Lead AI Engineer, LearnWith.AI (Remote) - $200,000/year USD
About the role
EdTech companies struggle with a fundamental issue: creating learning content that both captures attention and adapts to each student's individual requirements. The marketplace is saturated with one-size-fits-all solutions that fail to deliver meaningful results. Studies show that educational resources which don't resonate with learners or adjust to their distinct learning preferences lead to dramatic decreases in engagement, widening the gap in quality education delivery. This burden falls heavily on teachers, who must deliver customized, high-caliber instruction while managing limited time and resources.
LearnWith.AI is addressing this challenge directly through advanced AI technology that transforms how content is developed. Our focus extends beyond simply creating AI utilities—we're engineering intelligent systems that produce adaptive, individualized learning resources. Imagine an AI-enabled "Second Brain" for disciplines such as History or Science—a sophisticated knowledge engine that generates compelling, responsive educational materials efficiently and at scale. This groundbreaking methodology distinguishes us in a saturated marketplace and expands what AI can achieve in educational contexts, making learning more attainable, impactful, and engaging.
This position differs from conventional AI engineering positions. You won't spend your time confined to routine coding tasks or theoretical model development. You'll spearhead initiatives that reshape student learning by architecting and deploying AI-powered systems that deliver genuinely personalized educational journeys. This opportunity isn't suited for those drawn to predictable workflows or gradual enhancements—it's designed for driven innovators ready to apply advanced technology to create measurable real-world change.
In this critical team position, you'll architect AI-powered educational platforms with the capacity to fundamentally alter the learning environment. You'll deploy LLMs as subject matter authorities to construct contextual knowledge frameworks and intelligent tutoring systems, guaranteeing our AI produces content that is substantive and transformative. If the prospect of leveraging AI to reinvent education excites you and you're prepared to own projects that challenge conventional limits, we want to connect with you.
What You Will Be Doing
Developing Self-Improving AI Content Generation Systems – Creating agent-based workflows that produce educational materials and continuously enhance themselves through evaluation loops and systematic experimentation. Building Evaluation Sets & Experiment Harnesses – Assembling curated datasets (inputs → expected outputs) alongside scoring mechanisms used to assess, benchmark, and refine the quality of AI-generated educational content. Architecting Context Packs – Developing structured knowledge resources that deliver domain expertise and enable systems to produce precise, superior educational content across multiple subjects.
Lead AI Engineer Key Responsibilities
Drive LearnWith.AI's competitive differentiation by producing engaging and personalized educational content through AI-powered tools
Basic Requirements
Minimum of 4 years of experience as a software engineer Professional experience integrating LLMs into a software product (experience building a chatbot or using simple coding assistants is not sufficient) Experience shipping a production system where a self-improving agent drove the iteration on the system itself (e.g., designed its own tools, refined its own reward function, etc.) Experience curating evaluation or regression sets driving self-improving systems and defining measurable success criteria Experience with modern agent-orchestration tooling (e.g., LangChain, LangGraph)
About LearnWith.AI
LearnWith.AI is an edtech startup that leverages AI and subject matter experts to cultivate a new way of learning. Our unique approach leverages 50+ years of learning science, cutting-edge data analytics and AI-powered coaching. In doing so, we can help students learn more, learn faster, and learn better - and have fun while doing it. We are a remote-first company that hires globally via Crossover.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5532-CA-COUNTRY-LeadAIEngineer
Not the right fit? Search for AI Engineer, LearnWith.AI - $200,000/year USD jobs in Canada
About Crossover
Crossover is a global recruitment company, founded in 2014. We're the world's largest recruiter that specializes in elite full-time remote jobs, hiring the top 1% of tech talent from every corner of the planet.
We find awesome talent in overlooked places, by posting jobs all over the world, and giving everyone an equal opportunity to prove their skills are world-class. Our system of AI-powered assessments is based on objective factors that are scientifically proven to predict high performance (e.g. cognitive aptitude).
𝐇𝐄𝐋𝐏𝐅𝐔𝐋 𝐋𝐈𝐍𝐊𝐒: 🧑 Reviews from people we've hired: crossover.com/reviews 💼 Current openings: crossover.com/jobs 💎 Hire someone for your company: crossover.com/hire ♟️ How the process works: crossover.com/selection-process ❓ FAQs: crossover.com/help
𝑵𝒐𝒕𝒆: Crossover jobs are are fully compliant with LinkedIn's policies, as well as the applicable laws in every country where we advertise.
Allow us to clarify some common misconceptions:
1) The reason we post so many job ads is because LinkedIn organizes all job postings by location. So, the only way to reach candidates all over the world is to post multiple ads in every city you want to hire from. Most recruiters don't bother because it's too time consuming... but we're not most recruiters.
2) We mostly recruit independent contractors, not employees, because labor laws vary so much from one country to another that it's near-impossible to recruit globally otherwise (which is why it's still uncommon even though most jobs can now be done remotely).
3) As is standard for any self-employed person, the stated pay is the entire compensation package. Because they are not employees, each contractor is responsible for handling the things that an employer would take care of e.g. taxes, equipment, vacation time, health insurance. One of the major reasons that Crossover jobs pay so much more than local jobs is to overcompensate for these costs.
It's hard, but it's worth it!
