Ready to reshape education with AI that actually works? At LearnWith.AI, we're not chasing education buzzwords—we're delivering measurable learning outcomes that transform how students master concepts. We need a Principal Product Manager who thrives on weekly impact metrics, not quarterly roadmaps.This role demands outcome obsession. You'll receive one clear goal tied to real student achievement, then make it happen through rapid iteration and data validation. You'll codify deep learning insights into structured "Brain Lifts" that enhance both human and AI understanding, driving weekly product improvements until results are undeniable. You won't just ship features—you'll ship proven educational breakthroughs.LearnWith.AI isn't patching the broken education system; we're building its replacement. We combine decades of learning science with AI-powered coaching to deliver personalized instruction at scale. From recovering pandemic learning loss to accelerating AP exam performance, we're demonstrating that education can be both individualized and dramatically more effective.
What You Will Be Doing
- Develop and maintain "BrainLifts"—structured repositories of deep domain insights that align teams, power AI systems, and drive decision-making excellence
- Execute rapid OODA (Observe-Orient-Decide-Act) Loops that identify the Most Important Problem, deliver high-impact solutions within one week, and measure success through objective metrics
- Transform educational challenges into measurable outcomes by synthesizing learning science, user feedback, and performance data
- Collaborate directly with founders to prioritize initiatives that maximize student achievement gains
What You Won’t Be Doing
- Managing traditional product roadmaps or dictating implementation details to engineering teams
- Starting with solutions before mastering the domain and understanding user needs
- Overseeing month-long development cycles; our cadence demands weekly feature delivery and refinement
- Designing technical architecture or coding solutions; your focus remains on educational outcomes
- Creating vanity metrics that don't directly correlate to improved student learning
Basic Requirements
Principal Product Manager key responsibilities
- Minimum 4 years in product leadership positions where you personally crafted product vision and owned the core problem-solution hypothesis
- Proven track record launching at least one successful product from conception to market, achieving minimum $1M revenue with real external users
- Demonstrated professional expertise integrating AI tools into your daily workflow for research, analysis, synthesis, and strategy
- Exceptional analytical capabilities with the ability to translate complex educational challenges into actionable product decisions
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 $100 USD/hour, which equates to $200,000 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-5599-IN-COUNTRY-PrincipalProdu.013
