IT System Administrator (1099 Contract)

About the Role

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. 

Responsibilities:

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

Qualifications: 

• 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

Preferred Qualifications:

• Prior experience operating in a GCC-High (Microsoft 365 Government) environment
• Familiarity with DoW/DoD security and compliance frameworks (e.g., NIST SP 800-171, CMMC, or DISA STIGs)
• Relevant certifications such as AWS Certified SysOps Administrator/Solutions Architect, Microsoft Certified: Azure Administrator, or Microsoft 365 Certified
• Experience administering third-party managed IT and security SaaS platforms across categories such as endpoint/mobile device management (RMM/MDM), IT service management and ticketing, managed detection and monitoring, security awareness training, and compliance automation tooling
• Experience with infrastructure automation, monitoring, or configuration management tooling
• Active or eligible for a US security clearance

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

Engagement Details 

• Schedule: Flexible; scope and expected hours to be defined in the contractor agreement
• Compensation: Competitive hourly/contract rate, commensurate with experience (rate range to be finalized)
• 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.