Top Tech Jobs & Startup Jobs in Chicago, IL

Annotate Japanese PDF pages by identifying, bounding, typing, and ordering document regions; link related components; transcribe all text exactly, including handwritten and vertically arranged content; capture metadata; and flag illegible or unsuitable pages. Experienced annotators also review colleagues’ work. Native Japanese fluency and command of kanji, hiragana, katakana, furigana, and variant characters are essential.

Capture and evaluate natural voice interactions with an AI assistant in Traditional Mandarin Chinese. Complete voice-based tasks on a Mac, create and clean transcripts, rate AI responses, organize task data in tracking sheets, and upload recordings. The four-week project requires native or near-native Taiwan Mandarin proficiency, English instruction comprehension, familiarity with productivity apps, structured data-entry skills, and an Apple Silicon Mac running macOS Sequoia 15.0 or newer.

Build and validate challenging codebase-exploration tasks for AI agents using production Python repositories. Responsibilities include investigating runtime behavior and issue history, rewriting questions, refining rubrics and foils, running validation workflows, documenting solutions, and addressing expert review. The role is fully remote, asynchronous, contract-based, and task-paid, with work performed in a dedicated Studio environment.

Capture and evaluate natural Korean voice interactions with an AI assistant using a Mac. Complete voice-driven tasks across everyday applications, transcribe and clean spoken queries, rate AI responses, record task data, and upload supporting recordings. Candidates must be native or near-native Korean speakers, understand English instructions, use productivity applications regularly, and perform detailed data entry and quality reviews independently.

Own the organization’s digital reputation across search engines, media, online platforms, and customer communities. Lead SEO, GEO, content strategy, digital PR, reputation monitoring, customer advocacy, and crisis-response initiatives. Improve page-one visibility, secure media placements, manage brand narratives, identify reputation risks, and track performance metrics. Collaborate with internal teams and senior leadership while adapting strategies to changing search algorithms, AI discovery, and digital trends.

Reviews securities and wealth-management compliance work products, including periodic client reviews, Reg BI and DOL rollover attestations, marketing communications, and structured-product or alternative-investment supervision. Identifies deficiencies, cites applicable controls and regulations, drafts audit-trail entries and reviewer dispositions, and evaluates compliance with FINRA, SEC, suitability, and supervisory requirements.

Develop regulatory law evaluation scenarios, reference compliance memoranda, regulatory filings, enforcement responses, and expert rubrics for AI systems. Work spans US and international regulatory frameworks, including financial services, healthcare and FDA, antitrust, privacy and cybersecurity, environmental, and energy regulation. Apply regulatory interpretation, compliance risk assessment, agency interaction, enforcement strategy, and rulemaking expertise.

Capture and evaluate natural voice interactions with an AI assistant in Brazilian Portuguese. Complete everyday tasks by voice on a Mac, transcribe and clean spoken queries, rate AI responses, record task data in tracking sheets, and upload supporting recordings. The four-week project requires native or near-native Brazilian Portuguese, English comprehension, familiarity with productivity apps, and an Apple Silicon Mac running macOS Sequoia 15.0 or newer.

Create realistic FP&A and treasury scenarios, including budgets, forecasts, variance analysis, cash-flow forecasts, cash positioning, bank administration, FX revaluation, debt compliance, and financial models. Review AI-generated outputs, assess assumptions, provide written feedback, and collaborate asynchronously with researchers.

Develops complex civil litigation and dispute-resolution evaluation tasks for AI systems. Responsibilities include creating scenarios, reference pleadings, discovery responses, motions, trial memoranda, and evaluation rubrics across commercial, class action, appellate, discovery, evidence, trial, settlement, and arbitration matters. The role requires applying US or international procedural and evidentiary rules, litigation technology, and experienced senior-litigator judgment.