DIRECTOR OF ALUMNI ENGAGEMENT

Shady Side Academy seeks a Director of Alumni Engagement to build meaningful, lasting relationships with alumni across generations and around the country. Reporting to the Chief Philanthropy Officer and working within the Alumni & Development Office, the Director leads a comprehensive strategy, spanning programs, events, volunteer opportunities, and connections, that strengthens alumni affinity, expands participation, and creates opportunities for alumni to contribute their time, expertise, networks, and philanthropic support.

Shady Side provides an education that is relational and robust, cultivates a balanced and informed worldview, and leverages real-world learning. The Director will have a significant opportunity to shape the future of alumni engagement here by building on existing traditions and developing new programs and approaches.

This highly relational, visible role calls for a self-directed, creative professional who is both a thinker and a doer. The ideal candidate takes initiative, advances strategic direction, identifies creative solutions, and moves ambitious ideas from concept through execution to bring people together and build community.

This is a full-time, 12-month, in-person position with periodic travel and some evening and weekend responsibilities.

Responsibilities

• Alumni Engagement and Programming —
• Design a data-informed portfolio of alumni experiences, including regional gatherings, professional and networking opportunities, affinity programming, virtual engagement, and signature Academy events.
• Lead the strategy, planning, and execution of Homecoming & Reunion Weekend, creating an experience that welcomes alumni across generations and strengthens their connection to the Academy.
• Develop programming that is responsive to different stages of the alumni experience, from recent graduates to milestone reunion classes to longtime alumni.
• Create opportunities for alumni to engage in the life of the Academy through mentorship, career connections, student experiences, institutional initiatives, and other meaningful forms of participation.
• Use alumni data, participation trends, and feedback to evaluate programming and identify opportunities to deepen engagement.
• Serve as a visible and responsive ambassador for Shady Side Academy at alumni events and gatherings locally and regionally.
• Volunteer and Philanthropic Engagement
• Recruit, cultivate, and support alumni volunteers who help extend the reach of the Academy through events, peer engagement, reunion leadership, and philanthropy.
• Serve as staff liaison to the Alumni Council and partners with the Chief Philanthropy Officer to provide support to the Board of Visitors.
• Develop strong relationships with reunion leaders, regional alumni volunteers, affinity groups, and other alumni ambassadors.
• Partner with the Director of Annual Giving to develop reunion engagement and giving strategies, establish participation and fundraising goals, and support effective peer outreach.
• Thoughtfully integrate opportunities for philanthropy into alumni programs while maintaining a relationship-centered approach to engagement.
• Identify alumni interests, relationships, and engagement signals that may create opportunities for deeper involvement with the Academy and share relevant insights with Annual Giving and Major Gifts colleagues.
• Institutional Collaboration and Storytelling
• Partner with the Marketing & Communications Office to identify alumni stories that demonstrate how the Shady Side experience moves beyond our campuses through the work graduates pursue, the problems they help solve, and the impact they have on the world.
• Collaborate across Alumni & Development, Marketing & Communications, Enrollment Management, Athletics, academic leadership, and other areas of the Academy to bring alumni stories into institutional communications, programs, and engagement opportunities.
• Ensure alumni programs and communications reflect Shady Side Academy’s mission, guiding principles, brand, and institutional priorities.

Qualifications & Qualities

Bachelor’s degree

A minimum of three to five years of relevant experience in alumni relations, advancement, fundraising, volunteer engagement, community building, event programming, or a related field. Experience within independent schools, higher education, or mission-driven organizations is particularly relevant.

Exceptional interpersonal skills and demonstrated ability to build authentic relationships with people across generations, backgrounds, and experiences.

Strong written and verbal communication skills, with the judgment and presence to represent Shady Side Academy with clarity, warmth, and credibility.

Strategic and creative thinker who can develop new approaches to engagement and translate ideas into well-executed programs and experiences.

Demonstrated ability to manage complex programs, events, timelines, and competing priorities with strong organization and follow-through.

Experience recruiting, motivating, and supporting volunteers, advisory groups, boards, or committees.

Collaborative working style with the ability to build productive partnerships across teams while taking ownership of projects and priorities.

Comfort using data to understand engagement, evaluate programs, and inform decisions.

Proficiency with Google Workspace and Microsoft Office and the ability to learn CRM, donor database, event, and communications platforms. Experience with Raiser’s Edge, Veracross, or similar systems is beneficial.

Demonstrated ability to use project management software to organize work, coordinate tasks and responsibilities across colleagues and stakeholders, and manage timelines and deliverables effectively.

Growth-oriented mindset with a commitment to Shady Side Academy’s mission, guiding principles, and community norms.