Lead AI Engineer, LearnWith.AI (Remote) - $200,000/year USD

Company: Crossover

Educational technology companies confront a significant obstacle: creating learning content that captures student interest while adapting to their individual requirements. The market is saturated with one-size-fits-all solutions that fail to deliver meaningful results. Evidence shows that educational resources that don't resonate with learners or accommodate their distinct learning preferences lead to sharp declines in engagement, leaving a void in productive educational experiences. This burden falls heavily on teachers, who must deliver customized, high-caliber instruction within tight time and budget limitations.
LearnWith.AI is addressing this challenge directly through advanced AI technology that transforms how content is developed. Our focus extends beyond mere AI tool creation—we are engineering intelligent systems that produce dynamic, learner-centered educational materials. Envision an AI-powered "Second Brain" for disciplines such as History or Science—a sophisticated knowledge system that generates compelling, responsive content on demand. This approach distinguishes us in an oversaturated marketplace and expands what AI can accomplish in education, making learning more attainable, impactful, and engaging.
This position differs from typical AI engineering roles. Your work will extend well beyond routine coding or theoretical model development. You will spearhead the transformation of student learning by architecting and deploying AI-powered workflows that deliver genuinely individualized educational experiences. This opportunity is not suited for those seeking routine assignments or gradual enhancements—it demands bold innovators ready to leverage advanced technology for tangible, real-world outcomes.
In this pivotal role, you will architect AI-powered educational platforms capable of reshaping the learning environment. You will employ LLMs as specialized domain authorities to construct contextual knowledge frameworks and intelligent tutoring systems, ensuring our AI produces content with substance and relevance. If the prospect of applying AI to revolutionize education excites you and you are prepared to drive projects that challenge existing limits, we encourage you to apply.
What You Will Be Doing
* Developing Self-Refining AI Content Generation Platforms – Agent-based workflows that produce educational materials and continuously enhance themselves through evaluation cycles and systematic experimentation.
* Constructing Evaluation Datasets & Experiment Frameworks – Carefully selected datasets (inputs → anticipated outputs) and scoring mechanisms deployed to assess, benchmark, and refine the quality of AI-produced content.
* Engineering Context Packs – Organized knowledge structures that deliver domain-specific grounding and empower systems to produce precise, superior educational content spanning multiple subjects.
Lead AI Engineer Key Responsibilities
* Help LearnWith.AI distinguish itself in a competitive landscape by producing compelling and individualized educational content through AI-driven tools
Basic Requirements
* Minimum of 4 years of professional experience as a software engineer
* Demonstrated professional experience embedding LLMs into software products (simple chatbot development or basic coding assistant usage does not meet this requirement)
* Track record of deploying production systems where self-improving agents directed system iteration (e.g., autonomous tool design, reward function refinement, etc.)
* Proven experience building evaluation or regression datasets that guide self-improving systems and establishing quantifiable success metrics
* Hands-on experience with contemporary agent-orchestration frameworks (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-RO-COUNTRY-LeadAIEngineer

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