Top Tech Jobs & Startup Jobs in Chicago, IL

Manage end-to-end procurement contract lifecycle: draft, review, negotiate, and execute NDAs, MSAs, SOWs, and order forms. Maintain contract repository, coordinate internal reviews with legal, security, finance and procurement, provide stakeholder guidance, prepare summaries and risk analyses, and improve templates, workflows, and compliance processes across jurisdictions.

Evaluates AI-generated investment analysis, valuation, and credit work products, including documents, spreadsheets, and presentations. Applies expert financial judgment to assess accuracy, rigor, factual correctness, aesthetics, and domain quality against structured rubrics. Provides clear written feedback on identified issues. This is a fully remote, flexible independent-contractor engagement paid hourly.

Create technical accounting scenarios, memos, schedules, SEC filings, footnotes, and disclosures for AI training. Review AI-generated accounting outputs for standards-accurate conclusions, apply complex ASC guidance, and provide written feedback. The role requires deep experience with ASC 606, 842, 718, and 805, SEC reporting, and technical accounting in a Big Four or public-company environment. Work is fully remote, asynchronous, and performed as an independent contractor.

Creates realistic external audit, internal audit, and SOX controls scenarios for AI training. Reviews AI-generated audit outputs for accuracy, evidence, and professional judgment; provides written feedback; and collaborates asynchronously with a research team. Responsibilities include audit planning, risk assessment, substantive testing, workpapers, audit reporting, PBC support, SOX walkthroughs and testing, issue tracking, and remediation validation.

Adjudicate transaction-monitoring, sanctions, adverse-media, fraud, dispute, and communications alerts; review KYC/CDD onboarding packets; resolve beneficial ownership structures; document dispositions, remediation requirements, and SAR narratives. The role involves timed mock-case assessments, requires defensible written rationales and knowledge of FinCEN, FATF, OFAC, SAR, and CDD standards. This is a fully remote independent contractor position for approximately 15 hours per week.

Develop enterprise mechanical engineering evaluation tasks for AI systems in Fortune 500 product design and manufacturing contexts. Create complex design, analysis, manufacturing, reliability, certification, and regulatory scenarios; produce reference designs, engineering analyses, technical narratives, and judgment-focused rubrics. Work across CAD, FEA/CFD, thermal and fluid systems, structural analysis, DFM/DFA, Six Sigma, GD&T, and enterprise PLM tools under ASME and ISO standards.

Evaluate AI-generated documents, spreadsheets, and presentations for accuracy, rigor, domain quality, and presentation quality in incident management, reliability, and SRE. Apply specialized rubrics, identify factual and aesthetic errors, and provide structured written feedback. This is a fully remote, flexible independent-contractor engagement requiring at least five years of relevant professional experience, English fluency, and proficiency with Microsoft Office and Google Workspace.

Evaluate AI-generated engineering, manufacturing, and technical operations work products, including documents, spreadsheets, and slide decks. Assess outputs for factual accuracy, rigor, aesthetics, presentation quality, and adherence to domain-specific rubrics. Identify errors and provide clear, structured written feedback. This is a fully remote, flexible independent contractor engagement paid hourly on a weekly basis.

Evaluate AI-generated documents, spreadsheets, and slide decks related to public-sector procurement and RFI responses. Assess outputs for factual accuracy, rigor, presentation quality, and adherence to domain-specific rubrics. Identify errors and provide clear, structured written feedback. This is a fully remote, flexible independent-contractor engagement requiring at least five years of relevant professional experience.

Evaluate AI-generated documents, spreadsheets, and slide decks related to pricing, ROI, and revenue economics. Assess accuracy, rigor, factual correctness, aesthetics, and presentation quality against domain-specific rubrics, then provide clear, structured written feedback. This is a fully remote, hourly independent contractor engagement with flexible scheduling and weekly payments.