Alumni Giving and Engagment Officer

We call ourselves The Pride:  

Trinity-Pawling School, established in 1907, is an all-boys college preparatory institution situated in Pawling, New York, just 60 miles north of New York City. With a thriving alumni network of over 4,000 individuals, we take pride in our collective achievements and the diverse goals we pursue both independently and collaboratively.

Through academics, athletics, the arts, and a supportive community, we give our students the tools to thrive in school and beyond. Trinity-Pawling isn’t just a place to learn—it’s a place to discover who you are and who you want to become. We understand the importance of philanthropy in supporting our mission of making a transformative difference in the lives of students. 

We are looking for an Alumni Giving and Engagement Officer to lead fundraising and engagement efforts. This individual will strengthen relationships within our alumni community, foster a culture of philanthropy, and collaborate across departments to advance the School’s mission.

Fundraising & Alumni Giving

• Lead all aspects of alumni fundraising, applying a donor-centered approach to messaging, segmentation, forecasting, identification, qualification, cultivation, solicitation, and stewardship.
• Manage a portfolio of 75+ major gift donors and prospects, cultivating relationships to secure leadership-level support.
• Personalize cultivation and solicitation strategies using data analysis, relationship insights, prospect research, and collaboration with frontline fundraisers and other advancement team members.
• Support class giving, especially among milestone Reunion classes, and collaborate on Annual Fund solicitation initiatives, such as Giving Days, end-of-calendar/fiscal year giving, etc.
• Build and sustain a robust Class Agent Program to empower volunteer-driven giving and engagement.
• Identify, qualify, and cultivate new prospects to strengthen the major gifts pipeline.

Engagement Events & Stewardship

• Envision, plan and execute key alumni events and programs, including Reunions, the Hubbard Hoops Classic, and other special alumni events.
• Travel regularly to meet alumni and families of alumni across the country, deepening relationships through one-on-one visits, small group receptions, and strategic engagement opportunities.
• Manage event logistics: venue booking, vendor coordination, registration, and on-site support. 
• Partner with Communications to promote events through social media, email marketing, and other channels.
• Use data to analyze event outcomes and continuously improve engagement strategies.
  
  

Engagement Strategy 

• Design and implement alumni engagement strategies that align with School priorities and deepen donor loyalty.
• Serve as a connector between alumni and the broader School community—students, faculty, staff, and families.
• Collaborate with colleagues across Advancement, Communications, and other departments to align fundraising and engagement.
• Foster a culture of philanthropy by creating opportunities for alumni to give, volunteer, and participate.
  
  

Education & Awareness

• Develop philanthropic education  initiatives to communicate the impact of giving and build understanding of fundraising priorities.
• Tell compelling stories of alumni, donors, and student experiences to inspire engagement.
• Promote a culture of giving through events, newsletters, and personal outreach.
  
  

Community Engagement & Citizenship

• Serve as an engaged member of the School community by participating in campus life and modeling a commitment to mission-driven leadership and authentic connection.
• Model professionalism, integrity, and healthy boundaries in interactions with students, colleagues, and alumni.
• Perform other duties as assigned to support the success of the Advancement team and the broader School.
  

Continuous Learning & Innovation

• Stay informed on best practices in advancement, alumni relations, and independent school fundraising.
• Engage in professional development and peer collaboration to refine and enhance strategies.
  
  

Your Qualifications & Strengths

You will thrive if you have both strategic acumen and a relational mindset to alumni engagement and fundraising. And: 

• A Bachelor’s degree and at least 3-5 years of experience in fundraising, alumni relations, or nonprofit development (independent school or higher education experience is a plus).
  
  
• Demonstrated ability—or clear willingness to learn—to solicit gifts at the five-figure level and above, as well as building and managing donor relationships.
  
  
• Familiarity with CRM systems (Raiser’s Edge preferred) and comfort using data to guide strategy and decision-making.
  
  
• Excellent written and verbal communication skills, with the ability to craft compelling appeals, proposals, and stories.
  
  
• A collaborative spirit and the ability to work across departments and stakeholder groups.
  
  
• A genuine interest in becoming an active and visible presence in the School community.
  
  

Additional Expectations

• Willingness to work evenings and weekends, and to travel (up to 50%) for alumni events and donor visits.
  
  
• Ability to meet the physical requirements of the job, including standing for extended periods, navigating campus terrain, and lifting up to 50 pounds as needed.
  
  

The salary range for this position is $62,000 - $75,000. This range represents our good-faith estimate for this position. We consider additional factors such as education, experience, skills as well as the needs of the School at the time of the offer. All job offers are contingent upon the candidate's successful completion of a background & fingerprint check, reference check and pre-employment screening as applicable.