- Advanced techniques for integrating AI into product development workflows
- Cutting-edge approaches to personalized learning and educational technology
- How to drive measurable outcomes through rapid, data-informed iteration cycles
- The science of effective learning and how to translate it into scalable product features
Director of AI Product Development $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 AI Product Visionaries Only: Transform Education Through Rapid, Measurable Impact
At LearnWith.AI, we're not just talking about AI in education—we're rebuilding the entire learning paradigm. We seek a Director who can translate learning science into revolutionary product outcomes that demonstrably improve student success. This isn't about managing a product roadmap; it's about driving weekly, measurable impact that transforms how students learn.
You'll receive one clear goal tied to student outcomes. Your mission: make it happen through rapid experimentation, data-driven iteration, and deep domain expertise. Working alongside our founders and elite team of engineers and educators, you'll codify your thinking into structured "Brain Lifts" that power both human and AI decision-making. The result? Learning experiences that adapt to individual students at scale, breaking free from the outdated one-size-fits-all education model.
This position demands exceptional product leadership from someone who thrives on autonomy, embraces accountability, and possesses the intellectual rigor to convert complex learning challenges into elegant solutions. If you're prepared to prove your impact with hard data every week while building something that genuinely matters, we should talk.
What you will be doing
- Develop and maintain "BrainLifts"—structured repositories of deep domain insights that align teams, inform AI systems, and drive consistent decision-making across the organization
- Execute rapid OODA Loops (Observe-Orient-Decide-Act) that identify the Most Important Problem, deliver high-impact solutions within one week, and measure success through objective metrics
- Transform learning science principles into product features that demonstrably improve student outcomes across diverse learning scenarios
- Collaborate directly with founders to prioritize initiatives that maximize educational impact while supporting business growth
- Synthesize user research, learning data, and market insights to continuously refine our approach to AI-powered personalized education
What you will NOT be doing
- Managing traditional product roadmaps or getting lost in long-term planning exercises that delay immediate impact
- Starting with solutions rather than deep domain understanding—we solve real problems, not imagined ones
- Overseeing month-long development cycles—our weekly shipping cadence demands rapid iteration and continuous validation
- Dictating technical implementation details or architectural decisions—we have engineering experts for that
- Creating features disconnected from measurable student outcomes—every product decision must demonstrably improve learning
Key responsibilities
Drive measurable improvements in student learning outcomes through rapid product iteration cycles powered by deep domain expertise and data-driven decision making.
Candidate requirements
- Minimum 4 years in product leadership roles with direct responsibility for product vision and core problem-solution hypotheses
- Proven track record launching at least one successful product from conception to market, reaching external users and generating minimum $1M in revenue
- Demonstrated proficiency integrating AI tools into your professional workflow for research, analysis, synthesis, and strategic planning
- Exceptional analytical capabilities with the ability to translate complex educational challenges into structured, solvable problems
- Results-oriented mindset with experience delivering measurable outcomes through rapid experimentation and iteration
Nice to have
- Experience in educational technology or learning science
- Background in cognitive science, educational psychology, or related fields
- Previous success building AI-powered products or platforms
- Experience working in high-growth startups with weekly shipping cadences
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 6
Accept job offer.
STEP 5
Pass
proctored test.
Frequently asked questions
What you will learn
Work examples
- Identifying that students struggle most with maintaining consistent study habits, then designing and shipping a personalized notification system that increased weekly engagement by 40%
- Creating a "BrainLift" document that codifies how different learning styles respond to various content formats, enabling both the team and our AI systems to deliver more effective personalization
- Analyzing user data to identify a critical gap in our algebra curriculum, then collaborating with subject matter experts to develop and deploy targeted interventions that improved mastery rates by 25% within two weeks
Reviews
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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.
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AI-first remote workers.