Lead Preschool Teacher – Where Little Learners Grow Big Dreams!

Location: 4401 S. Kedzie Ave. | Chicago, IL 60632
Schedule:  Monday–Friday | 9:30 AM – 6:00 PM
Pay: $19.25 per hour

Why You’ll Love Working With Us

We believe that early education should be as joyful as it is meaningful. Here, your creativity, compassion, and care help shape the next generation of thinkers and dreamers. You’ll be part of a supportive team that values your growth just as much as our children’s.

We Offer:

• $19.25/hr
• 10 days of PTO and Paid Holidays
• Discounted Childcare
• 401(k) Plan
• Comprehensive Medical Benefits

What You’ll Be Doing:

• Inspire Learning: Help lead classroom activities that spark curiosity and confidence.
• Build Bonds: Create lasting, positive relationships with children and families.
• Foster Growth: Maintain a safe, clean, and nurturing environment where every child feels seen, supported, and celebrated.

What You Bring:

• Education: Associate’s in Early Childhood Education or higher
• Experience: 1 year in a licensed childcare facility
• Certifications: Food Handler’s, CPR, and First Aid
• Other Requirements: Must be 18 or older and able to pass a background check

Join Us

If you’re passionate about creating meaningful early learning experiences and thrive in a team that values collaboration and care, we want to meet you. Apply today and help us nurture tomorrow’s brightest minds—one smile, one story, one discovery at a time.

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

At Guidepost Montessori, our Assistant Spanish 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 Spanish Guide, you’ll support a mixed-age Montessori Spanish 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!

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

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!

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

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!

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!

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

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!

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

At Guidepost Montessori, our Infant Assistant Guides play a meaningful role in helping children ages 0–3 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 Infant Assistant Guide, you’ll support a mixed-age Montessori classroom, 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 0-3 in a school, nursery, or childcare setting
• A positive, adaptable, and collaborative mindset
• A genuine love for working with babies and 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!

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

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 Spanish Guide, you’ll support a mixed-age Montessori Spanish 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!

Shape a child’s very first learning experiences. At Guidepost Montessori, our Lead Infant Guides create calm, nurturing environments where infants are respected as capable individuals from the very beginning.

If you’re passionate about early development and want to lead a thoughtfully designed classroom that supports independence, movement, and discovery, we’d love to meet you.

As a Lead Infant Guide, you’ll lead a mixed-age infant classroom (ages 0–3) in a Montessori environment intentionally designed to support each child’s natural development.

In Montessori, the environment and the guide work together to nurture independence, curiosity, and confidence. You’ll thoughtfully prepare the classroom, observe each child closely, and provide individualized care that honors their unique rhythms and needs.

Most importantly, you’ll help infants develop trust in themselves and the world around them laying the foundation for lifelong learning.

What You’ll Do

• Observe each child to understand and support their physical, emotional, and cognitive development
• Respect and follow each child’s natural rhythms for sleeping, eating, and toileting
• Prepare and maintain a beautiful, orderly environment that fosters trust, movement, and exploration
• Support independence by encouraging children to participate in care activities
• Build warm, meaningful relationships with children and families
• Partner closely with parents to support each child’s growth and development
• Lead and collaborate with classroom team members to create a strong, respectful community

The Montessori Prepared Environment

Every Guidepost infant classroom is fully equipped with high-quality Montessori materials and thoughtfully designed to support movement, exploration, and independence.

Our infant environments include:

• Open floor space for movement and exploration
• Child-sized furniture and materials
• Curriculum that supports independence in feeding, dressing, and toileting
• Scientifically designed materials for fine and gross motor development
• Natural elements like real plants, cozy rugs, and abundant natural light
• Beautiful, breakable materials made from wood and metal rather than plastic
• Opportunities for climbing, crawling, and discovery without restrictive devices

What We’re Looking For

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

What We Offer

• Sponsored Montessori diploma training and ongoing professional development
• Competitive salary: $40,000 - $50,000 depending on experience and education
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 75% tuition discount for up to two children at any Guidepost school
• A collaborative community of peers and mentors
• Clear pathways 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 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 passionate about early childhood, excited to partner with families, and ready to lead with purpose, we’d love to welcome you to our community.

