Director of AI/ML Engineering at Chess

About Us

Chess.com is one of the largest gaming sites in the world and the number one platform for playing, learning, and enjoying chess. Our team includes 600+ fully remote people across 60+ countries supporting over 200M players worldwide with product, content, and tooling. We are a tech, gaming, and content company that values a mission-driven, flat, life-celebrating, no-corporate culture.

About You

You are an AI expert and visionary, comfortable with hands-on delivery and empathetic leadership. You have a demonstrated track record of building and supporting engineering teams that deliver AI and ML products and tools at scale. You care about team growth, cross-functional collaboration, and applying AI responsibly. You can navigate strategic conversations at all levels and shift between coaching and individual contribution as needed. Experience or strong interest in gaming and chess is a plus.

What you'll do

• Integrate AI across the company - Work across business, product, and operations to craft and integrate AI and ML initiatives into products and workflows.
• Build AI-first teams - Recruit, grow, and support a team of AI-first engineers and applied ML practitioners.
• Deploy scalable infrastructure - Design and deploy scalable AI and ML infrastructure, MLOps pipelines, and model serving systems in production.
• Lead model development - Drive development and deployment of models to production, including monitoring, feedback loops, and lifecycle management.
• Promote data governance and ethics - Ensure AI initiatives follow data governance, privacy, and ethical standards across teams.
• Foster learning culture - Support a culture of experimentation, continual learning, and collaboration across remote teams.

What We're Looking For

• 2-4+ years in AI/ML engineering, and 6+ years in leadership roles overseeing engineering teams.
• Deep knowledge of models, prompt and context engineering, workflows, feedback loops, AI frameworks, and MLOps best practices.
• Proven success delivering scalable, impactful AI solutions in production.
• Strong leadership, communication, and cross-functional collaboration skills in distributed environments.
• Ability to align AI strategy with product and business goals and to operationalize model deployment and monitoring.

Preferred Skills

• Experience with MLOps and tooling such as WandB, Langchain, Langfuse, or similar platforms.
• Familiarity with model providers and orchestration tools such as Cursor, Claude, Vertex AI.
• Experience with graph databases like Neo4j and data engineering practices.
• Languages and platforms such as Java, Python, Golang, Node, PHP, and Typescript.
• Experience operating on Kubernetes, Linux, and cloud platforms like Google Cloud.
• Experience with deep learning, generative models, and production ML pipelines.
• Chess players and lifelong learners are encouraged to apply.

About the Opportunity

This is a full-time role and Chess.com is 100% remote - work from anywhere. You will lead AI/ML strategy and engineering across our distributed teams and have the opportunity to shape how intelligent systems power a global chess platform. Learn more about our remote culture:

• How Chess.com virtual team works together
• About Chess.com

Apply

If this role excites you, please apply via the job listing. We look forward to meeting you and learning how you can contribute to Chess.com.