IT System Administrator, DEFCON AI

• 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

Desirable

• DEFCON AI is seeking an experienced IT System Administrator to support and maintain the infrastructure that keeps our cloud environments, identity systems, and end-user services running reliably and securely
• This is a 1099 independent contractor engagement supporting a fast-moving team operating across commercial and government cloud environments
• As the IT System Administrator, you will own day-to-day administration across our multi-cloud footprint—spanning AWS and Microsoft Azure—as well as our Microsoft 365 collaboration and identity stack
• You will be the hands-on technical resource responsible for provisioning, monitoring, hardening, and troubleshooting the systems our workforce depends on, while helping ensure our environment meets the security and compliance expectations of a company operating in Department of War (DoW) mission spaces
• This role is well suited to a self-directed contractor who is comfortable working independently, documenting their work clearly, and balancing routine operational tasks with project-based infrastructure improvements
• This role is a 1099 contract opportunity, with full time hours
• Cloud Infrastructure Administration:
• 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 that deliver high-quality, real-world insights
• Design and implement novel heuristics and optimization models to solve complex problems in various industries, ensuring efficiency and scalability
• Stay up to date with the latest advancements in decision science and implement best practices for our customers
• The communication of complex technical concepts and findings to non-technical stakeholders clearly and concisely
• Collaborate with cross-functional teams to understand business requirements and translate them into actionable solutions
• Microsoft 365 & Identity Management:
• Administer the Microsoft 365 tenant, including Entra ID (Azure AD), Exchange Online, SharePoint, Teams, and related services
• Manage user lifecycle (provisioning/deprovisioning), licensing, group and role assignments, and conditional access policies
• Support mail flow, security baselines, and collaboration platform configuration
• Systems Operations & Support:
• 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
• Managed IT & Security Application Support:
• Administer and support the organization's portfolio of managed IT and security SaaS platforms, ensuring proper configuration, integration, and reliable day-to-day operation
• Maintain tooling that spans endpoint and mobile device management (RMM/MDM), patching, and IT service management/ticketing and user-facing support workflows
• Support security-focused managed services, including managed detection and monitoring, security awareness training, and compliance automation and evidence-collection tooling
• Manage user access, licensing, integrations, and vendor coordination across these platforms; serve as the internal administrator and escalation point for configuration and operational issues
• Automation & Scripting:
• Develop and maintain basic scripts (e.g., PowerShell, Bash, or Python) to automate repetitive administrative tasks
• Support reporting, monitoring, and provisioning workflows through scripting and native cloud/M365 tooling
• Security & Compliance Support:
• 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
• What Success Looks Like:
• Cloud and M365 environments that are reliable, secure, well-documented, and consistently maintained
• Routine administrative and provisioning tasks handled promptly and accurately
• Repetitive workflows reduced through practical automation and scripting
• Security and compliance configurations applied and maintained in line with DoW expectations
• A dependable, self-directed technical partner who requires minimal oversight
• Schedule: Flexible; scope and expected hours to be defined in the contractor agreement

• As an independent contractor, you will be responsible for your own taxes, insurance, and applicable business expenses. Equipment and tooling arrangements will be specified in the contractor agreement