Position: Interim Upper School Learning Specialist
Department: Academic Skills Center
Location: Wigglesworth Hall, Milton Academy Campus, Milton, MA
Hours: Full-time or part-time with the flexibility to work on nights and weekends
FLSA: Exempt
Classification: Faculty (Academic Year)
Base Salary: For the 2026-27 academic year, full-time 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.
Milton Academy is an independent college preparatory K-12 school, boarding and day in grades 9-12, located just outside of Boston.
Milton Academy cultivates in its students a passion for learning and a respect for others. Embracing diversity and the pursuit of excellence, we create a community in which individuals develop competence, confidence and character. Our active learning environment, in and out of the classroom, develops creative and critical thinkers, unafraid to express their ideas, prepared to seek meaningful lifetime success and to live by our motto, “Dare to be true.”
Summary of Position:
Milton Academy is seeking a learning specialist for an opening in the Academic Skills Center in the Upper School for the remainder of the 2026-2027 academic year. The Upper School learning specialist will work in collaboration with the broader school community, including faculty members, administrators, counselors, and staff, to advocate for and promote an inclusive academic environment that supports all learners.
Please note this is an interim position for 2026-2027; the position may be eligible for renewal depending on school needs.
Schedule and Flexibility:
We are open to full-time and part-time candidates, with flexibility in both hours and scheduling. Our priority is finding the right person and developing a schedule that works for everyone.
Essential Responsibilities:
- Provide skill and strategy instruction for students using research-based practices
- Offer one-on-one and group instruction focusing on study skills, time management, note taking, test preparation and other academic skills
- Communicate regularly with students and their families, providing information about available academic support resources, including tutors, therapists, and other allied professionals
- Empower students to develop self-advocacy skills and take ownership of their learning
- Support students returning from medical leaves and other extended absences by coordinating re-entry plans and working with teachers to prioritize essential coursework
- Coordinate assessment administration for students with accommodations
- Collaborate with Milton faculty and staff to support their ability to deliver effective and differentiated classroom instruction and appropriate implementation of accommodations
- 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
- Establish contact with advisors, teachers, families, and outside providers to foster a team approach to student support
- Communicate closely with the Counseling Center team in consultation and collaboration
- Attend department meetings with the Director of Academic Support and Upper School learning specialist 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, community, and residential life activities, among others. Please see the full job description for more information.
The school seeks candidates who could contribute to the broader student experience, from co-curricular to athletic to residential life programming.
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, such as advising a student activity, acting as a faculty sponsor to a student club, coaching an athletic team, leading an intramural sport or acting as an affinity group advisor.
- Complete all chaperone and/or supervisory duty, as assigned; lead and facilitate weekend programming / activities and supervise recreational activities both on and off campus.
Other Professional Expectations and Responsibilities
- Work cooperatively with students, parents, peers, administration, and community members.
- Act in a manner that is respectful, generous toward others, supportive of colleagues, and based in a belief in the competence and good intentions of all members of the community.
- Communicate openly and promptly, supporting colleagues, students, and the integrity of the institution in conversations with students and parents.
- Create and maintain classroom and campus environments that are open and flexible, reflecting the school’s values related to diversity, equity, and belonging.
- Strive to grow and improve professionally, demonstrating a commitment to continuing professional development in alignment with the upper school’s growth statements.
- Exhibit skills in collaborative problem-solving, critical thinking, and teamwork.
- Meet deadlines.
- Attend all school-wide, divisional, and faculty meetings and events and serve on committees as required.
- Prepare for and participate in opening of school programming, family visit days, graduation, and all other key student/family moments that are part of the school calendar.
- Complete school-required training.
- Abide by the school’s policies and procedures as outlined in the provided handbooks.
- Communicate with the appropriate supervisor when unable to meet any professional obligation.
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.