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. Key Responsibilities Annual Giving