Window Server Engineer

Contract: 8-12 Months

Location: Lutz, FL

Core Windows Server Upgrade Skills

• Proven experience performing in‑place upgrades from Windows Server 2016 to 2019 and/or 2022
• Strong understanding of Windows Server upgrade paths, edition compatibility, and licensing implications
• Ability to assess and remediate pre‑upgrade blockers (deprecated roles, drivers, legacy applications)
• Hands‑on experience reviewing and resolving setupact.log / setuperr.log issues
• Knowledge of supported .NET, PowerShell, and role dependencies across Windows Server versions
• Experience validating post‑upgrade OS health (services, roles, performance, event logs)

VMware vSphere & Virtual Machine Operations

• Experience working with VMware vSphere / ESXi virtual machines
• Ability to safely perform:
• VM snapshots (pre‑upgrade and rollback planning)
• Disk space checks and expansion if required
• VMware Tools verification and upgrades
• Understanding of vCPU, memory, and virtual hardware compatibility with newer Windows Server versions

Pre‑Upgrade Planning & Risk Mitigation

• Ability to:
• Run and interpret Windows Upgrade Readiness checks
• Verify application and vendor support for target OS
• Confirm backup validity and recovery options
• Experience documenting:
• Upgrade plans
• Rollback procedures
• Success criteria and validation steps
• Familiarity with change management and maintenance window execution

Application & Role Awareness

• Experience upgrading servers with common roles such as:
• Active Directory Domain Services (non‑FSMO or with coordination)
• DNS / DHCP
• IIS
• File & Print Services
• SQL Server (OS upgrade support validation)
• Ability to identify workloads not suited for in‑place upgrade and recommend alternatives

Security & Compliance Considerations

• Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versions
• Ability to validate:
• Antivirus / EDR compatibility post‑upgrade
• GPO and local policy behavior after upgrade

EEO Statement

Brooksource is an equal opportunity employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth, lactation and related medical conditions), gender identity or gender expression, sexual orientation, marital status, military service and veteran status, physical or mental disability, protected medical condition as defined by applicable state or local law, genetic information, or any other characteristic protected by applicable federal, state, or local laws and ordinances.

Benefits & Perks

Benefits & Perks: Brooksource offers competitive medical, dental, vision, Health Savings Account, Dependent Care FSA, and supplemental coverage with plans that can fit each employee’s needs. We offer a 401k plan that includes a company match and is fully vested after you become eligible, paid time off, sick time, and paid company holidays. We also offer an Employee Assistance Program (EAP) that provides services like virtual counseling, financial services, legal services, life coaching, etc.

Pay Disclaimer

The pay range for this job level is a general guideline only and not a guarantee of compensation or salary. Additional factors considered in extending an offer include (but are not limited to) responsibilities of the job, education, experience, knowledge, skills, and abilities, as well as internal equity, alignment with market data, applicable bargaining agreement (if any), or other law.