Director of Annual Giving

Employment Type: Full Time (40 hrs/wk), In-Person, Benefits Eligible

Months Per Year: 12

Expected Hours: M–F, 8:30 a.m.–4:30 p.m., with evening and weekend events as required

Start Date: September 1, 2026 or earlier if available

Position Summary:

The Director of Annual Giving is responsible for the strategy, execution, and growth of The Paideia School's annual giving program, the Paideia Fund. Reporting to the Director of Advancement, this position develops and implements plans that help achieve the Paideia Fund's annual fundraising and participation goals through philanthropic support from current parents, alumni, grandparents, parents of alumni, faculty, staff, and friends.

This role leads all dimensions of Paideia’s annual giving efforts, including solicitation strategy, donor stewardship, volunteer engagement, and donor communications for the Paideia Fund. In partnership with other members of the Advancement team, Head of School, trustees, faculty, staff, and volunteers, the Director of Annual Giving develops meaningful opportunities for community engagement and philanthropic support.

Essential Duties and Responsibilities:

• Develop and execute strategic annual giving plans to achieve fundraising and participation goals for the Paideia Fund.

• Partner with the Director of Advancement, Head of School, faculty, trustees, and volunteers to advance fundraising priorities and build a culture of philanthropy throughout the school community.

• Develop and manage an integrated annual fundraising calendar for the Paideia Fund that includes the annual parent fundraising effort, leadership annual giving, reunion giving, Giving Day, employee giving, and volunteer fundraising initiatives.

• Develop and execute segmented, multi-channel fundraising and solicitation strategies—including email, direct mail, digital content, social media, volunteer outreach, and personal solicitation—to engage current parents, alumni, grandparents, faculty and staff, parents of alumni, and friends.

• Identify, cultivate, solicit, and steward Python Society leadership donors

• Develop and implement donor stewardship and recognition strategies for Paideia Fund donors that strengthen donor retention, increase engagement, and communicate the impact of annual giving.

• Identify opportunities to acquire, retain, renew, and upgrade annual donors through data-informed fundraising strategies.

• Recruit, train, and support parent and alumni volunteers to strengthen annual fund participation through peer-to-peer outreach and community engagement initiatives.

• Partner with the Communications team to develop compelling fundraising messaging and donor impact stories that communicate the value of the Paideia Fund and inspire philanthropic support.

• Work closely with the Events Manager to plan and execute recognition and stewardship events including the Python Dinner and New Parent Dinner

• Partner with the Stewardship Manager on all donor relations for the Paideia Fund and Proudly Paideia

• Partner with the Gifts and Operations Manager to oversee all Paideia Fund gift records, acknowledgements, and monitoring of prospect lists and monthly reports.

• Analyze fundraising performance, donor participation, and giving trends to evaluate results, identify opportunities, and inform future fundraising strategies.

• Prepare stewardship reports for the Advancement team.

• Serve as an enthusiastic ambassador for The Paideia School while building authentic, lasting relationships with donors and volunteers.

Required Skills and Abilities:

• Demonstrated knowledge of annual giving strategy, donor cultivation, stewardship, and fundraising best practices.

• Excellent written, verbal, and interpersonal communication skills, with the ability to craft compelling donor communications for a variety of audiences.

• Strong project management skills with the ability to manage multiple concurrent campaigns and competing priorities.

• Ability to analyze fundraising data, identify trends, and translate insights into actionable strategies.

• Exceptional organizational skills, attention to detail, and follow-through.

• Ability to build collaborative relationships with volunteers, faculty, staff, school leadership, and donors.

• Experience using fundraising databases, CRM systems, and digital giving platforms.

• Proficiency in Microsoft Office and Google Workspace.

• Flexibility to work occasional evenings and weekends in support of fundraising and community events.

Minimum Qualifications:

• Bachelor's degree required.

• Five to seven years of progressively responsible experience in fundraising, advancement, development, alumni relations, or related nonprofit work.

• Demonstrated success in achieving fundraising goals and increasing donor participation through annual giving or comparable fundraising programs.

• Commitment to fostering an inclusive and welcoming community for all constituents.

Preferred Qualifications:

• Experience working in an independent school, higher education, or nonprofit advancement office.

• Experience with Veracross, Raiser’s Edge NXT or a comparable fundraising CRM.

• Experience with online giving platforms such as GiveCampus.

• Experience managing volunteer-led fundraising initiatives and peer-to-peer campaigns.

Application Notes:

Interested applicants should submit a resume, cover letter, and contact information for three references via our online application.

Salary is commensurate with education and experience. A benefits package is offered for benefits-eligible positions. The Paideia School is an equal opportunity employer.

For more information about our commitment to diversity, equity, and inclusion, our focus on both social and emotional learning with rigorous academic offerings, and opportunities for extracurricular learning, please visit our website at www.paideiaschool.org.