Top Tech Jobs & Startup Jobs in Chicago, IL

Creates realistic tax compliance, provision, planning, notice-response, and controversy scenarios from professional experience. Reviews AI-generated tax outputs for technical accuracy, provides written feedback, and collaborates asynchronously with an AI research team. The role covers corporate, individual, partnership, SALT, and international tax specialties.

Creates M&A, due diligence, valuation, purchase accounting, and LBO scenarios for AI training data. Reviews AI-generated advisory analyses for accuracy, assumptions, and professional judgment, then provides written feedback to improve performance. Requires transaction advisory, corporate development, investment banking, or valuation experience; hands-on QoE, valuation, or deal-model ownership; strong writing; and a finance, accounting, or related degree. CPA, ASA, ABV, or CFA credentials are advantageous.

Performs investment operations and fund-accounting exercises, including ledger-to-statement reconciliations, NAV variance attribution, trade-break investigations, corporate-action processing, payment exception handling, and merchant or vendor descriptor matching. Produces adjusting entries, variance commentary, root-cause narratives, and other analyst deliverables. The role is contract, remote, US-based, and approximately 15 hours per week.

Design insurance policy-processing scenarios, create operational reference materials, evaluate AI-generated responses, and provide feedback on policy lifecycle accuracy. The role covers intake, binding, issuance, endorsements, billing, renewals, cancellations, reinstatements, documentation, quality control, and servicing workflows. Candidates need at least two years of policy administration, underwriting operations, insurance servicing, or premium operations experience, along with strong process discipline and knowledge of policy administration systems.

Contribute subject matter expertise to a project for a leading AI laboratory by creating challenging, high-quality domain problems and data to improve large language models. Applicants should have a PhD, advanced degree, or equivalent industry experience in a listed STEM domain, along with strong attention to detail and excellent written and verbal communication skills. The role includes a brief interview, task, and paid onboarding.

Reviews AI-generated documents, spreadsheets, and slide decks for accuracy, rigor, presentation quality, and domain-specific compliance. Evaluates outputs using quality rubrics, identifies factual and aesthetic errors, and provides structured written feedback. The role requires deep expertise in data quality and CRM operations, strong English fluency, and proficiency with Microsoft Office and Google Workspace. It is a fully remote, flexible independent-contractor engagement.

Capture and evaluate natural Hindi voice interactions with an AI assistant using a Mac. Complete voice-based tasks across productivity applications, transcribe and clean spoken queries, rate AI responses, maintain structured task logs, and upload recordings. Native or near-native Hindi proficiency, English comprehension, detailed data entry, and quality-review skills are required. The project lasts four weeks and begins immediately.

Use a specialized Mac app to complete everyday voice tasks in Italian, including composing messages, generating content, formatting documents, applying spreadsheet formulas, and summarizing files. Record and clean spoken transcripts, evaluate AI responses, enter task data into structured tracking sheets, and upload recordings. The four-week project requires native or near-native Italian, English comprehension, an Apple Silicon Mac running macOS Sequoia 15.0 or newer, familiarity with productivity apps, and careful self-directed quality review.

Evaluates AI-generated investment analysis, valuation, and credit work products, including documents, spreadsheets, and presentations. Applies expert financial judgment to assess accuracy, rigor, factual correctness, aesthetics, and domain quality against structured rubrics. Provides clear written feedback on identified issues. This is a fully remote, flexible independent-contractor engagement paid hourly.

Create technical accounting scenarios, memos, schedules, SEC filings, footnotes, and disclosures for AI training. Review AI-generated accounting outputs for standards-accurate conclusions, apply complex ASC guidance, and provide written feedback. The role requires deep experience with ASC 606, 842, 718, and 805, SEC reporting, and technical accounting in a Big Four or public-company environment. Work is fully remote, asynchronous, and performed as an independent contractor.