Head of Product Growth, LearnWith.AI

6 days ago


Toronto, Canada Crossover Full time

Head of Product Growth, LearnWith.AI (Remote) - $400,000/year USD We are seeking a seasoned product leader to take charge of our Education vertical and champion the mission of making learning more effective for students. This full‑time, independent‑contractor role offers a base pay of $200 per hour ($400,000 per year) in a remote‑first environment. Base pay range : $200.00/hr – $200.00/hr Are you a product leader prepared to harness AI to reshape the education landscape? This position focuses on driving fundamental change, not simply rolling out incremental improvements. This role is driven by ownership of a strategic outcome rather than process management. You will set an objective for our Education vertical and be empowered to achieve it, crafting the master “Brain Lift” that encodes our strategy and establishes a dynamic portfolio roadmap. The portfolio should ensure all our educational products function as a unified system. You will guide a team of talented Product Owners, serving as a player‑coach who stays deeply involved in the most vital initiatives. The conventional one‑size‑fits‑all model of education consistently falls short in serving individual learners. Our methodology constructs a new system grounded in learning science and AI to provide genuinely individualized instruction, demonstrating that education can be simultaneously deeply personal and profoundly impactful. This position differs from a conventional VP of Product role. If you favor managing processes instead of owning outcomes or wish to delegate essential strategic work, this opportunity is not the right match. We seek a leader who is intensely analytical, a clear first‑principles thinker, and unrelenting in pursuing the defined goal. You will collaborate directly with the founders to direct the entire vertical. The metric of your success is straightforward: clear, data‑supported evidence that your strategy measurably enhanced how students learn. If you are prepared for this magnitude of challenge and accountability, let’s connect. What You Will Be Doing Architecting the Domain Knowledge: Take ownership and advance the master “Education Domain BrainLift,” distilling team and market insights into one cohesive strategy that unifies the entire vertical around critical product decisions. Driving the Portfolio Roadmap: Convert the Domain BrainLift into an outcome‑focused roadmap for the entire product portfolio. You will establish the work sequence that generates compounding value and provides the strategic rationale to guide your team's execution. Player‑Coach Execution: Operate as a player‑coach, conducting your own OODA loops on critical outcomes to establish the standard, while coaching your team by assessing their iterations and refining their insights for unified portfolio execution. What You Won’t Be Doing Serving as a pure people manager. Your main function is to guide the vertical’s strategy and establish the execution standard, not simply manage headcount, budgets, and processes. Implementing a top‑down strategy that has been delivered to you. You are expected to personally compose the cohesive, comprehensive strategy for the entire vertical, synthesizing insights from the ground up. Building static, long‑range roadmaps. The portfolio roadmap is a dynamic document that you will navigate with agility, leveraging weekly learnings from your team’s iterations and your own. Managing a “feature factory.” Your success is measured by accomplishing the strategic outcome for the vertical. This demands fostering genuine cross‑pollination between products, not merely shipping more features in isolation. Key Responsibilities & Qualifications 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 to launch, achieving at least $1 million in revenue. Professional experience using AI in your daily work (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 draws on 50+ years of learning science, cutting‑edge data analytics, and AI‑powered coaching to help students learn more, learn faster, and learn better – and enjoy the process. Working with Us This full‑time (40 hours per week), long‑term position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level is $200 USD per hour, which equates to $400,000 USD per year assuming 40 hours per week and 50 weeks per year. Payment is weekly. #J-18808-Ljbffr



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