Sr. DevOps Engineer II (Remote Eligible in Bulgaria)

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking.

That is magic at work, and it’s what we show up for every day. We are seeking a Senior DevOps Engineer to join the team that owns and operates Smartsheet's edge proxy platform and internal engineering tooling. The edge proxy is a custom-built, high-performance reverse proxy that serves as the entry point for all traffic across Smartsheet's commercial and FedRAMP-authorised US Government environments.

The team owns the full lifecycle of this platform: from maintaining the proxy binary and its configuration tooling, to provisioning and operating the multi-region AWS EKS infrastructure it runs on, to managing the observability and on-call story for every service that routes through it. Beyond the edge layer, the team also drives the evaluation and adoption of internal developer tooling — from developer portals to productivity platforms — that improves the engineering experience across the company. You will work remotely from Bulgaria and will be reporting to an engineering leader.

You Will: Own and evolve the edge proxy platform: Maintain, upgrade, and extend a high-performance reverse proxy — including maintaining the proxy binary and its configuration tooling, writing Go and Python automation, managing the full container image lifecycle on hardened Linux base images, and working across the broader edge layer, including CDN, WAF, and traffic management capabilities. Build and maintain cloud infrastructure as code: Design and implement Terraform/Terragrunt modules and live environment configurations managing EKS clusters, load balancers, IAM roles, VPC networking, ECR registries, and supporting AWS services across multiple regions including GovCloud. Operate Kubernetes clusters at scale: Manage multi-region, multi-cluster EKS deployments via FluxCD GitOps workflows and Helm charts, including node AMI rotation, add-on lifecycle management, and horizontal pod autoscaling.

Build and own CI/CD pipelines: Design, maintain, and improve shared GitLab CI/CD pipeline templates used across all team repositories; build and operate alternative pipeline workflows for isolated government cloud environments. Automate operational toil: Build and maintain tooling for tasks such as container image patching, EKS AMI rotation, air-gapped ECR image sync to GovCloud, and automated MR creation for monthly version-bump patching cycles. Manage observability and on-call: Provision and maintain Datadog SLOs, monitors, and dashboards via Terraform; participate in the team's on-call rotation responding to edge proxy incidents across production and GovCloud environments.

Support FedRAMP/GovCloud operations: Operate the GovCloud environment with its unique constraints — air-gapped image distribution, infrastructure automation in isolated networks, and alert management with compliance-aware data handling. Evaluate and adopt internal developer tooling: Research, prototype, and drive the adoption of internal tools that improve engineering productivity across the company — including developer portals, platform self-service capabilities, and other tooling that raises the bar for the developer experience at Smartsheet. Mentor and collaborate: Share knowledge across the team through code reviews, architecture discussions, and runbook authorship; foster a culture of engineering excellence and operational rigour.

Strategically apply AI tools: Strategically apply and champion AI tools within your team's domain to improve project execution, infrastructure design, quality, and debugging, leading adoption of AI best practices.