Senior Product Manager, Chess AI at Chess

Chess.com is one of the world's largest gaming sites and the #1 platform for playing, learning, and enjoying chess. We are a team of 600+ fully remote individuals across 60+ countries, dedicated to serving the global chess community. Our mission is to support over 200M+ chess players worldwide with the best possible product, content, and tools. We are a tech company, a gaming company, and a content company, driven by passion and commitment to the game. Above all, we value our mission-driven, flat, life-celebrating, no-corporate culture, and we look forward to meeting you and learning what you can bring to the team.

About You

First and foremost, you love to play chess and are eager to help others discover that same joy. You are intimately familiar with Chess.com products and have a keen interest in the history of chess as a proving ground for AI advancement. Secondly, you possess extensive experience as a Product Manager, having shipped consumer-facing products with Large Language Model (LLM) and/or AI/ML-powered features. You have collaborated deeply with engineering teams to define success in ambiguous environments and communicate effectively with executive stakeholders. Finally, you possess technical know-how; you work closely with engineering throughout the delivery process, driving execution. You understand pipelines and data, enabling clear and productive conversations with engineering teams.

What You'll Do

• Shape the AI/ML roadmap and vision: In close partnership with leadership, you will define both the near-term roadmap and the long-term vision for AI/ML at Chess.com, focusing on helping users learn, improve faster, and deepen their engagement with chess. You will expand the role of AI in products like Game Review, Play Coach, and FairPlay, and lead new initiatives such as human-like bots, personalized coaching, and novel AI-powered concepts.
• Bring ideas and sharpen them with the team: You will arrive with your own clear perspective on what should be built and why, without waiting to be told. Concurrently, you will seriously engage with feedback from leadership and peers, internalizing it, pushing back where you disagree, and using it to enhance the work. The vision is collectively built, and you will be a strong, informed voice in its development.
• Operate in public: As a globally remote company spanning many time zones, asynchronous Slack communication is how decisions are made. You will work transparently in channels: brainstorming openly, posing incisive questions, making decisive small calls with clear reasoning, and explicitly distinguishing between urgent and non-urgent matters. You will engage with depth and without ego, pulling in the right people by name to build alignment. You will optimize synchronous meeting time by addressing the most significant questions.
• Partner deeply with engineering, early and through to delivery: You will collaboratively shape the technical approach alongside engineering partners, write specifications that are crisp on intent and honest about trade-offs, and serve as a driving force through to execution. You will unblock, reprioritize, and ensure delivery.
• Define success and uphold the quality bar, even without precedent: You will frame the problem, partner with engineers and researchers to establish evaluation criteria, and make decisions with incomplete data that you revisit as you gain further insights. You will determine what "good enough to ship" entails and how to seamlessly integrate qualitative product feedback with quantitative models.
• Use AI to prototype, de-risk, and accelerate: You will build mocks, test flows, evaluate models, and pressure-test ideas yourself before significant engineering investment. You will bring working artifacts into discussions, rather than solely relying on presentations.

Preferred Skills

• 7+ years in product management, with 4+ years shipping consumer AI/ML products. You have successfully delivered consumer-facing products powered by both LLMs and quantitative ML models.
• Excellent product taste, particularly within the chess context. You instinctively know what feels good and what doesn't. You understand what users with varying levels of chess experience need from a Coach and can articulate why a response that resonates with a 1200-rated player might fall flat for a 400-rated player.
• Technically fluent: You collaborate deeply with engineers, understand complex systems, and are comfortable reading or producing AI-assisted code. You are adept at model evaluations, can interpret what a metric is indicating, and connect engineering discussions back to the product and ultimately the user experience.
• AI-native: You actively use AI daily to prototype, explore ideas, and accelerate execution. You build working prototypes as the foundation for discussions.
• High-velocity communicator: You communicate clearly and concisely at speed and across multiple projects. You act as the central point of coordination across design, engineering, stakeholders, product peers, and executives, delving into engineering specifics in one conversation and then zooming out to executive-level outcomes in the next. You operate primarily through written communication, and your output is high enough that multiple workstreams progress 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 involve most key stakeholders across the US. While we offer flexibility regarding your location, we require clear and substantial overlap with both Eastern and Pacific hours.

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