Top Tech Jobs & Startup Jobs in Chicago, IL

Reviews and evaluates operations, program management, and project documents for accuracy, quality, clarity, completeness, and alignment with requirements. Provides structured feedback, identifies gaps and risks, analyzes reports and presentations, compares work against standards, and documents recommendations. The role requires independent work, strong analytical and written communication skills, attention to detail, and proficiency with Microsoft Office. This is a fully remote independent contractor opportunity with variable project workloads.

Evaluate AI-generated JSON outputs using detailed grading rubrics. Read and parse structured data, apply rubric-based scores consistently, identify discrepancies or missing information, and produce evidence-based justifications while meeting turnaround requirements and working independently without AI-assisted tools.

Part-time remote role reviewing and improving AI-generated electrical engineering content. Provide expert answers, identify technical inaccuracies, recommend standards/resources, and share practical engineering workflows and documentation to improve AI model quality.

Evaluate and review finance workflows and task designs for realism and accuracy in real assets, project finance, infrastructure, energy, mining, and natural resources. Identify missing assumptions, ambiguous instructions, impractical constraints, and edge cases. Provide concise, structured written feedback and recommendations, collaborate with other experts, and participate in synchronous review sessions as needed.

Work with research and engineering teams to design realistic marketing tasks, create reference solutions, and evaluate AI/LLM outputs with structured rubrics. Maintain evaluation guidelines, ensure dataset quality, and collaborate with SMEs to improve AI model performance on marketing challenges.

Evaluate and review AI-generated mechanical engineering content for technical accuracy and real-world applicability; provide expert answers and feedback; recommend standards and references; share design, manufacturing, and testing insights; identify errors and collaborate with subject-matter experts to improve AI model quality. Part-time, remote, contractor (~10 hrs/week).

Design task-specific grading criteria for B2B sales deliverables and evaluate AI-generated and human work against those rubrics. Provide detailed, evidence-based written justifications, refine rubrics with senior reviewers, and ensure consistent, reproducible evaluations across large volumes of work.

Design evaluation rubrics and scoring frameworks for marketing deliverables, assess AI-generated and human-created marketing work with evidence-based judgments, provide written justifications, and iterate with stakeholders to improve consistency and scoring quality.

Review and evaluate quantitative finance tasks for technical accuracy and real-world realism. Identify missing assumptions, unrealistic constraints, edge cases, and data or backtesting issues. Provide concise, structured written feedback and actionable recommendations. Collaborate with other experts to calibrate evaluations and maintain consistent quality standards throughout a high-engagement, remote contractor sprint.

Conduct 20-minute structured interviews with subject-matter experts, evaluate domain expertise and communication using a rubric, verify availability and work authorization, provide evidence-based hiring recommendations (Advance/Hold/Pass), coordinate scheduling, document outcomes, and collaborate with the program team to ensure consistent evaluation standards. Approximately 10 hours/week, fully remote with U.S. Eastern Time overlap.