Senior Product Manager, Chess AI

Role Description

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.
• Operate in public.
• Partner deeply with engineering, early and through to delivery.
• Define success and hold the quality bar, even when there's no precedent.
• Use AI to prototype, de-risk, and accelerate.

Qualifications

• 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.
• Technically fluent.
• AI-native.
• High-velocity communicator.

Requirements

• 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.
• 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.
• You already use AI daily to prototype, explore ideas, and accelerate execution.
• You communicate clearly and concisely at speed and across many projects.

Benefits

• This is a full-time opportunity.
• We are 100% remote (work from anywhere!).
• US time zone overlap.