Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Serve as the internal customer advocate and pre-sales technical lead for finance-focused enterprise deals. Configure complex billing, pricing, metering, invoicing, and revenue recognition workflows; build demo environments; engage finance leaders; support RFPs and sandbox configurations; document solutions and handoffs; feed product and engineering with customer insights.

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.

Senior sales hunter responsible for acquiring new enterprise clients for Analytics, AI/ML, GenAI, Data Science, and Data Engineering consulting services. Build CXO relationships, manage full sales cycle from prospecting to close, hit revenue quotas, leverage strategic partnerships (Microsoft, Databricks), and travel nationally to engage clients.

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.

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.

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.

Manage and optimize end-to-end account reconciliations, intercompany eliminations, and chart-of-accounts governance. Identify discrepancies, perform variance analysis, and implement AI-driven automation and anomaly detection to reduce manual effort and accelerate close. Collaborate with cross-functional teams to resolve mismatches and improve financial data quality and reporting accuracy.

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.