Learning Specialist

Title: Learning Specialist

Reports To: Senior Director of Student Life and Community

Status: Full-time, exempt

Start Date: August 24, 2026

Salary Range: $45,585 - $63,386*

About Woodstock Day School

Founded in 1973, Woodstock Day School (WDS) is a progressive, independent school set on a

40-acre campus in New York’s Hudson Valley. Located midway between the towns of

Woodstock and Saugerties and roughly two hours north of Manhattan, WDS is accredited by

NYSAIS and offers a unique and inclusive educational experience to approximately 175

students from nursery school through grade twelve.

Our combination of purposefully small class sizes, intensely committed faculty and a culture of

individual respect empowers our students to shape and achieve their personal goals while

preparing them to make a positive difference in a complex world. WDS actively seeks to build a

diverse community of educators and collaborators.

Please visit www.woodstockdayschool.org to learn more.

Summary

Woodstock Day School is seeking a full time Learning Specialist with experience working with

students Kindergarten-6th Grade. WDS Learning Specialists work with students as part of our

Learning Lab to provide targeted support both in and out of the classroom, including regular 1:1

sessions. The Learning Specialist is a key member of the Student Support Team and works

closely with the Senior Director of Student Life and Community to provide regular and ongoing

communication regarding those services with faculty, parents, and other staff as needed. Ideal

candidates embrace a range of pedagogical approaches, are excited about teaching in a

progressive community and have demonstrated a commitment to addressing issues of diversity,

equity, and inclusion within and outside the classroom.

Additional expectations include attending staff meetings, in-service days including a week in

August and a week after school ends in June, and to participate in the life of the school. Faculty

hours on campus are 8:00 am to 4:00 pm, with a weekly Tuesday staff meeting until 5 pm.

Key Responsibilities

Student Support

• Provide one-on-one and small-group instruction for students in both push-in and pull-

out environments

• Review classroom assessments on a frequent basis to inform instruction, monitor

growth, and determine if further assessment is needed

• Develop and share individual learning goals that will target students’ specific

curricular/learning needs

• Meet and collaborate with teaching staff regularly, offering resources, strategies, and

assistance to enable faculty to better meet the needs of all learners

• Communicate and meet with parents to discuss the progress of Learning Lab

students being supported, and to make recommendations

• Attend Parent Teacher Conferences and work with classroom teachers to write

semesterly reports

• Develop and oversee 504 plans as needed

Professional Development / Support for classroom teachers

• Provide coaching to teachers on creating access and removing barriers for students

with IESPs and 504s

• Meet and collaborate with teaching staff regularly, offering resources, strategies, and

assistance to enable faculty to better meet the needs of all learners

• Develop and maintain communication and documentation related to learning support

for all faculty

• Work with the Senior Director of Student Life and Community and the Director of

Curriculum and Instruction to provide professional development to faculty on working

with students with learning differences, especially on creating access, and removing

barriers to learning

Collaboration and Information Sharing

• Assume an active role in Student Support Team (SST) meetings

• Gather documentation, write and manage 504 plans including communication with

families and faculty

• Attend administrative week in August to coordinate set-up for Learning Lab and

Special Education services

• Attend CSE meetings as appropriate

Qualifications and Dispositions

• Bachelor’s or Master’s degree in Special Education

• At least three years of experience as a learning specialist or in a related role

• Orton Gillingham or Wilson trained a plus

• Familiarity with NYS legislation related to IESPs and 504 plans

• Deep knowledge of Universal Design for Learning principles, and

neurotypical/neurodivergent populations

• Ability to collaborate with faculty, staff, administration, and parents

• Strong organizational skills, attention to detail and commitment to follow

through

• Ability to communicate clearly and effectively, verbally and in writing

• Experience working in a progressive school or knowledge of progressive

education is preferred

How to Apply

To apply, please submit a letter of interest, explaining why you would succeed in this position,

resume, and three professional references as attachments (to be contacted later in the

interview process), via e-mail to careers@woodstockdayschool.org. Please include

Mathematics Teacher in the subject line.

*In order to maintain equity among faculty and staff, WDS utilizes a tiered salary band system

to ensure that pay is commensurate with employees' experience and qualifications. Area of

education, level of education, and duration of relevant work experience are the key factors

taken into consideration when selecting an initial salary band for a prospective employee to be

placed into.

*****

The Woodstock Day School is committed to a work environment in which all individuals are

treated with respect and dignity. WDS prohibits all forms of unlawful discrimination, harassment

and retaliation, including behavior which targets an individual or group based on perceived or

actual characteristics, such as but not limited to: race, color, religion, creed, sex (including

pregnancy, childbirth and related medical conditions), national origin, age, disability, military

service, veteran status, marital status, partnership status, sexual orientation, familial status,

gender identity, gender expression, transgender status, genetic predisposition or carrier status,

alienage, citizenship status, caregiver status, status as a victim of domestic violence, sex

offense or stalking, unemployment status, status as a certified medical marijuana patient or any

other legally protected classification.

Pay: $45,585.00 - $63,386.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Tuition reimbursement
• Vision insurance

Work Location: In person

Salary : $45,585 - $63,386