Overview

Experience: 6+ years (on-prem Windows/IIS and Azure) | Project - Insurance Platform

Client currently hosts on its own Windows/IIS servers and is moving to Azure. We need a DevOps engineer to own delivery to both targets. That means reliable, automated, zero-downtime releases to the on-prem IIS estate today, and building the Azure platform the services will move to. Both targets are deployed from the same pipelines and the same artifacts.

Key Responsibilities

• Own CI/CD to Client's on-prem IIS servers.
• Build pipelines that deploy the .NET 10 services and the React SPA to Windows Server/IIS inside the Quincy network, using self-hosted build agents or deployment groups behind the firewall.
• Manage IIS hosting for ASP.NET Core:
• Hosting Bundle versions
• App pools, site bindings, and SSL certificates
• In-process vs out-of-process hosting
• web.config and environment configuration per server
• Deliver zero-downtime releases on-prem. Use side-by-side sites or app pools behind ARR or the load balancer for a blue-green swap, with health checks and fast rollback. Avoid appoffline outages.
• Automate server configuration with PowerShell (WebAdministration/IISAdministration), WinRM, and Web Deploy (MSDeploy), or DSC, so servers are reproducible rather than hand-built.
• Run a hybrid build-once model. A single versioned artifact deploys to either IIS or Azure App Service, with target-specific configuration injected at release time.
• Handle on-prem secrets and data. Manage secrets on-prem (no Managed Identity there), and gate migrations against on-prem SQL Server and PostgreSQL the same way as in Azure.
• Plan and run the move from on-prem IIS to Azure. That includes parity testing, DNS and traffic cutover, and rollback.

Required Skills

• 3+ years deploying .NET applications to on-prem Windows Server/IIS through automated CI/CD, not manual copy-and-paste.
• Hands-on with self-hosted agents or runners (Azure DevOps agents, deployment groups, or GitHub self-hosted runners) inside restricted corporate networks.
• Strong IIS administration: app pools, bindings, certificates, URL Rewrite/ARR, and ASP.NET Core Hosting Bundle.
• Advanced PowerShell for deployment and server automation (WinRM, Web Deploy).
• Experience delivering zero-downtime or near-zero-downtime releases on IIS behind a load balancer.

Preferred Skills

• Migrating workloads from on-prem IIS to Azure App Service.
• Azure Arc, or hybrid monitoring of on-prem servers in Azure Monitor.
• Load balancers such as F5, NetScaler, or Windows NLB.
• On-prem observability: Windows Event Log, performance counters, and an OpenTelemetry collector forwarding from inside the network.

Interview Focus Areas

• On-prem release: design a pipeline that deploys to three IIS servers behind a load balancer with no downtime and a rollback path.