Systems Administrator II
The Judge Group
IT
Remote
System Administrator
Location: Remote
About the job
This role goes far beyond standard Active Directory administration. As a hands-on Active Directory and Identity & Access Management (IAM) Engineer, you will tackle complex tenant migrations, domain consolidations, and identity integration initiatives driven by continuous acquisitions.
Operating in a fast-moving, high-volume, and evolving infrastructure, you will be expected to step in with minimal ramp-up time to troubleshoot intricate integration issues, decommission legacy systems, and ensure seamless site-by-site cutovers. This is a highly collaborative, execution-focused role requiring independence, composure under pressure, and the technical depth to navigate non-standard, multi-tenant environments successfully. You will not just be keeping the lights on; you will be actively untangling technical debt and designing solutions for large-scale domain mergers.
Responsibilities
Execute Migrations & Consolidations: Lead and execute M365 and tenant migrations, handling site-by-site cutovers, domain mergers/divestitures, and domain controller decommissioning.
Identity Integration: Manage and troubleshoot identity and access management integrations (Okta, Azure AD/Entra ID), resolving corrupted data, access problems, and onboarding friction during acquisitions.
Automation & Scripting: Develop and deploy PowerShell scripts for onboarding, migrations, and the automation of complex, routine tasks.
System Administration & Support: Support, design, customize, and maintain servers, Active Directory Domain Services (ADDS), and all associated components. Provide break/fix support and resolve legacy tech debt (e.g., Server 2008/2012 cleanup).
Infrastructure Optimization: Maintain system reliability and performance through proactive monitoring, patch management, and trending utilization.
Technical Problem Solving: Collaborate with stakeholders to identify system requirements, manage Azure app registrations, and implement Microsoft Certificate Authority (MSCA) services.
Stakeholder Communication: Act as a strong communicator who can calm high-pressure situations, establish credibility through data-driven decisions, and troubleshoot critical incidents independently without needing step-by-step direction.
Minimum qualifications
5+ years of hands-on experience supporting Active Directory, network technology, and computing in a complex enterprise environment.
Proven, real-world experience executing M365 and tenant migrations, domain consolidations, and mergers/divestitures (not just project participation).
Strong proficiency in Active Directory Domain Services (ADDS), Azure Entra ID, AD Connect, DNS, and DHCP.
Demonstrated experience writing and utilizing PowerShell for automation and scripting.
Ability to work in a hybrid or fully remote capacity, including 24-hour on-call support with occasional night and weekend availability for critical issue resolution and project milestones.
Preferred qualifications
Bachelor’s degree in Business, Computer Science, or a related technical discipline.
Extensive background working in unstructured, legacy, or M&A-heavy environments (rather than strictly clean, polished enterprise settings).
Hands-on experience with Okta workflows, AWS/Azure cloud services, and VMware virtualization.
Strong understanding of KMS, RDP licensing, and TCP/IP Subnetting.
Exceptional critical thinking skills with the ability to act proactively, manage stakeholder expectations, and identify project risks and resource constraints.