Senior System Administrator

Description

Who We Are:

Veteran Benefits Guide (VBG) was founded by a former United States Marine with the goal of ensuring that Veterans receive accurate disability benefits in a timely manner. Since it was founded, VBG has guided more than 35,000 Veterans through the complicated Veteran Affairs (VA) disability claims process. As a company founded by a Veteran and staffed by many Veterans and families of Veterans, VBG is committed to advocating for policies that protect the rights and interests of former service members.

What We Are Looking For :

Veteran Benefits Guide (VBG) is seeking a Senior System Administrator to join our growing IT team. In this pivotal role, you will bridge Support Services, Dev Ops, and IT Security to deliver secure, efficient, and resilient IT operations across multi-site environments. You will lead the architecture, implementation, and maintenance of hybrid infrastructure spanning on-premises systems, SaaS platforms, and cloud environments, while driving automation, compliance, and innovation across the enterprise.

This is a high-impact role for a strategic technologist who can thrive at the intersection of infrastructure, security, and Dev Ops.

Requirements

Essential Functions:

Reasonable accommodation may be made to enable individuals with disabilities to perform essential functions.

Support Services & End-User Experience

• Serve as the Tier 3 escalation point for Help Desk, owning complex troubleshooting and resolution across multi-site operations.
• Define, track, and report SLA/KPI metrics (system uptime, incident resolution time, user satisfaction).
• Mentor Support Services staff and cross-train San Diego users for basic IT support functions.

Infrastructure & Cloud Operations

• Install, configure, and maintain physical, virtual, and cloud-hosted systems, including servers, desktops, laptops, firewalls, switches, routers, access points, and VPNs.
• Administer and optimize Windows Server, Windows 10/11, Linux, and other enterprise operating systems.
• Manage VMware, Hyper‑V, AWS, Azure environments with a focus on cost efficiency and scalability.
• Implement and manage Infrastructure as Code (IaC) using Terraform, Cloud Formation, or equivalent.

Own network infrastructure:

• Unifi Dream Machine SE, Giga Switches, and APs for LAN/Wi‑Fi.
• Rapid Scale Velo Cloud with Forti Gate EMS for SD‑WAN, VPN, and secure remote access.

Dev Ops & Automation

• Collaborate with Dev Ops teams to integrate infrastructure into CI/CD pipelines (Git Hub Actions, Jenkins, Azure Dev Ops).
• Deploy and manage containerized workloads using Docker and Kubernetes.
• Automate configuration, patching, and deployment with Ansible, Intune (Windows & Android), JAMF (Mac/iOS), and scripting (Power Shell, Bash, Python).
• Support application release processes through environment preparation, infrastructure readiness, and rollback planning.

Security & Compliance

• Partner with the Security Team to design and implement Zero Trust Architecture and micro‑segmentation strategies.
• Integrate and maintain EDR/SIEM solutions (Wazuh, Microsoft Defender, Splunk, Datadog) for proactive threat detection and response.
• Ensure compliance with NIST, CIS v8, ISO 27001, SOC 2 standards.
• Lead vulnerability remediation efforts and coordinate penetration testing follow‑up.
• Maintain role‑based access controls (RBAC) and identity governance with Azure AD/Entra .
• Support physical security by maintaining  door access control and office cameras in coordination with Facilities.

Disaster Recovery & Business Continuity

• Implement and validate backups for cloud and on‑premises workloads, ensuring compliance with the IT Disaster Recovery Plan.
• Manage cloud‑to‑cloud SaaS backups (Barracuda for Microsoft 365, OWN for Salesforce).
• Participate in Business Continuity exercises and maintain documentation for multi‑site recovery.

Observability & Monitoring

• Integrate systems with modern observability platforms (Datadog, New Relic) to ensure proactive issue detection.
• Leverage Down Detector and external monitors for vendor outage visibility.
• Develop automated remediation workflows for recurring incidents.

Documentation & Asset Management

• Maintain up‑to‑date technical documentation, including…