Job Title: DevOps Engineer
Duration: 6+ month contract
Location: Morton Grove IL 60053
About the Role
We are seeking an experienced DevOps Engineer to support and modernize our Windows-based application landscape. This role will focus on infrastructure reliability, application migration and modernization, automation, CI/CD optimization, and operational excellence across our IaaS environments.
The ideal candidate combines strong hands-on Windows infrastructure experience with DevOps practices and automation capabilities. You will collaborate closely with development, infrastructure, and security teams to ensure stable, scalable, and secure platforms.
Key Responsibilities
Infrastructure & Platform Engineering
- Support and lead migration of applications from legacy Windows Server environments to modern Windows Server versions (2022+).
- Manage and maintain IIS-hosted applications and Windows Services.
- Ensure stability, performance, and security of IaaS-based environments.
- Support SQL Server connectivity, configuration, and service account management.
Automation & DevOps Practices
- Design and maintain CI/CD pipelines (TeamCity, Octopus Deploy, or similar tools).
- Improve deployment reliability and release processes.
- Contribute to Infrastructure-as-Code standards and practices.
- Reduce manual operational tasks through scripting and automation.
Modernization & Cloud
- Participate in modernization initiatives (replat forming, refactoring where applicable).
- Assist in improving monitoring, logging, and observability practices (ELK, monitoring tools, etc.).
- Support Azure-based workloads and hybrid environments.
Documentation & Governance
- Document environments, architecture decisions, and operational processes.
- Identify technical risks and propose mitigation strategies.
- Contribute to change management processes and enterprise governance standards.
- Ensure compliance with internal security and operational policies.
Collaboration
- Work closely with development, security, infrastructure, and project teams.
- Provide technical guidance during design and migration planning.
- Participate in troubleshooting and root cause analysis for production incidents.
Required Skills & Experience
- 4+ years of experience in DevOps, infrastructure engineering, or related roles.
- Strong hands-on experience with:
o IIS administration and application deployment
o Windows Server administration
o Windows Services configuration and troubleshooting
- Experience migrating legacy workloads to modern environments.
- Practical understanding of SQL Server (connection strings, permissions, service accounts).
- CI/CD pipeline design and maintenance (TeamCity, Octopus Deploy, or comparable tools).
- PowerShell scripting for automation.
- Experience working in Azure or hybrid cloud environments.
- Solid understanding of networking fundamentals and Active Directory.
- Strong troubleshooting and root cause analysis skills.
- Familiarity with .NET application environments.
Desirable / Nice-to-Have
- Azure infrastructure provisioning and configuration (Terraform, PowerShell, ARM/Bicep where applicable).
- Exposure to containerization technologies (Docker, Kubernetes).
- Knowledge of observability tools (ELK stack, APM tools).
- Security hardening and vulnerability remediation experience.
- Experience with enterprise-scale change management environments.
Soft Skills
- Clear and professional written and verbal communication.
- Ability to work independently while collaborating cross-functionally.
- Structured and detail-oriented approach to problem solving.
- Strong analytical and troubleshooting mindset.
- Proactive attitude with continuous improvement focus.
- Willingness to learn and adapt to evolving technologies.
Experience & Other Requirements
- 4+ years of relevant experience.
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