Apply today and help shape the earliest years of learning.

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.

Our toddler environments feature:

• 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

• Sponsored Montessori diploma training and ongoing professional development
• Competitive salary: $40,000 - $50,000 depending on experience and education
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 75% 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.

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.

Our toddler environments feature:

• 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

• Sponsored Montessori diploma training and ongoing professional development
• Competitive salary: $40,000 - $50,000 depending on experience and education 
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 75% 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.

Looking for a flexible role working with children in a meaningful, supportive environment?

Join our on-call Substitute Teacher team at Guidepost Montessori!

We’re always excited to welcome warm, dependable substitute guides to support our mixed-age Montessori classrooms when our full-time teachers are out. No formal Montessori training is required, we’ll provide training as part of your orientation and onboarding.

About the Role

This is an on-call, as-needed position, ideal for individuals seeking flexible hours while making a positive impact on young children.

As a Substitute Teacher, you’ll support multiple classrooms serving children ages 0–6, helping maintain a calm, engaging, and nurturing learning environment.

Many of our substitute teachers go on to become full-time Assistant Teachers, making this a great opportunity to get your foot in the door at Guidepost Montessori.

What You’ll Do

• Step into classrooms as needed to support children and maintain consistency
• Assist with daily routines and classroom activities across mixed-age groups
• Help create a warm, safe, and engaging environment for children
• Collaborate with school staff to ensure smooth transitions and continuity of care
• Model patience, professionalism, and kindness in every interaction

Schedule & Flexibility

• Hours and days vary based on school needs
• Perfect for those seeking part-time, flexible, or supplemental work

Minimum Qualifications

• Negative TB test within the last 12 months
• Valid state background check
• Strong interpersonal and communication skills
• Warm, friendly, and dependable demeanor
• Passion for working with young children

Preferred (but not required):

• Early Childhood Education (ECE) units
• Recent experience working with children ages 0–6

Why Guidepost Montessori?

Guidepost Montessori is a global community of educators dedicated to transforming education through independence, curiosity, and respect for each child.

We are committed to expanding high-quality, authentic Montessori programs across the U.S. and around the world creating environments where children and educators alike can thrive.

If you love children, value flexibility, and are looking for a meaningful way to grow in early childhood education, we’d love to meet you.

Apply today and become part of our school community!

Looking for a flexible role working with children in a meaningful, supportive environment?

Join our on-call Substitute Teacher team at Guidepost Montessori!

We’re always excited to welcome warm, dependable substitute guides to support our mixed-age Montessori classrooms when our full-time teachers are out. No formal Montessori training is required, we’ll provide training as part of your orientation and onboarding.

About the Role

This is an on-call, as-needed position, ideal for individuals seeking flexible hours while making a positive impact on young children.

As a Substitute Teacher, you’ll support multiple classrooms serving children ages 0–6, helping maintain a calm, engaging, and nurturing learning environment.

Many of our substitute teachers go on to become full-time Assistant Teachers, making this a great opportunity to get your foot in the door at Guidepost Montessori.

What You’ll Do

• Step into classrooms as needed to support children and maintain consistency
• Assist with daily routines and classroom activities across mixed-age groups
• Help create a warm, safe, and engaging environment for children
• Collaborate with school staff to ensure smooth transitions and continuity of care
• Model patience, professionalism, and kindness in every interaction

Schedule & Flexibility

• Hours and days vary based on school needs
• Perfect for those seeking part-time, flexible, or supplemental work

Minimum Qualifications

• Negative TB test within the last 12 months
• Valid state background check
• Strong interpersonal and communication skills
• Warm, friendly, and dependable demeanor
• Passion for working with young children

Preferred (but not required):

• Early Childhood Education (ECE) units
• Recent experience working with children ages 0–6

Why Guidepost Montessori?

Guidepost Montessori is a global community of educators dedicated to transforming education through independence, curiosity, and respect for each child.

