Top Tech Jobs & Startup Jobs in Chicago, IL

The Senior Backend Engineer will develop the Payroll product, overseeing the entire development cycle from design to deployment, in a microservices architecture.

Lead the Benefits Administration product: define and deliver features, write requirements, manage roadmap, perform customer research, measure impact, and collaborate cross-functionally to build compliant, scalable enrollment, carrier integration, and employee self-service experiences that improve HR efficiency and adoption.

Own and operate production-grade Kubernetes infrastructure on AWS, build GitOps CI/CD with GitHub Actions and ArgoCD, develop AI agents and internal DevOps tooling, maintain Datadog-based observability, and manage on-call incident response while collaborating with engineering teams to improve reliability and delivery speed.

As a Product Support Specialist, you will provide expert support to customers, troubleshoot issues, guide users, and collaborate with teams for improvements.

As a Mid Market Account Executive, you will manage the sales cycle, build relationships, prepare product demos, and forecast revenue in the HR tech space.

The role involves supporting customers with benefits administration issues, troubleshooting complex problems, and collaborating with multiple teams to improve product functionality and customer experience. Candidates should have a strong background in US benefits administration and exceptional problem-solving skills.