Top Tech Jobs & Startup Jobs in Chicago, IL

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

Own the Gameplay product roadmap and long-term vision for Chess.com, covering live games, daily games, and bot play. Partner with design, engineering, leadership, and executives to define product quality, scope, metrics, and success. Develop ideas, communicate asynchronously, run experiments, prototype with AI, and ship delightful consumer products at scale. The role requires deep chess knowledge, strong product judgment, high-velocity communication, and substantial overlap with Eastern US hours.

Own and scale paid acquisition across Meta, Google, App Store Ads, YouTube, and DSPs for a global consumer subscription platform. Build incrementality testing, saturation analysis, ROAS and LTV frameworks; manage budgets, vendors, attribution, creative testing, and channel strategy. Partner with growth, social, content, and leadership teams to optimize spend around product launches, seasonal events, and viral moments.

Full-time remote engineering internship with Product Engineering and AI/ML Engineering tracks. Interns may build and optimize scalable product features, contribute to architecture and design decisions, develop data pipelines and machine learning models, deploy AI applications, and integrate LLM-powered capabilities into Chess.com products. Applicants should be enrolled students or equivalent bootcamp participants with strong communication, ownership, teamwork, and relevant programming, database, machine learning, or AI experience.

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.

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.