We are committed to expanding high-quality, authentic Montessori programs across the U.S. and around the world creating environments where children and educators alike can thrive.

If you love children, value flexibility, and are looking for a meaningful way to grow in early childhood education, we’d love to meet you.

Apply today and become part of our school community!

Shape a child’s very first learning experiences. At Guidepost Montessori, our Lead Infant Guides create calm, nurturing environments where infants are respected as capable individuals from the very beginning.

If you’re passionate about early development and want to lead a thoughtfully designed classroom that supports independence, movement, and discovery, we’d love to meet you.

As a Lead Infant Guide, you’ll lead a mixed-age infant classroom (ages 0–3) in a Montessori environment intentionally designed to support each child’s natural development.

In Montessori, the environment and the guide work together to nurture independence, curiosity, and confidence. You’ll thoughtfully prepare the classroom, observe each child closely, and provide individualized care that honors their unique rhythms and needs.

Most importantly, you’ll help infants develop trust in themselves and the world around them laying the foundation for lifelong learning.

What You’ll Do

• Observe each child to understand and support their physical, emotional, and cognitive development
• Respect and follow each child’s natural rhythms for sleeping, eating, and toileting
• Prepare and maintain a beautiful, orderly environment that fosters trust, movement, and exploration
• Support independence by encouraging children to participate in care activities
• Build warm, meaningful relationships with children and families
• Partner closely with parents to support each child’s growth and development
• Lead and collaborate with classroom team members to create a strong, respectful community

The Montessori Prepared Environment

Every Guidepost infant classroom is fully equipped with high-quality Montessori materials and thoughtfully designed to support movement, exploration, and independence.

Our infant environments include:

• Open floor space for movement and exploration
• Child-sized furniture and materials
• Curriculum that supports independence in feeding, dressing, and toileting
• Scientifically designed materials for fine and gross motor development
• Natural elements like real plants, cozy rugs, and abundant natural light
• Beautiful, breakable materials made from wood and metal rather than plastic
• Opportunities for climbing, crawling, and discovery without restrictive devices

What We’re Looking For

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

What We Offer

• Sponsored Montessori diploma training and ongoing professional development
• Competitive salary: $40,000 - $50,000 depending on education and experience
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 75% tuition discount for up to two children at any Guidepost school
• A collaborative community of peers and mentors
• Clear pathways 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 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 passionate about early childhood, excited to partner with families, and ready to lead with purpose, we’d love to welcome you to our community.

Apply today and help shape the earliest years of learning.

About the Role
We are looking for a hands-on Amazon DSP expert to support the launch and management of our first wave of Amazon DSP clients. You will serve as the execution lead during our Alpha phase, working directly with our Smart Services team to ensure flawless campaign delivery while helping us build the internal processes and documentation needed to scale.

This is a client-facing, highly collaborative role where you'll be both a doer and a teacher.

What You'll Do:

• Own campaign execution across PG (Programmatic Guaranteed) and auction/performance campaigns: including setup, QA, pacing, troubleshooting, and optimization

• Act as the client facing DSP lead for early implementations, supporting communications and strategic guidance on campaign performance

• Build the playbook: develop SOPs, setup checklists, safety controls, workflow documentation, and reporting templates for repeatable use by the internal team

• Train Smart Services through live work and structured knowledge transfer sessions

• Quantify lift: track and document time/effort across campaign types to help establish benchmark models distinguishing PG vs. auction/performance support needs

What We're Looking For:

• 3+ years of hands-on Amazon DSP experience, with demonstrated expertise in both CTV/Programmatic Guaranteed and auction/performance buying

• Proven ability to manage and troubleshoot live campaigns with high spend accountability

• Strong client communication skills and comfortable presenting and advising directly with brand partners

• Experience building SOPs or training teams is a strong plus

• Ability to start immediately and operate with minimal ramp time

Perks & Benefits…

• Five weeks paid time off (PTO), 11 company paid holidays, unlimited sick days
• Generous healthcare packages & mental health benefits
• Monthly wellness benefit and learning reimbursement opportunities 
• 401K plus matching & equity grants for all new Smartlies
• Volunteer time off days & company donation matching opportunities 
• Choice of computer (MAC or PC)
• And so much more… 

