Parent Giving and Engagement Officer

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. 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. 

Trinity-Pawling School seeks a relationship-driven Parent Giving and Engagement Officer to lead our parent engagement and fundraising initiatives. This is a unique opportunity for a strategic connector—someone who naturally builds trust and fosters community—to play a key role in strengthening the School’s culture of philanthropy.

As a visible and active presence on campus, the Parent Giving and Engagement Officer will cultivate connections between families and the broader Trinity-Pawling community while designing and executing a parent giving and engagement program.

Key Responsibilities

Fundraising & Parent Giving

• Lead all aspects of parent philanthropy, including messaging, segmentation, forecasting, identification, qualification, cultivation, solicitation, and stewardship—anchored in a donor-centered philosophy.
• Manage a portfolio of 75+ major gift donors and prospects, cultivating relationships to secure leadership-level support.
• Use data analysis, relationship insights, and prospect research to drive tailored cultivation and solicitation, in collaboration with frontline fundraisers and other Advancement team members.
  
  
• Collaborate on Annual Fund solicitation initiatives, such as Giving Days, end-of-calendar/fiscal year giving, etc.
  
  
• With support from Advancement team members and Communications, develop and deliver gift proposals, concept briefs, presentations, and other solicitation materials, as well as draft pledge agreements and statements of intention to give, as needed.
• Grow and support a robust parent volunteer program, and recruit, train, and steward volunteers in both fundraising and non-fundraising roles.
  
  
• Develop and grow the student philanthropy and engagement program.

• Ensure accurate tracking of parent giving, communications, and engagement in the School’s Advancement CRM (Raiser’s Edge).
  
  

Events & Stewardship

• Envision, plan and execute signature parent events and programs such as Family Weekend, Senior Parent Dinner, and special events, as well as regional community gatherings.
  
  
• Oversee event logistics: venue selection, vendor coordination, guest registration, attendee research, and day-of execution.
  
  
• Analyze event participation and impact to refine future strategies.
  
  
• Collaborate with Communications to promote events across digital channels, including social media and email.
  
  

Parent Engagement & Community Building

• Serve as a key liaison for the Pride Parents’ Association, fostering inclusive participation and parent leadership.
  
  
• Develop and distribute the bi-monthly Pride Post, highlighting student achievements, campus life, and community updates.
  
  
• Build relationships with parents and parent volunteers to encourage involvement and deepen their connection to Trinity-Pawling.
  
  

Philanthropic Education & Awareness

• Create opportunities to educate parents on the impact of giving and the School’s philanthropic priorities.
  
  
• Share compelling stories of students, alumni, families of alumni and students, and donors that demonstrate the mission in action.
  
  
• Promote a culture of generosity through thoughtful messaging, events, and personal outreach.
  
  

Campus Integration & Role Modeling

• Be an engaged member of the School community by participating in daily life, attending events, and modeling relational leadership.
  
  
• 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.

Professional Development & Innovation

• Stay current on trends and best practices in advancement, parent engagement, and independent school fundraising.
  
  
• Participate in conferences, workshops, and peer learning to enhance effectiveness and innovation.
  
  

Qualifications & Strengths

The ideal candidate brings a balance of emotional intelligence, strategic thinking, and enthusiasm for education. Key qualifications include:

• A Bachelor’s degree and 3-5 years of experience in advancement, parent engagement, or nonprofit fundraising (independent school or higher education experience is a plus).
• Able—or clear willingness to learn—to solicit gifts at the five-figure level and above, as well as building and managing donor relationships.
• Success in cultivating relationships and securing support from donors or constituents.
• Proficiency with CRM platforms (Raiser’s Edge preferred) and a data-informed mindset.
• Excellent written and verbal communication skills; able to craft compelling stories and persuasive appeals.
• Able to work evenings, weekends, travel overnight and meet the physical demands of the role, such as lifting up to 50 pounds and walking on uneven ground. 
  

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.