IT System Administrator (1099 Contract)

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.

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

• 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

• 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
• 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.