Windows Systems Administrator / DevOps

Title - Windows Systems Administrator / DevOps

Location: Boston, MA (Hybrid)
Duration: 2-3 months plus extension.
Schedule: 35 Hours/Week
Employment Type: Contract

Job Overview

Our client is seeking a senior-level Windows Systems Administrator / DevOps professional to lead a critical Active Directory modernization project. The primary focus of this engagement will be upgrading the organization's Active Directory domain from Windows Server 2019 to Windows Server 2025, improving security, scalability, performance, and overall infrastructure stability.

The ideal candidate will have extensive experience managing enterprise Active Directory environments, executing domain and forest upgrades, and administering Windows Server environments in mid-to-large organizations.

Key Responsibilities

• Lead the Active Directory domain upgrade from Windows Server 2019 to Windows Server 2025.
• Create and deploy five new domain controllers using VMware infrastructure.
• Perform testing and validation in the development environment before production deployment.
• Manage and maintain Active Directory, Organizational Units (OUs), and Group Policies (GPOs).
• Handle forest and domain upgrades, FSMO role transfers, and domain migration activities.
• Administer Kerberos authentication, Certificate Authority (CA) services, and Windows DNS.
• Develop custom scripts and automate administrative processes.
• Collaborate with Infrastructure and ITS teams to ensure successful project delivery.
• Maintain system security, performance, and compliance throughout the migration process.

Required Qualifications

• Bachelor's degree in information technology, computer science, or a related discipline.
• Minimum 5 years of experience managing Active Directory environments in mid-to-large organizations.
• Strong expertise in:
  • Active Directory Administration
  • Group Policy (GPO) Creation and Management
  • OU and Domain Management
  • Windows Server 2019, 2022, and 2025
  • Windows DNS
  • Kerberos Authentication
  • Certificate Authority (CA) Management
  • VMware Administration
• Experience with:
  • Domain and Forest Upgrades
  • FSMO Role Transfers
  • Active Directory Migration Projects
  • PowerShell or custom scripting

Preferred Qualifications

• Prior experience leading Windows Server 2025 domain upgrades.
• Experience with Ansible and Jenkins.
• DevOps and infrastructure automation experience.
• Higher education or enterprise IT environment experience.

Work Arrangement

• Hybrid position located in Boston, MA.
• Initial onsite training/probation period of approximately 3–4 weeks.
• After successful completion of the probation period, candidates may work remotely up to 50% of the time.
• Local candidates are strongly preferred due to the hybrid requirement.

Required Skills

• Active Directory Administration
• Group Policy Objects (GPO)
• Windows Server 2019/2022/2025
• VMware
• Forest & Domain Upgrades
• FSMO Role Transfers
• Windows DNS
• Kerberos
• Certificate Authority (CA)
• PowerShell / Custom Scripting
• Ansible (Preferred)
• Jenkins (Preferred)
• DevOps Practices