Senior IT Systems Administrator (Azure Windows Admin)

CHAOS Industries • Washington, DC

5h • $140,000 - $200,000 • Onsite

About The Position

CHAOS Industries is seeking a Senior IT Systems Administrator to design, build, secure, and operate Windows and Azure infrastructure in a defense environment. The role owns the Windows Server and Azure environments, including architecture, patching, monitoring, backup and recovery, and hardening. As a senior member of the IT organization, this person will lead systems engineering standards, take on complex technical issues, mentor teammates, and partner with cybersecurity, service desk, engineering, and program teams.

The role leads infrastructure initiatives such as server and cloud migrations, new site standups, and environment consolidations. It also supports Microsoft 365 and endpoint management, maintains compliance documentation and audit evidence, and contributes to infrastructure planning. The position includes participation in an on-call rotation, occasional after-hours maintenance windows, and minimal travel of up to roughly 10% to company offices and new sites. Work is primarily sedentary at a computer, with occasional lifting of equipment up to 25 lbs and work in server or network rooms.

Requirements

• Bachelor’s degree in Information Technology, Computer Science, Information Systems, or a related field, or equivalent work experience.
• At least 7 years of progressive experience administering enterprise Windows Server and Microsoft Azure environments.
• Deep expertise with Active Directory, Group Policy, DNS, DHCP, and Microsoft Entra ID identity and access management, including MFA and conditional access.
• Experience designing and implementing Azure solutions, including virtual machines, virtual networking, storage, role-based access control, and hybrid connectivity.
• Advanced PowerShell scripting to automate administration, patching, and reporting at scale.
• Experience owning patch management, monitoring, backup, and disaster recovery, including restore testing and meeting recovery objectives.
• Experience hardening systems and remediating vulnerabilities in a regulated environment, such as NIST SP 800-171 or CMMC.
• Track record of leading infrastructure projects and mentoring other engineers; strong troubleshooting, documentation, and communication skills.
• U.S. person status, as required for access to CUI and export-controlled data (ITAR/EAR).

Nice To Haves

• Experience with Azure Government or Microsoft GCC High environments and other cloud platforms such as AWS (EC2, VPC, IAM) in multi-cloud or hybrid environments.
• Experience with Okta for single sign-on, MFA, and identity lifecycle management, including integration with Entra ID and cloud applications.
• Cloud or Microsoft certification such as Azure Administrator Associate, Azure Solutions Architect Expert, or AWS Solutions Architect; or security certification such as Security+ or CISSP.
• Experience with infrastructure as code or configuration management tools such as Bicep, Terraform, ARM templates, or Ansible across cloud platforms.
• Experience supporting CMMC, NIST 800-171, or FedRAMP assessments, and an active U.S. government security clearance or ability to obtain one.

Responsibilities

• Architect, administer, and maintain physical and virtual Windows Server environments, including provisioning, configuration, patching, monitoring, and lifecycle management.
• Design, deploy, and manage Azure resources—including virtual machines, networking, storage, identity, and monitoring—in commercial and government cloud environments using templates and infrastructure as code.
• Administer and improve Active Directory, Microsoft Entra ID, Group Policy, DNS, DHCP, and certificate services, including identity lifecycle, privileged access, MFA, and conditional access policies.
• Act as technical lead and final escalation point for complex incidents, perform root-cause analysis, and drive permanent fixes.
• Mentor and coach junior systems administrators and service desk staff; set technical standards, best practices, and peer review practices.
• Lead infrastructure projects from planning through delivery, including site buildouts, server and cloud migrations, and integration of newly acquired environments.
• Develop and maintain PowerShell and other scripting automation for provisioning, patching, reporting, and routine administration.
• Own backup, disaster recovery, and business continuity design, including regular restore testing and recovery objectives.
• Apply and maintain security baselines such as DISA STIG and CIS benchmarks, remediate vulnerabilities, and partner with cybersecurity to close findings.
• Support CMMC, NIST SP 800-171, and FedRAMP requirements by maintaining configuration documentation, logs, and access reviews and providing audit evidence.
• Review technical designs and changes, follow change control, and communicate maintenance windows and impacts to stakeholders.
• Evaluate and recommend tools and technologies; contribute to the infrastructure roadmap, capacity planning, and budget inputs.
• Support Microsoft 365 and endpoint management services, including device compliance and configuration policies, in partnership with the service desk.
• Create and maintain system documentation, runbooks, and architecture diagrams.
• Participate in an on-call rotation and occasional after-hours maintenance windows for critical systems.
• Travel occasionally, up to roughly 10%, to company offices and new sites.

Benefits

• Medical, dental, and vision benefits fully paid for by the company.
• 401(k) with a 50% company match up to 6% of pay.
• Flexible spending account (FSA), health savings account (HSA), and life insurance.
• Free daily lunch while working onsite and a fully stocked kitchen.
• Unlimited PTO.
• Casual dress code.
• Generous pre-IPO stock option grants.
• Relocation assistance.
• Annual bonuses are described as coming soon.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior