AI Product Strategy Lead $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
Elite Product Minds Wanted: Transform Education Through AI-Powered Learning
At LearnWith.AI, we're not iterating on the broken education system—we're rebuilding it from first principles. We seek a strategic product leader who can translate learning science into measurable student outcomes through rapid, data-driven innovation cycles. This role demands intellectual rigor, relentless execution, and the ability to leverage AI as both a product feature and a force multiplier for your own thinking.
Our mission is clear: personalize education at scale by combining cutting-edge AI with decades of learning science. While traditional classrooms remain trapped in a one-size-fits-all model, we're proving that technology can deliver truly individualized instruction that helps students recover from learning loss or excel in advanced coursework—with the data to prove it.
What you will be doing
- Develop and maintain "BrainLifts"—structured repositories of deep domain insights that align teams, inform AI systems, and drive strategic decision-making
- Execute tight OODA loops (Observe-Orient-Decide-Act) with weekly product iterations focused on solving the Most Important Problem, as validated by objective metrics
- Transform learning science principles into concrete product features that deliver measurable improvements in student outcomes
- Collaborate directly with founders to identify critical growth opportunities and rapidly implement solutions
What you will NOT be doing
- Managing traditional product roadmaps or backlogs that aren't directly tied to measurable student outcomes
- Starting with solutions before mastering the domain and understanding user needs
- Engaging in prolonged development cycles; our rhythm demands meaningful feature delivery weekly, not monthly
- Writing code or designing technical architecture—we need your strategic insight, not your engineering skills
- Creating presentations or strategy documents that don't translate into immediate action
Candidate requirements
- Minimum 4 years in product leadership positions 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 minimum $1M in revenue
- Demonstrated proficiency using AI tools to enhance your professional work (research, analysis, strategy)
- Exceptional analytical capabilities with the ability to translate complex data into actionable insights
- Self-directed work style with the ability to define and achieve outcomes without prescriptive direction
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
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School sucks. So we’re fixing it.
The education Olympics
It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game.
Salary without side gigs
Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.
Skills make the grade
Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.
Join America’s largest community of 
AI-first education leaders.