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.

For the 2025-2026 academic year, we are seeking a dedicated educator who is passionate about recognizing the unique potential in every student and guiding them toward academic success and personal growth to join our dynamic team at the Center for Learning Achievement (CLA).  As a national model for teaching and learning, the CLA provides students with the strategic support and proven skills they need to achieve academic independence and intellectual empowerment. 

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: 

Teaching & Instruction

• Ensure students’ academic success by following individualized support plans and implementing strategies such as study skills, time management techniques, and self-advocacy training. 
• Monitor student progress, adjusting support plans and programs to ensure optimal outcomes.
• Advocate for students by collaborating with faculty to implement appropriate accommodations and modifications in the classroom.
• Facilitate regular communication with parents and guardians, providing updates on student progress and involving them in the support process.

Program Support and Implementation

• Make academic content accessible with the Language through Enrichment, Analysis, and Development (LEAD) Program and using Orton-Gillingham tools.  
• Using the English Mastery Program, teach English literacy to international students by guiding them through reading comprehension, active listening, and advanced writing skills. Help prepare them for academic success and TOEFL testing through personalized instruction and targeted skill development.
• Develop students’ essential executive functioning skills such as planning, organization, problem-solving, and self-monitoring with the Executive Skills Program,
• Promote the CLA program by speaking with prospective parents and students, assessing applicational materials, providing insights into academic programs, and explaining the school's educational offerings.

Mission, Vision & Strategic Alignment 

• Advance the School's mission by enthusiastically engaging in experiential and project-based learning, promoting, and contributing to the School's signature Institute programming, and actively supporting Winter Session initiatives.
• Support and advance the School's commitment to a student-centered environment by engaging in campus-wide mentorship and advocating for student growth and development.
• Participate in the continual assessment and iteration of signature programs to ensure innovation and excellence in boys' education.
• Collaborate with faculty and administration to enhance curricular offerings and optimize technology for a forward-thinking educational experience.

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.
• 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 regular updates, meaningful conversations, and constructive feedback.
• Participate fully in campus life, engaging in extracurricular activities to connect with students beyond the classroom.
• Instill a strong sense of belonging and connectedness that promotes personal growth and mutual support.

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 and/or
• Engage with students beyond the classroom through regular participation and attendance  in extracurricular activities, school traditions, and community events

Your Qualifications & Strengths:

To be successful, you will have a Bachelor’s degree in Education, Special Education, or a related field (Master’s degree preferred) and demonstrated best practices in differentiated instruction and engaging students with varied learning styles as well as experience working with students with diverse learning needs, including implementing individualized support plans. It would be helpful if you are familiar with the Orton-Gillingham method or other structured literacy approaches and if you can read educational testing (such as neuropsychological education, 504s, IEPs, etc).

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;
• 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 frequent 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.

All job offers are contingent upon the candidate’s successful completion of a background & fingerprint check, reference checks, and 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 as well the needs of the School at the time of the offer.

About www.trinitypawling.org

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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