Upper Elementary Special Education Assistant

Faculty / Full-Time

Oak Meadow School, Littleton, MA



Oak Meadow School seeks an experienced educator to be a full-time Upper Elementary Special Education Teaching Assistant for the 2023-24 school year for grades 4-6. This person  will work with all students including those with a variety of mild-moderate learning disabilities and/or mild social-emotional challenges. The role of the Special Education Teaching Assistant is to support the implementation of learning plans for students with disabilities in a Montessori environment. The Special Education Teaching Assistant will provide both small group and 1:1 instructional support needed for student progress under the direction of the Upper Elementary Lead Teachers and the Director of Education. 


This position will involve collaboration with all areas of the school, with the following primary responsibilities:



  • Assist with specific student supports, either as individual or small group, with guidance from teaching staff in the implementation of Learning Plans, benchmarks to readiness, and related support plans
  • Support the social and emotional needs of students through positive relationship building, appropriate support and engaging instruction
  • Collect data across settings and domains under the supervision of the Learning Support Office in order to inform the team of the progress and challenges experienced by assigned students
  • Reinforce learning of materials or skills introduced by classroom teachers
  • Work in conjunction with classroom teachers to support the learning experiences in the classroom, focusing first on the identified students with Learning Plans and then for the broader group of students
  • Be actively engaged in the learning environment, providing support for all learners
  • Implement strategies, accommodations and reinforce the learning, and social-emotional, goals of students
  • Perform other job-related tasks and duties as assigned
  • As appropriate, provide coverage for teachers. 
  • Participate in in-service trainings and meetings, as well as, training programs specific to Montessori and Learning Disabilities
  • Maintain a record of regular attendance, arrive and depart at specified contractual times, and notify appropriate personnel when absent
  • Ensure confidentiality regarding all personal information and educational records concerning students and their families
  • Maintain professional boundaries with students and their families
  • Have a flexible attitude, work well in teams, be responsive and able to adjust when changes in routines are made
  • Adapt and acquire new skills and knowledge and use them consistently to support student engagement with learning activities and social interactions
  • Provide coverage during lunch and recess times for all learners. 



Oak Meadow School was founded in 1977 as a Montessori school for early childhood students. Over the years, elementary and middle school, and most recently, toddler grade levels have been added. Oak Meadow now has a reputation for one being one of the finest independent schools in the country, matriculating its graduates to the most selective independent high schools in New England. 

Oak Meadow School has dedicated their focus and commitment to professionalism, transparency, excellence, and inclusivity. The school’s Diversity, Equity, Inclusion and Justice (DEIJ) Task Force (composed of teachers, staff, parents, and trustees) has significantly advanced the school’s commitment to equity, inclusion, anti-racism, and justice. 

Littleton, Massachusetts is located just northwest of Concord, in one of the top growth areas outside of Boston, and attracts families who value the best educational options available. Train service to Boston is easily accessible, and the beautiful outdoor resources of New Hampshire, Vermont, Maine, Cape Cod, and the Berkshires are a short drive away. 


Oak Meadow School is rooted in the child-centered Montessori philosophy, which fosters academic excellence, personal growth, and cultural awareness while nurturing children’s spirits. A diverse community of life-long learners, we cultivate confident, independent, and compassionate human beings by providing the tools and experiences needed to embark on rich, meaningful journeys as responsible citizens of the world. 

We commit to being equitable and inclusive, providing all candidates equal opportunities to demonstrate their knowledge, skills and abilities. We welcome candidates representing the diversity of the world in our educational program, admission policies, financial aid program, staff hiring, and other school-administered programs. Our goal is to actively recruit, reach, identify, hire, promote, and retain the best people possible.


  • Bachelor’s Degree, Master’s preferred
  • Demonstrated Special Education experience
  • Reading Intervention specialization preferred


  • A cover letter describing your interest in the position 
  • A current resume
  • A brief statement (not more than one page) of your educational philosophy including your background and experience with children and education, as well as your knowledge of and experience in Diversity, Equity, Inclusion and Justice.


Lee Waterhouse, Education Director – employment@oakmeadow.org
Applications must be received via email.

Oak Meadow School

Littleton, MA
Infant / Toddler, Early Childhood, Elementary, Middle School
All Gender