Job Description

Senior Windows Server Infrastructure Analyst

Location: Lutz, FL (North Tampa Area)
Pay Rate: $60-$65/hr

Overview: 

We are seeking a Senior Windows Server Infrastructure Analyst to support a large-scale server upgrade and modernization initiative. This role focuses on upgrading existing Windows Server environments (2016 → 2022/2025), improving system performance, and ensuring stability across a complex enterprise infrastructure.

This is a hands-on execution role, not a greenfield build position. You will be working within an established environment, helping modernize and stabilize critical systems.

What You’ll Do

Windows Server Upgrades & Modernization

• Execute in-place upgrades from Windows Server 2016 to 2022/2025
• Migrate key server roles (Active Directory, DNS, DHCP, File Services, IIS, Certificates)
• Validate application compatibility and system functionality pre- and post-upgrade
• Plan and execute testing, rollback strategies, and production cutovers
• Decommission legacy systems after successful migrations

Active Directory Management

• Maintain and optimize Active Directory across multiple versions
• Monitor replication, FSMO roles, and overall AD health
• Clean up and improve Group Policy (GPO) performance
• Troubleshoot authentication issues (Kerberos, SPNs)
• Ensure secure AD configurations aligned with company policies

VMware & Virtual Infrastructure

• Support VMware ESXi hosts and vCenter environments
• Coordinate virtual machine migrations during upgrades
• Manage snapshots and rollback processes
• Adjust system resources (CPU, memory, storage) as needed

Troubleshooting & Support

• Diagnose and resolve server, network, and authentication issues
• Use structured troubleshooting methods to identify root causes
• Escalate hardware issues and coordinate vendor support
• Handle complex technical incidents in an enterprise environment

Security & Compliance

• Apply security hardening standards to upgraded systems
• Ensure compliance with internal IT security policies
• Address vulnerabilities identified during system assessments
• Support firewall rules and secure system segmentation

Disaster Recovery & Documentation

• Update disaster recovery plans and documentation
• Participate in DR testing and validation
• Maintain accurate system diagrams and configurations

What You Bring

Required:

• 5+ years of hands-on experience with Windows Server environments
• Proven experience upgrading Windows Server 2016 to newer versions (2022/2025)
• Strong expertise in Active Directory administration
• Experience with VMware ESXi and vCenter
• Solid troubleshooting skills across servers, networking, and virtualization

Preferred:

• Experience in enterprise environments
• Familiarity with Cisco networking (switching/routing)
• Experience supporting firewalls and SAN storage
• Bachelor’s degree (or equivalent experience)

Technical Environment

• Windows Server 2016 (legacy) → 2022/2025
• Microsoft Active Directory
• VMware ESXi & vCenter
• Cisco networking
• Enterprise firewalls
• SAN storage systems

Additional Requirements

• Must be able to work onsite 4 days per week (5 days during critical phases as needed)
• Candidates must meet company safety and compliance requirements

Why Join Us

• Be part of a large-scale infrastructure modernization effort
• Work in a complex, enterprise-level environment
• High-impact role with visibility across IT operations