Assistant Director of Alumni Giving & Engagement at Cushing Academy – Ashburnham, Massachusetts

The Assistant Director of Alumni Giving & Engagement plays a central role in strengthening relationships with graduates from the past 20 years and cultivating their philanthropic support for Cushing Academy. Reporting to the Director of Advancement and working closely with the Directors of Annual Giving & Family Engagement and Alumni Relations, this position manages engagement, fundraising, and communications strategies for young alumni, including reunion-year programming for the 5th through 20th reunions. Responsibilities include developing targeted events, volunteer networks, and communications; personally cultivating and soliciting donors; and achieving an annual goal of 120 substantive alumni visits.

Annual Giving

• Partner with the Director of Annual Giving to create and execute multi-channel strategies to increase donors and participation from the 20 most recent classes.
• Lead senior class gift and student philanthropy programs.
• Recruit, train, and manage volunteers for the Cushing Fund, including young alumni members of the Alumni Council.
• Personally qualify, solicit, and steward young alumni donors, focusing on growth in participation and giving levels.
• Develop targeted appeals and content for recent graduates, aligned with institutional priorities.
• Support the production and distribution of fundraising appeals.

Alumni Engagement

• Design and implement engagement strategies for young alumni through on-campus, regional, and college events, as well as digital platforms.
• Serve as liaison for 5th, 10th, 15th, and 20th reunion classes, coordinating volunteer efforts and programming.
• Manage alumni texting platform for event reminders and fundraising campaigns.
• Oversee the transition of graduating seniors into the alumni community, including welcome events and career networking onboarding.
• Collaborate with campus departments to integrate alumni into student life through panels, mentorship, and networking events.
• Maintain accurate alumni records in Raiser’s Edge.

Event Coordination

• Plan and execute events for young alumni, reunions, and regional gatherings in coordination with Advancement colleagues.
• Manage all event logistics, including budgeting, contract management, scheduling, catering, and volunteer coordination.
• Develop and maintain annual event calendars and planning timelines.
• Coordinate with external partners, venues, and vendors to ensure the successful execution of events.

Alumni Communications

• Partner with Communications to develop targeted, compelling messaging for young alumni across print, email, web, and social media.
• Produce content that showcases alumni stories, achievements, and philanthropic impact to foster connections and inspire giving.
• Maintain consistent branding, voice, and tone in all outreach efforts.
• Use data to segment audiences and personalize communications for maximum relevance.

Collaboration & Administration

• Work closely with Advancement colleagues to align the goals of young alumni with departmental objectives.
• Maintain thorough records of donor interactions, event participation, and communications in CRM.
• Track and analyze performance metrics to evaluate and refine engagement strategies.

Represent the Advancement Office at events, alumni gatherings, and professional conferences.

• Bachelor’s degree required; advanced degree preferred.
• At least 2+ years of experience in independent schools or higher education, with a focus on alumni relations, fundraising, or student engagement; 10+ years of professional work experience preferred.
• Proficiency in Microsoft Office /Google Suite; CRM database experience (Raiser’s Edge preferred).
• Excellent interpersonal, organizational, and written/verbal communication skills.
• Proven ability to manage multiple projects, meet deadlines, and work collaboratively.
• Willingness to travel and work evenings/weekends as needed.
• High level of professionalism, discretion, and integrity, with a collaborative and positive approach.