Top Tech Jobs & Startup Jobs in Chicago, IL

Review AI-generated finance outputs, verify figures and rules against authoritative sources, perform quantitative checks and recomputations, assess financial reasoning, provide structured feedback on model performance, and collaborate with researchers to improve models.

Review and evaluate two AI-generated legal responses for accuracy and client-readiness, provide written feedback to improve model behavior, and join onboarding and calibration sessions. Role is part-time (6–15 hours/week) and requires employment/labor law expertise, strong legal research and writing, and a U.S. law degree and license.

Author and classify expert-level cybersecurity prompts, evaluate and annotate model responses for technical accuracy and safe handling of sensitive content, and apply structured guidelines to label prompts and conversations. Part-time role (15–25 hrs/week) requiring strong cybersecurity knowledge, technical writing, and sound security judgment.

Perform market research and competitive analysis, build business cases and go-to-market strategies, synthesize insights into presentations and models, collaborate with stakeholders on metrics, and support strategic planning and scenario modeling.

Part-time private equity role (minimum 10 hours/week) requiring at least 2 years PE experience at top firms. Responsibilities include financial modeling, TAM/market sizing, investment memos, CIM creation and due diligence, NDA/legal document processing, and deal sourcing.