Role Summary

We’re looking for a Digital Content & AI Automation Manager to lead our transition to 'Vibe Marketing.' Inspired by the shift toward Vibe Coding, we want to bridge the gap between creative intent and digital execution. You’ll move Okta away from manual tickets and rigid CMS forms toward an agentic, self-service model—building the tools that allow marketers to describe a goal in natural language and see it manifest across our digital ecosystem.

This is a test, learn, build, iterate role. You aren't just managing a stack; you’re building an autonomous engine that empowers every marketer to be a creator.

What You’ll Actually Do

• Build the "Vibe Marketing" tools: Create the workflows and agentic layers that allow non-technical stakeholders to manage and scale digital content across its entire lifecycle using natural language and AI assistance.
• Develop Agentic Support Models: Prototype and deploy AI agents that act as "co-pilots" for Marketing Managers—handling everything from automated tagging and metadata to complex distribution across our headless ecosystem.
• Architect Self-Service Systems: Reduce the "time-to-live" by building modular, reusable content structures that agents can manipulate, moving us beyond the constraints of traditional platforms like Adobe Experience Manager.
• Operate Like a Lab: Run rapid experiments with emerging AI tools and automation platforms. Build scrappy prototypes—not just strategy decks—to prove that "vibe-based" creation works at enterprise scale.
• Partner Across Teams: Bridge the gap between "what if" and "here’s how," working with Marketing, Engineering, and Digital teams to turn agentic concepts into production-ready workflows.

What We’re Looking For

• The "Vibe" Mindset: You understand the shift from "doing the work" to "directing the agents." You’ve followed the Vibe Coding movement and are itching to apply it to Marketing Tech.
• 4–8 Years of Experience: You’ve seen the limitations of legacy CMS architectures and are ready to bypass those bottlenecks by building a modern, agent-led content supply chain.
• Hands-on AI & Automation: You don't just prompt; you build. You have experience with APIs, MCP, LLM orchestration, and connecting tools to create seamless loops.
• Technical Fluency: You aren't a full-stack engineer, but you understand how to navigate enterprise complexity—you're comfortable with structured content, and the logic of how data flows between a headless CMS, an LLM, and the front-end.

#LI - Hybrid

P24086_3333054

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

At Guidepost Montessori, our Lead Toddler Teacher 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 Teacher, 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 Teachers 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 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, 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.

Who We Are 

At 8th Light, we bring life to the best ideas.

Founded in 2006 and headquartered in Chicago, we are a technology solutions provider that partners with organizations to solve meaningful challenges and drive sustainable growth. From early-stage startups to global enterprises, we work across industries to optimize our clients’ digital products through product strategy innovation, experiential design, AI solutions, and deep engineering expertise. 

Our commitment to quality means we deliver solutions we’re truly proud of, while our curiosity sparks innovation and breakthrough thinking. 8th Lights thrive in an environment that champions continuous education, fueling our growth through mentorship and hands-on work. We foster an open, collaborative culture grounded in honesty that builds trust, and believe true success is measured by the outcomes we create for our clients.

If this kind of work and our kind of people energizes you, you’ve found the right place. 

Who You Are

You’ve shown long-term repeated success on a variety of projects, typically over the course of 10+ years. You are a trusted expert and leader, often called upon to guide ambiguous initiatives and architect scalable solutions. You bring a blend of deep consulting acumen, technical expertise, and product thinking that drives measurable and impactful outcomes. In your previous experience, you have:

