Middle School Learning Specialist (2026-2027 Coverage)

Job Description

Job Description

Position: Middle School Learning Specialist (2026-2027 Coverage)

Department: Middle School

Location: Ware Hall, Milton Academy Campus, Milton, MA

Hours: Full-time

FLSA: Exempt

Classification: Faculty (2026-2027)

Milton Academy is an independent college preparatory K–12 school, boarding and day in grades 9–12, located just outside of Boston.

In our ongoing work to create an environment that confronts bias, injustice, and bigotry, we encourage each other to be open to learning, explore our histories and identities, and seek to understand the world around us with a critical lens. At Milton, we prepare students to partner with their future communities to create a more just world, and to have the courage to speak up and live by our motto, “Dare to be true.”

Base Salary: For the 2026–27 academic year, faculty salaries range from $50,000 to $120,000 annually. Placement within this range is determined by years of experience, in alignment with Milton Academy’s faculty salary scale designed to ensure equitable pay progression.

Housing Stipend: Faculty members who reside off-campus will also receive an annual stipend of $13,000 (in 2026-27) in addition to the base salary listed above.

Summary of Position:

Milton Academy is seeking a full-time Learning Specialist to join the Middle School for the 2026-2027 academic year, beginning in August 2026. The Middle School learning specialist will work in collaboration with the Middle School community to offer academic support to students.

Milton Academy is committed to supporting employee growth and development. This position may be eligible for professional development funding to support continued learning, skill enhancement, and career growth.

Essential Responsibilities:

• Provide skill and strategy instruction for students using research-based practices

  • Offer one-on-one and group instruction

  • Communicate regularly with students and their families, providing information about available academic support resources, including tutors and other allied professionals

  • Empower students to develop self-advocacy skills and take ownership of their learning

• Collaborate with the MS Director of Academic Support to share theory, research, and resources to support best instructional practices; serve as a resource in understanding diverse learning profiles; Maintain regular communication to ensure partnership in meeting students’ needs

• Collaborate with the Director of Academic Support to establish contact with advisors, teachers, families, and outside providers to foster a team approach to student support

• Meet multiple times a week with the Director of Academic Support to discuss plans, progress, and concerns regarding individual students, as well as plan and implement school initiatives

• Other responsibilities as assigned

Other faculty member responsibilities at Milton Academy encompass advising and other Middle School community responsibilities.

Community

• Be a visible, accessible presence around campus.

• Contribute to creating a positive community culture that ensures students are heard, seen, valued, and cared for.

• Share in the enforcement of our expectations for students.

• Actively participate in greater community enrichment activities

• Complete all supervisory duty, as assigned

Other Middle School Responsibilities

All middle school employees are expected to attend morning assemblies and advisories, faculty and staff meetings, grade-level meetings, departmental meetings, and professional development. All Middle School employees are expected to be ready to welcome students into our space at 8:00 a.m. and, in this role, to remain on campus until 4:00 p.m.

A variety of community responsibilities are also an essential component of our program. All middle school employees are responsible for:

• Weekly lunch supervision

• Weekly study hall supervision

• Facilitation of one semester-long activity

Supervision to be received: Supervised by the Director of Academic Support.

Supervision to be exercised: None.

Education/Certification/Licensure

Required: A bachelor’s degree in special or inclusive education or a related field

Preferred: A master’s degree in education or a related field

Experience

Required: A minimum of three years of proven experience in working with students with documented learning profiles, preferably in a school setting

Competencies

Required:

• Possess an expert knowledge of learning differences and brain-based teaching and learning principles.

• Knowledge of best practices in providing academic accommodations to support students with learning differences.

• Skilled in teaching foundational academic skills and strategies.

• Ability to mentor and support faculty in their understanding of academic support needs and effective instructional strategies.

• Strong advocacy for students with learning differences within the school community.

• Empathy and a student-centered approach, ensuring that students’ unique needs are heard, understood, and addressed.

• Ability to track and monitor student progress, assess the effectiveness of support services, and make necessary adjustments.

• Ability to work collaboratively with internal and external constituencies.

• Excellent verbal and written communication skills.

• Demonstrated computer expertise, including proficiency in Google Workspace

• Understanding of confidentiality and related issues.

• Receptive to supervision and professional development.

• Desire to be a part of a dynamic educational community.

Physical Abilities

Required:

• Must be able to work at a computer for up to 8 hours each day in conjunction with OSHA requirements.

• Must be able to teach in a classroom setting and use relevant instructional technology.

• Must be able to move around the Milton Academy campus without restriction.

• Must be able to lift up to 10 pounds.

All interested internal candidates must complete an application for promotion or transfer and inform your supervisor as soon as possible.

The essential functions and basic skills have been included in this job description; it is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

Milton Academy is an equal opportunity employer. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of any category protected by federal, state, or local law, including but not limited to race, color, sex, sexual orientation, gender identity, gender expression, religion, disability, age, genetic information, veteran status, ancestry, citizenship or national or ethnic origin.