AI Product Director, .AI; Remote

Position: AI Product Director, LearnWith.AI (Remote) - $400,000/year USD

AI Product Director, Learn With.

AI (Remote) - $400,000/year USD

Join to apply for the AI Product Director, Learn With.

AI (Remote) - $400,000/year USD role at Trilogy .

This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range

$200.00/hr - $200.00/hr

Ready to revolutionize education through AI? We are seeking a visionary AI Product Director to spearhead our Education vertical with a mission that matters: helping students learn more effectively through personalized instruction. This isn’t about incremental improvements—it’s about fundamentally reimagining how education works.

As the strategic architect of our Education vertical, you’ll craft the vision that unifies our educational products into a cohesive ecosystem. You’ll author our definitive “Brain Lift” strategy document and translate it into action through a dynamic portfolio roadmap. Leading a team of exceptional Product Owners, you’ll remain hands-on with critical initiatives while providing strategic direction.

We’re challenging the one-size-fits-all education model by building a system grounded in learning science and AI that delivers truly individualized learning experiences. Our mission is to prove that education can be simultaneously personal and transformative.

This position transcends traditional product leadership roles. We’re looking for an analytical first-principles thinker who thrives on accountability and measurable outcomes—not someone who simply manages processes or delegates strategic thinking. Your success will be measured in concrete data showing improved learning outcomes for students.

If you’re energized by the challenge of working alongside founders to transform education through AI innovation and delivering measurable impact, we want to hear from you. What You Will Be Doing

• Craft and evolve our “Education Domain Brain Lift”—the strategic blueprint that synthesizes market insights and team knowledge into a unified vision guiding all vertical decisions
• Develop and continuously refine an outcome-focused portfolio roadmap that creates compounding value across products, providing the strategic rationale for your team’s execution priorities
• Embed the player-coach model by personally driving critical OODA (Observe-Orient-Decide-Act) loops while mentoring your team through thoughtful review and refinement of their work to ensure portfolio cohesion What You Won’t Be Doing
• Functioning solely as a people manager—your value comes from strategic leadership and execution standards, not administrative oversight of headcount and budgets
• Implementing pre-defined strategies handed down from above—you will be the author and architect of the vertical’s comprehensive strategy, building it from first principles
• Creating rigid, unchanging roadmaps—your portfolio strategy will evolve continuously, incorporating weekly insights and learnings from across the team
• Running a “feature factory” with siloed products—success means achieving strategic outcomes through thoughtful integration across the product ecosystem, not simply shipping isolated features AI Product Director

Key Responsibilities

This section was empty in the original job description. Basic Requirements

• 6+ years in product leadership positions where you personally crafted product vision and owned the fundamental problem-solution hypothesis
• Track record of successfully launching at least one complete product (not a feature or module) from conception to market, reaching real external users and generating minimum $1M in revenue
• Demonstrated professional experience integrating AI tools into your daily workflow for research, analysis, strategic synthesis, or other high-value activities Nice-to-have Requirements About Learn With.

AI

Learn With.

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…