Hillside School, a Junior Boarding School serving grades 4-9, with a Lower School serving grades K-3, is seeking an enthusiastic Learning Specialist with a strong academic background and passion for providing exceptional student learning support starting in September 2026.

The Learning Specialist provides differentiated and targeted instruction, intervention, and assessment to students in grades four through nine, especially those enrolled in Hillside’s Tutorial program, in the areas of reading, writing, math, and executive functioning. The candidate must possess an understanding of students with diverse learning profiles and should be familiar with neuropsychological and educational evaluations as well as creating and working with student learning plans. We are seeking a collaborative educator who will work closely with the Director of the Tutorial Center and all faculty to support student growth, differentiate instruction, and monitor progress to meet students’ needs. Finally, the Learning Specialist must be confident in communicating with families and building relationships to support them in understanding their child’s learning both in and out of the classroom. 

Qualified candidates should embrace boarding school life.  They must be willing to teach a full schedule (16-20 periods per week), coach two seasons of sports, and cover scheduled dorm duties on evenings and weekends. Interested candidates should send a cover letter and resume to Thomas Pipoli, Dean of Faculty and Academics at tpipoli@hillsideschool.net.

Responsibilities include but are not limited to:

• Plan, develop, and administer individual and small group instruction based on student learning needs and goals in the areas of reading, writing, executive functioning and math if possible. Tutorials that the Learning Specialist may teach include: Executive Functioning, Foundations of Language, Math, and/or Advanced ESL in grades 4-9
• Assist students to develop learning strategies that support individual success. This may include executive functioning strategies, compensatory study skills and test taking strategies, course tutoring, etc.
• Assist students with understanding individual course requirements, developing short- and long-term plans to meet requirements, and reviewing progress
• Communicate and work collaboratively with faculty and staff to ensure students are accessing the curriculum and receiving appropriate and reasonable accommodations in the classroom, where applicable
• Create learning profiles for students based on neuropsychological and educational evaluations
• Maintain and update confidential files and records pertaining to students
• Meet with families to report student progress, including parent-teacher conferences
• Attend team meetings to monitor student progress and suggest strategies 
• Ability to act as a resource and provide professional development for faculty
•  Perform miscellaneous job-related duties as assigned

Prior Experience/Qualifications Required

• Bachelor’s degree in a related field required; master’s degree preferred
• At least two years of experience working as a learning specialist or special educator and/or working with students with learning disabilities strongly preferred
• Strong preference given to applicants with Orton-Gillingham certification, Wilson or specialized Reading certification and experience
• Must have an understanding of learning disabilities and experience in reading and writing instruction.
• Experience with math supports would be preferred but not required.
• Familiarity with teaching executive functioning skills/strategies and ESL specific supports or a willingness to be trained

About Hillside School

For over 100 years, Hillside School has been teaching boys the core values of compassion, determination, honesty, respect, and brotherhood. Since its founding, Hillside School has committed to offering an all-boys educational experience in a structured, inclusive, supportive environment. Our boarding and day program for boys in grades four through nine is unique in its ability to meet each student at his learning threshold and then truly maximize his potential, creating a transformative experience for our students. In 2025, Hillside will be opening its new coed Lower School, serving grades K-3.

Connections working at Hillside School