The base pay range for this position is as mentioned below per year, plus annual bonus. We take into consideration an individual’s background, expertise, and experience in determining final salary. In addition to annual salary, Smartly’s total rewards provide employees with stock options, medical/dental/vision insurance, retirement savings benefits, parental leave, 5 weeks vacation, unlimited sick days, life insurance and disability benefits. To learn more visit https://www.smartly.io/careers#our-benefits. This information is provided in accordance with applicable law. Base pay information is based on market location.  

Location: Remote (U.S. or Canada)

Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor

About Human Agency

We're scaling rapidly and have a growing pipeline of opportunities that demand exceptional talent across disciplines. Our mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth.

We are a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don't insulate us from feedback or basics. We invite critique, learn quickly, and keep raising the bar. The best ideas win here, no matter where they come from, because clients trust us to deliver the strongest outcomes every time.

Our clients' missions, products, and bottom lines are sacred. We immerse ourselves in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset we create must be both beautiful and functional; practical, usable, and designed for real-world impact.

Humans are our most valuable resource, and we only grow by hiring people who push us forward. Across strategy, engineering, design, data, and operations, we seek out teammates who raise the bar and make us better. Always hire up, never down.

We partner with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We believe AI should amplify human potential, not replace it, and we build with that conviction in every engagement. From advisory and tooling to implementation and education, we meet clients where they are and help them integrate AI in ways that align with their mission and values. Our goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation.

And through it all, we lead with purpose, love, and adventure. We do meaningful work with people we care about, and we make the ride an adventure worth taking. Because at Human Agency, who we are and how we work are one and the same.

The Opportunity

This is not a traditional enterprise CISO role where you inherit a legacy infrastructure, manage a large team, and maintain the status quo. This is a hands-on, entrepreneurial builder role. You are joining at the frontier of AI security — designing systems that don't yet exist, solving problems the industry is only beginning to name, and treating security not as a cost center but as a strategic and commercial advantage.

We're deploying AI agents at scale across client environments, building our own AI-powered tools, and advising organizations on how to safely integrate autonomous systems into mission-critical workflows. That creates a unique security mandate: you must secure our internal operations, embed security directly into the AI products we build, and help clients deploy agents safely in regulated, high-stakes environments. You are architect, operator, and evangelist all at once.

You'll have the rare opportunity to shape how an entire category of technology gets secured. We're not asking you to retrofit old playbooks onto new problems — we're asking you to write the playbook. If you've been looking for a role where security is core to the product, where you can build things that matter, and where your work influences the broader conversation around AI safety and governance, this is it.

What You'll Own

Define and execute our security strategy from the ground up. You'll architect our internal security posture across infrastructure, data, and AI systems, establish governance models for how we deploy agents safely, and ensure we're prepared for compliance frameworks like SOC 2, ISO, and potentially FedRAMP as we scale into enterprise and government clients.

Build security into AI agent systems as a first-class product feature. You'll design guardrails, monitoring, and policy enforcement for autonomous agents — ensuring they operate within defined boundaries, audit their own actions, and surface anomalies in real time. This isn't theoretical; you'll implement these systems in production environments where they directly impact client outcomes.

Develop and potentially commercialize security products. The security tooling you build internally may become standalone offerings. You'll have the latitude to identify what's missing in the market, prototype solutions, and work with our product and engineering teams to turn internal infrastructure into revenue-generating products.

Lead incident response, threat modeling, and adversarial testing. You'll build and run red team exercises against our AI systems, model attack vectors that don't yet have names, and develop response frameworks for risks unique to agentic AI — things like prompt injection at scale, model extraction, or adversarial manipulation of agent behavior.

Serve as the public face of AI security for Human Agency. You'll represent us in client conversations, partner discussions, and industry forums. You'll publish, speak, and help shape the broader conversation around AI risk, alignment, and governance. If the industry doesn't yet have consensus on how to secure a given AI capability, you'll be one of the people defining it.

