IT System Administrator (1099 Contract)

Skills

About the Role

You will own day-to-day administration across a multi-cloud footprint spanning AWS and Microsoft Azure, as well as the Microsoft 365 collaboration and identity stack. You will be the hands-on technical resource responsible for provisioning, monitoring, hardening, and troubleshooting the systems the workforce depends on, while helping ensure the environment meets the security and compliance expectations of a company operating in Department of War mission spaces. You'll work independently as a self-directed contractor, documenting your work clearly and balancing routine operational tasks with project-based infrastructure improvements. This is a 1099 independent contractor engagement with full time hours.

Requirements

• 7+ years of hands-on IT system administration experience
• Strong, demonstrable expertise administering AWS environments
• Practical cloud administration experience across both AWS and Microsoft Azure
• Microsoft 365 administration expertise (Entra ID, Exchange Online, SharePoint, Teams, licensing, and identity management)
• Basic scripting experience (PowerShell, Bash, or Python) for automation of administrative tasks
• Some experience supporting or operating within Department of War (DoW) environments
• US Citizenship required
• Ability to work independently as a 1099 contractor with strong documentation and communication habits

Responsibilities

• Administer, monitor, and maintain workloads across AWS and Microsoft Azure, including compute, storage, networking, and identity resources
• Manage resource provisioning, cost visibility, tagging, and baseline security configuration across both cloud platforms
• Support hybrid and cloud-native architectures, troubleshooting connectivity, performance, and availability issues
• Integrate with an interdisciplinary team of experts in optimization and simulation to design, build, and optimize models
• Design and implement novel heuristics and optimization models to solve complex problems
• Communicate complex technical concepts and findings to non-technical stakeholders clearly and concisely
• Collaborate with cross-functional teams to translate business requirements into actionable solutions
• Administer the Microsoft 365 tenant, including Entra ID (Azure AD), Exchange Online, SharePoint, Teams, and related services
• Manage user lifecycle provisioning and deprovisioning, licensing, group and role assignments, and conditional access policies
• Support mail flow, security baselines, and collaboration platform configuration
• Perform routine system administration, patching, monitoring, and maintenance across endpoints and cloud-hosted systems
• Respond to and resolve escalated infrastructure and end-user support issues
• Maintain accurate documentation, runbooks, and configuration records
• Administer and support the organization's portfolio of managed IT and security SaaS platforms
• Maintain tooling spanning endpoint and mobile device management, patching, and IT service management and ticketing
• Support security-focused managed services, including managed detection and monitoring, security awareness training, and compliance automation
• Manage user access, licensing, integrations, and vendor coordination across platforms
• Develop and maintain scripts to automate repetitive administrative tasks
• Support reporting, monitoring, and provisioning workflows through scripting and native cloud/M365 tooling
• Apply and maintain security configurations consistent with DoW and applicable compliance requirements
• Support hardening, logging, access reviews, and audit-readiness activities
• Partner with security and compliance stakeholders to ensure administrative practices align with organizational policy