Flexible Classroom Support Teacher

guidepostmontessori· Substitute Guide
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📍 Wilton, Connecticut

About this role

 

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.

Frequently Asked Questions

Is the salary disclosed for the Flexible Classroom Support Teacher position at guidepostmontessori?
The salary for this Flexible Classroom Support Teacher role at guidepostmontessori is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the Flexible Classroom Support Teacher position at guidepostmontessori located?
This Flexible Classroom Support Teacher role at guidepostmontessori is based in Wilton, Connecticut. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Which team or department does the Flexible Classroom Support Teacher at guidepostmontessori belong to?
This Flexible Classroom Support Teacher position is part of the Substitute Guide department at guidepostmontessori. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Flexible Classroom Support Teacher position at guidepostmontessori?
Click the "Apply Now" button on this page. You will be redirected to guidepostmontessori's official application portal hosted on greenhouse where you can submit your application directly.
When was the Flexible Classroom Support Teacher job at guidepostmontessori posted?
This Flexible Classroom Support Teacher position at guidepostmontessori was posted on Jun 1, 2026. Apply as soon as possible — early applications are often reviewed first.
Flexible Classroom Support Teacher
guidepostmontessori
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