Chess.com
Senior Product Manager, Chess AI
Edtech.com's Summary
Chess.com is hiring a Senior Product Manager, Chess AI. The role involves shaping the AI/ML roadmap and vision to enhance chess learning and gameplay features, partnering closely with engineering to drive product development from concept to delivery while defining success criteria and iterating based on feedback.
Highlights
- Lead the AI/ML product roadmap, focusing on innovative chess features like Game Review, Play Coach, and FairPlay.
- Develop new AI-driven products such as human-like bots and personalized coaching.
- Collaborate closely with engineering teams to define technical strategies and execute product delivery.
- Use AI tools to prototype and validate ideas before engineering investment.
- Engage and align with global, remote teams through clear and asynchronous communication.
- Required experience: 7+ years in product management, with 4+ years shipping consumer AI/ML products.
- Technical fluency in AI systems and ability to interpret model evaluations and metrics.
- Passion for chess, strong product sensibility tailored to users with varied chess skill levels.
- Prefer candidates who actively use AI for prototyping and accelerating workflows.
- Requires substantial overlap with US Eastern and Pacific time zones.
Senior Product Manager, Chess AI Full Description
Senior Product Manager, Chess AI
Product
Product
Remote
About Us
Chess.com is one of the largest gaming sites in the world and the #1 platform for playing, learning, and enjoying chess.
We are a team of 600+ fully remote people in 60+ countries working hard to serve the global chess community. We are here to support 200M+ chess players worldwide with the best possible product, content, and tools to serve the community!
We are a tech company. A gaming company. A content company. And we do it all with passion and commitment to the game. Above all we prize our mission-driven, flat, life-celebrating, no-corporate culture, and we look forward to meeting you and learning more about what you can bring to the team.
About You
First off, you love to play chess and want to help others discover that same joy. You are intimately familiar with Chess.com products and have been interested in the history of chess as a proving ground for AI advancement.
Secondly, you have extensive experience as a product manager shipping consumer-facing products with LLM and/or AI/ML-powered features. You have worked deeply with engineering teams to define what success looks like in an ambiguous environment. You communicate regularly and successfully to executive stakeholders.
Finally, you have technical know-how. You work closely with engineering all the way through to delivery and drive on execution. You talk through pipelines and data so you can have clear and productive conversations with engineering.
What you'll do
- Shape the AI/ML roadmap and vision. In close partnership with leadership, shape both the near-term roadmap and the long-term vision for AI/ML at Chess.com, helping our users learn the game, improve faster, and deepen their relationship with chess. Expand the role of AI in products like Game Review, Play Coach, and FairPlay, and lead new bets like human-like bots, personalized coaching, and ideas no one has surfaced yet.
- Bring ideas and sharpen them with the team. Come with your own point of view on what's worth building and why. You don't wait to be told. At the same time, engage seriously with feedback from leadership and peers: internalize it, push back where you disagree, and use it to make the work better. The vision is built together; you're a strong, informed voice in it.
- Operate in public. As a globally remote company spanning many time zones, async slack communication is how decisions get made. Work out loud in channels: brainstorm openly, pose sharp questions, make decisive small calls with reasoning attached, and be explicit on what's urgent vs. not. Engage with depth and without ego, pull the right people in by name to build alignment. Make the most of sync meeting time by taking on the biggest questions.
- Partner deeply with engineering, early and through to delivery. Shape the technical approach alongside engineering partners, write specs that are crisp on intent and honest about tradeoffs, and be a force driving through to execution. Unblock, reprioritize, and ship.
- Define success and hold the quality bar, even when there's no precedent. Frame the problem, partner with engineers and researchers to set evaluation criteria, and make calls with incomplete data that you revisit as you learn. Work through what "good enough to ship” looks like and how to meld qualitative product feedback with quantitative models.
- Use AI to prototype, de-risk, and accelerate. Build mocks, test flows, evaluate models, and pressure-test ideas yourself before engineering invests. Bring working artifacts into discussions, not just decks.
Preferred Skills
- 7+ years in product management, 4+ shipping consumer AI/ML. You've shipped consumer-facing products powered by both LLMs and quantitative ML models.
- Excellent product taste, especially in the chess context. You know what feels good and what doesn't. You know what users with different levels of chess experience need to hear from a Coach and you can articulate why a response that lands for a 1200 will fall flat for a 400.
- Technically fluent. You collaborate deeply with engineers, understand systems, and aren't afraid to read or produce AI-assisted code. You're comfortable in model evals, can reason about what a metric is telling you, and connect engineering discussions back to the product and ultimately the user.
- AI-native. You already use AI daily to prototype, explore ideas, and accelerate execution. You build working prototypes as the basis for discussion.
- High-velocity communicator. You communicate clearly and concisely at speed and across many projects. You act as the focal point across design, engineering, stakeholders, product peers, and executives, digging into engineering specifics in one thread then zooming out to exec-level outcomes in the next. You operate primarily in writing, and your throughput is high enough that multiple workstreams keep moving without you becoming a bottleneck.
About the Opportunity
- This is a full-time opportunity
- We are 100% remote (work from anywhere!)
- US time zone overlap. This role will have most of it’s key stakeholders across the US. While we are flexible with your location, we would require clear and substantial overlap with both Eastern and Pacific hours.
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