Senior Product Manager, Chess AI

Chess.com is one of the largest gaming sites in the world and the #1 platform for playing, learning, and enjoying chess. The team is 600+ fully remote people in 60+ countries, working to serve 200M+ chess players worldwide with the best possible product, content, and tools. This role calls for someone who loves to play chess and wants to help others discover that same joy — someone intimately familiar with Chess.com products and interested in the history of chess as a proving ground for AI advancement. The ideal candidate has extensive experience as a product manager shipping consumer-facing products with LLM and/or AI/ML-powered features, has worked deeply with engineering teams to define success in ambiguous environments, and communicates regularly with executive stakeholders. What You'll Do: Shape the AI/ML roadmap and vision: Partner with leadership to shape the near-term roadmap and long-term vision for AI/ML at Chess.com — helping users learn the game, improve faster, and deepen their relationship with chess. Expand AI in products like Game Review, Play Coach, and FairPlay, and lead new bets like human-like bots and personalized coaching. Bring ideas and sharpen them with the team: Come with your own point of view on what's worth building. Engage seriously with feedback from leadership and peers, internalize it, push back where warranted, and help build the vision together. Operate in public: Work out loud in Slack channels across time zones — brainstorm openly, pose sharp questions, make decisive calls with reasoning attached, and build alignment by pulling the right people in. Partner deeply with engineering, early and through delivery: Shape technical approach alongside engineering, write specs that are crisp on intent and honest about tradeoffs, and drive execution through to shipping. Define success and hold the quality bar: Frame problems, set evaluation criteria with engineers and researchers, and make calls with incomplete data — revisiting as you learn. Use AI to prototype, de-risk, and accelerate: Build mocks, test flows, evaluate models, and pressure-test ideas before engineering invests, bringing working artifacts into discussions rather than just decks.

Preferred Skills: 7+ years in product management, with 4+ years shipping consumer AI/ML products powered by both LLMs and quantitative ML models Excellent product taste, especially in the chess context — understanding what different skill levels of chess players need from a Coach Technically fluent — collaborates deeply with engineers, understands systems, comfortable reading/producing AI-assisted code and reasoning about model evals and metrics AI-native — uses AI daily to prototype, explore ideas, and accelerate execution High-velocity communicator — communicates clearly and concisely at speed across many projects, acting as a focal point across design, engineering, stakeholders, and executives; operates primarily in writing with high throughput