Entrepreneur in Residence $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
Ready to be at the forefront of an AI-powered educational revolution? At LearnWith.AI, we're not just dreaming about the future of learning—we're building it. We're seeking a visionary Entrepreneur in Residence who can turn bold ideas into measurable student success stories.
Picture yourself as the architect of transformative learning experiences, where every week brings new opportunities to directly impact how students learn, grow, and succeed. We're dismantling the one-size-fits-all education model and replacing it with a sophisticated blend of cutting-edge AI, proven learning science, and expert-driven instruction.
This isn't your typical product role. It's an opportunity to pioneer solutions that make education more personal, effective, and accessible. You'll be working with a dynamic team of engineers, educators, and AI specialists, turning data-driven insights into features that revolutionize how students learn. If you're energized by rapid iteration, obsessed with measurable outcomes, and ready to leverage AI to amplify human potential, we want to hear from you.
What you will be doing
Your mission will revolve around two core pillars:
- Knowledge Amplification: Create and maintain "BrainLifts"—sophisticated knowledge frameworks that synthesize your deep domain insights to power both human and AI decision-making processes
- Rapid Impact Cycles: Lead high-velocity OODA (Observe, Orient, Decide, Act) loops that transform insights into actionable features within days, not months, always guided by concrete success metrics
What you will NOT be doing
To set clear expectations, this role is not about:
- Traditional product management or roadmap maintenance
- Jumping straight to solutions without deep user understanding
- Long development cycles (we move in weeks, not months)
- Technical architecture decisions or engineering management
Candidate requirements
Your track record should demonstrate:
- 4+ years of proven product leadership experience, with direct ownership of product vision and problem-solution validation
- A success story of launching a product from zero to $1M+ revenue, managing the entire journey from conception to market success
- Practical expertise in leveraging AI tools for professional analysis, research, and strategic planning
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.
Accept Job Offer.
Pass 
proctored test.
Frequently asked questions
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The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
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