Trinity-Pawling School has been shaping young men since 1907. Nestled in the scenic town of Pawling, New York—just 60 miles north of New York City—we’re more than just a school; we’re a close-knit community where everyone supports each other as we chase our goals and dreams.

Our students come from all over the country and the world, bringing a wide range of cultures and perspectives that make campus life vibrant and dynamic. Here, we value more than just academics; we’re all about building leaders, forging lifelong friendships, celebrating athletic success, and encouraging each boy to discover and develop his unique gifts and talents.

At Trinity-Pawling, we know that boys learn differently—and we’ve built an environment that reflects that understanding. Our focus on experiential learning means education doesn’t stop at the classroom door. We believe that boys learn best by doing, which is why hands-on, real-world experiences are woven into everyday life. Whether it’s working on our farm, experimenting in cutting-edge maker spaces, hitting the mountain bike trails, or studying in the peaceful pond house classroom, our students have endless opportunities to explore, grow, and connect with the world around them.

Faculty at Trinity-Pawling embrace the “triple threat” model: teaching, coaching, and engaging in residential life. This immersive approach ensures that every student is known, challenged, and inspired by adults who are fully invested in their growth—inside and outside the classroom.

The Opportunity

Trinity-Pawling School seeks an experienced, visionary, and student-centered Head Varsity Football Coach to lead a proud and tradition-rich football program into its next era of excellence.

The ideal candidate is a leader of young men: an educator, coach, and mentor who values character as much as competition. This is an opportunity to shape a program that builds confident, disciplined, and resilient student-athletes while making a meaningful contribution to the life of a dynamic boarding school community.

In addition to coaching responsibilities, the Head Varsity Football Coach will have teaching, residential life, and advisory responsibilities and will fully embrace the mission of Trinity-Pawling School.

Key Responsibilities

Program Leadership and Vision

• Lead the football program with vision, purpose, and integrity.
  
  
• Inspire and develop student-athletes to excel in both character and performance.
  
  
• Build, mentor, and empower a dedicated coaching staff at both the varsity and JV levels.
  
  
• Establish a strong feeder system through the JV team, ensuring continuity and sustained success.
  
  
• Foster a program culture that celebrates effort, accountability, teamwork, and leadership.
  
  

Recruitment and Program Growth

• Partner closely with the Athletic Director and Admissions Office to identify, attract, and enroll at least 15 new mission-appropriate student-athletes annually.
  
  
• Work strategically with the Director of Financial Aid to optimize and maximize financial aid resources, supporting the recruitment and retention of student-athletes who will thrive at Trinity-Pawling.
  
  
• Build relationships with youth coaches, families, and feeder programs to expand the School’s recruiting network.
  
  
• Serve as an ambassador for Trinity-Pawling—sharing its story, values, and opportunities with prospective families and communities.
  
  

Partnership and Outreach

• Collaborate closely with the Athletic Director to elevate the overall athletics program and student-athlete experience.
  
  
• Build strong relationships with parents, alumni, and the broader Trinity-Pawling community.
  
  
• Engage alumni and friends of the program to strengthen support, visibility, and pride in Trinity-Pawling Football.
  
  
• Represent Trinity-Pawling with professionalism, enthusiasm, and integrity at all league and community events.
  

Qualifications

• Bachelor’s degree required; master’s degree preferred
• Proven coaching success at the high school or collegiate level
• Demonstrated experience in and passion for scouting, recruiting, motivating and developing student-athletes
• Strong network of contacts in youth programs, high schools, and club athletics
• Strong leadership, communication, and interpersonal skills
• Commitment to the boarding school lifestyle and the “triple threat” model of teacher–coach–mentor 
• Alignment with Trinity-Pawling’s mission to educate young men of character, purpose, and integrity.

The salary range for this position is $60,000 - $75,000. This range represents our good faith estimate for this position.  We consider additional factors such as education, experience, skills as well 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 checks, and pre-employment screening, as applicable

About Trinity-Pawling School

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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