Top Tech Jobs & Startup Jobs in Chicago, IL

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.

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.

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.

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.

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.

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).

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.

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.