Top Tech Jobs & Startup Jobs in Chicago, IL

Execute end-to-end US accounts payable and payroll tasks using Deel, Brex, and QuickBooks. Reconcile AP transactions, manage vendor invoices and employee expenses, support month-end/year-end close, maintain financial controls, resolve invoice discrepancies, and improve processes while operating in a fast-paced global environment.

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.

Act as the internal voice of the customer, partnering with Sales, Product, and Engineering to design and configure billing, revenue recognition, and invoicing solutions. Lead discovery with finance leaders, build demo/sandbox environments, respond to RFPs, document handoffs, and create onboarding materials while advocating customer needs to Product and Engineering.

Design institutional-quality, transaction-oriented financial modeling tasks and gold-standard reference models to train AI. Build and review integrated 3-statement models, DCFs, LBOs, M&A and growth equity frameworks, perform diligence and sensitivity analyses, document assumptions, and collaborate asynchronously with AI researchers.

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.

Provide supply chain, procurement, manufacturing, and logistics domain expertise to improve generative AI training data: create annotation standards, design real-world tasks, evaluate outputs, and collaborate with research teams to close knowledge gaps and improve 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.

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.

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.

Evaluate and assess financial statements, reports, models, and business documents for accuracy and completeness. Provide structured feedback per guidelines, identify inconsistencies, and recommend improvements while following detailed evaluation frameworks.