Cheshire Academy seeks a full-time instructor for The Roxbury Center for Learning & Leadership for the 2026–27 academic year. This position focuses on teaching and coaching students to become adaptable, self-aware learners who can apply effective learning, executive function, and leadership strategies across their academic, athletic, and personal lives.

The Roxbury Center for Learning & Leadership advances the school’s mission to develop character, critical thinking, and confidence. Grounded in Mind, Brain, and Education research and practice, the Center offers five specialized pathways that provide targeted, research-informed support for diverse learners: Academic Excellence, Student Athlete, Aspiring Leader, Executive Function & Cognitive Strengthening, and English Language Learners. Through these pathways, instructors help students build the habits, mindsets, and skills essential for academic success, purposeful leadership, high-level performance, and lifelong growth.

Preference will be given to candidates with experience in English Language Learning instruction to support the Center’s English Language Learners pathway. This pathway helps students achieve high levels of academic English, express ideas clearly, understand complex material, and perform strongly across subjects. In alignment with the Center’s coaching model, this work also supports students in developing executive function, self-awareness, and learning strategies to apply their language skills effectively across academic contexts.

Center Instructors receive ongoing support in our unique coaching model, a research-informed, strengths-based approach to student learning and leadership development. Instructors work one-on-one and in small groups to build executive function skills, strengthen metacognition, guide goal setting, and teach personalized learning strategies. Collaboration among instructors, classroom teachers, dorm parents, families, and the broader student success team is essential.

Additional responsibilities include:

Serving as an advisor.

Contributing to the co-curricular program.

Participating in weekend team responsibilities.

Performing residential/dormitory duties if campus housing is provided.

Holding a valid driver’s license with the ability to obtain a CT “A” endorsement for transporting students.

While there are other ways to contribute to the cocurricular program, current coaching needs that we are looking to fill include:

ESports

JV Volleyball

Basketball

Fencing

JV Tennis

Golf

Please express coaching interest in your cover letter.

School provided housing is not guaranteed for the academic year of 2026-2027.

Salary and benefits are competitive. Candidates must be able to pass a criminal background check.

Must be eligible to work in the U.S. to be considered.

A Bachelor’s degree is required, preferably in education, special education, or a related field; a Master’s degree is preferred.

Candidates with advanced degrees, experience supporting diverse learners at the secondary or post-secondary level, and a demonstrated commitment to fostering belonging are strongly encouraged to apply. A background in classroom teaching is beneficial, and the ability to teach in a subject area of expertise is a plus.