Head of AI Products, LearnWith.AI

7 days ago

Bulacan, Philippines Trilogy Full time

Head of AI Products, LearnWith.AI (Remote) - $400,000/year USD

Join the Head of AI Products, LearnWith.AI (Remote) - $400,000/year USD role at Trilogy

Elite Product Visionaries Only: Lead AI's Educational Revolution

We're seeking the rare product leader who can transform education through AI—not incrementally, but fundamentally. As Head of AI Products for our Education vertical, you'll own a mission that matters: helping students learn more effectively through personalized AI instruction. This isn't about managing processes—it's about delivering measurable outcomes that prove we've changed how education works.

You'll author our strategic "Brain Lift" that unifies our educational products into a cohesive ecosystem. Operating as a player-coach, you'll lead sharp Product Owners while remaining personally engaged in critical strategic work. Your mission: replace one-size-fits-all education with a learning science-backed AI system that delivers truly individualized instruction.

What You Will Be Doing

  • Architect the Education Domain Knowledge: Create and evolve the master "Education Domain BrainLift"—a comprehensive strategic framework that synthesizes team insights and market intelligence into actionable direction for the entire vertical.
  • Drive Portfolio-Level Strategy: Transform your Domain BrainLift into a precise, outcome-driven roadmap that sequences work for maximum impact and provides the strategic "why" behind every product decision.
  • Execute as Player-Coach: Set the standard through direct engagement with critical outcomes while simultaneously mentoring your team, reviewing their iterations, and ensuring cohesive portfolio execution.

What You Won’t Be Doing

  • Managing administrative processes. Your focus is strategic leadership and execution excellence, not headcount administration or budget oversight.
  • Implementing pre-determined strategies. You will author the overarching vertical strategy from first principles, not execute someone else's vision.
  • Building static roadmaps. Your portfolio strategy will evolve continuously based on weekly learnings and rapid iteration cycles.
  • Running a feature factory. Success means achieving transformative educational outcomes through an integrated product ecosystem, not shipping isolated features.

Head Of AI Products Key Responsibilities

Transform education through AI by developing and executing a cohesive product strategy that delivers measurable improvements in student learning outcomes.

Basic Requirements

  • Minimum 6 years in product leadership positions where you personally shaped product vision and owned core problem-solution hypotheses
  • Proven track record launching at least one successful product from conception to market, reaching real users and generating minimum $1M in revenue
  • Demonstrated professional experience leveraging AI tools in your strategic workflow (research, analysis, synthesis, strategy development)

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.

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 $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year.

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