Director of AI/ML Engineering

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

You are an AI expert and visionary, who is prolific with hands-on delivery and an empathetic Engineering leader. You’re looking for an opportunity to lead AI + ML across all teams, systems, and features, and have a proven track record of building and supporting engineering teams that deliver successful AI + ML products and tools at scale. You’re known for caring and supporting the people around you, and have experienced many processes for product development, understanding the nuances required to optimize how we work. Navigating conversations with all levels of the organization is not foreign to you, and neither is pivoting quickly between being a teacher and being a student. You know when to lead from the front and coach, and when to step aside. Rolling up your sleeves is second nature, but you are humble, with a sense of humor and don’t take yourself too seriously. You have been working in or dreamed of working in the gaming industry and are ready to turn your talents towards chess!

What you'll do

• Work across business, product, and operations to craft and integrate AI + ML.
• Build and support a team of AI-first engineers.
• Deploy innovative, scalable AI + ML infrastructure.
• Lead the development and deployment of models in production.
• Support our culture of learning, creativity, and continuous improvement.
• Ensure all AI initiatives align with data governance and ethical standards.

What We're Looking For

• 2-4+ years in AI/ML engineering, with 6+ in leadership roles.
• In-depth knowledge of models, prompt + context engineering, workflows + feedback loops, AI frameworks and MLOps practices.
• Proven success in delivering scalable, impactful AI solutions.
• Excellent leadership and communication skills.
• Ability to work collaboratively across remote teams.
• Passion for innovation and strategic problem-solving.

Preferred Skills

• WandB, Langchain, Langfuse, Cursor/Claude, Vertex, Neo4j
• Java, Python, Golang, Node/Typescript, PHP
• Kubernetes, Linux, GCP
• Data science, Data Engineering
• Experience with deep learning and generative models
• Chess Player
• Life-Long Learner

About the Opportunity

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

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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