Deploy and operate security infrastructure hands-on. You'll implement zero-trust architectures, secure multi-agent systems, deploy monitoring and detection tools, and build secure data pipelines. This is not a role where you delegate all technical work — you write code, you configure systems, you debug in production when necessary.

Who You Are

Experience & Skills

• You've served as a CISO, VP of Security, or Head of Security at a high-growth tech company, ideally one building or deploying AI systems at scale.
• You have deep, hands-on experience securing AI and machine learning systems — not just theoretical knowledge, but real work protecting LLM architectures, model training pipelines, and inference infrastructure.
• You've built and operated cloud-native security programs across AWS, GCP, or Azure, including zero-trust frameworks, identity and access management, and secure multi-tenant architectures.
• You understand threat modeling and red teaming deeply, and you've led adversarial exercises against complex systems — ideally including AI-specific attack vectors like prompt injection, model inversion, or data poisoning.
• You've designed and implemented security monitoring, incident response, and compliance programs that scale — you know what good looks like at every stage from startup to enterprise readiness.
• You have a track record of building or contributing to security products, not just internal programs — something you shipped that customers used, or tooling that became infrastructure for others.

Mindset & Traits

• You think like a founder. You see security as a competitive advantage and a product opportunity, not just a compliance checkbox. You want to build things, not just manage them.
• You are comfortable with ambiguity and energized by unsolved problems. The fact that no one has secured autonomous AI agents at scale yet doesn't intimidate you — it excites you.
• You are product-minded and commercially aware. You understand that security decisions have business implications, and you can articulate trade-offs in language that non-security stakeholders understand and respect.
• You are technical enough to earn respect from engineers and pragmatic enough to earn trust from clients. You can debug a containerized agent deployment in the morning and present to a CFO in the afternoon.
• You are a teacher and a builder of institutional knowledge. You document what you learn, you share what you know, and you leave systems better than you found them.
• You care deeply about doing the right thing. You take security seriously because real people and real organizations depend on it, and you hold yourself to the highest standard even when no one is watching.

Equal Opportunity Commitment

Human Agency is an Equal Opportunity Employer. We value diverse perspectives and are committed to building inclusive, high-performing teams where everyone can do their best work.

Location: Remote (U.S. or Canada)

Type: US Applicants – Full-Time; Canadian Applicants – Independent Contractor

About Human Agency

We're scaling rapidly and have a growing pipeline of opportunities that demand exceptional talent across disciplines. Our mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth.

We are a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don't insulate us from feedback or basics. We invite critique, learn quickly, and keep raising the bar. The best ideas win here, no matter where they come from, because clients trust us to deliver the strongest outcomes every time.

Our clients' missions, products, and bottom lines are sacred. We immerse ourselves in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset we create must be both beautiful and functional; practical, usable, and designed for real-world impact.

Humans are our most valuable resource, and we only grow by hiring people who push us forward. Across strategy, engineering, design, data, and operations, we seek out teammates who raise the bar and make us better. Always hire up, never down.

We partner with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We believe AI should amplify human potential, not replace it, and we build with that conviction in every engagement. From advisory and tooling to implementation and education, we meet clients where they are and help them integrate AI in ways that align with their mission and values. Our goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation.

And through it all, we lead with purpose, love, and adventure. We do meaningful work with people we care about, and we make the ride an adventure worth taking. Because at Human Agency, who we are and how we work are one and the same.

The Opportunity

This is not a traditional enterprise CISO role where you inherit a legacy infrastructure, manage a large team, and maintain the status quo. This is a hands-on, entrepreneurial builder role. You are joining at the frontier of AI security — designing systems that don't yet exist, solving problems the industry is only beginning to name, and treating security not as a cost center but as a strategic and commercial advantage.

