Guidepost Montessori is a network of authentic, high-fidelity, community-based schools. With over 80 locations, find a Guidepost Montessori near you. Searching by office will allow you to see all of the open roles in your area.
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.
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Assistant Teacher
Guidepost Montessori
Wilton, Connecticut
Assistant Guide5d ago
Flexible Classroom Support Teacher
Guidepost Montessori
Wilton, Connecticut
Substitute Guide5d ago
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Do work that matters! Every single day. We are hiring Assistant Guides for our lovely Guidepost Montessori school at Wilton!
At Guidepost Montessori, our Assistant Guides play a meaningful role in helping children ages 0–6 develop independence, confidence, and a lifelong love of learning.
If you’re passionate about working with young children and want to grow in a supportive, purpose-driven environment, we’d love to meet you.
Your Impact
As an Assistant Guide, you’ll support a mixed-age Montessori classroom (Infant, Toddler, and Children’s House ages 3–6), helping create a calm, engaging environment where children are empowered to explore, learn, and grow at their own pace.
In a Montessori classroom, the environment and the guide work together to support each child’s development. You’ll assist in preparing beautiful, intentional learning spaces and support children through individualized and small-group activities—always with respect, patience, and care.
Most importantly, you’ll help children build confidence in themselves and discover what they’re capable of achieving.
What You’ll Do
Observe children closely to understand and support their individual needs
Help prepare and maintain a beautiful, orderly classroom environment
Support individual and small-group learning activities
Build warm, respectful relationships with children and families
Collaborate with Lead Guides and fellow team members to create a strong classroom community
What We’re Looking For
Experience working with children ages 3–6 in a school or childcare setting
A positive, adaptable, and collaborative mindset
A genuine love for working with young children
Interest in learning and growing within the Montessori approach (prior Montessori experience is welcome but not required)
What We Offer
Fully sponsored Montessori diploma training through the Prepared Montessorian Institute
Ongoing professional development and mentorship
75% tuition discount for up to two children at any Guidepost school
Competitive pay
Health, dental, and vision insurance
Paid time off and paid holidays
Abundant opportunities for growth and career advancement
A supportive network of peers who value collaboration and shared best practices
About Guidepost Montessori
Guidepost Montessori is a growing network of over 100 schools across the U.S. and Asia, serving children from 3 months to 6 years old.
We believe children are capable and we design an education that nurtures independence, curiosity, and joy. Our mission is to transform education by helping every child reach their highest potential academically, socially, and emotionally.
If you love working with children and are looking for a role where you can grow, make an impact, and be part of something meaningful, we’d love to hear from you.
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.
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)
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.
