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 • 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 Benefits • Top-of-market competitive salary, bonus, and equity package • 100% employer paid comprehensive health insurance including medical, dental and vision for you and your family • Unlimited PTO, with your manager’s approval • 14 weeks of fully paid parental leave • Occasional travel to our offices in Washington D.C or alternative locations to collaborate with your team in person • Opportunities for professional development and continued learning