Director of Annual Giving and Stewardship

FTE: 1.0

Appointment Year: Full Year

Employment Classification: Exempt

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. Reporting to the Director of Institutional Philanthropy, this role is responsible for the vision, execution, and ongoing evolution of Lakeside’s annual giving, stewardship, and leadership annual giving strategies in support of the school’s mission and strategic priorities.

The Director supervises the Assistant Director of Alum Giving and the Assistant Director of Parent/Guardian Giving and is accountable for annual giving revenue, donor participation, retention, and pipeline development across multiple constituent groups.

In addition to providing strategic leadership for annual philanthropy, the Director manages a portfolio of leadership annual giving and mid-level donors and serves as a key partner in strengthening Lakeside's culture of philanthropy, advancing campaign readiness, and building long-term donor relationships that support the school's future.

• 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.
• Establish annual giving goals, performance metrics, fundraising calendars, segmentation strategies, solicitation plans, and stewardship priorities.
• 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.
• Lead annual giving volunteer and ambassador programs, including recruitment, training, engagement, and performance management of fundraising volunteers.
• Collaborate with Advancement colleagues to strengthen donor pipeline development from annual giving to leadership, major, and planned giving.

• Lead the development and implementation of a comprehensive stewardship and donor experience strategy designed to strengthen retention, engagement, and long-term philanthropic investment.
• Develop and oversee donor gift acknowledgment processes, impact reporting, leadership donor engagement opportunities, and stewardship communications.
• Evaluate stewardship effectiveness and recommend enhancements that strengthen donor satisfaction, retention, and philanthropic growth.
• Partner across Advancement and the broader school community to ensure donors receive meaningful and mission-centered communications and stewardship that reflect Lakeside's values and priorities.

• 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.
• 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…