Top Tech Jobs & Startup Jobs in Chicago, IL

Contract role combining actuarial science, risk management, and AI to improve portfolio performance. Responsibilities include loss and combined ratio analysis, portfolio risk assessment, catastrophe and exposure modeling, stress testing, and integrating ML to enhance pricing, reserving, and risk selection while collaborating with underwriting, finance, and product teams.

Work with research teams to close mathematical knowledge gaps in LLMs by creating and evaluating advanced math problems and solutions, and providing clear written feedback to improve AI model performance. Remote, part-time independent contractor role (15-20 hrs/week) with potential extension.

Validate and stress-test AI-generated insurance outputs across pricing, reserving, underwriting, and risk models. Review actuarial projections for accuracy and regulatory compliance, provide structured feedback, tag content by insurance domain, and support benchmarking of AI capabilities. Work remotely as an independent contractor on a part-time, short-term project.

Lead architecture and delivery of real-time stream-processing pipelines using Apache Flink and Java. Design scalable, event-driven, low-latency systems; optimize performance and reliability; deploy and manage cloud/containerized services; enforce CI/CD, testing, and observability; troubleshoot production issues; collaborate with cross-functional teams; and mentor engineering teams.

Lead AI-enabled financial planning and strategic analysis, build data-backed business cases, refine unit economics, deliver executive-level insights, integrate ML into FP&A, and track KPIs to drive profitability and strategic decisions.

Design and implement AI/NLP solutions to automate insurance policy administration (issuance, endorsements, renewals). Translate policy language into models and rule engines, integrate with PAS, ensure regulatory compliance, monitor model performance, and support underwriting, operations, and exception handling.

Review, validate, and refine AI-generated accounting analyses, audit reports, and financial statements for compliance with GAAP/IFRS. Tag content, provide structured feedback on accuracy and clarity, and support benchmarking of AI model performance in financial domains.

Lead integration of AI-driven tools into tax provision, planning, and multi-jurisdictional compliance. Design ML/analytics solutions for sales and payroll tax, enhance regulatory filings, support audits, and collaborate with finance, legal, and technology teams. Monitor tax regulation changes, document AI tax models for transparency and governance, and continuously refine models for scalability, reliability, and compliance.

Drive net-new enterprise IT services revenue by owning full sales lifecycle: prospecting, executive engagement, solution positioning, collaboration with presales/delivery, pipeline management, and closing multi-year managed services, application modernization, and digital transformation deals to meet $5M–$10M annual targets.