Job Description

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

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