Winston Preparatory School is seeking a knowledgeable, engaging educator to join our Norwalk, CT campus as a full-time History/Focus teacher. If you are seeking a school environment where your expertise is appreciated, your professional growth is supported, and your work has a direct and lasting impact on students’ lives, we encourage you to apply now for the 2026-2027 school year. The hired candidate will begin in August 2026.

The nature of the position allows for someone with a varied background. Currently, Winston Prep faculty and staff include traditional educators, special educators, social workers, reading specialists, SLPs, learning specialists, and school psychologists. Our classroom teachers have equally diverse and interesting backgrounds. We are proud of our diverse student body and are actively seeking candidates who reflect the diversity of our school community.

As a member of the Winston Prep faculty, you will be part of a professional, collegial team that values collaboration, shared responsibility, and reflective practice. Teachers receive regular coaching and mentorship, participate in professional development, and are trusted with the autonomy to design engaging, responsive curriculum. Our culture encourages curiosity, professional growth, and open dialogue, while prioritizing the development of both academic skills and the Qualities of a Sustainable and Independent Learner (QSIL).

This role is ideal for an educator who:

• Is passionate about making history accessible, engaging, and relevant
• Enjoys breaking down complex concepts into clear, structured, manageable steps and teaching the skills in a primary way to access content
• Understands how to differentiate instruction for diverse learners
• Values building strong relationships with students in both small-group and 1:1 settings
• Sees executive functioning, problem solving, and critical thinking as integral parts of math and science instruction

About Winston Preparatory School

Winston Preparatory School is a co-ed private day school for 3-12th-grade students with learning differences, including dyslexia, NVLD, expressive or receptive language disorders, and executive functioning difficulties (ADHD). 

The Connecticut campus is located in Norwalk, CT. 

Our mission is to facilitate the independence and meaningful participation of students with specific learning disorders through a Continuous Feedback System that develops skill acquisition and the Qualities of a Sustainable and Independent Learner. Winston Preparatory School also seeks to influence the field of education with research and implementation models that achieve these ends, in this way.  

At Winston Prep, Focus teachers provide individualized remediation for students struggling with a wide range of learning differences, while coordinating and facilitating consistent communication between classroom teachers and families. Classroom teachers deliver instruction in core content areas (Math, Science, English/Language Arts, History/Social Studies, etc.) with a focus on flexibly integrating a wide range of skills and content tailored to the individual needs of student class groupings. 

Learn more about Winston Preparatory School at www.winstonprep.edu.

Essential Tasks

(These are intended only as illustrations of the various types of work performed. The omission of specific duties does not exclude them from the position if the work is similar, related, or a logical assignment to the position.)

• Provide direct and indirect instructional support to students in a positive environment
• Teach students in a 1:1 and/or small class setting
• Employ special educational strategies and techniques during class instruction to improve skills, including comprehension,  abstract reasoning, executive function, and written language   
• Instruct students using a variety of techniques, including multi-sensory strategies, to generalize skills and to meet students’ varying needs and interests
• Plan and conduct activities for a balanced program of instruction, demonstration, and work time that provides students with opportunities to observe, question, and investigate
• Establish and enforce rules for behavior and procedures for maintaining an environment conducive to learning for all students
• Maintain accurate and complete student records and prepare reports on children and activities, as required by laws, school policies, and administrative regulations
• Communicate with parents to discuss their children’s progress and to determine priorities for their children and their individualized educational needs
• Establish clear objectives for all lessons, units, and projects, and communicate those objectives to students
• Confer with parents, administrators, testing specialists, social workers, and other outside professionals to develop individualized education programs (IEPs) designed to promote students’ educational, physical, and social/emotional development
• Collaborate with students’ teams and document weekly updates that will be shared with families, including observations in both academic and social-emotional realms
• Maintain professional competence by participating in staff development activities, curriculum development meetings, and other professional opportunities
• Perform related work as required

Qualifications

• Bachelor’s degree (BA or BS) required; Master’s degree (MA or MS) preferred
• Candidates should have experience teaching diverse learners and experience teaching High School History coursework
• Experience with special education is a plus
• Strong writing and verbal communication skills, effective classroom management, excellent organization, team-oriented, and a collaborative, flexible mindset
• Proficiency in Google Workspace, Meet, and Classroom

Benefits and Other Compensation Offered:

• Health Insurance
• Health Savings Accounts (HSA)
• Flexible Savings Accounts (FSA)
• Paid Time Off (Sick leave)
• Professional Development for instructional staff
• Retirement Plan with employer match after 2 years of employment
• $700 annual employer health care contribution every January following 1 year of service
• Pre-tax commuter benefits
• Additional compensation is available for extra-curricular responsibilities such as after-school clubs, exam proctoring, and tutoring

We are proud of our diverse student body and actively seek candidates who reflect the diversity of our school community.  This position requires the successful candidate to work in person and on campus in Norwalk, CT.

The salary range for this position is $65,000-75,000, commensurate with education and experience.

Ready to apply? Interested candidates should submit their resume to:

Stephanie Zabar

Head of School

szabar@winstonprep.edu

About Winston Preparatory School

Founded in 1981, Winston Preparatory School is a network of eight campuses, both physical and virtual, for students ages 8-21+ with learning differences such as dyslexia, executive functioning difficulties (ADHD), and nonverbal learning disorder (NVLD). Our model is based on an in-depth understanding of each student, which results in grouping by learning profile and precisely designed programming. Winston Prep accomplishes this through its Continuous Feedback System. Our expert faculty continually assess how a student is responding to their skill development plan and adjust our teaching approach based on that. Students also participate in a daily one-to-one session called Focus, designed to serve as the diagnostic, instructional, and mentoring centerpiece of their experience. At the high school level, students with appropriate levels of skill mastery may participate in college courses. For students ages 17-21+ needing more time to prepare for life beyond high school, Winston Transitions offers programming that is individually tailored to meet academic, social-emotional, employability, and life skills. Our Winston Online campus offers flexible and engaging program options for students across the country and overseas.

Connections working at Winston Preparatory School