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

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Posted on: 3 October, 2025

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

Are you a product leader ready to use AI to transform how education works? We’re looking for someone to lead our Education vertical and own the mission of helping students learn more effectively. This role is about driving systemic change, not just delivering incremental features.

This role is defined by owning a strategic outcome, not managing the process. You will be responsible for defining an objective for our Education vertical and be empowered to achieve it. You will personally author the master “Brain Lift” that codifies our strategy and defines the portfolio roadmap that makes all our educational products work as one. You’ll lead a team of sharp Product Owners, operating as a player-coach who remains deep in the most critical work.

The standard one-size-fits-all education model fails to serve the individual student. Our approach is to build a new system from a foundation of learning science and AI to deliver truly individualized instruction. We are proving that education can be both deeply personal and highly impactful.

This role is different from a typical VP of Product position. If you prefer managing process over owning outcomes, or want to delegate core strategic work, this is not the right fit. We’re looking for a leader who is deeply analytical, a clear first-principles thinker, and relentless in achieving the stated goal.

You will lead a sharp team of product owners and work directly with the founders to steer the entire vertical. The measure of your success is simple: clear, data-backed proof that your strategy measurably improved how students learn. If you’re ready for a challenge of this scope and accountability, let’s talk.

What You Will Be Doing

  • Architecting the Domain Knowledge: Own and evolve the master “Education Domain BrainLift,” synthesizing team and market insights into a single, cohesive strategy that aligns the entire vertical on key product decisions.
  • Driving the Portfolio Roadmap: Translate the Domain BrainLift into an outcome-driven roadmap for the whole product portfolio. You will define the sequence of work that creates compounding value and provides the strategic “why” to direct your team’s execution.
  • Player-Coach Execution: Act as a player-coach: drive your own OODA loops on critical outcomes to set the standard, while mentoring your team by reviewing their iterations and sharpening their insights for cohesive portfolio execution.

What You Won’t Be Doing

  • Acting as a pure people manager. Your primary role is to lead the vertical’s strategy and set the standard for execution, not just manage headcount, budgets, and process.
  • Executing a top-down strategy that has been handed to you. You are expected to personally author the cohesive, overarching strategy for the entire vertical, synthesizing insights from the ground up.
  • Creating static, long-term roadmaps. Your portfolio roadmap is a living document. You will steer the portfolio with agility, drawing on weekly learnings from your team’s iterations and your own.
  • Overseeing a “feature factory.” Your success is defined by achieving the strategic outcome for the vertical. This requires creating true cross-pollination between products, not just shipping more features in silos.

Head Of Product Growth Key Responsibilities

Lead and execute the strategic vision for our Education vertical, delivering measurable improvements in student learning outcomes through AI-powered personalized education solutions.

Basic Requirements

  • At least 6 years of experience in a product leadership role where you personally shaped the product vision and owned the core problem-solution hypothesis
  • Previous experience launching at least one successful product (not just a feature or a module) that reached real users (not internal tools) from scratch (not joining partway through the development process) to launch (achieving at least $1 million in revenue)
  • Professional experience using AI in your daily work (e.g., research, analysis, synthesis, strategy)

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 $200 USD/hour, which equates to $400,000 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-5660-AU-Melbourn-HeadofProductG.001

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