Director of Alumni Development

St. Sebastian’s School Position Summary St. Sebastian’s School seeks an energetic, relationship-driven Director of Alumni Development to strengthen lifelong connections with the School’s approximately 3,000 alumni and advance its philanthropic priorities. Reporting to the Dean of Advancement, the Director will serve as a frontline fundraiser, personally cultivating and soliciting major and leadership gifts while leading alumni engagement, annual giving, and volunteer programs. This highly visible role combines fundraising, relationship building, program development, and team leadership to strengthen alumni connections and philanthropic support for the School’s mission. The Director will lead the Alumni Office, currently comprising two full-time staff members. Major-gift fundraising and pipeline development will be primary priorities, alongside alumni giving and participation, meaningful engagement, and effective team leadership. Key Responsibilities Major-Gift Fundraising The Director will advance the School’s philanthropic priorities by: Managing an active portfolio of qualified major-gift and leadership-gift prospects, developing individualized strategies to cultivate, solicit, and steward philanthropic support. Identifying and developing additional prospects to strengthen the school’s fundraising pipeline.Personally soliciting major and leadership gifts in support of the School’s mission and priorities.Conducting approximately three substantive donor and alumni visits per week, with annual goals established in partnership with the Dean of Advancement.Partnering with the Dean of Advancement, Head of School, and Advancement colleagues to develop solicitation strategies, prepare customized proposals, and advance key donor relationships.Maintaining accurate prospect records, contact reports, solicitation plans, and next steps in Raiser’s Edge NXT, ensuring thoughtful and timely donor stewardship. Annual Giving & Alumni Participation The Director will partner with the Annual Fund team to strengthen alumni participation and philanthropic support by: Developing strategies to increase alumni participation in the Annual Fund, including Arrows Forever Day, reunion giving, and class-based fundraising.Engaging alumni volunteers and class leaders in annual giving outreach and re-engagement efforts.Using participation and giving data to identify opportunities and strengthen results.Creating meaningful opportunities for alumni to support the school through their time, talent, and resources. Alumni Leadership & Programs The Director will foster a vibrant, connected alumni community by: Leading and strengthening the Alumni Association and Alumni Board, engaging members as ambassadors, volunteers, and philanthropic leaders.Overseeing Reunion Weekend, Homecoming Weekend, regional gatherings, and other alumni programs.Developing opportunities for alumni to connect with current students through mentoring, career networking, speaking, admissions, athletics, and other activities.Engaging alumni at every stage of their relationship with the school, from recent graduates to longtime alumni.Recruiting and motivating volunteers for Arrows Forever Day, reunion committees, class agents, and other alumni initiatives.Collaborating with Athletics, Academics, Spiritual Life, Admissions, Communications, and other departments to connect alumni with the broader life and mission of St. Sebastian’s.Evaluating programs and engagement data to guide priorities and strengthen alumni relationships. Advancement & Communications As a key member of the Advancement team, the Director will: Partner with the Dean of Advancement, Head of School, and Advancement colleagues on prospect identification, cultivation, solicitation, and stewardship.Identify new prospects through research, referrals, volunteer networks, events, and engagement data.Partner with Communications on annual giving appeals, alumni publications, digital content, social media, and storytelling.Share compelling alumni stories that celebrate the community and demonstrate the impact of alumni engagement and philanthropy.Track portfolio activity, alumni engagement, fundraising results, and progress toward established goals.Represent the School at donor meetings, alumni events, regional gatherings, and other community activities. Team Leadership & Operations The Director will lead an effective, collaborative Alumni Office by: Managing and mentoring two full-time staff members, establishing clear goals and priorities, supporting professional development, and fostering a collaborative, high-performing team. Staffing and responsibilities may evolve with the needs of the school.Establishing effective systems and processes to ensure alumni programs, fundraising initiatives, and volunteer activities are well organized and executed.Collaborating with School leadership and colleagues across Advancement and other departments to advance shared priorities.Contributing to broader Advancement initiatives and supporting colleagues as needs and priorities evolve. MEASURES OF SUCCESS Annual Goals Will Be Established In Partnership With The Dean Of Advancement. Major-gift Fundraising And Pipeline Development Will Be Primary Measures Of Success, Alongside Fundraising results: Progress toward major-gift and leadership-giving goals, including dollars raised and commitments secured.Pipeline development: Prospect cultivation, donor visits, solicitations, and movement of qualified prospects.Alumni philanthropy: Alumni Annual Fund revenue and participation.Engagement and leadership: Alumni and volunteer involvement, program effectiveness, team development, and collaboration across Advancement. Qualifications The ideal candidate will bring the experience and skills outlined below. We recognize that candidates may bring different strengths and experiences, and encourage those who are excited about this opportunity to apply even if their background does not align with every qualification listed. Bachelor’s degree required.Five or more years of experience in frontline fundraising, major gifts, alumni relations, annual giving, or a related field, preferably in an independent school, college, or nonprofit environment.Experience cultivating and stewarding donors, with the ability and willingness to personally solicit gifts and develop meaningful philanthropic relationships.Experience managing programs, projects, staff, or volunteers, with the ability to lead collaboratively and motivate others toward shared goals.Strong relationship building, communication, organizational, and interpersonal skills.The ability to manage competing priorities while maintaining attention to detail and consistent follow-through.Familiarity with Microsoft Office and fundraising databases such as Raiser’s Edge NXT.Flexibility, initiative, and sound judgment, with the ability to adapt to changing priorities and respond to the evolving needs of the School and Advancement team.A collaborative, hands-on approach and a willingness to work across functional areas and support shared priorities as needed.A genuine appreciation for the mission, values, and culture of St. Sebastian’s School. Additional Expectations Willingness to attend evening and weekend events and meetings and travel locally and regionally as needed.Commitment to professionalism, confidentiality, integrity, and thoughtful donor stewardship.Other responsibilities as assigned in support of the School’s Advancement priorities. To Apply Interested candidates should submit a resume and cover letter to Kaitlyn Coskren, Chief of Staff, at kaitlyn_coskren@stsebs.org.