Learning Strategist, Middle School (Contract

Full Time
  • Full Time
  • Toronto


Learning Strategist, Middle School

Two Year Contract Starting Late August 2024

The York School is a gender-inclusive, independent school in midtown Toronto that offers the International Baccalaureate (IB) from Junior Kindergarten to Grade 12. We’re proud to be at the forefront of education excellence, attracting curious learners who thrive in belonging to an inclusive community of high performance.

We’re seeking a globally minded professional who’s fueled by curiosity, inspired by innovation and energized by collaboration to join our dynamic community of educators, staff, students, parents and alumni.


As a valued member of our Wellbeing department, you’ll collaborate closely with passionate faculty members to provide tailored academic support to students, aligning with our school’s mission, vision, and values. Using a flexible approach, you’ll work with students throughout the day, employing both push-in and pull-out models to meet their diverse learning needs. Reporting to the Associate Head, Wellbeing, you’ll play a vital role in ensuring every student receives the support they need to thrive, working collaboratively with the Middle School Principal and the Student Support team.

If you’re passionate about making a difference in students’ lives and are committed to educational excellence, we encourage you to apply and be part of our inclusive and supportive community at The York School.


Work closely with the faculty, counsellor and principal to provide academic support to students

Read and interpret psycho-educational assessments to create and maintain the student learning plans of all identified students.

Work closely with faculty to help determine viable learning strategies for identified students

Assist with the provision of assessment accommodations

Participate in co-teaching of classes, including unit planning and teaching

Provide opportunities for success in the classroom by fostering the development of learning skills and by promoting positive interactions

Support the implementation of outlined accommodations and instructional needs to allow students to develop effective academic learning skills

Assist with the provision of assessment accommodations

Collaborate with Learning Strategist in the Junior, Middle and Senior school divisions to share strategies, plans and to ensure continuity of support

Communicate with parents regarding the strategies used to support their child, including the arrangement of parent meetings and faculty roundtables.

Create and implement Transition Plans for students who are new to the school and for students moving between divisions

Work with the Learning, Innovation, and Technology department to train students in assistive technology

Perform supervision duties as assigned


A Bachelor’s degree, B.Ed. and membership in good standing with the Ontario College of Teachers

Minimum or 3-4 years experience teaching within the Middles Years Programme (MYP) required

Special Education Additional Qualifications (Parts 1 and 2) or equivalent training

Experience working with students of diverse learning needs, one-on-one, in small groups and in whole-class situations

Strong ability to work as part of a collaborative team

Excellent written, verbal and interpersonal communication skills

Ability to interact with students, parents and teachers cheerfully, enthusiastically, courteously, patiently and with discretion

Strong organisational and time management skills

A proactive team player who is flexible and self-motivated with a “How can I help?” attitude

Considerable proficiency in navigating a technologically rich school environment, with expertise in Google Workspace considered an asset


Flexibility & Adaptability

Breadth of Contribution

Relationship Focused

Service Orientation

Communication & Collaboration Inclusivity

Integrity & Trust


Flexibility & Adaptability

Breadth of Contribution

Relationship Focused

Service Orientation

Communication & Collaboration Inclusivity

Integrity & Trust


Planning & Preparation for Student Learning

Delivery of Instruction

Managing Classroom Culture & Environment


The York School Campus, Toronto

Occasional evening, overnight and weekend travel for school trips required


Within the Greater Toronto Area, The York School ranks among the top CIS Ontario Schools for compensation. Our comprehensive benefits package includes health and dental coverage that is effective on your first day of employment, and participation in the Ontario Teachers’ Pension Plan.

You’ll enjoy professional development opportunities that support your career growth, and will be welcomed by a community that values relationships and is dedicated to wellbeing and belonging. Learn more about the benefits of working at The York School.


The York School embraces diversity and is committed to creating an inclusive and accessible workplace. We actively encourage applicants from all equity seeking groups.

Our goal is to attract, develop and retain highly talented employees from diverse backgrounds so our community will benefit from a wide variety of experiences and perspectives.

We are committed to providing barrier-free and accessible recruitment and employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require accommodation through any stage of the recruitment process, please make it known when contacted and we will work with you to meet your needs.


All qualified candidates are encouraged to apply online here by submitting their application by April 10, 2024.

As a condition of employment, successful candidates will need to provide a current criminal record check with vulnerable sector screening from the police jurisdiction in which they reside.

We thank all candidates for their applications; however, only those selected for an interview will be contacted.


To apply, please visit the following URL: