Principal Product Manager, LearnWith.AI (Remote) - $200,000/year USD

Elite Product Leaders Only: Transform Education Through AI-Powered Learning OutcomesAt LearnWith.AI, we're not iterating on education—we're reinventing it. We seek a Principal Product Manager who delivers measurable student success through rapid, data-driven execution. Your mission: make specific learning outcomes happen every week, prove it with data, and scale personalized education that works.This role demands exceptional product leadership to combine learning science with AI-powered coaching that delivers individualized instruction at scale. You'll work directly with founders to transform how students learn—whether recovering from learning loss or mastering advanced coursework—through a platform that adapts to each learner's unique needs.The U.S. education system wasn't built for personalization. We are. Join us to create the learning experience students deserve.

What You Will Be Doing

• Develop and maintain "BrainLifts"—structured knowledge frameworks that codify deep customer and domain insights to align teams, enhance AI capabilities, and drive decisive action
• Execute rapid OODA Loops (Observe-Orient-Decide-Act) with weekly product iterations focused on solving the Most Important Problem with measurable impact
• Transform learning science research into practical product features that demonstrably improve student outcomes
• Collaborate directly with founders and cross-functional teams to prioritize initiatives that maximize educational impact
  

What You Won’t Be Doing

• Managing traditional product roadmaps or backlog prioritization exercises
• Starting with solutions before deeply understanding the domain and user needs
• Conducting lengthy development cycles; we ship meaningful features weekly, not monthly
• Defining technical architecture or writing code (though you'll work closely with those who do)
• Creating products without clear, measurable learning outcomes
  

Principal Product Manager Key Responsibilities

Drive measurable improvements in student learning outcomes through rapid product iterations that combine learning science expertise with AI innovation.

Basic Requirements

• Minimum 4 years in product leadership roles where you personally shaped product vision and owned core problem-solution hypotheses
• Proven track record launching at least one successful product from conception to market, reaching real users and generating at least $1M in revenue
• Demonstrated proficiency using AI tools in your professional workflow for research, analysis, synthesis, and strategy development
• Exceptional analytical capabilities with a data-driven approach to product development and outcome measurement
• Ability to rapidly develop domain expertise and translate complex educational concepts into practical product features
  

Nice-to-have Requirements

• Experience in education technology or learning science
• Background working with AI/ML products or platforms
• History of successful product launches in high-growth environments
• Experience with personalization algorithms or adaptive learning systems
  

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.010