Senior Product Manager, Chess AI

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 f