Jobs at Chess.com

Lead Chess.com’s direct digital advertising sales business, owning strategy, prospecting, negotiations, execution, account management, and revenue growth. Sell web and app advertising solutions, build relationships with brands and agencies, respond to RFPs, and develop market awareness. Partner with Business Development, Product, Engineering, and Data teams to create effective, brand-compliant advertising solutions while delivering positive experiences for advertisers and the chess community.

Own Learn Chess with Dr. Wolf end to end, including roadmap planning, feature prioritization, user research, metrics, business operations, and direct development on iOS and Android. Use agentic AI coding tools to prototype, ship features, and fix bugs while improving the learning experience through feedback, data, and chess education expertise.

Own the design and front-end implementation of Chess.com’s internal growth, AI knowledge, agent, and admin platforms. Create polished UI/UX, translate designs into production-ready interfaces, improve interaction and motion quality, and evolve the design system. Prototype rapidly with Cursor and Claude, design AI-native workflows, collaborate across a distributed team, review code, and ship end-to-end frontend experiences.

Own and operate Chess.com's Elasticsearch/OpenSearch platform: capacity planning, cluster architecture, performance tuning, incident response, migrations, and GitOps-driven infrastructure. Provide on-call incident leadership, snapshot/disaster recovery, index and mapping guidance, and enable cross-team use of dashboards and query optimizations at massive scale.

Lead a small data science team to build production algorithms and models across product and fair-play, partner with cross-functional teams to ship features, design cheating-detection systems, mentor data scientists, and communicate results to stakeholders.

Analyze player behavior and drive product innovation through data-driven insights. Collaborate with teams to design and evaluate experiments, maintaining data quality and delivering meaningful insights.

The Site Reliability Engineer will manage infrastructure stability and scalability, lead cloud migrations, and optimize performance across systems while mentoring team members.

Write high-converting copy across onboarding, upsells, lifecycle emails, paid ads, and sale moments. Partner with product, design, and marketing to craft tests, iterate on A/B results, set tone of voice, and drive subscription revenue while preserving brand voice.

Lead and evolve Chess.com’s creative vision and visual identity across marketing, product, and brand. Design and art direct major campaigns, launches, and performance marketing; mentor and grow the creative team; partner with Product, Marketing, Partnerships, and Content to translate strategy into compelling multi-channel creative; advance brand guidelines and design systems; manage creative resourcing and asset pipelines to deliver work that builds brand equity and drives measurable business growth.

Lead roadmap and vision for Chess.com core product; collaborate with engineering, design, and leadership to define specs, run experiments, and move engagement and retention metrics. Prototype with AI, operate asynchronously, and drive features through to delivery.

As a Senior Product Manager for Chess AI, you'll shape the AI/ML roadmap, partner with engineering, and define product success metrics, while collaborating with stakeholders to enhance user engagement and experience in chess.