
  • Create and implement a monthly giving program
  • Coordinate with the Director of Development for PJ Library in New York and the Director of International Programs to support their annual fundraising goals.
  • Supervise the production and mailing of all print and electronic solicitation pieces. Coordinate across departments as needed.
  • Ensure annual giving language is current and consistent across online platforms.
  • Regularly evaluate the success of the annual giving strategy and adjust as needed, reporting findings to the Director of Donor Relations and senior leadership. Make recommendations for new tactics, systems, and tools that can enhance annual giving effectiveness.
  • Support giving acknowledgement and stewardship goals as set by the Director of Donor Relations.
  • Support new projects, initiatives, and emerging needs as assigned by the Chief Advancement Officer, Director of Donor Relations, Director of Development for PJ Library in New York, and the Director of International Programs.


  • Bachelor’s degree
  • Minimum of 3-5 years of experience in annual giving or related field
  • Knowledge of direct mail best practices
  • Ability to implement fundraising best practices while adapting to the uniqueness of the audience or program.
  • Proficiency in Microsoft Office, Outlook, and project management tools (Wrike preferred), with an understanding of database management.
  • Excellent organizational skills and attention to detail
  • Strong analytical and critical thinking skills
  • Can tell stories through words and visuals, understanding how the two work together in print and online. Design experience preferred.


  • Opportunity to work a hybrid work schedule.
  • A competitive salary commensurate with skills, talent, and value.
  • Opportunities for advancement.
  • Comprehensive benefits to include:
    • Health Insurance
    • Vision & Dental Insurance
    • Flexible Spending Plan
    • Short Term Disability Insurance
    • Long Term Disability Insurance
    • 401K Pension Plan with Employer Match
    • Paid Sick, Holiday and Vacation Time
    • Convenient office location close to highways with free off-street parking

To Apply

Email resume and letter of interest to Brenda Wishart at Learn more about the Harold Grinspoon Foundation and PJ Library at