• Demonstrated long-term success on high-stakes consulting engagements across multiple language paradigms, stacks, ecosystems, technical environments, and client industries 
• Built high-quality, maintainable software collaboratively, incrementally, and through an approach tailored towards the unique needs of the clients you’ve served 
• Led the development and delivery of production-grade software using a variety of languages and frameworks, including but not limited to: Python, Java, JavaScript, TypeScript, React, Ruby, Scala, R, SQL, and Go
• Evaluated and strategically applied AI-assistive development tools to accelerate delivery and improve quality
• A track record of understanding, assessing, and embracing new tooling and trends within the software industry
• Experience building or integrating AI/ML-powered features into products or systems (e.g., recommendation engines, NLP models, computer vision, predictive analytics) 
• Used context-appropriate automated testing to inform software design choices and catch bugs
• Successfully led modernization efforts to align legacy systems with short and long-term business needs
• Remedied architecture-level concerns such as scalability, security, reliability, and performance
• Facilitated alignment and collaboration across technical and non-technical stakeholders to move initiatives forward in the face of ambiguity and complexity while balancing technical considerations with product and user needs
• Provided mentorship and team support at scale, while sharing knowledge and improving team practices 
• Actively sought out and effectively given feedback
• Collaboratively led stakeholders to balance technical considerations with product and user needs

What You’ll Do At 8th Light

As a go-to technologist and strategist within 8th Light, you’ll work with a variety of clients, typically one to two in a year, while continuing to deepen your and our collective domain expertise over the course of your career with us. You’ll be responsible for:

• Rapidly building trust with clients, demonstrating technical expertise and understanding of their domain and objectives 
• Guiding technical direction, solving complex problems, and demonstrating best practices while remaining deeply engaged within the codebase
• Working pragmatically to balance technology choices while delivering high-quality work within deadlines
• Advising clients on architecture, scalability and platform evolution, connecting technical decisions to product and business outcomes
• Collaborating on systems that involve the full ML lifecycle from data ingestion and preprocessing, to model deployment, integration, and performance monitoring
• Driving innovation by proactively surfacing new technical approaches and product solutions
• Leading or initiating formal feedback conversations with teams and clients via retrospectives
• Clearly articulating and documenting outcomes and driving forward action items
• Contributing to the health of your team and 8th Light’s culture by modeling our Values
• Designing and managing high-level technical roadmaps for large engagements
• Building your network and maintaining relationships with clients and other industry leaders within your domain
• Coaching client engineering teams, transferring knowledge and leveling up practices
• Influencing client CTOs and executive decisions. Planning and execute technical work that involves stakeholders outside of project boundaries such as across a client's technical organization
• Participating in account planning; opportunity identification.
• Facilitating retrospectives, strategy sessions, and technical deep-dives to improve team and project outcomes
• Identifying, mitigating, and resolving blockers to team progress
• Contributing to 8th Light by serving as a mentor, leading or designing workshops internally or for clients, representing 8th Light in the tech community, or supporting our hiring processes
• Demonstrating leadership in scalable system design, modular architecture, and platform- or product-oriented development.
• Bringing depth in testing strategies, observability, fault tolerance, and secure engineering practices.
• Applying architectural patterns to evaluate tradeoffs and drive clear, documented design rationale.

Strongly Preferred Skills

We work across many areas, and encourage anyone with the experience listed above to apply. We would particularly like to encourage applicants with experience in the following areas:

• Delivering and advising on enterprise-grade AI systems, including RAG pipelines, vector search, and agentic frameworks (e.g., LangChain, LlamaIndex, Crew AI, AutoGen, n8n), ensuring scalable, production-ready solutions that empower developers and align with business outcomes.
• DevSecOps & DevOps
• MLOps
• Infrastructure as Code
• Data Engineering: including platforms like Databricks for data processing and analytics.

Building a truly diverse, equitable, and inclusive workplace is an ongoing journey, and we’re excited to keep learning and growing together. We have a proud tradition of hiring talented colleagues with real-world career experiences. 

How You’ll be Supported

At 8th Light, we believe our people are our greatest asset. Their growth, well-being, and success shape our future. 

Our wellness package is designed with the Whole YOU in mind and includes:

• A robust L&D program featuring unlimited access to thousands of books, courses, and expert-led training on the O'Reilly learning platform.
• Annual financial stipend and time allotment for learning & development
• Coworking support for our global team
• Flexible PTO 
• 12 weeks of new parent leave available for eligible employees

See our full list of Benefits. 

A Note on Compensation

At 8th Light, we are committed to a compensation philosophy that is transparent, fair, and helps us attract and retain top talent in alignment with our company’s strategic growth goals and clients’ needs.

