Senior IT Systems Administrator (Azure Windows Admin)

CHAOS Industries was founded in 2022 and has raised a total of $1 billion in funding from leading investors, including 8VC, Accel, and Valor Equity Partners. The company is headquartered in Los Angeles, with offices in Washington, D.C., San Francisco, San Diego, Seattle, and London. For more information, please visit www.chaosinc.com.

Role Overview:

CHAOS Industries is looking for a Senior IT Systems Administrator to design, build, secure, and operate the Windows and Azure cloud infrastructure our teams rely on every day. You will keep servers, identity services, and cloud workloads healthy, patched, and compliant in a defense environment where uptime and data protection are both non-negotiable. As a senior member of the IT organization, you will act as a technical lead for systems engineering: setting standards, owning the hardest problems, and mentoring teammates, while partnering with cybersecurity, service desk, engineering, and program teams.

• Team mandate: keep the core platforms running reliably, securely, and predictably, and automate the repetitive work so the team can spend its time on improvements. You will be the escalation point for complex systems issues and a trusted advisor on infrastructure decisions.
• Ownership: technical ownership of the Windows Server and Azure environments, including architecture, patching, monitoring, backup and recovery, and hardening, plus leadership of infrastructure projects such as server and cloud migrations, new site standups, and environment consolidations as the company grows.

Responsibilities:

• Architect, administer, and maintain Windows Server environments (physical and virtual), including provisioning, configuration, patching, monitoring, and lifecycle management.
• Design, deploy, and manage Azure cloud 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.
• Serve 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, and set technical standards, best practices, and peer review for the team.
• Lead infrastructure projects from planning through delivery, including site buildouts, server and cloud migrations, and the integration of newly acquired environments.
• Design and maintain automation with PowerShell and other scripting tools to streamline 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 compliance requirements (such as CMMC, NIST SP 800-171, and FedRAMP) by maintaining configuration documentation, logs, and access reviews, and providing evidence for audits.
• Review technical designs and changes, follow the change control process, and communicate maintenance windows and impacts to stakeholders.
• Evaluate and recommend tools and technologies, and 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: minimal, up to roughly 10% (occasional trips to company offices and new sites).
• Physical demands: primarily sedentary work at a computer; occasional lifting of equipment up to 25 lbs and work in server or network rooms.

Minimum Requirements:

• Minimum education:
• Bachelor’s degree in Information Technology, Computer Science, Information Systems, or another related field or equivalent work experience
• 7+ years of progressive experience administering enterprise Windows Server and Microsoft Azure environments.
• Deep expertise with Active Directory, Group Policy, DNS, and DHCP, and with 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, and backup and disaster recovery, including testing restores 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, with strong troubleshooting, documentation, and communication skills.
• U.S. person status, as required for access to CUI and export-controlled data (ITAR/EAR).

Preferred Requirements:

• Experience with Azure Government or Microsoft GCC High environments, and with 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 integrating Okta with Entra ID and cloud applications.
• Cloud or Microsoft certification such as Azure Administrator Associate, Azure Solutions Architect Expert, or AWS Solutions Architect; security certification such as Security+ or CISSP.
• Experience with infrastructure as code or configuration management (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 the ability to obtain one.

Why CHAOS?

• Health Benefits: Medical, dental, and vision benefits 100% paid for by the company
• Additional benefits: 401k (+ 50% company match up to 6% of pay), FSA, HSA, life insurance, and more
• Our Perks: Free daily lunch while you're working onsite, fully-stocked kitchen, unlimited PTO, casual dress code
• Compensation Components: Competitive base salaries, generous pre-IPO stock option grants, relocation assistance, and (coming soon!) annual bonuses
• Team Growth: 500+ employees and counting across 5 global offices

Salary Range: $140,000 - $200,000

The stated compensation range reflects only the targeted base compensation range and excludes additional earnings such as bonus, equity, and benefits. If your compensation requirements fall outside of the range, we still encourage you to apply. The salary range for this role is an estimate based on a range of compensation factors, inclusive of base salary only. Actual salary offer may vary based on (but not limited to) work experience, education and/or training, critical skills, and/or business considerations.

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