Top Tech Jobs & Startup Jobs in Chicago, IL

Design and author realistic, multi-step software engineering benchmarks in Python; create reproducible reference solutions and validation checks; evaluate AI-generated code, identify failures, and improve benchmark quality; review peers tasks and collaborate with AI researchers to refine evaluation methodologies.

Review, create, and evaluate professional operational finance deliverables (P&L reconciliations, month-end close, AP/P2P, three-statement models, pro forma analysis, covenant and partnership accounting). Analyze complex documents, assess AI-generated financial work for technical accuracy and completeness, and produce executive-ready summaries with assumptions, variances, impacts, and recommendations.

Evaluate finance workflows and tasks for realism, technical accuracy, and practical applicability in trading, derivatives, and crypto markets. Identify ambiguous assumptions, unrealistic constraints, missing edge cases, and provide concise, actionable feedback. Collaborate with domain experts to maintain consistency and ensure high-quality assessments throughout a fast-paced, remote sprint engagement.

Remote contract role to create, review, and refine high-quality consulting deliverables (M&A, post-merger integration, corporate strategy, operational improvement). Analyze due diligence, financial models, and market research to produce client-ready presentations, memos, and financial models. Provide rigorous evaluation and structured feedback to improve analytical rigor, business judgment, and decision-ready recommendations.

Provide insurance subject-matter expertise to improve generative AI models: design insurance tasks, create reference solutions, evaluate AI outputs with structured rubrics, refine scoring guidelines, and collaborate with research and engineering teams to produce high-quality training and evaluation data. Commitment of 35+ hours/week and proven senior insurance experience required.

Design real-world computer vision tasks, build reference solutions and evaluation components in Python, assess AI model outputs, identify failure modes, and develop structured rubrics and guidelines. Collaborate with experts to maintain high-quality training data and evaluation standards for multimodal and generative vision systems. Part-time, remote contractor role (~20 hours/week).

Evaluate and annotate physics content, create problem sets and technical documentation, and assess AI-generated responses for scientific accuracy. Contribute to dataset creation and provide expert feedback to improve AI model training. Collaborate remotely with project teams to ensure timely, high-quality deliverables and improve evaluation methodologies.

Evaluate and review AI-generated legal content for accuracy and quality, answer legal questions, recommend authoritative references, share real-world legal workflows and standards, and collaborate with a multidisciplinary team to improve AI performance in legal domains. Part-time, remote contractor role (~10 hours/week).

Contribute financial expertise to train and evaluate AI language models: design finance tasks, produce reference solutions, evaluate AI outputs with rubrics, collaborate with SMEs, and identify knowledge gaps to improve AI reasoning in finance. Independent contractor role requiring at least 10 hours/week.

Contractor engineering SME to review and create technical engineering content for AI training: analyze documentation, develop examples and datasets, evaluate AI outputs for technical accuracy, and collaborate with teams to improve model performance and processes.