Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate and improve LLM financial reasoning by designing real-world finance tasks, creating reference solutions, scoring AI outputs with structured rubrics, refining evaluation frameworks, and collaborating with researchers to raise data quality and model performance. Must provide detailed feedback and identify gaps to enhance AI across finance use cases.

Design realistic chip architecture and RTL, build verification environments and testbenches, evaluate AI-generated hardware solutions, provide technical feedback, and collaborate to improve AI understanding of digital design, verification, and semiconductor workflows. Commit 20–40 hours/week remotely as an independent contractor.

Assess finance tasks and workflows for professional realism, clarity, and completeness. Identify missing assumptions, ambiguities, edge cases, and impractical constraints. Validate workflow logic, evaluate whether tasks measure professional finance capabilities, and provide concise, structured written feedback and improvement recommendations while collaborating with other finance experts during a high-engagement remote sprint.

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.

Validate and harden AI evaluation benchmarks by designing test cases, reviewing tasks and reference solutions, debugging Python evaluation scripts, identifying edge cases and exploits, developing repeatable QA processes, and collaborating with researchers to ensure reliable, reproducible benchmark results.

Collect and evaluate Egyptian Arabic voice interactions for an AI voice assistant. Use a Mac to perform voice-driven tasks, record transcripts, clean transcripts, assess AI responses for quality, maintain logs, upload recordings, and follow project guidelines during a ~3-week remote engagement.

Design realistic, multi-step data analysis benchmark tasks and create reproducible reference analyses. Evaluate AI-generated analyses for correctness, statistical validity, and interpretation. Collaborate with researchers to improve benchmark quality and document methodologies in Jupyter/Colab notebooks.

Remote full-time MLOps Engineer role to design, evaluate, and improve ML infrastructure and large-scale training systems. Develop and review challenging MLOps tasks, optimize GPU kernels (Pallas/Triton), create evaluation rubrics, and collaborate with researchers to improve model reasoning and training pipelines. Requires production JAX/PyTorch experience and strong distributed training knowledge.

Evaluate and score AI-generated and human consulting deliverables by developing task-specific evaluation criteria, applying structured frameworks, and providing evidence-based written justifications. Assess strategic thinking, financial reasoning, market analysis, and executive communication; collaborate to refine guidelines, improve scoring consistency, and enhance AI training datasets. Work independently in a remote, asynchronous review environment and continuously calibrate evaluation quality against peers.

Evaluate and record Turkish voice interactions using a Mac, perform everyday voice-driven tasks, transcribe and correct speech, rate AI responses for quality, maintain task logs, upload recordings, and follow project quality standards.