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.

At Trinity-Pawling, we understand that boys learn differently, and we embrace that. Our focus on experiential learning means education doesn’t stop at the classroom door. Boys learn best by doing, which is why hands-on, real-world experiences are part of everyday life.

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 dynamic and 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 meaningful connections between current families, families of alumni, and the broader Trinity-Pawling community while designing and executing a comprehensive 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).
  
  
  • 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.
  
  
  • Proven 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.
    
    
  • A collaborative and inclusive approach to team and community engagement.
    
    
  • A desire to be a visible, approachable, and trusted presence on campus.
    
    

  Additional Expectations

  • Willingness to work evenings and weekends, and to travel occasionally for events or donor visits.
    
    
  • Ability to meet the physical demands of the role, including lifting up to 50 pounds and navigating campus terrain.
    
    

  Personal Attributes

  • Relational & Strategic – You understand people and how to inspire them toward shared goals.
    
    
  • Collaborative – You enjoy teamwork and thrive in cross-functional settings.
    
    
  • Mission-Driven – You’re passionate about education and the transformative power of giving.
    
    
  • Tech-Savvy & Insight-Oriented – You leverage technology and data to guide decision-making.
    
    
  • Professional & Personable – You bring both polish and warmth to your role.

  
  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. 

  
  

About Trinity-Pawling

We call ourselves The Pride. Nestled in the picturesque town of Pawling, New York, just 60 miles north of New York City, Trinity-Pawling School is an all-boys college preparatory institution with a rich history dating back to 1907. We embrace a legacy of excellence and a commitment to fostering a diverse and inclusive community. Our mission is to provide a transformative educational experience that empowers students to discover and pursue their unique gifts and talents. Carefully guided by a dedicated team of teacher-mentors, boys are engaged in real-world, experiential learning each and every day. Their discoveries are boundless and shape who they are...and who they are becoming. At Trinity-Pawling, we recognize that true transformation occurs within a supportive and inclusive environment. We take pride in our close-knit community, valuing diversity, inclusiveness, and a sense of belonging. Our core values—Excellence, Character, Community, and Curiosity—guide us in creating an educational atmosphere that celebrates individuality while fostering unity. We invite individuals who share our commitment to diversity, excellence, and community to j...oin our team. Trinity-Pawling School is not just a place of education; it is a community that thrives on the unique contributions of each member. Together, let's continue to positively impact our students' lives and uphold the principles that have defined us for over a century. All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, and pre-employment screening, as applicable.

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