We benchmark our salaries using Geographic Structures to establish competitive pay ranges within the regions where 8th Lights live. Our pay ranges for our Principal Engineer position within our four US structures are as follows:

• Structure 1 (Tampa Metro, Ohio, Tennessee, Wisconsin)
• RANGE: $151,535-$189,418 USD
• Structure 2 (Chicago Metro, Miami Metro, Philadelphia Metro, Raleigh Metro ) 
• RANGE: $159,240-$199,050 USD
• Structure 3 (Austin Metro, Boston Metro , DC Metro)
• RANGE: $169,513-$211,892 USD
• Structure 4 (Los Angeles, Seattle, New York City)
• RANGE: $176,705- $220,881 USD

Reach out to recruiting@8thlight.com for more relevant information pertaining to your local market.

8th Light Hubs and Geographies

As a remote-first company, 8th Light's culture is rooted in strong connections that extend across our teams, regions, and beyond client work. We are a distributed team across the United States, Canada, and the United Kingdom, with hubs in Chicago, London, Los Angeles, New York, and Seattle. 

If you are hired into a hub, you will be a part of a team with regular rituals around co-working and community building. For team members outside of those cities, we offer access to coworking spaces to foster continued collaboration and connection across our global team. 

In most cases, our consulting engagements do not require travel.

We hope to see you apply! 

_#LI-Remote

Senior Software Engineer - [Chicago | Atlanta | Boston]

Who We Are 

At 8th Light, we bring life to the best ideas.

Founded in 2006 and headquartered in Chicago, we are a technology solutions provider that partners with organizations to solve meaningful challenges and drive sustainable growth. From early-stage startups to global enterprises, we work across industries to optimize our clients’ digital products through product strategy innovation, experiential design, AI solutions, and deep engineering expertise. 

Our commitment to quality means we deliver solutions we’re truly proud of, while our curiosity sparks innovation and breakthrough thinking. 8th Lights thrive in an environment that champions continuous education, fueling our growth through mentorship and hands-on work. We foster an open and collaborative culture grounded in honesty that builds trust, and believe true success is measured by the outcomes we create for our clients.

If this kind of work and our kind of people energizes you, you’ve found the right place. 

Who You Are

You’ve shown repeated success on a variety of projects, typically over the course of 4+ years. You have a broad range of expertise that allows you to make an immediate impact on projects. In your previous experience, you have:

• Successfully contributed to high-stakes consulting engagements from discovery to production 
• Written production-quality code using a variety of languages and frameworks, that include: Python, Java, JavaScript, TypeScript, React, Ruby, Scala, R, SQL, and Go
• Built high-quality, maintainable software collaboratively, incrementally, and through an approach tailored towards the unique needs of the clients you’ve served 
• Leveraged AI-assistive development tools for tasks like scaffolding, refactoring, debugging, test generation, and documentation, where appropriate
• Experience building or integrating AI/ML-powered features into products or systems (e.g., recommendation engines, NLP models, computer vision, predictive analytics) 
• Used context-appropriate automated testing to inform software design choices and catch bugs
• Debugged and refactored pre-existing code to incrementally improve it
• Collaborated with teams using Git, MacOS/Linux, and CI/CD
• Remedied architecture-level concerns such as scalability, security, reliability, and performance
• Contributed to forums that encourage idea sharing, collaboration, and problem solving
• Made thoughtful recommendations and set direction in the face of ambiguity
• Mentored and shared knowledge with colleagues
• Actively sought out and effectively given feedback
• Communicated empathically with stakeholders and colleagues
• Influenced stakeholders to balance technical considerations with product and user needs

What You’ll Do At 8th Light

As a senior technologist on projects, you’ll work with a variety of clients, typically one to two in a year, through a variety of technologies and frameworks over the course of your career with us. You’ll work with colleagues who share your passion for technology solutions. You’ll invest time developing your skills and sharing what you know. You’ll be responsible for:

