Teaching and Learning Specialist


The Winsor School, Boston, MA

The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Our diverse, vibrant community values intellectual curiosity, authentic engagement, and personal integrity and prepares young women to pursue their aspirations and contribute to the world. Winsor strives to create an environment of respect and inclusion.


Working from a combination of broad experience and deep research, the Teaching and Learning Specialist supports Winsor’s mission by providing academic support across the school, from individual student meetings to presentations to the entire faculty on best practices in the classroom. The Teaching and Learning Specialist observes and supports students new to the school as they acclimate to the Winsor program, works with any students experiencing academic challenges that have not been fully addressed within the classroom, offers peer coaching and feedback for individual teachers as they seek to refine their practice, and leads professional development work for the entire faculty from time to time. The successful candidate will help students and teachers work more effectively together and will be part of the team helping students move toward self-advocacy and overall academic success. A demonstrated commitment to diversity, equity, and inclusion is important, as is an ongoing commitment to professional development around pedagogy, assessment, peer coaching, and overall educational trends. This is a 10-month position and reports to the Division Heads.


Roles and Responsibilities:

  • Works with faculty on best practices in pedagogy and classroom practices
  • Provides peer coaching and instructional strategies for classroom teachers
  • Advises Deans and Class Coordinators about academic challenges and successes within the school
  • Coordinates and implements academic support for all students in Classes I-VIII
  • Meets regularly with students who need organizational and academic support, and provides regular updates to advisors and parents as needed
  • Provides content-specific support in math and writing in the Lower School
  • Develops work plans for students who have missed significant class time
  • When appropriate, provides referrals for outside tutoring and/or educational testing
  • Interprets psychoeducational testing results and develops plans for students who may need accommodations
  • Serves as the SSD Coordinator for the College Board and submits requests for accommodations for all standardized testing
  • Advises the Admission Office on interpreting admission testing
  • Collaborates with the Class V dean to support students as they transition to the Upper School
  • Coordinates and run the Peer Tutoring program
  • Advises in the Lower School
  • Other duties as assigned


Minimum Qualifications

  • Bachelor’s degree in education or related subject, Masters preferred
  • Minimum of five years of experience working with students in an academic program
  • Ability to develop and provide differentiated instruction to meet the learning needs of a range of students
  • Experience working with faculty around best practices in education

The Winsor School

Boston, MA
Elementary, Middle School, High School