Lead AI Engineer

360learning

Remote· lead

This is a hands-on leadership role that puts you in control of real technical decisions from day one. You'll set the direction for AI across 360learning's product, own the hard architectural problems, and grow a team of engineers around you—all while staying close to the code. If you want to lead without leaving engineering behind, this is the move.

You'll coach a growing team of AI Engineers, partner with product and design, and drive shipping agentic features that thousands of users rely on. Recent wins include conversational search, bulk operations agents, AI-generated courses, and personalized recommendations. You'll own the technical vision for what comes next and make the calls on how the team scales.

You're a strong engineer who can think in systems—someone who's shipped real ML or data work and knows how to mentor others without micromanaging. You don't need a decade of experience; you need clarity on architecture, comfort with ambiguity, and the ability to grow people as you grow yourself. A portfolio of projects (personal or professional) speaks louder than a degree.

To apply, visit CareerJumpShip and submit your resume, a link to your work (GitHub, deployed projects, or case studies), and a brief note on why this role appeals to you. 360learning will review applications on a rolling basis.

About this role

Introduction to the Team & Role AI is central to 360Learning's strategy: our AI Squad ships agentic features that help users discover, create, and administrate content. Over the last year, we have shipped 5+ AI features powering thousands of users monthly: Catalog Companion: An AI agent performing bulk catalog operations (sharing, archiving, tagging, author assignments) Smart Search: conversational search helping users discover the right content Conversational BI: Analytics and insights delivered through natural conversation AI Course & Question Generation: Creating questions and full courses from documents and titles Content Recommendations: Personalized content discovery We're now looking for a Lead AI Engineer to drive the technical vision for AI in 360Learning’s product and to coach our AI Engineers as the team grows. This is a hands-on leadership role: you'll set technical direction, own the hardest architectural decisions, and grow the people around you, while staying close to the code. You'll coach our team of AI Engineers (2 today, growing), and partner closely with 1 Product Manager, 1 Product Designer, and our Full-Stack Developers. You'll report directly to the Head of AI/Data.

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