• Making immediate contributions to projects, rapidly building trust with your clients and team
• Working pragmatically to balance technology choices while delivering high-quality work within deadlines
• Contributing to architecture and software design discussions
• Collaborating on systems that involve the full ML lifecycle from data ingestion and preprocessing, to model deployment, integration, and performance monitoring
• Generating new potential solutions to challenges (technical and non-technical) in partnership with team members and clients
• Contributing to formal feedback conversations with teams and clients via retrospectives
• Clearly articulating and documenting outcomes and driving forward action items
• Regular syncs with your delivery team to provide status updates, and for identifying and evaluating risks and presenting potential solutions
• Identifying, mitigating, and resolving blockers to team progress
• Pursuing opportunities to further your skills to grow your career and keep pace with the rapid changes within the technology industry 
• Contributing to your team culture by building connections with your fellow 8th Lights, showing up on camera, and leveraging collaboration opportunities, such as coworking spaces and local team gatherings, where appropriate
• Confidently predicting the next World Series Win for the Chicago White Sox. 

Strongly Preferred Skills

We work across many areas, and encourage anyone with the experience listed above to apply. We would particularly like to encourage applicants with experience in the following areas:

• MLOps: including tools like LangChain for application development and managing the ML lifecycle
• Data Engineering: including platforms like Databricks for data processing and analytics
• DevSecOps & DevOps
• Infrastructure as Code

Building a truly diverse, equitable, and inclusive workplace is an ongoing journey, and we’re excited to keep learning and growing together. We have a proud tradition of hiring talented colleagues with real-world career experiences. 

How You’ll be Supported

At 8th Light, we believe our people are our greatest asset. Their growth, well-being, and success shape our future. 

Our wellness package is designed with the Whole YOU in mind and includes:

• A robust L&D program featuring unlimited access to thousands of books, courses, and expert-led training on the O'Reilly learning platform
• Coworking support for our global team
• Flexible PTO 
• 12 weeks of new parent leave available for eligible employees
• Transparent semi-annual promotion panel

See our full list of Benefits. 

A Note on Compensation

At 8th Light, we are committed to a compensation philosophy that is transparent, fair, and helps us attract and retain top talent in alignment with our company’s strategic growth goals and clients’ needs.

We benchmark our salaries using Geographic Structures to establish competitive pay ranges within the regions where 8th Lights live. Our pay ranges for our Senior Engineer position within Chicago, Illinois is: $104,160-$130,200 USD. 

Reach out to recruiting@8thlight.com for more relevant information pertaining to your local market.

8th Light Hubs and Geographies

As a remote-first company, 8th Light's culture is rooted in strong connections that extend across our teams, regions, and beyond client work. We are a distributed team across the United States, Canada, and the United Kingdom, with hubs in Chicago, London, Los Angeles, New York, and Seattle. 

If you are hired into a hub, you will be a part of a team with regular rituals around co-working and community building. For team members outside of those cities, we offer access to coworking spaces to foster continued collaboration and connection across our global team. 

In most cases, our consulting engagements do not require travel.

We hope to see you apply! 

_#LI-Remote

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 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, 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.

Inspire curiosity. Build independence. Shape a lifelong love of learning.

At Guidepost Montessori, our Lead Children’s House Guides empower children ages 3–6 to grow into confident, capable learners through thoughtfully prepared environments and respectful, individualized guidance.

If you’re passionate about early childhood education and excited to lead a classroom where independence and joy take center stage, we’d love to meet you.

Your Role

As a Lead Children’s House Guide, you’ll lead a mixed-age preschool classroom in a Montessori environment designed to nurture concentration, confidence, and deep learning.

Montessori guides carefully prepare their classrooms to spark curiosity and independence. Through close observation, individualized lessons, and intentional language, you’ll support each child’s academic, social, and emotional development meeting them where they are and helping them grow.

Children in Montessori classrooms have the freedom to choose meaningful work, repeat activities until mastery, and take pride in their accomplishments. Your guidance helps every child develop focus, confidence, and a strong belief in their own abilities.

