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Chess.com

Senior Product Manager, AI/ML

🇺🇸 Remote - US

🕑 Full-Time

💰 TBD

💻 Product Development

🗓️ August 14th, 2025

Edtech.com's Summary

Chess.com is hiring a Senior Product Manager, AI/ML. The role involves shaping and executing the product roadmap focused on AI innovations to enhance user engagement with chess, collaborating with engineering to prototype and deliver AI-driven features, and leading initiatives such as developing human-like chess bots and an interactive AI chess coach.

Highlights
  • Lead product growth in AI-enhanced features like Game Review, Play Coach, and FairPlay.
  • Develop new AI initiatives including human-like chess bots and LLM-driven chess coaching tools.
  • Collaborate closely with engineering to prototype, de-risk, and execute AI model integration.
  • Align cross-functional teams with AI/ML-powered product vision and drive excitement for these features.
  • Require 7+ years of product management experience with consumer-facing AI/ML products.
  • Experience shipping interactive LLM-based products and quantitative ML model-driven consumer products.
  • Strong collaboration skills with engineering teams to evaluate AI model performance.
  • A passion for chess and its AI-related history is essential.
  • Full-time position with a fully remote work arrangement.

Senior Product Manager, AI/ML Full Description

Senior Product Manager, AI/ML

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 have been interested in the history of chess as a proving ground for AI advancement.

Secondly, you are an experienced product manager who has shipped consumer-facing products with AI/ML-powered features. You have worked with engineering teams to define what success looks like in an ambiguous environment and can communicate successfully to executive stakeholders.

What you'll do
  • Shape and execute the near-term roadmap and long-term vision of Chess.com’s product growth in the AI space, helping our users learn chess and deepen their relationship with the game. Expand the use of AI in existing products such as Game Review, Play Coach, FairPlay, and beyond. Lead new initiatives to develop human-like chess bots, an interactive LLM-driven chess coach, and things we haven’t even thought of yet.
  • Collaborate closely with engineering on planning and execution. Find ways to iteratively prototype between products and the underlying models. De-risk opportunities by creating proofs of concept. Lead on innovation and ensure our best abilities meet our toughest problems.
  • Collaborate with the entirety of the product org to integrate AI-driven features into existing products. Align teams to the vision by creating excitement for and developing interest in AI/ML-powered experiences for our users. Act as a trusted expert who can create trust across teams.

Preferred Skills
  • You have 7+ years experience in product management related to consumer-facing products with AI/ML-powered features.
  • You have shipped interactive, consumer-facing LLM products.
  • You have shipped consumer-facing products driven by quantitative ML models.
  • You are comfortable collaborating closely with engineering teams to help evaluate the AI models underlying your products.
  • You have a passion for chess.

About the Opportunity
  • This is a full-time opportunity
  • We are 100% remote (work from anywhere!)
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