Top Tech Jobs & Startup Jobs in Chicago, IL

Perform contract drafting, review, redlining, and simulated negotiations while evaluating AI-generated legal responses. Identify contractual risks, assess legal accuracy using structured rubrics, and provide actionable feedback to improve AI systems for contract review. Collaborate with legal, product, engineering, and research teams on datasets, evaluation guidelines, and quality standards.

Designs challenging data science and machine learning tasks, builds reproducible environments and verified reference solutions, and develops automated tests and evaluation frameworks for AI-generated code. The role analyzes AI agent performance, identifies bugs, leakage, overfitting, and methodological weaknesses, documents technical requirements, and iteratively improves task reliability and complexity.

Evaluates AI-generated software for correctness, quality, efficiency, security, and maintainability. Designs programming challenges, reference solutions, test cases, and evaluation criteria. Reviews technical reasoning related to debugging, architecture, and system design, then provides structured feedback and documentation. The role requires strong programming fundamentals, software testing and code review experience, analytical problem-solving ability, and clear technical communication.

Prepare and review individual U.S. income tax returns, identify complex tax edge cases, validate product outputs against professional tax software, and collaborate with engineers and founders to improve tax product functionality, roadmap, and user experience. The role requires substantial tax-season experience, strong federal tax knowledge, and expertise with professional tax preparation platforms.

Prepare and review individual U.S. income tax returns, identify complex tax scenarios and product edge cases, validate tax engine outputs against professional tax software, and collaborate with engineers on tax rules, product improvements, and user experience. Serve as a tax subject matter expert embedded within an early-stage product and engineering team.

Reviews and evaluates domain-specific documents, providing structured feedback on quality, accuracy, and relevance. The role requires strong analytical and written communication skills, detailed document review, proficiency with spreadsheet and presentation software, and the ability to follow structured guidelines. Candidates must have a bachelor’s degree, at least three years of relevant professional experience, English proficiency, and reside in the United States, Europe, the United Kingdom, or Canada.

Builds a talent network of experienced data scientists for potential future AI evaluation projects. Responsibilities may include creating grading criteria, evaluating AI-generated or human-produced data science work, writing evidence-based justifications, applying consistent judgment, and incorporating reviewer feedback. Candidates should have professional data science experience, strong Python and SQL skills, expertise in statistical modeling, machine learning, experimentation, causal inference, and excellent technical communication.

Develop and evaluate realistic Excel tasks and solutions for AI training data. Apply advanced Excel capabilities including formulas, PivotTables, data modeling, dashboards, Power Query, Power Pivot, and VBA across multiple industries and business functions. Provide written feedback, close research knowledge gaps, improve model performance, and collaborate with subject matter experts. Requires reliable weekday availability, initially 40 hours per week and 20 hours thereafter.

Design and manage compensation and equity programs, including salary bands, leveling frameworks, annual compensation cycles, incentive structures, option and RSU programs, 409A valuations, grant administration, equity modeling, and employee communications. Valuable experience includes pay equity, pay transparency, global or contractor compensation, benefits design, HRIS and compensation tooling, executive compensation, plan governance, and IPO readiness.

Evaluate AI-generated legal analyses involving civil legal services and access-to-justice issues. Review housing, family, consumer, foreclosure, and debt scenarios; assess legal reasoning and procedural guidance; identify inaccuracies and access-to-justice considerations; and provide structured written feedback. The role requires a Juris Doctor, active U.S. bar admission, civil legal practice experience, pro bono initiative experience, and strong legal writing and analytical skills.