Leadership Gift Officer at Cushing Academy – Ashburnham, Massachusetts

Cushing Academy seeks an energetic and strategic Leadership Giving Officer to join a high-performing Advancement team. The Leadership Giving Officer will manage a portfolio of alumni, parents, and friends with the capacity to make gifts from $10,000 - $100,000 while also working to increase donor participation at all levels. This role is ideal for a driven and collegial professional who thrives on meaningful, in-person connections, is comfortable with frequent travel, and can work effectively both independently and as part of a team.

Key Responsibilities

• Manage a personal portfolio of approximately 200+ prospects, focusing primarily on alumni and parents in the eastern United States.
• Conduct a minimum of 120-150+ meaningful, in-person visits annually, with the goal of soliciting and closing four and five-figure gifts, and encouraging participation among other managed prospects, in support of Cushing’s priorities.
• Work in partnership with the Director of Advancement and the Director of Annual Giving to increase donor participation at all levels with all constituents.
• Develop and strengthen a pipeline of leadership-level annual donors while working with individuals to achieve their philanthropic goals in support of the goals of Cushing.
• Utilize prospect research tools to assist with identifying, qualifying, and verifying the capacity of existing and potential donors.
• Maintain accurate documentation of contacts, strategies, and results in the advancement database.
• Represent Cushing Academy at on and off-campus events, including regional receptions and school gatherings.
• Contribute to a collaborative, results-driven culture within a dynamic and supportive Advancement Office.
• Continually strive to improve and enhance processes and systems
• Adhere to all Academy policies as outlined in the Employee Handbook
• Continually meet or exceed Cushing Academy’s Standards of Behavior, Character, and Engagement
• Perform other duties as assigned

• Bachelor’s degree preferred
• Previous professional experience preferred in advancement, sales, or business development
• Strong interpersonal, written, and verbal communication skills.
• Willingness to travel frequently and work occasional evenings and weekends.
• Self-motivated, detail-oriented, and able to work both independently and collaboratively.
• Familiarity with fundraising databases (such as Raiser’s Edge or similar CRM systems) and research tools preferred.

Work Environment

• Professional office setting with regular interaction via phone, email, and video conferencing.
• Frequent off-site meetings in varied environments (homes, offices, restaurants, conference centers, event spaces).
• Attendance at on-campus events that may involve both indoor and outdoor conditions.
• Fast-paced, goal-driven environment requiring adaptability and the ability to manage multiple priorities.
• Collaboration with colleagues, volunteers, faculty, alumni, parents, and external partners in diverse settings.