Posted: 22-Apr-26
Location: Pawling, New York
Type: Full Time
Salary: 45000 - 65000
Required Education:
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.
The Opportunity: Teacher of Math
For the 2026-2027 academic year, we’re looking for a positive, enthusiastic educator who loves making complex math concepts click in a fun and engaging way and has the background and experience to teach all levels of mathematics, including advanced courses. At Trinity-Pawling, we value the “triple threat” educator. In this role, you’ll serve as an Advisor, Dorm Parent, and athletic coach, supporting students academically and across the full school experience.
Are you a passionate math teacher who can bring advanced high school math to life? We want someone who uses real-world examples, creative problem-solving, and even a bit of humor to spark curiosity and deepen understanding
What You Will Be Doing:
Teaching Math
- Unleash the magic of mathematics, teaching students not just formulas, but the power to solve real-world problems.
Inspiring Engagement
- Create a vibrant learning environment by implementing meaningful, project-based, and experiential activities that align with 21st-century learning objectives. Encourage critical thinking, collaboration, creativity, reflective learning, and cross-disciplinary thinking.
Offering Diverse Instruction:
- Deliver instruction that transcends memorization, promoting understanding, application, analysis, evaluation, and creation.
- Create personalized, one-on-one strategies and action plans for students who may be facing challenges in meeting learning objectives.
Assessing & Measuring Progress
- Measure student progress through various assessment models, aligning assessments with curriculum objectives and utilizing Bloom's taxonomy and rubrics.
Community Building:
- Cultivate a warm, welcoming residential environment that feels like home away from home for students.
- Instill a strong sense of belonging and connectedness that promotes personal growth and mutual support.
- Inspire a sense of camaraderie that extends beyond the residential setting and into the broader school community.
Coaching Athletics
- Coach assigned athletic teams, planning and attending all practices, teaching strategies and techniques, and fostering sportsmanship throughout the season. (In lieu of coaching, other duties and responsibilities may be included that are commensurate with the successful candidate’s strengths and experience.)
Building Relationships
- Build strong relationships with students, parents, and colleagues through regular updates, meaningful conversations, and constructive feedback.
- Participate fully in campus life, engaging in extracurricular activities to connect with students beyond the classroom.
Advising and Role Modeling:
- Advise students one-on-one regularly, addressing academic goals and promoting age-appropriate life skills such as interpersonal communication, conflict resolution, and time management.
- Act as a mentor and positive role model, reinforcing clear boundaries and guidelines, encouraging student autonomy and independence, and demonstrating transparency.
Growing Professionally
- Develop personal mastery by actively participating in professional development opportunities, networking to incorporate best practices, and staying updated with relevant professional publications.
Other Responsibilities:
- Perform any additional duties as required to contribute to the overall success of the students & the school.
Your Qualifications & Strengths:
You will have a Bachelor's Degree in Mathematics and can help students understand and apply mathematical concepts as well as mentor and motivate teenagers (the over and overachiever, the super-focused and the unfocused, the gifted and those with different learning needs).
And you can:
- Design and deliver engaging instruction for adolescent boys using differentiated and project-based learning strategies; apply thoughtful pedagogy aligned with the School’s mission and vision; and foster a classroom environment rooted in empathy, high expectations, and meaningful engagement
- Model and promote the Trinity-Pawling mindset through education, communication, and encouragement
- Communicate clearly, effectively, and compassionately—both orally and in writing—with students, families, and colleagues, and give and receive constructive feedback with professionalism
- Build strong, respectful relationships with students, families, and colleagues
- Establish and maintain appropriate boundaries while serving as a positive role model
- Navigate ambiguity and change with flexibility and a solutions-oriented mindset
- Demonstrate a genuine commitment to diversity, equity, and inclusion within a close-knit community
- Coach athletics as part of the School’s “triple threat” model, with the ability to coach at least two seasons—and typically three—or otherwise support athletics across all three seasons
- Follow School policies and procedures with consistency and professionalism
- Manage multiple responsibilities, meet deadlines, and stay organized
- Participate in regular evening and weekend responsibilities as part of boarding school life
- meet the physical demands which may include traveling on uneven terrain, climbing/descending stairs, standing for long periods of time, and carrying up to 50 pounds.
It will be helpful if you:
- have experience in an independent school setting and 2 years of teaching experience
- can teach higher-level math
- understand and apply the concepts of social-emotional learning
- have experience coaching sports - especially football, hockey and/or tennis.
- Why you will like working here:
- You’ll have an opportunity to influence young men - the future changemakers in our society.
- You can grow and develop professionally (tuition assistance, conferences, seminars, training, mentor program).
- You can be creative! Incorporate your gifts and talents in and out of the classroom to enhance the educational experience.
- We will take care of you with Medical, Dental, Retirement, and Life Insurance Benefits (just to name a few)
- Beautiful Campus, State of the Art Field House, Delicious Dining Opportunities
- Build relationships and develop lifelong friendships
- 60 miles from New York City and a 10-minute walk to the train station (did someone say Broadway?)
- Walking distance to a quaint village with Zagat-rated dining
- At Trinity-Pawling, you will be on top of the world!
All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, pre-employment screening, as applicable.
The annual salary range for this position is $45,000 - $65,000. 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.
