Cloud Systems Engineer

About the Role

DEFCON AI is hiring a Cloud Systems Engineer to administer AWS, Microsoft Azure, and our Microsoft 365 and Entra ID tenant. This is a single, senior seat covering both halves of the environment — the infrastructure that runs our workloads and the identity plane that governs who reaches them — with end-to-end ownership of each.

The work spans virtual machine provisioning and network architecture, Infrastructure as Code, tenant and identity administration, endpoint management, automation, and continuous monitoring. We operate under defense-sector compliance obligations, so security hardening and audit-ready documentation are part of the job rather than an afterthought. Experience in regulated or compliance-driven environments — defense, healthcare, or financial services — is a strong plus.

Responsibilities:

Cloud Infrastructure and Virtual Systems Administration

• Administer and maintain AWS and Azure environments, including day-to-day operations of virtual machines, networking, and storage across both providers.
• AWS: deploy, maintain, and optimize EC2, RDS, S3, IAM, KMS, Secrets Manager, and CloudTrail; manage VPCs, subnets, routing tables, security groups, and NACLs.
• Azure: administer virtual machines, virtual networks and NSGs, storage accounts, Azure Files, Key Vault, Azure Virtual Desktop, and Site Recovery across subscriptions.
• Build and manage hardened VM images and golden images for consistent, repeatable deployments.
• Implement and support high availability, auto-scaling, backup, and disaster recovery configurations.
• Support multi-account and multi-subscription governance structures — AWS Organizations, Azure Management Groups, and equivalent landing-zone constructs.

Identity & Microsoft 365 Administration

• Own the Microsoft 365 tenant end to end: Entra ID, Exchange Online, SharePoint, OneDrive, Teams, and licensing.
• Administer the identity plane — Conditional Access policies, MFA enforcement, RBAC and least privilege, privileged access, hybrid identity, and application registrations. and role assignments, and conditional access policies
• Run the full user lifecycle: provisioning, onboarding, role changes, offboarding, and access reviews, automated wherever the volume justifies it.
• Manage the endpoint fleet through Intune, including compliance policies, configuration profiles, patching, and device lifecycle.
• Administer single sign-on and provisioning integrations (SAML, SCIM) between Entra ID and the SaaS platforms we operate.
• Support data governance and protection through Purview, sensitivity labels, and DLP policy where applicable.

Infrastructure as Code and Automation

• Design and maintain infrastructure using Terraform — modular design, remote state management, and workspace strategy — across both AWS and Azure.
• Build reusable, secure baseline modules for network architecture, IAM roles, logging, monitoring, and encryption.
• Automate operational workflows in PowerShell, Bash, and Python, including Microsoft Graph API automation for identity and tenant tasks.
• Integrate infrastructure provisioning and security controls into CI/CD pipelines (GitHub Actions, GitLab CI, or equivalent) and maintain version-controlled infrastructure repositories.
• Implement automated drift detection and remediation, and enforce policy-as-code guardrails.

Security, Compliance & Monitoring

• Apply and maintain hardening baselines (CIS Benchmarks, DISA STIGs) across Linux and Windows systems and cloud tenants.
• Configure and monitor AWS CloudTrail, GuardDuty, Security Hub, and Config alongside Microsoft Defender and Entra ID sign-in and audit logging.
• Support SIEM integration (Splunk, Microsoft Sentinel, or equivalent) and assist with incident response.
• Maintain the vulnerability management lifecycle: patching, remediation tracking, and reporting.
• Support compliance aligned to NIST SP 800-171, CMMC, and FedRAMP or SOC 2 as applicable, including evidence collection for assessments.

AI Platform Administration

• Administer the AI platforms in our environment — Anthropic Claude, ChatGPT, AWS Bedrock, and Microsoft 365 Copilot — including seats and licensing, SSO and provisioning, retention and data controls, connector and agent governance, and spend limits.
• Enforce and communicate standards for what data may be placed into AI tooling, particularly where CUI or controlled data is involved.

Collaboration and Documentation

• Partner with engineering, security, and operations to deliver reliable, scalable services
• Produce and maintain architecture diagrams, runbooks, SOPs, and audit evidence artifacts without being asked for them
• Contribute to capacity forecasting, resource planning, and cloud cost management.

Qualifications: 

• 5+ years in systems administration, cloud operations, or infrastructure engineering.
• 3+ years hands-on administering AWS in production, including virtual machine administration, networking, and IAM.
• 2+ years administering a Microsoft 365 tenant with real admin rights — Entra ID, Exchange Online, Conditional Access, licensing, and user lifecycle. Help-desk support of Microsoft 365 does not meet this bar.
• Hands-on Microsoft Azure administration in a production environment.
• Demonstrated automation of operational workflows using PowerShell, Bash, or Python; working Terraform experience.
• Strong understanding of IAM, encryption (KMS, TLS), and network segmentation.
• Experience with Linux (RHEL or Amazon Linux) and Windows Server in a cloud context.
• Experience working in Department of Defense or Department of War environments and applying their security requirements.
• Disciplined documentation habits — runbooks, SOPs, and configuration records maintained as a matter of course.
• US Citizenship Required. All work must be performed within the United States.

Preferred Qualifications:

• Microsoft 365 GCC High tenant experience.
• Terraform depth including modular design, state management, and leading IaC migrations from legacy tooling.
• Container platform experience — Docker with ECS, EKS, or AKS.
• AWS certifications (Solutions Architect, SysOps Administrator, Security Specialty) or Azure equivalents (AZ-104); Microsoft 365 Administrator (MS-102); CompTIA Security+.
• AWS Control Tower, Landing Zones, or Azure Landing Zone governance tooling.
• SIEM platform experience (Splunk, Microsoft Sentinel).
• Administration of AI platforms at the tenant or account level - Anthropic, OpenAI, Bedrock and Copilot 
• Managed service provider background administering across many client tenants.
• Regulated-industry experience: defense (CMMC, NIST 800-171), healthcare (HIPAA), or financial services (SOC 2).
• Active DoD security clearance (Secret or above), or eligibility to obtain and maintain one.

Core Competencies

• Infrastructure and identity ownership — takes end-to-end accountability for the health, security, and performance of both the infrastructure and the identity plane.
• Automation mindset — proactively replaces manual processes with scalable, repeatable solutions.
• Security-first thinking — embeds security into every layer of design and operations rather than bolting it on.
• Cross-functional communication — translates technical complexity for business and compliance stakeholders.
• Disciplined documentation — produces clear, audit-ready artifacts without being prompted.
• Adaptability — comfortable across cloud providers, toolchains, and an evolving compliance landscape.

What Success Looks Like

• AWS, Azure, and the Microsoft 365 tenant are stable, secure, observable, and documented.
• Identity is governed: access follows least privilege, joiners and leavers are handled cleanly, and access reviews are routine.
• Infrastructure changes are repeatable through code, with clear review and rollback paths.
• Monitoring, logging, and vulnerability remidiation are routine rather than scramble-driven.
• Audit artifacts - diagrams, runbooks, evidence - stay current and usable.

What We Offer

• A fully remote, results-based environment
• 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
• Flexible work environment where you manage your work day
• 14 weeks of fully-paid parental leave

Salary Range: $160,000-$190,000. This represents the typical salary range for this position based on experience, skills, and other factors.