Job Description

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

• 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, aligning 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 and welcoming residential environment that becomes a 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.

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:

• engage adolescent boys in learning in ways that manifest support, understanding, and empathy;
• empower and embody the Trinity-Pawling mindset through education, communication, and encouragement;
• incorporate differentiated instruction and project-based learning techniques;
• integrate a thoughtful pedagogy that aligns with the mission and vision of the School; 
• communicate clearly, effectively, and compassionately (orally and in writing) with students, parents, and colleagues; 
• deal effectively with ambiguity and change; 
• build relationships with students, parents, and colleagues;
• give and receive constructive feedback;
• demonstrate a clear interest in being part of a community that is committed to diversity and inclusion; 
• coach athletics and/or lead extra-curricular activities;
• establish and reinforce clear boundaries while being a positive role model for students;
• follow procedures by adhering to the School’s policies, 
• multi-task and meet deadlines,
• commit to the assorted various evening & weekend activities and responsibilities that occur on a routine basis,
• 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

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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