What You’ll Do

• Observe each child closely to understand and support their physical, intellectual, and emotional development
• Prepare and maintain a beautiful, orderly classroom that fosters concentration and independence
• Encourage self-confidence by supporting children as they learn to “do it themselves”
• Provide individualized and small-group lessons in practical life, literacy, math, and beyond
• Build strong, respectful relationships with children and families
• Communicate and collaborate with parents to support each child’s growth
• Lead your classroom with warmth, professionalism, and purpose

The Montessori Prepared Environment

Every Guidepost Children’s House classroom is fully equipped with high-quality Montessori materials and designed around the principles of beauty, order, and accessibility.

A Guidepost Children’s House environment includes:

• Child-sized furniture and ample floor space for independent and small-group work
• Practical life materials for sweeping, food preparation, table setting, and care of the environment
• Curriculum that builds independence in dressing, feeding, and self-care
• Hands-on materials for literacy, math, science, and cultural studies
• Low shelves and child-level artwork for full accessibility
• Cozy reading spaces, real plants, and abundant natural light
• Beautiful, breakable materials made from wood, metal, and glass

What We’re Looking For

• Montessori diploma for ages 3–6, or willingness to obtain certification (fully sponsored)
• Experience working with children ages 3–6 in a group learning environment
• Alignment with child-led philosophies such as Montessori or Reggio Emilia
• Required ECE or Child Development credits
• Bachelor’s degree in (Child related field)

What We Offer

• Sponsored Montessori diploma training through the Prepared Montessorian Institute
• Ongoing professional development and mentorship
• 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 supportive network of passionate educators
• 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 ages 3 months to 6 years in our Nido, Toddler, and Children’s House programs.

We believe children are capable. Our mission is to transform education by designing learning environments that cultivate independence, joy, and lifelong curiosity for children, families, and educators alike.

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, daycare, preschool, 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 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, 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.

Inspire curiosity. Build independence. Shape a lifelong love of learning.

At Guidepost Montessori, our Lead Children’s House Guides empower children ages 3–6 to grow into confident, capable learners through thoughtfully prepared environments and respectful, individualized guidance.

If you’re passionate about early childhood education and excited to lead a classroom where independence and joy take center stage, we’d love to meet you.

Your Role

As a Lead Children’s House Guide, you’ll lead a mixed-age preschool classroom in a Montessori environment designed to nurture concentration, confidence, and deep learning.

Montessori guides carefully prepare their classrooms to spark curiosity and independence. Through close observation, individualized lessons, and intentional language, you’ll support each child’s academic, social, and emotional development meeting them where they are and helping them grow.

Children in Montessori classrooms have the freedom to choose meaningful work, repeat activities until mastery, and take pride in their accomplishments. Your guidance helps every child develop focus, confidence, and a strong belief in their own abilities.

What You’ll Do

• Observe each child closely to understand and support their physical, intellectual, and emotional development
• Prepare and maintain a beautiful, orderly classroom that fosters concentration and independence
• Encourage self-confidence by supporting children as they learn to “do it themselves”
• Provide individualized and small-group lessons in practical life, literacy, math, and beyond
• Build strong, respectful relationships with children and families
• Communicate and collaborate with parents to support each child’s growth
• Lead your classroom with warmth, professionalism, and purpose

The Montessori Prepared Environment

Every Guidepost Children’s House classroom is fully equipped with high-quality Montessori materials and designed around the principles of beauty, order, and accessibility.

A Guidepost Children’s House environment includes:

• Child-sized furniture and ample floor space for independent and small-group work
• Practical life materials for sweeping, food preparation, table setting, and care of the environment
• Curriculum that builds independence in dressing, feeding, and self-care
• Hands-on materials for literacy, math, science, and cultural studies
• Low shelves and child-level artwork for full accessibility
• Cozy reading spaces, real plants, and abundant natural light
• Beautiful, breakable materials made from wood, metal, and glass

What We’re Looking For

• Montessori diploma for ages 3–6, or willingness to obtain certification (fully sponsored)
• Experience working with children ages 3–6 in a group learning environment
• Alignment with child-led philosophies such as Montessori or Reggio Emilia
• Required ECE or Child Development credits
• Bachelor’s degree in (Child related field)

What We Offer

• Sponsored Montessori diploma training through the Prepared Montessorian Institute
• Ongoing professional development and mentorship
• 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 supportive network of passionate educators
• 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 ages 3 months to 6 years in our Nido, Toddler, and Children’s House programs.

