Senior Windows / .NET / AWS DevOps & Platform Engineer – Windows Server Migration

Project overview

For an established German B2B SaaS platform, we are looking for an experienced Senior DevOps / Platform Engineer to support an existing productive AWS/Windows environment.

This is explicitly a grown brownfield environment with existing business logic and productive customers - not a greenfield project and not a cloud rebuild.

The first concrete task is the analysis, planning, and subsequent secure migration of an existing Windows Server production environment to a currently supported Windows Server version.

We are not looking for a pure implementer, but a senior who can independently analyze existing systems, identify risks and dependencies, evaluate options, realistically estimate effort, and provide a pragmatic recommendation.

Current Environment:

First Task: Windows Server Migration

The engagement will initially be in two phases.

Phase 1 - Assessment and Migration Plan

Specifically expected:

The assessment itself should be estimated with a realistic hourly effort before starting. If additional analysis is required, we expect a re-estimate before further work.

Phase 2 - Migration

After approval based on the assessment:

Further tasks after successful collaboration.

Must-have Experience

Proven practical experience is sought with:

Expected Working Method

We explicitly seek a Senior Consulting Approach:

Analysis ? Options ? Trade-offs ? Recommendation ? Effort/Risks ? Approval ? Implementation ? Validation ? Documentation

We value:

Currently not the goal of the project:

Our approach is:

Modernize in place. Reduce risk. Improve maintainability.

Framework Conditions:

Please specify when applying:

Job facts: Direct client project

• AWS
• Windows Server / EC2
• IIS
• .NET / ASP.NET
• SQL Server on AWS RDS
• S3
• IAM / Secrets Management
• CloudWatch / Monitoring
• Bitbucket Pipelines
• Self-hosted Windows Runner
• separate Production and Test/Staging environments
• Recording of the existing Windows/EC2/IIS environment
• Identification of all relevant dependencies
• IIS Sites, Application Pools, and Bindings
• installed .NET Runtimes / Hosting Bundles
• Windows Services
• Scheduled Tasks
• Certificates and Private Keys
• local files and permissions
• Environment Variables / Configuration / Secrets
• Deployment components / Bitbucket Runner
• Network / Security Groups / DNS
• RDS and S3 dependencies
• Monitoring / Logging
• external integrations
• Evaluation of suitable Windows Server target versions
• Recommendation for the target version
• Evaluation of side-by-side vs. in-place migration
• Migration strategy
• Cutover concept
• Rollback concept
• Validation plan
• expected downtime / operational impact
• required input from the existing Senior .NET Developer
• effort estimation for Phase 2
• Prepare target environment
• Transfer necessary IIS/Windows/.NET components
• Migrate configuration and dependencies
• Validate Test/Staging
• Ensure backup/rollback position
• Production Cutover
• Technical and functional validation
• Rollback capability during the transition phase
• Documentation and handover
• Windows Server Administration
• Production Windows Server Migrations
• ideally Windows Server 2016/2019 ? 2022/2025
• AWS EC2
• .NET / ASP.NET Hosting
• SQL Server / AWS RDS
• VPC / Security Groups
• CloudWatch
• Bitbucket Pipelines or comparable CI/CD
• Self-hosted Windows Runners
• Backup / Restore / Disaster Recovery
• Production Troubleshooting
• Security / Least Privilege
• Brownfield production systems
• independent analysis of existing systems
• proactive identification of risks and dependencies
• realistic effort estimations before starting
• re-estimates for scope changes
• pragmatic and cost-effective solutions
• reuse of existing infrastructure where sensible
• clear communication to non-technical management
• independent responsibility for infrastructure topics
• involvement of the existing Senior .NET Developer only where application knowledge is necessary
• Kubernetes introduction
• Microservice rewrite
• complete cloud rebuild
• unnecessary re-architecture
• Infrastructure-as-Code as an end in itself
• additional platform complexity without concrete benefit
• Freelance
• Remote
• preferably Germany / DACH / EU
• direct collaboration
• no agencies or intermediaries
• Start possible on short notice
• Long-term collaboration possible with a good fit
• Communication in German or very good English
• Hourly or daily rate
• Current availability
• Possible start date
• Typical weekly capacity
• Brief description of a comparable Production Windows Server / IIS / .NET migration project
• What role you specifically took on yourself
• Experience with AWS EC2 / RDS
• Experience with Bitbucket or comparable CI/CD

Project details

• Start: ab sofort
• Remote: remote
• Location: Bei Nürnberg, Deutschland, DE
• Languages: German