Role : Windows & SQL Server In-place Upgrade Automation Engineer
Location: Remote (US)
Duration: Long Term
Note: We're looking for an experienced engineer to automate and support Windows Server and Microsoft SQL Server upgrades across virtual machine and clustered environments.
Key Responsibilities:
- Automate Windows Server in-place upgrades
- Automate SQL Server in-place upgrades
- Support standalone SQL Server environments
- Support SQL Server Failover Cluster Instances (FCI)
- Support SQL Always On Availability Groups
- Perform rolling cluster upgrades with minimal downtime
- Build PowerShell automation for upgrade, validation, and rollback activities
- Integrate upgrade workflows with GitLab CI/CD and GitLab Runners
- Integrate automation with MCM for orchestration and workflow tracking
- Perform automated pre-upgrade health checks
- Validate OS and SQL version compatibility
- Coordinate and validate VM snapshots and backups
- Validate SQL database and system database backups
- Automate DBCC CHECKDB and SQL health checks
- Automate cluster failover and failback
- Validate SQL services, databases, SQL Agent jobs, listeners, and application connectivity
- Build post-upgrade validation and reporting
- Develop rollback and recovery automation
- Troubleshoot failed Windows, SQL, cluster, and pipeline executions
- Maintain automation code in Git
- Follow change-management and production deployment processes
Core Technical Skills
- Windows Server 2016 / 2019 / 2022 / 2025
- Microsoft SQL Server 2016 / 2017 / 2019 / 2022+
- PowerShell automation
- Git and GitLab
- GitLab CI/CD pipelines
- GitLab Runner configuration and troubleshooting
- MCM workflow/orchestration integration
- Windows Server Failover Clustering
- SQL Server Failover Cluster Instance (FCI)
- SQL Always On Availability Groups
- VMware / virtual machine environments
- SQL Server backup and recovery
- Windows and SQL upgrade automation
- REST API integration
- JSON / YAML
- Production change-management experience
Preferred Automation Flow
MCM GitLab Pipeline GitLab Runner PowerShell Automation Prechecks Snapshot/Backup Windows/SQL Upgrade Cluster/AG Validation Postchecks Status back to MCM
Preferred Experience
Experience building large-scale automated Windows and SQL upgrade solutions using PowerShell, GitLab Runner, GitLab CI/CD, MCM, VM snapshots, backup validation, rolling cluster upgrades, post-validation, rollback, and centralized reporting.