We believe children are capable. Our mission is to transform education by designing learning environments that cultivate independence, joy, and lifelong curiosity for children, families, and educators alike.

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.

Inspire curiosity. Build independence. Shape a lifelong love of learning.

At Guidepost Montessori, our Lead Children’s House Guides empower children ages 3–6 to grow into confident, capable learners through thoughtfully prepared environments and respectful, individualized guidance.

If you’re passionate about early childhood education and excited to lead a classroom where independence and joy take center stage, we’d love to meet you.

Your Role

As a Lead Children’s House Guide, you’ll lead a mixed-age preschool classroom in a Montessori environment designed to nurture concentration, confidence, and deep learning.

Montessori guides carefully prepare their classrooms to spark curiosity and independence. Through close observation, individualized lessons, and intentional language, you’ll support each child’s academic, social, and emotional development meeting them where they are and helping them grow.

Children in Montessori classrooms have the freedom to choose meaningful work, repeat activities until mastery, and take pride in their accomplishments. Your guidance helps every child develop focus, confidence, and a strong belief in their own abilities.

What You’ll Do

• Observe each child closely to understand and support their physical, intellectual, and emotional development
• Prepare and maintain a beautiful, orderly classroom that fosters concentration and independence
• Encourage self-confidence by supporting children as they learn to “do it themselves”
• Provide individualized and small-group lessons in practical life, literacy, math, and beyond
• Build strong, respectful relationships with children and families
• Communicate and collaborate with parents to support each child’s growth
• Lead your classroom with warmth, professionalism, and purpose

The Montessori Prepared Environment

Every Guidepost Children’s House classroom is fully equipped with high-quality Montessori materials and designed around the principles of beauty, order, and accessibility.

A Guidepost Children’s House environment includes:

• Child-sized furniture and ample floor space for independent and small-group work
• Practical life materials for sweeping, food preparation, table setting, and care of the environment
• Curriculum that builds independence in dressing, feeding, and self-care
• Hands-on materials for literacy, math, science, and cultural studies
• Low shelves and child-level artwork for full accessibility
• Cozy reading spaces, real plants, and abundant natural light
• Beautiful, breakable materials made from wood, metal, and glass

What We’re Looking For

• Montessori diploma for ages 3–6, or willingness to obtain certification (fully sponsored)
• Experience working with children ages 3–6 in a group learning environment
• Alignment with child-led philosophies such as Montessori or Reggio Emilia
• Required ECE or Child Development credits
• Bachelor’s degree (Child related field)

What We Offer

• Sponsored Montessori diploma training through the Prepared Montessorian Institute
• Ongoing professional development and mentorship
• 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 supportive network of passionate educators
• 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 ages 3 months to 6 years in our Nido, Toddler, and Children’s House programs.

We believe children are capable. Our mission is to transform education by designing learning environments that cultivate independence, joy, and lifelong curiosity for children, families, and educators alike.

At Instawork, the safety of our marketplace is our highest priority. We are looking for a Trust & Safety Specialist who is, first and foremost, a meticulous and objective investigator. You will be responsible for protecting our community by resolving complex safety incidents with a firm commitment to evidence and policy.

To excel at the scale we operate, you must be highly proficient in modern operational leverage. This means using vibe coding (Natural Language to SQL) and AI-driven automation to gather facts, synthesize data, and streamline your workflow. We aren't looking for someone to just follow a manual—we want an investigator who uses the latest technology to find the truth faster and more accurately.

