Top Tech Jobs & Startup Jobs in Chicago, IL

Own the end-to-end customer-facing conversational agent across chat and voice: roadmap, conversation and interface design, partner discovery and launches, Figma-driven design, prototype building with AI tools, define quality metrics, and iterate agent behavior from production data.

The Finance & Strategy Manager will build systems for Hopper, partnering with leaders to make strategic decisions using AI and automated finance reporting, forecasting, and modeling tools.

The Principal Product Manager will define, build, and commercialize the HTS API Marketplace, coordinating across teams and managing the revenue model while utilizing AI tools for rapid prototyping.

Lead development of model-driven pricing intelligence, supplier performance signals, and automated financial reconciliation across flights, hotels, cars, and ancillaries. Define roadmaps, productionize predictive models, implement monitoring/drift detection, and deliver cross-functional, measurable systems that ensure revenue integrity and marketplace economics.

Lead a team of engineers to build distributed systems for B2B partners, manage technical integrations, and drive architectural excellence.

Own and build end-to-end partner invoicing, AR, and revenue recognition processes in NetSuite. Reconcile multi-source data, apply ASC 606, draft technical memos, manage collections and partner disputes, and automate revenue accounting with SQL-driven data validation and cross-functional collaboration.

Lead and modernize global payroll and equity operations, managing a small team, administering Shareworks equity processes, driving HRIS integrations and automation, strengthening payroll controls and compliance, partnering with HR Tech/IT/Finance, and resolving complex tax and market-specific payroll issues to scale a highly automated operating model.

Own the end-to-end customer-facing conversational agent across chat and voice. Set roadmap, drive conversation and interface design in Figma, prototype with AI coding tools, define agent behavior and quality metrics, partner with enterprise clients for requirements and launches, and iterate from production conversation data.

The Principal Product Manager will define and build the HTS API Marketplace, coordinating with teams to develop coherent, enterprise-grade API products, manage commercial models, and establish the go-to-market strategy while utilizing AI for rapid prototyping.