- How to leverage cutting-edge AI to solve complex educational challenges
- Deep expertise in learning science and cognitive development
- Techniques for rapid product iteration with measurable outcomes
- Methods for structuring knowledge to make both humans and AI systems smarter
Founder 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
Elite Product Visionaries Only: Redefine Education Through AI-Powered Learning
You don't just build products—you create transformative learning experiences that measurably change lives. At LearnWith.AI, we're dismantling outdated education models and constructing something revolutionary in their place. We seek exceptional product minds who can translate deep learning science into weekly, data-validated wins for students.
This is not product management—it's outcome engineering. You'll receive one crystal-clear goal tied directly to student success. Your mission: make it happen, prove it with data, and iterate until excellence is undeniable. You'll work alongside founders, engineers, and educators to create personalized learning experiences that combine five decades of learning science with cutting-edge AI.
The American education system was designed for an industrial era that no longer exists. We're building its replacement. If you're ready to apply your product expertise to something that genuinely matters—helping students learn faster, better, and with greater satisfaction—this role demands your attention.
What you will be doing
- Execute BrainLifts: Develop and maintain a structured knowledge repository of deep domain insights that align your team, power our AI systems, and drive strategic decision-making
- Master OODA Loops: Lead rapid, data-driven product iteration cycles that identify the Most Important Problem, deliver high-impact solutions within one week, and measure success through objective metrics
- Drive Measurable Outcomes: Transform product hypotheses into concrete student achievements with clear before-and-after performance indicators
- Collaborate Cross-Functionally: Work directly with founders and specialists to rapidly prototype, test, and refine features that advance our learning platform's effectiveness
What you will NOT be doing
- Managing Traditional Roadmaps: We don't need someone to maintain Gantt charts or define quarterly feature releases—we need an outcome-driven leader focused on weekly impact
- Starting With Solutions: You won't jump to building features before deeply understanding the domain and users—expertise comes first, solutions follow
- Extended Development Cycles: Forget month-long feature builds; our pace demands meaningful improvements shipping weekly
- Technical Architecture: Your focus is on defining success and outcomes, not dictating how engineers should build the solution
- Following Established Playbooks: This role requires creating new approaches to learning, not implementing standard product management methodologies
Key responsibilities
Transform learning outcomes for students by identifying critical educational challenges and rapidly implementing AI-powered solutions that demonstrably improve comprehension, retention, and engagement.
Candidate requirements
- Proven Product Leadership: Minimum 4 years in product leadership roles where you personally shaped product vision and owned the core problem-solution hypothesis
- End-to-End Product Success: Track record of launching at least one successful product from inception to market, reaching real users and generating minimum $1M in revenue
- AI Proficiency: Demonstrated professional experience leveraging AI tools in your daily workflow for research, analysis, synthesis, and strategy development
- Data-Driven Decision Making: Exceptional ability to define, measure, and optimize toward clear success metrics
- Rapid Learning Capacity: Demonstrated ability to quickly master new domains and translate complex concepts into actionable insights
Nice to have
- Experience in education technology or learning science
- Background in cognitive psychology or instructional design
- Previous startup experience, particularly in founder or early-stage roles
- Experience with LLM prompt engineering or AI system design
How it works
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.
STEP 1
Chat-style
screening interview.
STEP 2
Cognitive 
aptitude test.
STEP 3
Prove real-world 
job skills.
STEP 4
Interview with the hiring manager.
STEP 5
Accept Job Offer.
ONE LAST THING
Pass 
proctored test.
Frequently asked questions
What you will learn
Work examples
- Identifying that students struggle with maintaining focus during study sessions, then designing and implementing an AI-powered attention tracking system that increases average study effectiveness by 40%
- Creating a structured knowledge framework that enables our AI to provide personalized feedback on writing assignments, resulting in measurable improvement in student composition skills
- Developing a rapid testing methodology that validates new learning approaches within days rather than months
Reviews
Meet some people who've landed similar jobs
Why Crossover
Recruitment sucks. So we’re fixing it.
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.
Join the world's largest community of 
AI-first remote workers.