Who You Are:

• The Master Investigator: You have a "detective" mindset. You know how to weigh conflicting evidence, identify biases, and reach a fair conclusion under pressure.
• AI-Native & Tech-Fluent: You are proficient in using AI to enhance your productivity. You understand how to use natural language to interface with data (vibe analytics) and automate repetitive administrative tasks.
• High Agency: You take extreme ownership of your cases. You don't just "process" a ticket; you solve the underlying problem.
• Experience: 3+ years in Trust & Safety, Operations, or Compliance. Experience communicating with external stakeholders (clients, legal, or law enforcement) is a must.
• Data-Inquisitive: You are comfortable navigating internal systems and using data to build a narrative of facts.

What You’ll Do: 

• Lead Complex Investigations: Your primary focus is the end-to-end resolution of safety incidents. You will conduct objective, unbiased, and thorough evidence-based investigations to protect all stakeholders on the platform.
• Evidence-Based Resolution: Manage escalated support tickets with a cool head. You will communicate clearly and consistently with professionals and partners, ensuring that resolutions are grounded in facts and aligned with our terms.
• Vibe Analytics (NL-to-SQL): Proactively interrogate our databases using natural language to generate SQL queries. You will pull your own data to identify fraud patterns and safety trends without needing a technical intermediary.
• Policy Stewardship: Act as a subject matter expert on Instawork’s Community Guidelines. You will apply these policies with precision and help evolve them as the marketplace grows.
• Automated Workflow Design: Identify manual bottlenecks in the investigation process and use AI or low-code automation to build scalable enforcement solutions.

For IL-based applicants:

• The base salary for this position is $90,000 - $100,000
• This position is eligible for equity in the form of stock options
• This position is eligible for Instawork benefits, including:
• A variety of medical, dental, and vision plans with coverage beginning on the date of hire
• Flexible paid time off and paid company holidays
• Phone stipend
• Commuter stipend
• Supplemental pay on qualified leaves
• Employee health savings accounts (HSA) contribution
• Flexible spending plans
• 401K plan
• Employee discount program

#LI-Onsite

At Instawork, our labor marketplace tech company, we believe that even in the age of AI, the core of success comes down to good people doing honest work. To empower these individuals and ensure our technology truly serves them, we're seeking a curious and driven Product Operations Intern to help us operationalize our intelligent product features, ensuring they deliver value and efficiency to our users. This is a fantastic opportunity to grow your career at the intersection of product, data, and user experience.

To help us evaluate your skills in a hands-on context, you will receive an email invitation to complete a practical case study upon applying to this role. 

Who You Are:

• Currently enrolled in an undergraduate program with a strong interest in product operations.
• A Passion for Product & Tech: You are fascinated by how technology products are built, launched, and improved. You're eager to learn and contribute to the product lifecycle.
• Curious about AI: You don't need to be an expert, but you're an enthusiast interested in learning about the latest AI technologies and tools and their potential to improve user experiences.
• Analytical & Data-Curious: You have a knack for looking at data to find patterns and answer questions. You're comfortable with spreadsheets (Excel/Google Sheets) and are excited to learn more about data analysis.
• A Problem-Solver: You enjoy tackling challenges and are motivated to find efficient solutions. You're organized, detail-oriented, and not afraid to ask questions to get to the root of a problem.
• Eager to Learn Technical Skills: You have an interest in learning data analysis tools. Any exposure to SQL or other data tools is a plus, but a strong desire to learn is most important.
• Collaborative & Hands-On: You are a team player who is ready to roll up your sleeves and help with a variety of tasks, from testing new features to analyzing user feedback.

What You'll Do:

• Support Product Rollouts & Adoption: Work closely with product, design, and operations teams to help execute outreach and rollout plans for new features.
• Contribute to Product Development: Act as a key tester for new product capabilities. You'll document your findings, share user feedback with the product team, and help identify areas for improvement.
• Analyze Feature Performance: Assist in monitoring the performance of new features by tracking key metrics, analyzing user behavior, and summarizing insights for the team.
• Champion the User Experience: Be a voice for our users. You'll help gather, organize, and analyze user feedback from various channels to inform the product roadmap.
• Streamline Team Operations: Support the team by identifying opportunities to make our processes more efficient, whether through better documentation, improved feedback loops, or simple automations.

