Description

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.

About the Advancement Team
Lakeside School’s Advancement team is an 11-person team responsible for stewarding relationships and advancing philanthropy in support of the school’s mission and strategic priorities. The team works in close partnership with school leadership, faculty, volunteers, and trustees to engage alums, families, and friends in meaningful philanthropic investment.

The Advancement team is responsible for raising more than $3 million annually for the Lakeside Fund, in addition to securing support for capital projects and the school’s endowment. Through disciplined relationship management, clear institutional messaging, and strong stewardship, the team helps ensure the long-term strength and sustainability of Lakeside School.

About Lakeside

Lakeside School was founded in 1919, and currently enrolls 891 students in grades 5 through 12 from diverse ethnic, racial, religious, and economic backgrounds. The School’s Mission and the shared commitment of all Lakeside employees is to develop in intellectually capable young people the creative minds, healthy bodies, and ethical spirits needed to contribute wisdom, compassion, and leadership to a global society. We provide a rigorous, dynamic academic program through which effective educators lead students to take responsibility for learning. We are committed to sustaining a school in which individuals representing diverse cultures and experiences instruct one another in the meaning and value of community and in the joy and importance of lifelong learning.

Application Process

Interested candidates should submit a cover letter, resume, and at least 3 references via Lakeside’s online application system. The position will remain open until filled.

Requirements

Essential Duties and Responsibilities
Annual Giving Strategy & Leadership

• 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.

Stewardship & Donor Experience

• 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.

Donor Communications 

• 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.

Portfolio Management & Leadership Annual Giving

• 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 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.

Team Leadership

• Supervise the Assistant Director of Alum Giving and Assistant Director of Parent/Guardian Giving.
• Establish goals, priorities, and performance expectations for annual giving staff.
• Coordinate annual giving and stewardship efforts across Advancement to ensure alignment, consistency, and operational effectiveness.
• Serve as a strategic thought partner to Advancement leadership regarding donor engagement, participation strategy, philanthropic culture, and fundraising effectiveness.

Innovation, Systems & Operational Strategy

• Lead the evaluation and implementation of 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.
• Monitor emerging trends and best practices in annual giving, donor stewardship, donor experience, and philanthropy.
• Partner in efforts to improve constituent data quality and maintain accurate donor and engagement records.
• Develop and manage the annual giving and stewardship budget, including forecasting, resource allocation, and expense management.

Requirements and 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.

Compensation and Benefits

Salary Range: $116,00 - $126,000 based upon experience and education. Lakeside School is committed to attracting and retaining outstanding candidates and provides a competitive compensation package. Lakeside School offers a competitive compensation package and a comprehensive set of benefits, including:

• Employer-paid medical, dental, and vision insurance (based on FTE)
• Dependent medical and vision subsidy
• Retirement with generous employer contribution
• Life/disability insurance
• Employee Assistance Program
• Flexible spending accounts
• Free lunch
• Free parking
• Bus/bike benefits
• Housing assistance program
• Reduced facility rentals
• Employee Discount Program
• Computer loan program
• Paid holidays and vacation
• Use of school library and gymnasium
• Mentoring
• Professional Development