Entry Level Software Engineer Remote Jobs in Chicago, IL

Upbound is hiring a Senior Software Engineer to help us build and operate Upbound Spaces, the multiple control plane management software at the heart of the Upbound Platform. As part of the Spaces team, you will help us scale Upbound to reliably support thousands of control planes, while also extending enterprise control plane management and operations both in the cloud and on premises. Our team is expanding, and this is the perfect opportunity for you to make a significant engineering impact in both development and production operations.

• Actively build and operate Upbound Spaces in production, troubleshooting and resolving issues across multi-tenant SaaS environments, as well as contributing to Upbound's open-source projects, including Crossplane.
• Take ownership of building features in high demand by Upbound's customers and deliver new functionality that will delight and amaze our users.
• Investigate and debug complex issues in customer environments, including multi-control plane scenarios, resource reconciliation problems, and performance bottlenecks.
• Communicate through thoughtful and thorough design documents for new initiatives and detailed post-incident reviews that drive system improvements.
• Support the full project lifecycle for highly scalable and reliable services running in a cloud environment - discovery, analysis, architecture, design, review, documentation, building, migration, automation, deployment, production-readiness, and ongoing operational support.
• Write and maintain Go code that interfaces with the Kubernetes API, such as operators, controllers, add-ons, etc., with a focus on observability, debuggability, and operational excellence.
• Deploy, manage, and troubleshoot our Kubernetes services in production, using metrics, logs, and traces to identify and resolve issues quickly.
• Build and maintain operational tooling for debugging customer environments, analyzing control plane health, and automating incident response.
• Author documentation, user guides, runbooks, and blog posts to support and promote new features that you release.
• Support the software release cycle for Spaces self-hosted distributions, including diagnosing issues in customer-managed deployments.
• Participate in on-call rotation to support Upbound Cloud, responding to incidents and driving them to resolution.

• Have experience operating production cloud services at scale: monitoring, alerting, incident response, post-mortems, and continuous improvement of service reliability.
• Have strong debugging skills across distributed systems, including experience with observability tools (Prometheus, Grafana, OpenTelemetry, distributed tracing) and techniques for diagnosing issues in production environments.
• Have experience building and operating controllers that interact with the Kubernetes API server, including troubleshooting reconciliation loops, managing API rate limits, and optimizing controller performance.
• Are comfortable working directly with customers to understand, reproduce, and resolve complex technical issues in their environments.
• Take responsibility and ownership for solving problems even if they are outside your lane, especially during incidents affecting customer workloads.
• Demonstrate excellence in your work, constantly trying to improve your skills and the operational posture of the systems you build.
• Have empathy for customers and keep them in mind as you build solutions, understanding that reliability and debuggability are features.
• Realize the importance of clear communication and effective collaboration to work as a team, deliver great results, and support customers through technical challenges.
• Help create a safe environment where everyone can contribute, learn from failures, share on-call knowledge, and help each other grow as operators and engineers.

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