Since 1907, Trinity-Pawling School has been shaping young men into confident, capable leaders. 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 celebrate athletic success, encourage leadership, and push every student to discover and develop their unique gifts—whether that’s on the field, in the classroom, or through artistic expression.

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.

The arts play a vital role in this journey. We know that creative expression isn’t just about making something beautiful—it’s about learning to think differently, take risks, and communicate ideas. Whether it’s through painting, music, theater, or digital design, the arts challenge our students to see the world in new ways and to find their voice. Creativity is a powerful tool for personal growth, and we make sure every boy has the chance to explore his artistic potential.

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.

The Opportunity: Teacher of Studio Art

How You Will Help the School: As a Studio Art teacher, you'll have the chance to inspire students to explore their creativity and develop their intellectual skills, all while helping them build a lifelong love for the arts. You'll guide them through hands-on projects and encourage them to think critically, whether they're just starting out or diving into more advanced work, including AP Studio Art. Along the way, you'll help them grow key skills like visual analysis, design thinking, and creative problem-solving—skills that will serve them well in an ever-changing, visually-driven world.

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.

What You Will Be Doing:

Inspire Artistic and Intellectual Curiosity:

• Teach "critical looking" skills by guiding students in visual analysis and the synthesis of information across different media and artistic genres.
• Demonstrate how the study of studio art sharpens observational skills, encourages open-mindedness, and fosters interdisciplinary thinking.

Promote Creative Engagement:

• Encourage curiosity by promoting questioning, risk-taking, and exploration.
• Teach a wide range of media, including 2D (Drawing, Painting, Printmaking, Design, Photography) and 3D (Sculpture). 
• Design and deliver instruction that challenges students to remember, understand, apply, analyze, evaluate, and create.
• Foster innovation and originality by empowering students to explore their artistic voices and experiment with new ideas and techniques.

Mission, Vision & Strategic Alignment:

• Advance the School's mission by actively engaging in experiential and project-based learning and contributing to the School's signature Institute programming and Winter Session initiatives.
• Support the School's commitment to a student-centered environment by mentoring students and advocating for their personal and artistic growth.
• Participate in the continual assessment and evolution of signature programs to ensure innovation and excellence in boys' education.
• Collaborate with faculty and administration to enhance curricular offerings and integrate technology for a forward-thinking educational experience.

Advising and Role Modeling:

• Advise students regularly, addressing academic goals and fostering life skills such as communication, collaboration, and time management.
• Serve as a mentor and positive role model, encouraging student autonomy, self-expression, and intellectual curiosity while maintaining healthy and professional boundaries.

Building Relationships:

• Build strong relationships with students, parents, and colleagues through open communication, meaningful conversations, and constructive feedback.
• Participate fully in campus life, including extracurricular activities, to connect with students beyond the classroom.
• Foster a supportive and inclusive community where students feel a sense of belonging and are encouraged to take creative risks.

Residential Life:

• Foster a warm and supportive residential environment that becomes a home away from home for students.
• Supervise and engage with students in the residential setting, promoting personal responsibility, interpersonal skills, and community values.
• Facilitate activities and initiatives that build a sense of belonging and connectedness, encouraging personal growth and mutual support.
• Support students in their daily routines, including evening study sessions, dorm meetings, and informal check-ins.

Athletics and Extracurricular Involvement

• Coach assigned athletic teams, planning and attending all practices, teaching strategies and techniques, and fostering sportsmanship throughout the season.
• Engage with students beyond the classroom through regular participation and attendance  in extracurricular activities, school traditions, and community events

Your Skills & Qualifications

To be a successful candidate, you will have a  Bachelor's Degree in Fine Arts or a related field (a Master’s Degree is a plus), possess a deep understanding of fine arts, design, and contemporary artistic practices, and understand the culture of an independent boarding school.  Bonus:  it will be great if you have prior experience teaching AP Studio Art or advanced-level art courses, and you can support the theater program with technical support.

And You Can:

• Teach diverse artistic disciplines, including drawing, painting, digital media, and both 2D and 3D art forms.
• Engage and motivate adolescent learners by fostering a supportive, empathetic, and challenging learning environment.
• Employ differentiated instruction and project-based learning techniques to meet the needs of all learners.
• Communicate clearly, effectively, and compassionately with students, parents, and colleagues.
• Inspire and support students of varying abilities, including gifted learners and those with learning differences.
• Adapt to ambiguity and change with flexibility and a positive attitude.
• Build meaningful, supportive relationships within the school community.
• Give and receive constructive feedback with openness and professionalism.
• Champion diversity, equity, and inclusion in all aspects of school life.
• Meet the physical demands of the position, including traveling on uneven terrain, standing for extended periods, and lifting up to 50 pounds.

Candidate must upload a portfolio along with a resume and a cover letter.  

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 - $60,000. This range represents our good faith estimate for this position.  We consider additional factors such as education, experience, skills, and the needs of the School at the time of the offer.

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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