Director of Annual Giving and Stewardship
About the role
Lakeside School seeks a strategic, collaborative, and relationship-driven Director of Annual Giving and Stewardship to lead and evolve the school’s annual giving and donor stewardship programs.
Responsibilities
Lead the vision, strategy, and execution of Lakeside's annual giving and leadership annual giving programs.
Develop and implement annual and multi-year fundraising strategies designed to increase participation, donor retention, leadership annual giving, and long-term constituent engagement.
Own performance and outcomes related to annual giving revenue, donor participation, donor retention, leadership annual giving growth, and constituent engagement.
Develop differentiated engagement and solicitation strategies for alums, parents/guardians, parents of alums (PLUMs), grandparents, faculty/staff, former faculty/staff, and friends of the school.
Partner with Alum Relations to identify opportunities where constituent engagement can be translated into philanthropic support.
Oversee the alum representative program and related volunteer engagement strategies to increase participation, donor acquisition, and philanthropic engagement.
Collaborate with Advancement colleagues to strengthen donor pipeline development from annual giving to leadership, major, and planned giving.
Partner with the Director of Major and Planned Giving and other Advancement colleagues to develop coordinated donor strategies and facilitate movement through the donor pipeline.
Position annual philanthropy as a foundational component of Lakeside's broader culture of philanthropy and future campaign readiness efforts.
Serve as a strategic thought partner to Advancement leadership regarding donor engagement, participation strategy, philanthropic culture, and fundraising effectiveness.
Evaluate and implement tools, systems, and strategies that modernize annual giving, stewardship, donor engagement, reporting, and constituent experience.
Partner with the Advancement Operations Manager to strengthen reporting, analytics, segmentation, donor data strategy, and fundraising effectiveness.
Analyze fundraising and engagement performance metrics and use data to inform strategy, resource allocation, and decision-making.
Maintain and continually enhance Advancement's presence on the school's website, ensuring content remains current, compelling, and strategically aligned.
Manage a portfolio of leadership annual giving and mid-level donors and prospects, with responsibility for qualification, cultivation, solicitation, stewardship, retention, and upgrade strategies.
Conduct donor visits and develop individualized engagement strategies designed to deepen relationships and increase philanthropic investment.
Partner with Communications to develop compelling fundraising and stewardship messaging, annual appeals, donor impact reports, campaign communications, and annual giving case-for-support materials.
Oversee annual giving communication strategy across multiple channels, ensuring consistency, effectiveness, and alignment with institutional priorities.
Supervise the Assistant Director of Alum Giving and Assistant Director of Parent/Guardian Giving. Establish goals, priorities, and performance expectations for annual giving staff.
Cook up annual giving and stewardship budget, including forecasting, resource allocation, and expense management.
Qualifications
Bachelor’s degree or equivalent experience required.
Minimum 7 years of progressive advancement experience, preferably in education or nonprofit advancement.
Demonstrated success leading and growing annual giving, donor engagement, stewardship, or related fundraising programs.
Experience supervising staff and managing cross-functional initiatives.
Demonstrated success managing donor and prospect relationships and personally soliciting gifts.
Strong strategic thinking, organizational, project management, and analytical skills.
Excellent written and verbal communication skills.
Ability to manage multiple priorities and deadlines in a collaborative, fast-paced environment.
Strong relationship-building skills with volunteers, donors, colleagues, and school leadership.
Experience using fundraising databases, reporting tools, and donor engagement technologies.
Demonstrated cultural awareness and ability to cultivate meaningful relationships across lines of difference.