About Us (Ensono)

Ensono is an expert technology adviser and managed service provider. As a relentless ally, we accelerate clients’ digital transformation to achieve business outcomes that stand to last. Our dedicated team helps organizations optimize today’s systems across any hybrid environment with services such as consulting, mainframe and application modernization, public cloud migration and cloud-native development. With certified experts in AWS, Azure and Google Cloud and recognized as Microsoft Datacenter Transformation Partner of the Year, Ensono has over 3500+ associates globally and is headquartered in greater Chicago. We care about your success, offering comprehensive strategic and managed services for mission-critical applications. Our Advisory and Consulting services can help upfront with an application strategy or find the right places for your applications – whether it’s public, multi or hybrid cloud, or mainframe. And because we span across all mission-critical platforms, we can meet you wherever you are in your digital transformation journey, with 24/7 support when you need it. We are your relentless ally, flexing with you when challenges emerge so you don’t feel stuck in place. With cross-platform certifications and decades of experience, our technology experts have become an extension of your team so you’re continuously innovating – doing more with less while remaining secure. And that’s just the beginning.

Job Description – Windows L3 System Administrator (Terraform & Cloud Automation)

Job Summary

The Windows L3 System Administrator is responsible for advanced administration, engineering, automation, and support of enterprise Windows Server environments across on-premises and cloud platforms. This role serves as the highest technical escalation point for Windows infrastructure, driving automation through Terraform, supporting cloud-native deployments, ensuring platform stability, and leading complex troubleshooting, migration, and modernization initiatives.

Key Responsibilities

• Provide L3-level support for Microsoft Windows Server environments (2016, 2019, 2022 and later versions).
• Act as the final escalation point for complex Windows OS, Active Directory, and infrastructure-related incidents.
• Design, deploy, and maintain highly available Windows server infrastructures.
• Develop and manage Infrastructure as Code (IaC) solutions using Terraform.
• Create and maintain reusable Terraform modules for cloud and on-premise infrastructure deployments.
• Automate server provisioning, configuration, and infrastructure lifecycle management.
• Support Microsoft Active Directory, Group Policy, DNS, DHCP, DFS, and Windows Failover Clustering.
• Lead Windows OS upgrades, patching, security remediation, and lifecycle management activities.
• Implement and support cloud infrastructure on Azure and AWS using Terraform and automation tools.
• Administer virtualization platforms including VMware and Hyper-V.
• Perform performance tuning, capacity planning, and system optimization.
• Manage enterprise backup, disaster recovery, and business continuity solutions.
• Troubleshoot server, storage, networking, and application-related issues.
• Collaborate with application, database, network, cloud, and security teams on infrastructure solutions.
• Drive security hardening initiatives and ensure compliance with corporate and regulatory requirements.
• Lead Major Incident Management (MIM), Root Cause Analysis (RCA), and Problem Management activities.
• Develop automation using PowerShell, Terraform, and other enterprise automation tools.
• Mentor L1/L2 engineers and contribute to SOPs, standards, and knowledge management.
• Participate in 24x7 on-call support and planned maintenance activities.

Required Skills & Experience

• 8–10+ years of enterprise Windows Server administration experience.
• Strong expertise in:
• Windows Server 2016/2019/2022
• Active Directory (AD)
• Group Policy (GPO)
• DNS and DHCP
• Windows Failover Clustering
• Hands-on experience with Terraform for Infrastructure as Code (IaC).
• Experience developing and managing Terraform modules, state files, and remote backends.
• Strong PowerShell scripting and automation experience.
• Experience with VMware and/or Hyper-V virtualization platforms.
• Strong troubleshooting skills across server, OS, networking, and storage layers.
• Experience with patch management, vulnerability remediation, and security hardening.
• Knowledge of Azure and AWS infrastructure services.
• Experience with enterprise backup and disaster recovery solutions.
• Hands-on experience with ServiceNow or similar ITSM platforms.
• Strong understanding of networking concepts including TCP/IP, DNS, routing, load balancing, and firewall fundamentals.
• Experience supporting 24x7 mission-critical production environments.

Preferred Qualifications

• Microsoft Certified: Windows Server Hybrid Administrator Associate.
• HashiCorp Terraform Associate Certification.
• Azure Administrator (AZ-104) or Azure Solutions Architect certification.
• AWS SysOps Administrator certification.
• VMware VCP certification.
• Experience with Azure DevOps, GitHub Actions, Jenkins, or GitLab CI/CD.
• Experience with Ansible, PowerShell DSC, or other automation frameworks.
• Knowledge of container platforms such as AKS or Windows Containers.
• ITIL Foundation Certification.

Professional Attributes

• Strong ownership and accountability mindset.
• Excellent troubleshooting and analytical abilities.
• Ability to manage critical incidents under pressure.
• Strong verbal, written, and stakeholder communication skills.
• Ability to work effectively across infrastructure, application, and cloud teams.
• Strong documentation and process governance skills.
• Passion for automation, platform modernization, and continuous improvement.
• Team-oriented attitude with mentoring and knowledge-sharing capabilities.

We are an equal opportunity employer. All qualified applicants will be considered for employment without regard to caste, colour, creed, religion, gender, gender identity, sexual orientation, age, disability, HIV status, or any other status protected by law. Candidates with disabilities who require accommodations during the recruitment process are encouraged to contact our Talent Acquisition team to place a request.