Do work that matters! Every single day. We are hiring Assistant Guides for our lovely Guidepost Montessori school at Magnificent Mile!

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!