Lead Toddler Teacher Old Town, Chicago

Help toddlers discover who they are and what they can do.

At Guidepost Montessori, our Lead Toddler Guides create calm, purposeful environments where curiosity, independence, and confidence grow every day.

If you’re passionate about early childhood development and ready to lead a classroom designed for exploration and independence, this is your opportunity to make a meaningful impact.

Your Role

As a Lead Toddler Guide, you’ll lead a mixed-age toddler classroom in a Montessori environment thoughtfully designed to support children during one of the most formative stages of development.

Montessori guides prepare beautiful, orderly environments that invite exploration and support independence. Through careful observation, individualized lessons, and respectful guidance, you’ll help each child develop language, coordination, self-regulation, and confidence.

Your leadership will empower toddlers to explore freely, make choices, and take pride in what they can accomplish laying the foundation for lifelong learning.

What You’ll Do

• Observe each child closely to understand and support their physical, emotional, and cognitive development
• Prepare and maintain a beautiful, orderly classroom that fosters focus, independence, and exploration
• Support independence by encouraging toddlers to “do it themselves”
• Provide lessons in practical life skills, language development, and grace and courtesy
• Build warm, trusting relationships with children and families
• Communicate and collaborate with parents to support each child’s growth
• Lead classroom routines and collaborate with team members to create a respectful, joyful community

The Montessori Prepared Environment

Every Guidepost toddler classroom is fully equipped with high-quality Montessori materials and designed according to the principles of beauty, order, and independence.

• Open spaces that encourage movement and exploration
• Child-sized furniture and tools to support independence
• Curriculum that builds skills in dressing, feeding, and toilet learning
• Scientifically designed materials for fine and gross motor development
• Natural elements including cozy rugs, real plants, and abundant light
• Beautiful, breakable materials made from wood, metal, and glass
• Opportunities to climb, crawl, and explore without restrictive devices

What We’re Looking For

• Interest in pursuing fully sponsored Montessori certification through our Prepared Montessorian Institute, or a previously earned Montessori diploma
• Experience working with children ages 0–3 in a group care or early learning setting
• Alignment with child-led educational approaches (Montessori, Reggio Emilia, or similar)
• Required ECE or Child Development credits
• Bachelor’s degree (Child related field)

What We Offer

• Competitive salary: $40,000 - $50,000 depending on experience and education
• Health, dental, and vision insurance
• Paid time off and paid holidays75% tuition discount for up to two children at any Guidepost school
• A collaborative, supportive network of peers and mentors
• Clear opportunities for career growth and leadership advancement

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 in our Nido, Toddler, and Children’s House programs.

We believe children are capable and we intentionally design environments that empower them to explore, grow, and flourish. Our mission is to transform education by nurturing independence, joy, and lifelong learning.

If you’re inspired by toddler development, excited to partner with families, and ready to lead with purpose, we’d love to welcome you to Guidepost Montessori.

Apply today and help toddlers take their next big steps.

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.