Director of AI Product Development

Are you ready to revolutionize education with AI? Want to work on something actually important, which helps real students unlock their potential and learn faster, better, and happier? At LearnWith.AI, we’re building the future of personalized learning, and we need product minds who don’t just think fast, but learn fast.

This role isn’t about managing a product. It’s about making specific, measurable outcomes happen every week. You’ll get one clear goal tied to real student impact. Your job is to make that outcome true, then prove it with data. You’ll go deep into the learning problem space, codify your thinking into structured “Brain Lifts” that make both humans and AI smarter, and drive tight, weekly product iterations until the result is undeniable. You’ll be shipping meaningful features fast and refining them just as quickly.

At LearnWith.AI, we’re not layering technology onto a broken system. We’re building a new one. The U.S. education model is outdated, designed for the average student in a one-size-fits-all classroom. Our platform combines 50+ years of learning science with subject matter experts and AI-powered coaching to deliver individualized instruction at scale. Whether it’s helping a student bounce back from learning loss or crush their AP exams, we’re proving that education can be both personal and high-impact.

This job isn’t for people who want to hide behind abstract strategy or get lost in executional details. If you need someone to tell you the plan, or you prefer defining features over defining success, you won’t thrive here. But if you’re hungry to solve real-world problems, fluent in data, and excited to use AI to amplify your thinking, you’ll be in your element.

You’ll work alongside a tight team of engineers, educators, and AI power users, collaborating directly with founders to move the needle where it matters most: student outcomes. You’ll move quickly, learn obsessively, and leave with proof that your work made a measurable difference in how students learn. If that’s the kind of product challenge you’ve been waiting for, apply. Let’s transform education together.

What you will be doing

• BrainLifts: Maintain a structured body of deep insights you’ve gathered from building domain and customer expertise in order to align teammates, LLMs, and decision-making
• OODA Loops: Drive measurable outcomes through frequent, data-driven product iteration cycles that target the Most Important Problem, deliver high-impact changes in under a week, and track success with clear objective metrics

What you won’t be doing

• Managing roadmaps or defining what to build or how to build it
• Solution-first product management; instead, your approach should begin with becoming a domain expert and understanding your users
• Spending a whole month developing a new feature; we aim to ship new features on a weekly basis
• Building technical solutions or defining software architecture

AI-First Lead Product Owner key responsibilities

Basic Requirements

• At least 4 years of experience in a product leadership role where you personally shaped the product vision and owned the core problem-solution hypothesis
• Previous experience launching at least one successful product (not just a feature or a module) that reached real users (not internal tools) from scratch (not joining partway through the development process) to launch (achieving at least $1 million in revenue)
• Professional experience using AI in your daily work (e.g., research, analysis, synthesis, strategy)

About LearnWith.AI

LearnWith.AI is an edtech startup that leverages AI and subject matter experts to cultivate a new way of learning. Our unique approach leverages 50+ years of learning science, cutting-edge data analytics and AI-powered coaching. In doing so, we can help students learn more, learn faster, and learn better - and have fun while doing it. We are a remote-first company that hires globally via Crossover.