Top Tech Jobs & Startup Jobs in Chicago, IL

Contractor engineering SME to review and create technical engineering content for AI training: analyze documentation, develop examples and datasets, evaluate AI outputs for technical accuracy, and collaborate with teams to improve model performance and processes.

Remote contractor role to create and evaluate mathematical problems, proofs, and datasets to train and improve AI models. Assess AI-generated solutions for correctness, produce technical documentation, and collaborate with cross-functional teams to develop benchmark datasets and provide actionable feedback to improve model reasoning.

Evaluate and annotate physics content, create problem sets and technical documentation, and assess AI-generated responses for scientific accuracy. Contribute to dataset creation and provide expert feedback to improve AI model training. Collaborate remotely with project teams to ensure timely, high-quality deliverables and improve evaluation methodologies.

Contractor role to create original, high-quality financial documents (reports, analyses, models) with rich visuals (tables, charts, graphs) to train AI. Ensure accuracy, anonymize sensitive data, contribute long-form documents (10–100 pages), and clarify submissions as needed.

Build, manage, and scale cloud infrastructure using Terraform and IaC; automate deployments; ensure system reliability and security; collaborate within a security-focused environment. Requires 5–7 years DevOps experience.

Design, implement, and optimize AI-powered solutions to support financial compliance and controls. Monitor GAAP/IFRS adherence, automate controls and reporting, support internal/external audits, and manage complex accounting areas like revenue recognition and lease accounting while collaborating with finance, audit, and technology teams.

Design, implement, and monitor AI/ML models to improve underwriting risk assessment, pricing, and portfolio management. Translate underwriting rules into data models, integrate models into workflows, analyze datasets for risk patterns, build decision-support tools, ensure compliance and fairness, and collaborate with underwriting, actuarial, product, and engineering teams.

Lead modernization of month-end and year-end close processes using AI and automation. Prepare, review, and validate journal entries, accruals, and financial statements. Implement anomaly detection, automated reconciliations, variance analysis, and predictive insights. Collaborate with data teams to structure finance data for ML use cases and design audit-ready, scalable reporting workflows.

Design realistic, specialty-specific clinical case scenarios and gold-standard attending-level responses, evaluate and grade AI-generated outputs using structured rubrics, provide detailed written feedback to improve model clinical reasoning, and participate in onboarding, calibration, and review sessions in a fully remote, asynchronous contractor role (~20 hours/week).

Build, manage, and scale cloud infrastructure using Terraform/IaC on AWS; automate deployment pipelines; maintain system reliability and security for a real-time data detection platform.