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.

Perform structured evaluations of AI assistants using MCP and plugins: design realistic prompts, execute multi-step personal workflows (screen-recorded), assess outputs for usefulness and safety, identify failures, and write detailed reports and rubrics. Remote, US-based contractor role requiring 20+ hours/week and rapid task turnaround.

Design and evaluate performance engineering tasks for AI training/evaluation. Optimize runtime, compilers, memory, CPU/GPU and concurrency. Produce documented solutions, evaluate AI-generated code, and build evaluation frameworks and scoring rubrics while collaborating with researchers and SMEs.

Design real-world ML and NLP tasks, build reference solutions and evaluation frameworks in Python, assess LLM outputs for correctness and reasoning, identify failure modes, create scoring rubrics, and collaborate with experts to improve model capabilities. Part-time, remote contractor (~20 hours/week).

Create clear, structured rater guidelines, evaluation rubrics, and reviewer instructions for human evaluators across domains. Review and revise documentation to remove ambiguity, design scoring frameworks, handle edge cases, and collaborate with researchers and SMEs to ensure consistent, high-quality AI evaluations.

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.

Design and run red-team evaluations to find failure modes and edge cases in frontier LLMs. Create reproducible, multi-step benchmark tasks, document technical findings, and collaborate with researchers to refine grading and improve model robustness. Commit ~35 hours/week as a remote independent contractor.

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.

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.

Evaluate and document AI voice assistant interactions in German using a Mac with Apple Silicon. Complete voice-based tasks, transcribe and polish spoken content, assess AI responses for quality, maintain task logs, and upload recordings and files for multilingual voice-data collection.