Upper School Learning Specialist

Upper School Learning Specialist

Westtown School seeks a dynamic, student-centered Learning Specialist to join our Upper School Learning Support Team in August 2026. Qualified candidates will have experience supporting high-achieving students with diverse learning profiles, possess exceptional interpersonal communication skills, a strong facility with educational technology, and the ability to build meaningful partnerships with students, families, and colleagues throughout our intentionally diverse community. This position reports to the Learning Center Director and the Upper School Principal.

As a member of the Upper School faculty, the Learning Specialist also contributes to Westtown’s residential program as either a Dorm Parent or Dorm Affiliate. These roles include one weeknight of evening duty and designated weekend responsibilities scheduled throughout the school year. On-campus housing may be available for faculty participating in the residential program, though it is not guaranteed. 

Additional responsibilities include advising a small group of students, serving on school committees, and participating in the co-curricular program by coaching interscholastic sports, facilitating lifelong fitness programs such as yoga, or engaging in collaborative activities such as theater or the service network. Preference will be given to candidates with coaching experience in soccer, basketball, golf, lacrosse, or field hockey. 

Westtown School is an independent, Quaker pre-K to 12 college-preparatory day and boarding school located in suburban West Chester, PA, approximately 30 miles from Philadelphia. On a beautiful 600-acre campus, Westtown offers a program where our committed faculty and staff inspire and prepare our students to be stewards and leaders of a better world. 

Essential Responsibilities

• Collaborate with the Student Support Team to design, implement, and monitor individual Learning Support Plans;

• Communicate and work collaboratively with faculty and staff to ensure students are accessing the curriculum and receiving appropriate and reasonable accommodations in the classroom; 

• Work directly with students to develop executive functioning skills, including organization, time management, study strategies, test-taking, and note-taking; 

• Provide instructional coaching to teachers as needed to enhance day-to-day instructional practices and improve student learning;

• Actively participate in weekly faculty meetings and Student Support Team meetings;

• Prepare and submit documentation for ACT/SAT accommodation requests;

• Maintain accurate, confidential student records and documentation; 

• Facilitate annual Learning Support Plan review;

• Effectively communicate with teachers and families regarding student progress;

• Manage communications with tutors and parents;

• Collaborate with the Learning Center Director to design and deliver professional development, modeling best practices in supporting diverse learners;

• The ability to provide ESOL support for international students is desirable;

• Stay current with research and best practices in learning differences and executive functioning;

• Engage in continuing professional development related to student learning and support strategies.

Qualifications

• An advanced degree in Special Education, or a related education field, is preferred;

• 3 or more years of relevant experience as a Learning Support Specialist;

• Experience teaching and working with high-achieving high school-aged students with diverse learning profiles;

• Experience with standardized assessment administration;

• Ability to navigate difficult conversations with parents, colleagues, and others;

• Ability to work independently and effectively in a fast-paced and changing environment

• Flexible, collaborative, and solutions-oriented;

• Enthusiasm for full participation in the coaching, advising, and residential duties required of a full-time Upper School faculty member;

• Familiarity with Google products and the integration of a learning management system, Canvas, into best teaching practices;

• A demonstrated commitment to enhancing an inclusive school community based on cultural competence, commitment to social justice, and respect for all voices;

• A strong character with a team-oriented spirit, and the ability to connect meaningfully with students throughout our diverse community;

• Strong affinity for the mission of Westtown School and an educational philosophy consistent with the school’s Quaker values.

For additional information about Westtown School and to explore current career opportunities, please visit our website westtown.edu/careers. Interested applicants can apply online by submitting their resume, cover letter, and three professional references directly to the specific job posting on the faculty employment portal.