AI Product Director, LearnWith.AI (Remote) – $400,000/year USD
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$200/hour – $200/hour
Are you a product leader prepared to harness AI to reshape the way education functions? We are seeking someone to own our Education vertical and take full responsibility for the mission of enabling students to learn with greater effectiveness. This role centers on catalyzing systemic transformation, not simply delivering incremental product enhancements.
This position is distinguished by ownership of a strategic outcome rather than management of processes. You will define the objective for our Education vertical and be empowered to deliver it. You will personally write the master "Brain Lift" that encodes our strategy and establishes the portfolio roadmap uniting all our educational products into a coherent whole. You will lead a team of talented Product Owners as a player‑coach, staying deeply engaged in the most mission‑critical work.
The traditional one‑size‑fits‑all model of education does not serve individual students well. Our method is to construct a new system grounded in learning science and AI that provides genuinely individualized instruction. We are demonstrating that education can be both profoundly personal and remarkably effective.
This role differs from a conventional VP of Product position. If you are more comfortable managing process than owning outcomes, or if you prefer to delegate core strategic responsibilities, this is not the appropriate role. We seek a leader who is intensely analytical, a rigorous first‑principles thinker, and unwavering in pursuit of the defined goal.
You will guide a talented team of product owners and collaborate directly with the founders to direct the entire vertical. The metric of your success is straightforward: concrete, data‑driven evidence that your strategy meaningfully enhanced how students learn. If you are prepared for this level of challenge and accountability, we should speak.
What You Will Be Doing
* Architecting the Domain Knowledge: Own and refine the master "Education Domain BrainLift," distilling team insights and market intelligence into a unified, cohesive strategy that aligns the full vertical on critical product decisions.
* Driving the Portfolio Roadmap: Convert the Domain BrainLift into an outcome‑oriented roadmap spanning the entire product portfolio. You will establish the sequence of initiatives that generates compounding value and supply the strategic rationale guiding your team’s execution.
* Player‑Coach Execution: Operate as a player‑coach: run your own OODA loops on high‑stakes outcomes to establish the standard, while coaching your team through reviewing their iterations and refining their insights to ensure cohesive portfolio execution.
What You Won’t Be Doing
* Serving as a pure people manager. Your principal responsibility is to lead the vertical’s strategy and establish the execution standard, not simply administer headcount, budgets, and process mechanics.
* Implementing a top‑down strategy delivered to you. You are expected to personally craft the comprehensive, overarching strategy for the entire vertical, synthesizing insights from the ground up.
* Developing static, long‑range roadmaps. Your portfolio roadmap is a dynamic instrument. You will navigate the portfolio with agility, integrating weekly insights from your team’s iterations and your own.
* Running a "feature factory." Your success is measured by achievement of the strategic outcome for the vertical. This demands fostering genuine cross‑pollination between products, not merely shipping additional features in isolation.
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.
Working with us
This is a full‑time (40 hours per week), long‑term position. The role 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.
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