IT System Administrator (1099 Contract)

ABOUT DEFCON AI

RESILIENCE IN THE FACE OF DISRUPTION. DEFCON AI is an insights company that leverages artificial intelligence, mathematical optimization, data analytics, and software engineering for resilient optimization of complex systems.

In today’s dynamically changing world, DEFCON AI’s technology aligns outcomes with operational goals, better decision making, and empowers customers to anticipate assess, and mitigate the impacts of disruptions.

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, licen…