Nice To Have:

• Familiarity with Coding Agents: Extensive experience building with autonomous agents like Replit Agent and Cursor to move from natural language prompts to production-ready code and complex workflows.
• Data Analysis Exposure: Basic experience with SQL, Python (Pandas), or data visualization tools like Tableau or Looker.
• Internship or Project Experience: Previous internships or relevant project work in a tech, startup, or marketplace environment.
• Customer-Facing Experience: Experience in a role where you directly interacted with users or customers (e.g., customer support, community management).

For IL based applicants:

• The pay range for this position is $30 - $40 per hour

A variety of factors are considered when determining someone’s compensation including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed above.

Position Overview:

We are looking for a Senior Machine Learning Engineer to build the core Machine Learning foundations that power Nova’s agentic experiences. This role focuses on applied Machine Learning in production environments: retrieval systems, evaluation frameworks, and model integration layers that make AI features reliable, scalable, and repeatable. You will design and implement the underlying components that support rich, intelligent interactions in the Iterable platform.

You will work closely with backend, frontend, and product teams to shape how Machine Learning is introduced and maintained across the company. The work blends hands-on engineering with system design, and is ideal for someone who can drive complex efforts independently, make practical architectural decisions, and collaborate in a fast-moving, cross-functional product environment.

Responsibilities:

• Design and build Machine Learning platform components that support agentic systems, including retrieval pipelines, indexing strategies, and model integration layers.
• Introduce and operationalize RAG use cases, from data sourcing and embedding generation to runtime retrieval patterns.
• Develop generalized evaluation frameworks for LLM- and agent-based features, including offline metrics, golden datasets, and continuous monitoring.
• Implement abstractions, tooling, and reusable patterns that enable other teams to build ML- and LLM-powered experiences efficiently.
• Partner with backend engineers to productionize ML features with strong reliability, observability, and performance characteristics.
• Prototype applied ML solutions to validate feasibility before investing in full builds.
• Ensure secure, robust handling of data used in ML workflows and retrieval operations.
• Collaborate with product, design, and engineering to align ML system design with user experience and product goals.
• Contribute to iterative improvements of the Nova agent framework, including workflows built with Mastra and TypeScript.

Qualifications:

• 5+ years experience as a Machine Learning Engineer or similar role focused on production systems.
• Strong engineering skills with Python or TypeScript, including experience building ML workflows in frameworks like Mastra or comparable agent/LLM toolkits.
• Experience with retrieval systems, vector databases, search technologies, or RAG architectures.
• Prior work integrating ML or LLM-powered features into production applications.
• Understanding of ML evaluation techniques, experimentation design, and failure analysis.
• Ability to lead complex projects, make practical trade-offs, and work independently in areas of ambiguity.
• Strong communication and collaboration skills in a distributed environment.

Bonus Points

• Experience building ML or LLM platforms, tooling, or developer-facing frameworks.
• Prior work with embeddings, search–ranking systems, or advanced RAG architectures.
• Familiarity with event-driven systems or streaming architectures.
• Experience with model observability, performance monitoring, or proactive regression detection.
• Background in personalization, recommendations, or applied NLP.
• Experience working in remote-first engineering teams.

Perks & Benefits:

• Competitive salaries, meaningful equity, & 401(k) plan
• Medical, dental, vision, & life insurance
• Balance Days (additional paid holidays)
• Fertility & Adoption Assistance
• Paid Sabbatical
• Flexible PTO
• Monthly Employee Wellness allowance 
• Monthly Professional Development allowance 
• Pre-tax commuter benefits
• Complete laptop workstation

The US base salary range for this position at the start of employment is $133,500 - $212,000. Within this range, individual pay is determined by specific US work location, as well as additional factors, including job-related skills, experience, relevant education or training, and internal equity considerations.

Please note that the range listed above reflects only base salary. The total compensation package includes variable pay (where applicable), equity, plus a range of benefits, including medical, dental, vision, and financial. In addition, we offer perks such as generous stipends for health & fitness and learning & development, among others.