About the job
Are you a product leader prepared to leverage AI to reshape the fundamentals of education? We are seeking someone to take ownership of our Education vertical and champion the mission of making student learning more effective. This position centers on catalyzing systemic transformation, not simply advancing incremental improvements. This position is characterized by ownership of a strategic outcome rather than process management. You will define an objective for our Education vertical and be given the authority to accomplish it. You will personally write the master "Brain Lift" that encodes our strategy and establishes the portfolio roadmap unifying all our educational products. You'll guide a team of capable Product Owners, functioning as a player-coach who stays deeply engaged in the most essential work. The conventional one-size-fits-all education paradigm consistently underserves the individual learner. Our methodology builds a new system grounded in learning science and AI to provide genuinely individualized instruction. We are demonstrating that education can be simultaneously deeply personal and profoundly impactful. This position differs from a conventional VP of Product role. If you favor process management over outcome ownership, or wish to delegate foundational strategic work, this is not the appropriate fit. We are seeking a leader who is rigorously analytical, a clear first-principles thinker, and uncompromising in achieving the defined goal. You will guide a capable team of product owners and collaborate directly with the founders to direct the entire vertical. The benchmark for your success is straightforward: clear, data-supported evidence that your strategy measurably enhanced how students learn. If you're prepared for a challenge of this magnitude and accountability, let's talk. What You Will Be Doing • Architecting the Domain Knowledge: Take ownership of and advance the master "Education Domain BrainLift," consolidating team and market intelligence into a unified, cohesive strategy that aligns the entire vertical on critical product decisions. • Driving the Portfolio Roadmap: Convert the Domain BrainLift into an outcome-focused roadmap for the complete product portfolio. You will establish the sequence of work that generates compounding value and supplies the strategic rationale to guide your team's execution. • Player-Coach Execution: Operate as a player-coach: run your own OODA loops on critical outcomes to establish the standard, while coaching your team by reviewing their iterations and refining their insights for unified portfolio execution. What You Won’t Be Doing • Functioning as a pure people manager. Your core responsibility is to lead the vertical's strategy and establish the execution standard, not simply manage headcount, budgets, and process. • Implementing a top-down strategy that has been delivered to you. You are expected to personally author the comprehensive, overarching strategy for the entire vertical, synthesizing insights from the ground up. • Producing static, long-term roadmaps. Your portfolio roadmap is a dynamic document. You will steer the portfolio with agility, leveraging weekly learnings from your team's iterations and your own. • Managing a "feature factory." Your success is measured by achieving the strategic outcome for the vertical. This demands creating genuine cross-pollination between products, not merely shipping more features in isolation. Basic Requirements AI Product Director key responsibilities • 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) 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.
About the company
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.
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