Top Tech Jobs & Startup Jobs in Chicago, IL

Manage treasury operations for a regulated Futures Commission Merchant, including customer fund segregation calculations, cash positioning, liquidity, margin funding, wire controls, regulatory reporting, bank relationships, forecasting, and treasury governance. The role partners across Finance, Accounting, Compliance, Product, and Engineering in a high-growth, deadline-driven environment. WOOF WOOF

Supports esports trading operations by entering player and game statistics, grading projections, settling games, and monitoring real-time markets for accurate payouts. The role includes posting and pricing markets across esports titles and requires night and weekend availability. WOOF WOOF

Own and grow Underdog’s fraud program by designing detection rules, controls, signals, and decisioning strategies; configuring fraud platforms; analyzing trends and performance; advancing automation; and partnering with Product, Engineering, Data, Operations, and Legal/Compliance. Lead and develop the fraud team, identify program gaps, and drive ambiguous fraud initiatives through implementation. WOOF WOOF.

Build and own simulation-based sports prediction and pricing models from research through production monitoring. Apply Bayesian inference, statistical modeling, market data, and trader feedback to estimate fair value across sports and market types. Collaborate with Trading, Engineering, and Product to deploy reliable models, improve calibration and performance, and support new launches. Provide technical leadership through code reviews, modeling standards, documentation, and mentorship while using AI-assisted workflows to accelerate development.

Build and maintain a regulatory reporting data platform using SQL and dbt, including models, automated validations, data pipelines, and testing. Investigate data issues end to end, validate submissions, support audits and legal data requests, monitor upstream changes, collaborate with product, engineering, compliance, and leadership, and participate in on-call coverage. WOOF WOOF

Own and build Underdog’s regulatory reporting data platform, including dbt models, resilient pipelines, automated validations, monitoring, and reporting roadmaps. Partner with regulators, engineering, product, compliance, and leadership; lead audits, investigations, root-cause fixes, data governance, and on-call operations. WOOF WOOF.

Senior Product Designer leading end-to-end experiences for Growth and Promotions. The role simplifies complex rewards mechanics, builds referral and engagement loops, translates marketing campaigns into cohesive product experiences, and partners with Product, Engineering, Data, and Marketing. Responsibilities include research-driven design, experimentation, prototyping, interaction and visual design, stakeholder communication, and shaping future product opportunities. WOOF WOOF

Own and scale the core betting experience across mobile and web using React Native. Diagnose and fix critical client issues, lead cross-platform design reviews, partner with backend/product/design, use analytics to validate changes, coach engineers, and drive reliability, performance, and developer-velocity initiatives.