Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate and author high-quality computer science content to improve AI model reasoning and accuracy. Analyze complex CS problems, create scenarios/datasets, review AI outputs for correctness, and collaborate remotely to refine guidelines and documentation.

Design and author research-oriented, multi-step benchmark tasks for frontier AI models; create reference solutions and evaluation standards using Python and notebooks; review AI outputs to identify methodological and analytical flaws; collaborate with AI researchers to refine evaluation methodologies.

Contractor role to create original, high-quality financial documents (reports, analyses, models) with rich visuals (tables, charts, graphs) to train AI. Ensure accuracy, anonymize sensitive data, contribute long-form documents (10–100 pages), and clarify submissions as needed.

Develop and maintain engine-level systems, game modding tools, and editor extensions. Implement and optimize rendering pipelines and shaders using DirectX/Vulkan/OpenGL/Metal. Profile and optimize CPU/GPU/memory and multithreaded workloads, debug complex graphics issues, and collaborate with engineers, artists, and designers to deliver high-quality, maintainable C++ engine code.

Remote contractor role to create and evaluate mathematical problems, proofs, and datasets to train and improve AI models. Assess AI-generated solutions for correctness, produce technical documentation, and collaborate with cross-functional teams to develop benchmark datasets and provide actionable feedback to improve model reasoning.

Seeking an Engineering Manager or Principal Engineer to drive technical advancement. Must have extensive Java, Apache Flink, and Rust experience, strong background building scalable distributed systems, proven leadership, and a high-ownership, builder mindset in a security-focused company.

Lead architecture, development, and delivery of enterprise-scale real-time streaming solutions using Apache Flink and Java. Manage and mentor engineering teams, design fault-tolerant distributed systems, implement stream processing pipelines, and ensure performance, scalability, and production reliability. Collaborate with stakeholders across product, DevOps, and architecture to drive technical roadmaps and best practices.

Serve as the internal customer advocate and technical pre-sales lead for finance-heavy billing and revenue recognition solutions. Translate complex billing and revenue requirements into configured demos, sandbox environments, and solution documents. Partner with Sales, Product, and Engineering to support discovery, RFPs, implementations, and handoffs for enterprise customers.

Lead budgeting, forecasting, and variance analysis while building AI-driven financial models, scenario planning, KPIs, and dashboards. Automate FP&A processes, deliver insights to senior leaders, and collaborate with cross-functional teams to improve forecast accuracy and strategic decision-making.

Provide clinical expertise to improve AI mental-health tools: annotate clinical interactions, evaluate psychotherapy datasets, design psychological testing scenarios, apply CBT frameworks, collaborate with engineers, ensure ethical standards, and drive research-backed AI improvements.