Founder in Residence, LearnWith.AI (Remote) - $200,000/year USD

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This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$100.00/hr - $100.00/hr

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 At LearnWith.AI, we're dismantling outdated education models and constructing something revolutionary in their place.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.

• 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 Won’t 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

Transform learning outcomes for students by identifying critical educational challenges and rapidly implementing AI-powered solutions that demonstrably improve comprehension, retention, and engagement.

• 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

• 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

LearnWith.AI is an edtech startup that leverages AI and subject matter experts to cultivate a new way of learning. Our approach combines 50+ years of learning science, advanced data analytics, and AI-powered coaching. We are a remote-first company that hires globally via Crossover.

There is much to cover for this exciting role. If you are interested, hit the Apply button and we look forward to meeting you!

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. For more details, consult www.crossover.com/help-and-faqs.

Crossover Job Code: LJ-5599-GB-COUNTRY-FounderinResid.006

Seniority level

• Director

Employment type

• Full-time

Job function

• Business Development, Project Management, and Strategy/Planning

Industries

• Education Administration Programs, E-Learning Providers, and Venture Capital and Private Equity Principals

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