Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate AI- and human-created product designs by creating task-specific grading criteria, assessing work samples, and providing detailed, evidence-based written feedback across usability, accessibility, interaction, visual quality, and business objectives.

Author and verify rigorous multiple-choice legal assessment items for AI benchmarks across multiple legal specialties. Create clear, self-contained questions with one correct answer and nine plausible distractors, classify difficulty, provide structured solution explanations and references, and review/edit questions for legal accuracy and clarity. Work remotely, asynchronously, as an independent contractor, committing 10+ hours weekly.

Perform corporate treasury exercises: build 13-week cash forecasts, analyze FX and interest exposures, recommend hedging, assess working capital and covenants, optimize banking/fees, draft treasury policies, and produce decision-ready deliverables based on mock materials.

Coordinate AI research and training-data projects, manage cross-functional workflows, onboard and engage domain experts, maintain documentation, track milestones and metrics, identify risks and quality issues, and facilitate stakeholder communication to keep programs on schedule.

Author and verify rigorous multiple-choice computer science assessment items across many CS domains to create gold-standard benchmarks for AI research. Produce correct answers, nine plausible distractors, solution explanations, difficulty labels, and authoritative references. Review and edit questions for technical accuracy, clarity, and reproducibility. Contribute asynchronously as an independent contractor, ~10+ hours/week, fully remote.

Develop realistic enterprise GTM scenarios and evaluation rubrics for Fortune 500 sales and marketing contexts. Create deal strategies, account plans, marketing and RevOps scenarios using enterprise platforms, apply established sales methodologies, produce executive-level narratives, and refine evaluation outputs through reviewer feedback.

Evaluate AI-generated music for musicality, creativity, production and vocal quality, classify songs by genre/structure, identify subtle audio issues, and provide structured feedback to improve generative music systems. Must apply consistent criteria across genres and document observations in English.

Create realistic enterprise legal scenarios (in-house counsel, regulatory/compliance, corporate transactions, litigation), author high-quality reference responses and criterion-based evaluation rubrics, review for legal accuracy and relevance, and translate complex legal judgment into objective evaluation standards aligned with frameworks like ERM/COSO and regulations such as FCPA, SOX, GDPR, and HIPAA.

Perform end-to-end corporate development/M&A exercises: build valuation and transaction models, analyze and compare deal terms, prepare board/executive materials, conduct diligence and screening, develop synergy and carve-out analyses, and produce decision-ready deliverables for senior leadership.

Evaluate AI-generated and human marketing deliverables by creating task-specific grading criteria, assessing work against briefs and brand objectives, and providing detailed, evidence-based written justifications. Develop and refine reproducible evaluation frameworks and translate professional marketing judgment into consistent, defensible criteria across creative briefs, campaigns, messaging, and presentations.