1000+ Best it support Jobs in Boston, Massachusetts (March 2026) - page 18

Upper School Learning Specialist

4 days ago

Milton

Job Description Position: Upper School Learning Specialist Department: Academic Skills Center Location: Wigglesworth Hall, Milton Academy Campus, Milton, MA Hours: Full-time with the flexibility to work on nights and weekends FLSA: Exempt Classification: Faculty (Academic Year) 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. 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.” Summary of Position: Milton Academy is seeking a full-time learning specialist for an opening in the Academic Skills Center in the Upper School beginning August 2026. 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. Essential Responsibilities: * Interpret and summarize educational evaluations; use them to develop and deliver individualized student learning guides * Maintain confidential student records and submit accommodation applications to the College Board and ACT * 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 * 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 * 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 * 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, community, and residential life activities, among others. Please see the full job description for more information. Advising * Serve as an advisor to a group of up to nine students, engaging in advisor meetings each week. * Connect, support, communicate, encourage, and celebrate each advisee * Facilitate students' social-emotional learning and growth in alignment with all school programming through small group meetings. * Build deep relationships with each advisee and assist them in navigating challenges they may encounter. * Form relationships with and act as a liaison between the school and advisee families; serve as the first point of contact between the school and families. * Read and be familiar with all relevant materials, most importantly the Student Handbook and the sections of the US Faculty Handbook on academic regulations and diploma requirements. * Be informed about course offerings for the following year and help each advisee select programs that are challenging and appropriate, as well as areas of special interest. * Review each advisee’s grades and comments. * Craft formal advisor reports for each advisee two times per year, offering overarching perspectives on their progress, and acknowledging a broader view of their academic and community achievements at Milton. * Should an advisee need additional support in a particular area, be in steady contact with the advisee’s teachers, administrators, and/or other committees as needed. * Attend all upper school student required weekly assemblies, programming, and special events (e.g., community service day, pep rallies). * Attend class trips, retreats, and social events arranged by the director of student activities or the class dean. 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. Residential Life (if residing in on-campus housing) * Act as a mentor and role model in all areas of the residential program, demonstrating a commitment to the success of each student, especially in the areas of social and emotional development. * Contribute to creating a positive community culture within the dorms that ensures students are heard, seen, valued, and cared for. * Be on call (on duty) as a dorm parent in a residential dorm once a week and on rotational weekends and ensure that all responsibilities and rules outlined in the faculty handbook around dorm supervision are adhered to. * Facilitate and oversee programming when on duty and supervise recreational activities as assigned. * Communicate regularly with other house staff as an opportunity to check in about the students in the dorm. * Attend at least two dinners per week with the dorm community. 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.

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