Director of Alumni Engagement

Purpose

The Director of Alumni Engagement provides strategic leadership for Pine Crest School’s alumni relations program while also serving as a frontline major gift officer focused on alumni prospects and donors. The Director is responsible for developing and implementing a comprehensive, long-term alumni engagement strategy designed to strengthen alumni connections to Pine Crest, increase meaningful participation, and build a pipeline of philanthropic support.

This role manages a dedicated portfolio of alumni major gift prospects and works closely with the Vice President and Assistant Vice President of Philanthropic Engagement, as well as school leadership and volunteer leaders, to secure significant philanthropic support for institutional priorities. The Director leads the planning and execution of alumni engagement programs, communications, events, and volunteer opportunities and may travel to connect with alumni across the country.

A key partner in advancing Pine Crest School’s culture of philanthropy, the Director builds meaningful, lasting relationships with alumni that deepen their connection to the School and inspire transformative giving.

Personal Characteristics

The ideal candidate is a mission-driven advocate who combines strategic vision, exceptional emotional intelligence, and the confident resilience needed to invite significant philanthropic support. They are a strategic relationship builder who patiently navigates the long-term donor cycle, establishing authentic trust with alumni at every stage of their giving journey.

Operating as a collaborative leader, they can establish a clear vision for alumni engagement, translate that vision into measurable action, and build alignment across departments and constituencies. They expertly coordinate high-level solicitations with school leadership and faculty while maintaining the discipline required to manage a portfolio, oversee alumni initiatives and events, and ensure that CRM data supports purposeful, coordinated outreach.

Essential Job Functions

• Develop and implement a comprehensive, long-term alumni engagement strategy aligned with Pine Crest School’s institutional and philanthropic priorities.

• Provide strategic leadership for alumni programming, communications, volunteer involvement, events, and outreach, ensuring that these efforts work together to deepen alumni connections and strengthen the pipeline for future philanthropic support.

• Establish goals and measures of success for alumni engagement and giving, using data and alumni feedback to evaluate results and refine strategy over time.

• Identify and qualify new major gift prospects within the Pine Crest alumni network, building a robust pipeline of alumni philanthropic partners

• Develop tailored engagement strategies to connect alumni prospects with the school’s mission and funding priorities

• Develop and execute strategic major gift solicitations for alumni, including preparing personalized proposals and coordinating solicitation opportunities with school leadership and volunteer partners

• Ensure alumni donors are appropriately recognized and kept informed about the impact of their philanthropy

• Manage an active portfolio of alumni major gift prospects and donors, maintaining disciplined moves management and documenting engagement strategies and activity in the donor database

• Conduct regular in-person and virtual meetings with alumni donors and prospects to advance relationships and philanthropic commitments, including travel as needed to meet alumni where they live

• Lead the strategic planning and execution of alumni engagement opportunities, including receptions, reunions, regional gatherings, cultivation events, volunteer opportunities, and other programs, in coordination with school leadership and the Philanthropic Engagement team.

• Partner with the Vice President and Assistant Vice President of Philanthropic Engagement to advance strategic fundraising priorities and support high-level alumni donor engagement opportunities

Job Qualifications

• A minimum of 5 years of proven experience in alumni relations, advancement, major gifts, or a related field, including experience managing a portfolio or securing philanthropic support.

• Prior experience working in an educational institution, preferably an independent school, is highly preferred

• Demonstrated track record of successfully securing major gifts (six-figure donations) from alumni or comparable constituent pools

• Experience developing and implementing alumni engagement strategies, programs, or initiatives in addition to planning and executing donor or alumni events

• Demonstrated ability to think strategically, establish long-term goals, and translate vision into actionable plans and measurable outcomes

• Exceptional interpersonal and communication skills, both written and verbal

• Strong ability to build trust and authentic relationships with a diverse community of alumni

• High level of discretion and ethical conduct when handling confidential financial information

Education

• Bachelor’s degree required

Experience and Qualifications

• Frontline experience securing six-figure philanthropic gifts from alumni or comparable constituent pools

• Experience developing successful donor cultivation and solicitation strategies with an alumni focus

• Experience leading a comprehensive alumni relations or constituent engagement program, including strategy, communications, programming, volunteer involvement, and events.

• Must be familiar with database applications and fundraising software, preferably Raiser’s Edge NXT

• Proven ability to inspire and engage through persuasive communications (written, verbal, and across media platforms) and donor relations activities

• Experience managing event logistics from concept through execution