Flexible Classroom Support Teacher

guidepostmontessori

Wilton, Connecticut · Wilton · United States

Posted Aug 21, 2026

Part-time
Substitute Guide

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Job description

Looking for flexible work with purpose?

Join our Flexible Classroom Support (On-Call) team at Guidepost Montessori, where you can make a meaningful impact in children’s lives while maintaining a schedule that works for you.

We’re seeking warm, dependable individuals to step into our classrooms and support our teaching teams when they’re out for planned time off. This is a great opportunity for someone who values flexibility but still wants to be part of a consistent, supportive school community.

About the Role

This is an on-call, as-needed position, primarily supporting planned teacher absences (like PTO).

While the role is flexible, it’s also predictable, you’ll typically receive your schedule 2 weeks to a month in advance, allowing you to plan ahead with confidence.

You’ll support classrooms serving children ages 0–6, helping maintain a calm, engaging, and nurturing Montessori environment.

✨ Many of our on-call team members go on to become full-time Assistant Teachers—this is a great way to get your foot in the door!

What You’ll Do

Step into classrooms as needed to provide continuity and support
Assist with daily routines and classroom activities across mixed-age groups
Help maintain a calm, orderly, and engaging learning environment
Support children with care, consistency, and respect
Collaborate with school staff to ensure smooth transitions
Model patience, professionalism, and warmth in every interaction

Schedule & Flexibility

As-needed, on-call role (no guaranteed weekly hours)
Primarily supporting pre-planned absences (PTO coverage)
Advance scheduling typically provided 2 weeks to 1 month ahead
Ideal for those seeking flexible, supplemental, or part-time work

What We’re Looking For

Reliable and dependable with strong communication skills
Warm, calm, and engaging presence with children
Passion for working with children ages 0–6
Ability to adapt to different classrooms and teams

Required:

Ability to pass a state background check

Preferred (not required):

Early Childhood Education (ECE) credits
Experience working with young children

Why Guidepost Montessori?

Guidepost Montessori is a global network of educators committed to helping children grow through independence, curiosity, and respect.

We believe in creating environments where both children and adults thrive—and that includes offering flexible pathways into meaningful work in education.

Interested?

If you’re looking for a flexible role with purpose, where you can support children and be part of a mission-driven community—we’d love to connect.

Apply today and join our school community.

Guidepost Global Education and Guidepost Montessori are committed to a policy of Equal Employment Opportunity (EEO). We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, alienage or citizenship, disability, marital status, military or veteran status, or any other legally recognized protected basis under applicable federal, state or local laws, regulations or ordinances. Our leadership is dedicated to ensuring the fulfillment of this policy. When requested, we are committed to reasonably accommodate employees and applicants with disabilities or special needs that may require an accommodation.