Similar Jobs
Lead AI Engineer, LearnWith.AI (Remote) - $200,000/year USD
About the role
EdTech companies struggle with a fundamental issue: creating learning content that both captures attention and adapts to each student's individual requirements. The marketplace is saturated with one-size-fits-all solutions that fail to deliver meaningful results. Studies show that educational resources which don't resonate with learners or adjust to their distinct learning preferences lead to dramatic decreases in engagement, widening the gap in quality education delivery. This burden falls heavily on teachers, who must deliver customized, high-caliber instruction while managing limited time and resources.
LearnWith.AI is addressing this challenge directly through advanced AI technology that transforms how content is developed. Our focus extends beyond simply creating AI utilities—we're engineering intelligent systems that produce adaptive, individualized learning resources. Imagine an AI-enabled "Second Brain" for disciplines such as History or Science—a sophisticated knowledge engine that generates compelling, responsive educational materials efficiently and at scale. This groundbreaking methodology distinguishes us in a saturated marketplace and expands what AI can achieve in educational contexts, making learning more attainable, impactful, and engaging.
This position differs from conventional AI engineering positions. You won't spend your time confined to routine coding tasks or theoretical model development. You'll spearhead initiatives that reshape student learning by architecting and deploying AI-powered systems that deliver genuinely personalized educational journeys. This opportunity isn't suited for those drawn to predictable workflows or gradual enhancements—it's designed for driven innovators ready to apply advanced technology to create measurable real-world change.
In this critical team position, you'll architect AI-powered educational platforms with the capacity to fundamentally alter the learning environment. You'll deploy LLMs as subject matter authorities to construct contextual knowledge frameworks and intelligent tutoring systems, guaranteeing our AI produces content that is substantive and transformative. If the prospect of leveraging AI to reinvent education excites you and you're prepared to own projects that challenge conventional limits, we want to connect with you.
What You Will Be Doing
Developing Self-Improving AI Content Generation Systems – Creating agent-based workflows that produce educational materials and continuously enhance themselves through evaluation loops and systematic experimentation. Building Evaluation Sets & Experiment Harnesses – Assembling curated datasets (inputs → expected outputs) alongside scoring mechanisms used to assess, benchmark, and refine the quality of AI-generated educational content. Architecting Context Packs – Developing structured knowledge resources that deliver domain expertise and enable systems to produce precise, superior educational content across multiple subjects.
Lead AI Engineer Key Responsibilities
Drive LearnWith.AI's competitive differentiation by producing engaging and personalized educational content through AI-powered tools
Basic Requirements
Minimum of 4 years of experience as a software engineer Professional experience integrating LLMs into a software product (experience building a chatbot or using simple coding assistants is not sufficient) Experience shipping a production system where a self-improving agent drove the iteration on the system itself (e.g., designed its own tools, refined its own reward function, etc.) Experience curating evaluation or regression sets driving self-improving systems and defining measurable success criteria Experience with modern agent-orchestration tooling (e.g., LangChain, LangGraph)
About LearnWith.AI
LearnWith.AI is an edtech startup that leverages AI and subject matter experts to cultivate a new way of learning. Our unique approach leverages 50+ years of learning science, cutting-edge data analytics and AI-powered coaching. In doing so, we can help students learn more, learn faster, and learn better - and have fun while doing it. We are a remote-first company that hires globally via Crossover.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5532-CA-COUNTRY-LeadAIEngineer
Not the right fit? Search for AI Engineer, LearnWith.AI - $200,000/year USD jobs in Canada
About Crossover
Crossover is a global recruitment company, founded in 2014. We're the world's largest recruiter that specializes in elite full-time remote jobs, hiring the top 1% of tech talent from every corner of the planet.
We find awesome talent in overlooked places, by posting jobs all over the world, and giving everyone an equal opportunity to prove their skills are world-class. Our system of AI-powered assessments is based on objective factors that are scientifically proven to predict high performance (e.g. cognitive aptitude).
𝐇𝐄𝐋𝐏𝐅𝐔𝐋 𝐋𝐈𝐍𝐊𝐒: 🧑 Reviews from people we've hired: crossover.com/reviews 💼 Current openings: crossover.com/jobs 💎 Hire someone for your company: crossover.com/hire ♟️ How the process works: crossover.com/selection-process ❓ FAQs: crossover.com/help
𝑵𝒐𝒕𝒆: Crossover jobs are are fully compliant with LinkedIn's policies, as well as the applicable laws in every country where we advertise.
Allow us to clarify some common misconceptions:
1) The reason we post so many job ads is because LinkedIn organizes all job postings by location. So, the only way to reach candidates all over the world is to post multiple ads in every city you want to hire from. Most recruiters don't bother because it's too time consuming... but we're not most recruiters.
2) We mostly recruit independent contractors, not employees, because labor laws vary so much from one country to another that it's near-impossible to recruit globally otherwise (which is why it's still uncommon even though most jobs can now be done remotely).
3) As is standard for any self-employed person, the stated pay is the entire compensation package. Because they are not employees, each contractor is responsible for handling the things that an employer would take care of e.g. taxes, equipment, vacation time, health insurance. One of the major reasons that Crossover jobs pay so much more than local jobs is to overcompensate for these costs.
It's hard, but it's worth it!