Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end product design for Chess.com’s social and community features across web, iOS, and Android. Design polished interfaces, prototypes, interactions, and cohesive experiences for Home, Profiles, Friends, Messaging, Notifications, and related features. Partner with Product, Engineering, and Design to shape requirements, influence decisions, resolve ambiguity, and maintain design quality through implementation. Contribute to design critiques, improve design-system consistency, mentor peers through feedback, and identify product opportunities beyond assigned briefs.

Design and iterate polished user experiences for Chess.com features across web, iOS, and Android. Own projects from problem definition through implementation, create prototypes with Cursor and Claude, apply design systems, collaborate with product and engineering teams, present design rationale, and contribute proactively in a remote environment.

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.

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.

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

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.