Top Engineering Jobs in Chicago, IL

Designs and scales cloud-native development infrastructure supporting multiple engineering teams. Responsibilities include Kubernetes platform operations, infrastructure-as-code with Terraform and Helm, GitOps with ArgoCD, CI/CD modernization, automation, platform migrations, observability, reliability, security, and incident escalation. The role partners with application and SRE teams, establishes engineering standards, reduces operational toil, and mentors engineers while supporting Azure and AKS environments.

Own complex software initiatives across requirements, architecture, implementation, and delivery for iManage’s core cloud platform. Design scalable cloud-native systems using Java, microservices, and event-driven architectures. Partner with product and engineering teams, apply AI tools in development, communicate technical direction, and mentor engineers. The role requires hands-on development, architectural judgment, database and Linux experience, and familiarity with CI/CD, Docker, and Kubernetes.

Lead a team of 4–5 engineers building and operating a cloud-scale SaaS document management platform. Responsibilities include people development, architecture, technical decision-making, AI-native software development, partner collaboration, roadmap execution, and engineering best practices such as CI/CD, testing, code reviews, documentation, and observability.

Develop and maintain Python-based automated tests for Windows desktop applications. Build UI automation suites with WinAppDriver or Appium, manage Azure test environments, integrate testing into GitHub Actions, and write PowerShell setup scripts. Diagnose flaky tests and CI failures, document defects and test coverage, participate in code reviews, and collaborate with QA, development, and DevOps teams to support reliable releases.

Lead incident response and reliability improvements for iManage Cloud. Triage large-scale production issues, build observability and automation, run postmortems, partner with product and engineering, and proactively detect and eliminate systemic problems to improve uptime and customer experience.

The Senior Site Reliability Engineer will focus on automating infrastructure, enhancing cloud resilience, supporting deployments, and mentoring teams in reliability best practices, while participating in on-call rotations.