Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate AI-generated and human brand and design deliverables by creating task-specific grading criteria, scoring work against professional standards, and providing detailed, evidence-based written feedback on visual quality, strategic alignment, consistency, usability, and brand effectiveness.

Evaluate and improve AI-generated fund-related legal work by drafting, reviewing, negotiating, and redlining fund documents; develop evaluation frameworks and scoring rubrics; collaborate with product, research, and engineering teams to refine AI training data and legal guidelines; identify contractual risks and provide expert legal feedback.

Part-time contractor M&A attorney to draft, review, negotiate, and redline transaction documents; evaluate AI-generated legal outputs; develop evaluation frameworks and scoring rubrics; provide subject-matter expertise to improve AI training data and legal analysis; collaborate with product, research, and engineering teams to refine legal guidelines and best practices.

Part-time contractor role evaluating and training AI for contract review. Draft, review, negotiate, and redline commercial technology agreements; assess AI-generated contract responses; develop evaluation criteria and scoring rubrics; collaborate with product, research, and engineering teams to improve AI legal workflows and identify contractual risks.

Paid remote research study recruiting senior design professionals to participate in structured, recorded sessions (4-5 hours) to discuss design decision-making, critique, quality standards, and readiness to ship. Participants may act as interviewees or interviewers. Requires a professional portfolio and strong ability to articulate design rationale and trade-offs.

Build, integrate, and stress-test full-stack applications and backend services that leverage advanced AI models. Develop production APIs, front-end features, databases, and cloud infrastructure; troubleshoot integrations; prototype rapidly and deliver high-quality code and documentation in fast-moving environments.

Provide senior-level legal expertise to design, evaluate, and benchmark AI systems for legal tasks. Review AI outputs, create task specifications and reference solutions, develop evaluation frameworks and scoring guidelines, and give structured feedback. Collaborate with researchers, engineers, and program teams to translate professional legal judgment into consistent evaluation standards.

Define rigorous evaluation standards and rubrics for character and facial performance-transfer technology. Curate benchmarks, evaluate subtle facial and body performance differences, document visual insights, and collaborate with specialists to shape consistent human-review processes. Provide expert feedback and help develop reviewer profiles and annotation workflows. Part-time, remote with monthly in-person sessions in Los Angeles or New York.

Build and maintain full-stack production applications and services that integrate frontier LLMs. Design, test, and stress-test systems, diagnose failures, prototype rapidly, and collaborate with engineering and research teams to deliver reliable, deployable software and evaluation tooling.

Evaluate and test complex AI benchmark tasks by designing test cases, executing tasks, debugging environments, reviewing grading logic, identifying shortcuts, and developing repeatable QA processes while collaborating with researchers to maintain rigorous quality standards.