Top Tech Jobs & Startup Jobs in Chicago, IL

Contract Electronics Engineer supporting AI training through robotic system video annotation. Reviews electrical and electronic observations, interprets schematics, identifies system events and anomalies, documents technical explanations, refines annotation guidelines, and collaborates asynchronously with engineering and machine learning teams.

Conduct equity research analysis for AI training datasets, including earnings analysis, estimate revisions, peer benchmarking, financial modeling, valuation analysis, and investment thesis development. Review company models, assess revenue, margin, cash flow, and valuation drivers, produce concise research summaries and event updates, identify sector trends and catalysts, and provide feedback to improve research-content quality.

Create realistic business scenarios using Excel, PowerPoint, and Word; interact with LLMs; review and compare AI-generated Office documents; and provide detailed feedback on accuracy, quality, and business relevance. The role requires strong analytical, communication, and document-review skills, with expertise in complex business models, reports, analyses, and presentations.

Contract equity research contributor evaluating AI tools for financial research. The role involves expert interviews, testing AI-generated analysis, reviewing financial content for accuracy and industry relevance, assessing sell-side research workflows, and documenting actionable feedback. Candidates should have recent sell-side equity research experience covering public companies, including published research, ratings, price targets, earnings notes, or coverage initiations.

Design production-style DevOps tasks covering CI/CD, containers, orchestration, infrastructure as code, monitoring, and incident response. Develop reproducible reference solutions with setup and validation instructions, evaluate AI-generated outputs, identify failures, provide precise corrections, and maintain high standards for correctness. Share structured feedback to improve future task design. The contract role requires at least 20 hours weekly and professional English proficiency.

Analyze product and design challenges; explain design and frontend trade-offs; create design documents, usability reports, research summaries, RFCs, and ADRs; evaluate Figma-based design systems, accessibility, and frontend architecture; synthesize complex information; and provide structured expert feedback on project artifacts. The role supports AI training through high-quality analytical and explanatory work.

Reconstructs and enhances PowerPoint presentations, improving slide structure, visual storytelling, data visualization, content clarity, and narrative flow. The contractor analyzes complex materials, edits and refines content, provides constructive feedback, and delivers polished presentation assets remotely. Prior client-facing management consulting experience is required, with contributions supporting AI model training and evaluation.

Create and validate complex datasets for AI benchmark tasks, including files with malformed records, missing data, truncations, and inconsistent formatting. Define correct final states, write detailed grading rubrics, and assess AI outputs for accuracy and completeness. The role requires exceptional attention to detail, error detection, format reconciliation, accurate documentation, and clear asynchronous communication in regulated or audit-sensitive contexts.

Evaluate AI model outputs on data science, statistics, machine learning, experimentation, and quantitative problems. Develop expert prompts, datasets, and reference solutions; identify statistical and methodological errors; and provide structured feedback to improve model performance. The role requires Python, machine learning, statistics, data analysis, experimentation, Pandas, and data modeling skills.

Reconstructs and redesigns data-driven presentations in Microsoft PowerPoint, creating visualizations and analytics reports that communicate complex insights clearly. Reviews and edits content for accuracy, flow, and narrative impact; applies data analysis and statistical reasoning; and refines slides based on feedback. The role supports AI training projects through high-quality presentation and analytical deliverables.