Top Tech Jobs & Startup Jobs in Chicago, IL

Create tax research, calculation, compliance, and evaluation tasks for AI agents. Develop original tax scenarios and reference solutions involving corporate income tax, indirect taxes, withholding, reconciliations, and related areas. Prepare accurate calculations, workpapers, supporting schedules, and authoritative citations. Evaluate agent performance, identify jurisdictional and factual errors, and assess unsupported deductions or outdated rules.

Create realistic financial reporting tasks and reference solutions for AI agents. Prepare scenarios involving financial statements, consolidation, cash flow reporting, disclosures, intercompany eliminations, foreign currency translation, and technical accounting. Evaluate agent outputs for accuracy, completeness, presentation, accounting compliance, and reporting-tool usage. Identify errors, omissions, inconsistencies, and unsupported conclusions in reporting workflows.

Designs audit workflow tasks for AI agents, develops reference solutions, and evaluates agent performance using financial records, audit documentation, spreadsheets, and analytical tools. Responsibilities include assessing risk, materiality, controls, testing, sampling, evidence sufficiency, professional skepticism, documentation quality, financial statement assertions, exceptions, and conclusion support.

Create accounting workflow tasks and reference solutions for AI agents. Evaluate bookkeeping, journal entries, accounts payable and receivable, reconciliations, financial statements, transaction classification, discrepancy correction, period-end adjustments, and accounting software usage. Define accuracy and traceability criteria, identify accounting errors, and document accounting treatments. The role is remote, project-based, and flexible.

Create realistic public accounting tasks and reference solutions, then evaluate AI agents completing bookkeeping, adjusting entries, trial balances, financial statements, reconciliations, and client accounting workflows. Develop scoring criteria for technical accuracy, documentation, consistency, and client communication. Assess how agents handle incomplete records, misclassifications, missing information, accounting judgments, and clarification requests using spreadsheets, accounting platforms, and supporting documents.

Develop and evaluate AI-agent tasks focused on budgeting, forecasting, variance analysis, cash flow planning, unit economics, and scenario modeling. Build transparent reference financial models, document assumptions, reconcile outputs, and assess analytical accuracy. Identify modeling errors, inconsistent assumptions, double counting, and unsupported conclusions. The role requires strong FP&A expertise, financial statement knowledge, advanced spreadsheet skills, and clear written communication.

Create corporate accounting tasks and reference solutions covering journal entries, reconciliations, accruals, prepayments, intercompany transactions, and month-end close. Evaluate AI agents’ accounting work for accuracy, completeness, documentation, compliance, errors, and audit-trail quality using spreadsheets, accounting software, and financial records.

Design, build, and maintain automation workflows and data pipelines across admissions, education, career services, and billing. Create BI dashboards, ensure data accuracy, manage lightweight databases (e.g., Supabase), and support cross-functional teams to improve operational efficiency and scalability.