Top Tech Jobs & Startup Jobs in Chicago, IL

Evaluate and improve AI-generated enterprise sales workflows, create gold-standard examples for prospecting through proposals, design evaluation rubrics, perform simulated end-to-end sales tasks in modern platforms, produce executive-facing sales materials, and collaborate with researchers and SMEs to enhance AI sales reasoning.

Design original Olympiad-level math problems, evaluate AI-generated solutions for correctness and rigor, and produce clear, high-quality reference solutions and reviews to improve AI mathematical reasoning.

Design reproducible coding environments and high-quality reference solutions to train AI. Create and validate complex programming challenges, debug and optimize codebases, refactor legacy systems, document technical decisions, and review technical submissions while collaborating remotely.

Lead end-to-end recruitment marketing campaigns: plan and execute paid and organic content, manage content pipelines and calendars, measure campaign performance across channels, generate optimization insights, and coordinate with recruiters and stakeholders to improve candidate attraction and conversion.

Remote contract role applying equity research expertise to train and evaluate AI models. Review AI-generated financial analyses, analyze SEC filings and financial statements, create evaluation tasks and structured datasets, and collaborate with AI researchers to improve financial reasoning and assessment criteria. Minimum 2 years equity research experience; 10 hours/week minimum commitment.