Roxbury Center Learning & Leadership Instructor

Description

PLEASE INCLUDE A COVER LETTER TO BE CONSIDERED

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 to help students become adaptable, self-aware learners with the capacity to 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 (MBE) 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 cultivate the habits, mindsets, and skills essential for academic success, purposeful leadership, high-level performance, and lifelong growth.

Center Instructors receive ongoing support in our unique coaching model, a research-informed, strength-based approach to supporting students’ 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 and communication among instructors, classroom teachers, dorm parents, families, and the broader student success team are essential to the success of this work.

• Work individually and in small-group settings with assigned students to implement the Roxbury Academic Coaching Model with fidelity.
• Help students understand themselves as learners, teaching strategies and skills to help them to leverage their strengths and best meet and overcome academic challenges.
• Support students in building self-advocacy, agency, resilience, and the confidence to take on leadership when appropriate.
• Maintain clear and consistent communication with the Roxbury Director, classroom teachers, and other campus partners regarding student progress.
• Communicate regularly with parents and caregivers, providing feedback on progress and strategies for continued growth.
• Document individual session notes and track student goals and outcomes.
• Effectively plan sessions for and with students, understanding that each student requires individual preparation, focus, and support.

• 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 co-curricular program, current coaching needs that we are looking to fill include:

• Robotics
• 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 .

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.

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