Senior System Administrator

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, DevOps, 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 DevOps.

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, CloudFormation, or equivalent.

Own network infrastructure:

· Unifi Dream Machine SE, Giga Switches, and APs for LAN/Wi-Fi.

· RapidScale VeloCloud with FortiGate EMS for SD-WAN, VPN, and secure remote access.

DevOps & Automation

· Collaborate with DevOps teams to integrate infrastructure into CI/CD pipelines (GitHub Actions, Jenkins, Azure DevOps).

· Deploy and manage containerized workloads using Docker and Kubernetes.

· Automate configuration, patching, and deployment with Ansible, Intune (Windows & Android), JAMF (Mac/iOS), and scripting (PowerShell, 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 ID.

· Support physical security by maintaining Alarm.com 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 diagrams, SOPs, and knowledge base articles in Confluence and SharePoint.

· Manage hardware/software inventory and lifecycle using Snipe-IT and Smartsheet.

Communication & Collaboration

· Ensure reliable communication through Microsoft Teams, RingCentral, and Zoom.

· Collaborate with internal stakeholders (Support, DevOps, Security, Engineering, Product, and Data teams) to align IT services with business needs

Qualifications or Competencies:

· 5+ years in system administration, hybrid cloud management, and IT operations, with experience managing multi-site environments.

Technical Expertise:

· OS: Windows Server, Linux

· Cloud: AWS, Azure

· Virtualization: VMware, Hyper-V

· Networking: Unifi (UDM SE, switches, APs), FortiGate SD-WAN/VPN

· Automation: Intune, JAMF, Ansible, Terraform, CloudFormation, scripting (PowerShell, Bash, Python)

· DevOps: CI/CD (GitHub Actions, Jenkins, Azure DevOps), Docker, Kubernetes

· Security: Wazuh, Microsoft Defender, Barracuda, Zero Trust, compliance frameworks

· Backups: Barracuda (M365), OWN (Salesforce), Box

Soft Skills: Strong problem-solving ability, cross-team collaboration, and effective communication.

Preferred Certifications: 

· CompTIA Security+, AWS SysOps Administrator, AWS DevOps Engineer, MCSA, CISSP, Kubernetes Administrator (CKA).

Education and Previous Work Experience:

· Bachelor’s degree preferred (Engineering, Computer Science, Information Systems major preferred) or equivalent experience.

Why Join Us
At Veteran Benefits Guide, you’ll play a critical role in securing and advancing IT systems that support our mission to serve U.S. Veterans. You’ll be part of a collaborative, fast-paced team environment where innovation and reliability matter. 

EEOC:

Veteran Benefits Guide (VBG) provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, national origin, ancestry, physical disability, mental disability, medical condition, marital status, sex (including pregnancy, childbirth, breastfeeding, or related medical conditions), gender (including gender identity and gender expression), genetic characteristic, sexual orientation, registered domestic partner status, age, military or veteran status, hair style or hair texture, reproductive health decision making, or any other characteristic protected by federal, state, or local laws.