Product Manager, Learn Chess with Dr. Wolf

Chess.com is one of the largest gaming sites in the world and the #1 platform for playing, learning, and enjoying chess.

Millions of students have learned chess from the kind and patient Dr. Wolf. What started as an indie labor of love has grown into a real product with a devoted following, and there’s so much more to build.

This is a rare opportunity to independently grow a product with an established user base. You’ll run the roadmap, ship code, talk to users, and make real decisions that affect real learners every day.

You’ll use agentic AI coding tools as your primary way of building as a genuine force multiplier that lets one person do the work of a small team.

• This is a full-time opportunity.
• We are 100% remote.
• Working hours must include at least 4 hours of overlap with US East Coast business hours.

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You can learn more about us here:

• https://www.chess.com/article/view/how-chess-com-virtual-team-works-together
• https://www.chess.com/about
• learnchesswithdrwolf.com
• Dr. Wolf joins Chess.com

You do projects for fun. You enjoy learning new things and messing around with technology. You like games, and teaching. You’ve made apps or websites before.

You’re comfortable with ambiguity. You don’t need a spec to get started. When something’s broken, you fix it. When something could be better, you prototype it.

You’re also someone who genuinely loves chess and cares about teaching it. You understand what it’s like to learn the game. The confusion, the breakthroughs, the way a good explanation can unlock something that felt impossible five minutes ago. That empathy is what makes this product work.

• →Own the product end-to-end. Plan features, review user feedback and stats, make prioritization calls, and talk directly to learners.
• →Ship your own code. Build features and fix bugs on the iOS and Android apps yourself, using agentic AI coding tools as your primary development environment.
• →Use AI as a creative and execution multiplier. Prototype ideas quickly, explore mechanics, automate the mundane, and keep moving. The best person in this role will look like a small team.
• →Design what’s next. Use data, user feedback, and your own judgment to shape what makes Dr. Wolf more effective as a learning experience.
• →Stay close to users. Talk to learners and teachers regularly. Understand where they’re getting stuck, what’s clicking, and what they’re asking for that doesn’t exist yet.
• →Run the business side. Keep the lights on, track the metrics that matter, and make sure the product is growing healthily for both users and the business.

• Projects with real users. An app, game, tool, or website you built mostly on your own and shipped to people who actually used it. A personal project or side project is totally fine.
• Hands-on experience with AI coding tools. You’ve used them to build real things, not just experiment. You know what they’re good for and where they fall short.
• A genuine connection to chess and chess education. You’ve learned the game, taught it, or thought seriously about what makes it hard to learn. You care about helping people get better.
• Comfort with ambiguity and independent ownership. You’ve made product or project decisions without waiting for direction, and you’re energized by that, not anxious about it.
• Curiosity and follow-through. You finish things. You learn by doing. You pick up new technical skills when the problem requires it.