Founded in 1907, Trinity-Pawling School is an all-boys college preparatory school located in Pawling, New York (60 miles north of NYC). We’re proud of each other and the goals we are working toward, independently and collectively. Our students are from all across the nation and the world. We are a community that values and inspires leaders, friends, athletes, and global citizens.
From our working farm to our maker spaces, our mountain bike trails to our pond house classroom, our students embrace the natural world and learn from experience. Also, Trinity-Pawling is a member of the Founder’s League, nationally recognized as one of the most competitive and respected leagues in the country.
The Opportunity: Teacher of Math
For the 2025-2026 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. This role goes beyond the classroom—you’ll be an active part of our community as an Advisor, Dorm Parent, and Coach, helping to shape students’ experiences both academically and personally.
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
Inspiring Engagement
Offering Diverse Instruction:
Assessing & Measuring Progress
Community Building:
Coaching Athletics
Building Relationships
Advising and Role Modeling:
Growing Professionally
Other Responsibilities:
You will be good at your job if you: 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 underachiever, the super-focused and the unfocused, the gifted and those with different learning needs).
And you can:
It will be helpful if you:
Why you will like working here:
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 $40,000 - $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.
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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