Job Specifications
Lead Windows System Administrator - Previous experience working in the Retail Industry is required.
We’re seeking a talented Lead Windows System Administrator with deep expertise in Microsoft and VMware technologies, Azure cloud services, and Microsoft 365 to join our dynamic team managing the core infrastructure that drives business operations.
In this role, you’ll support both on‑premises and cloud environments, play a key role in infrastructure initiatives, and ensure the ongoing security, stability, and performance of enterprise systems. The Windows Administration Team is responsible for maintaining and advancing the Microsoft ecosystem, including Active Directory, Microsoft 365, SharePoint Online, SQL, and the broader Microsoft Collaboration Suite. In addition, the team supports key service platforms such as VMware, compute, storage, backup, and other critical infrastructure technologies.
This position requires participation in an on‑call rotation and offers a primarily remote schedule, with on‑site presence approximately four days per month or as needed based on project or support requirements.
A Day in the Life
Design and implement hybrid infrastructure solutions using Azure IaaS/PaaS and on‑prem vSphere
Manage Azure services including VMs, networking, storage accounts, Azure AD, backup, and monitoring
Oversee VMware infrastructure (vCenter, ESXi hosts, HA/DRS clusters, vSAN)
Administer enterprise storage platforms
Automate system tasks using PowerShell, Azure CLI, and Terraform
Lead incident response, root cause analysis, and performance tuning
Collaborate with security and networking teams to enforce compliance and governance
Participate in an on‑call rotation and provide support as needed for projects and escalations
Mentor junior administrators and contribute to infrastructure roadmaps
You’ll Come With
Bachelor’s degree in Computer Science, Information Technology, or a related field (preferred)
5+ years of systems administration experience, including Windows Server (2016, 2019, 2025)
Experience with Active Directory, Azure AD, and Microsoft 365 administration
Expertise with VMware (ESXi, vCenter, vSphere) and virtualization best practices
Solid understanding of core infrastructure services: DNS, DHCP, DFS, IIS, Group Policy, RDS
Experience supporting Microsoft SQL Server infrastructure
Experience with Azure cloud services and Azure DevOps (CI/CD pipelines, infrastructure automation)
Expertise with Veeam Backup & Replication, including VeeamONE
Advanced PowerShell scripting skills for automation and configuration management
Experience with security best practices, patch management, and compliance standards
Expertise with enterprise server hardware (Cisco, HP rack‑mounted and blade systems)
Extensive experience with shared storage platforms and architectures
Working knowledge of monitoring and endpoint management tools such as BigFix, Datadog, or SolarWinds
Familiarity with ITIL, COBIT, and project management methodologies
Additional Qualifications
Strong background in risk and compliance, ideally within the payments or financial services space
Experience with process documentation, including creating documentation from scratch
Ability to assess and support controls, risks, and operational processes end‑to‑end
About the Company
The Judge Group is an international leader in business technology consulting, talent solutions, and learning and development.
With over 30 locations across the U.S., Canada & India, Judge is proud to partner with the best and brightest companies in business today, including over 60 of the Fortune 100. We serve organizations in financial services, healthcare, life sciences, insurance, government, aerospace & defense, manufacturing, and technology & telecommunications.
Judge has always been committed to doing what's right ...
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