Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as a domain expert in electrical engineering to identify and close knowledge gaps in LLMs. Collaborate with research teams to design and evaluate complex problems, provide detailed written feedback, and improve AI model performance. Remote, contractor role with weekly pay and flexible hours.

Provide real-world financial planning expertise to train and evaluate AI systems. Review scenarios, assess AI recommendations for accuracy, compliance, and suitability, document client conversations, define planning methodologies, give structured feedback, identify compliance/referral needs, and improve AI workflows and financial planning processes.

Design, implement, and optimize AI-driven solutions across the claims lifecycle (intake, investigation, adjudication). Build ML models for data extraction, fraud detection, reserve setting, subrogation, and adjudication decision engines. Collaborate with underwriting, fraud, legal, and IT to integrate models into operations and improve efficiency, accuracy, and compliance.

Guide research teams to close knowledge gaps in Statistics for LLMs: design and evaluate complex statistical problems and solutions, and provide clear written feedback to improve AI model performance.

Drive data-informed capital allocation by building financial models (NPV, IRR), applying AI/ML for forecasting and scenario planning, creating build-vs-buy and prioritization frameworks, implementing decision-support systems, collaborating with cross-functional stakeholders, and monitoring post-investment performance to refine allocation models.

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.

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.

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.

Support the executive by cutting administrative workload 50% within 30 days, convert tribal knowledge into SOPs, manage weekly/6-month/2-year OKRs and org chart, configure productivity tools, proactively solve problems, and ensure clear, error-free communication across teams.