We're deploying AI agents at scale across client environments, building our own AI-powered tools, and advising organizations on how to safely integrate autonomous systems into mission-critical workflows. That creates a unique security mandate: you must secure our internal operations, embed security directly into the AI products we build, and help clients deploy agents safely in regulated, high-stakes environments. You are architect, operator, and evangelist all at once.

You'll have the rare opportunity to shape how an entire category of technology gets secured. We're not asking you to retrofit old playbooks onto new problems — we're asking you to write the playbook. If you've been looking for a role where security is core to the product, where you can build things that matter, and where your work influences the broader conversation around AI safety and governance, this is it.

What You'll Own

Define and execute our security strategy from the ground up. You'll architect our internal security posture across infrastructure, data, and AI systems, establish governance models for how we deploy agents safely, and ensure we're prepared for compliance frameworks like SOC 2, ISO, and potentially FedRAMP as we scale into enterprise and government clients.

Build security into AI agent systems as a first-class product feature. You'll design guardrails, monitoring, and policy enforcement for autonomous agents — ensuring they operate within defined boundaries, audit their own actions, and surface anomalies in real time. This isn't theoretical; you'll implement these systems in production environments where they directly impact client outcomes.

Develop and potentially commercialize security products. The security tooling you build internally may become standalone offerings. You'll have the latitude to identify what's missing in the market, prototype solutions, and work with our product and engineering teams to turn internal infrastructure into revenue-generating products.

Lead incident response, threat modeling, and adversarial testing. You'll build and run red team exercises against our AI systems, model attack vectors that don't yet have names, and develop response frameworks for risks unique to agentic AI — things like prompt injection at scale, model extraction, or adversarial manipulation of agent behavior.

Serve as the public face of AI security for Human Agency. You'll represent us in client conversations, partner discussions, and industry forums. You'll publish, speak, and help shape the broader conversation around AI risk, alignment, and governance. If the industry doesn't yet have consensus on how to secure a given AI capability, you'll be one of the people defining it.

Deploy and operate security infrastructure hands-on. You'll implement zero-trust architectures, secure multi-agent systems, deploy monitoring and detection tools, and build secure data pipelines. This is not a role where you delegate all technical work — you write code, you configure systems, you debug in production when necessary.

Who You Are

Experience & Skills

• You've served as a CISO, VP of Security, or Head of Security at a high-growth tech company, ideally one building or deploying AI systems at scale.
• You have deep, hands-on experience securing AI and machine learning systems — not just theoretical knowledge, but real work protecting LLM architectures, model training pipelines, and inference infrastructure.
• You've built and operated cloud-native security programs across AWS, GCP, or Azure, including zero-trust frameworks, identity and access management, and secure multi-tenant architectures.
• You understand threat modeling and red teaming deeply, and you've led adversarial exercises against complex systems — ideally including AI-specific attack vectors like prompt injection, model inversion, or data poisoning.
• You've designed and implemented security monitoring, incident response, and compliance programs that scale — you know what good looks like at every stage from startup to enterprise readiness.
• You have a track record of building or contributing to security products, not just internal programs — something you shipped that customers used, or tooling that became infrastructure for others.

Mindset & Traits

• You think like a founder. You see security as a competitive advantage and a product opportunity, not just a compliance checkbox. You want to build things, not just manage them.
• You are comfortable with ambiguity and energized by unsolved problems. The fact that no one has secured autonomous AI agents at scale yet doesn't intimidate you — it excites you.
• You are product-minded and commercially aware. You understand that security decisions have business implications, and you can articulate trade-offs in language that non-security stakeholders understand and respect.
• You are technical enough to earn respect from engineers and pragmatic enough to earn trust from clients. You can debug a containerized agent deployment in the morning and present to a CFO in the afternoon.
• You are a teacher and a builder of institutional knowledge. You document what you learn, you share what you know, and you leave systems better than you found them.
• You care deeply about doing the right thing. You take security seriously because real people and real organizations depend on it, and you hold yourself to the highest standard even when no one is watching.

Equal Opportunity Commitment

Human Agency is an Equal Opportunity Employer. We value diverse perspectives and are committed to building inclusive, high-performing teams where everyone can do their best work.