Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Design and own the Courses product experience across web and mobile. Collaborate with Product, Engineering, and content teams to craft engaging, habit-forming learning flows, build high-fidelity prototypes, ensure design-to-code alignment, and iterate using user insights. Contribute to the design system, provide peer feedback, and improve product consistency and social engagement.

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.

Build and maintain cloud-native, service-based systems connecting users across Chess.com. Develop and ship code to Kubernetes, use AI tools (Cursor/Claude), perform code reviews, and design scalable software serving millions of users while building telemetry and dashboards.

Design and own core Chess.com product experiences (gameplay, puzzles, bots, learning, tournaments). Partner with cross-functional teams to create polished web and mobile interfaces, build interactive prototypes, ensure design-to-code alignment, present design rationale, and proactively propose product improvements to elevate user experience for millions of players.

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.

As a Senior ML Engineer, you'll own ML-driven features from modeling to deployment, drive innovation in generative AI, and mentor junior members.