System Administrator - Bridgeway Benefit Technologies

About the Role

Bridgeway is seeking a System Administrator to serve as the front line of our internal technology experience — owning ticket intake, triage, and escalation against defined SLAs while administering the identity, endpoint, and collaboration systems our employees and hosting customers rely on daily.

Reporting to the Sr. Manager, IT, the role also covers customer hosting support, remote-access management, and incident command for internal and customer-facing disruptions across our portfolio of healthcare benefits administration products. You'll pair strong troubleshooting instincts across Windows, Linux, networking, and virtualization with the discipline to work inside established security policy and the communication skills to keep users, customers, and executives clearly informed under pressure.

This is a fully remote position. Candidates in the Eastern time zone are preferred.

Responsibilities

• Serve as first point of contact for technical issues, managing the ticket queue to defined response and resolution SLAs.
• Diagnose and resolve hardware, software, network, and account access issues, protecting uptime and the end-user experience.
• Escalate to other technical teams per defined criteria, with a clean handoff and follow-through to resolution.
• Categorize and prioritize incidents and serve as incident command for internal and customer-facing disruptions, coordinating responding teams and owning communications to users, customers, and executives through restoration, root-cause analysis, and remediation tracking.
• Deploy and maintain end-user devices, peripherals, and workstation software, including mobile device management, endpoint packaging, and allow-listing.
• Administer corporate collaboration and productivity systems (mailboxes, mail groups, Teams, SharePoint, OneDrive) and manage licenses and renewals, including AI-tooling enablement (e.g., Claude Desktop, Copilot) under Security-defined policy.
• Operate corporate networking (cloud and end-user VPN) and support customer hosting environments — access and remote-access troubleshooting, scheduled customer jobs, and batch file processes.
• Administer Linux servers supporting workloads — package and repository management, service and daemon configuration, log and performance troubleshooting, filesystem and storage management, and SSH key and sudo access administration under least privilege.
• Administer and maintain remote-access infrastructure — RD Web gateways and Azure Virtual Desktop (AVD) — serving corporate and customer access, including host pool and session host lifecycles, image builds, FSLogix profile management, capacity tuning, and user session troubleshooting.
• Administer identity and directory services — Entra ID tenants and on-prem Active Directory (users, groups, GPO, OUs), SSO/federated authentication (Entra, Auth0, FusionAuth), and MFA and Conditional Access.
• Own onboarding and offboarding provisioning and internal access requests; run periodic dormant-account and access reviews for SOC 2 and HIPAA audit compliance.
• Administer privileged credentials and vaults (1Password), and manage service-account and API-key lifecycles.
• Execute patching for workstations, Windows/Linux servers, and third-party applications, along with backup validation and restore testing.
• Track ticket metrics and trends to recommend automation or self-service options.
• Create and maintain end-user knowledge base articles, FAQs, and troubleshooting guides.
• Share the team's Tier 1 on-call rotation for end-user and infrastructure support.
• Write and maintain shell scripts (Bash, PowerShell) and scheduled jobs to automate routine administration and checks.

Requirements

• 2+ years of experience in IT support or system administration, including hands-on Linux server administration in production alongside Windows server setup, configuration, and maintenance.
• Intermediate understanding of networking protocols, VPN and remote connectivity, and security practices.
• Experience with virtualization and virtual desktop platforms, including hands-on Azure Virtual Desktop administration.
• Ability to perform system backups, restore testing, and disaster recovery procedures against defined playbooks and schedules.
• Strong troubleshooting skills for hardware, software, and network issues.
• Hands-on administration of Entra ID and on-prem Active Directory, including SSO, MFA, and Conditional Access.
• Experience administering Microsoft 365 collaboration services and managing SaaS licenses.
• Endpoint management experience covering device deployment, MDM, software packaging, and patching.
• Experience managing an ITSM ticket queue to defined SLAs with strong written communication skills.
• Comfort operating in a SOC 2 / HIPAA-regulated environment, executing access reviews, and participating in a Tier 1 on-call rotation.
• Experience using generative AI tools (such as Claude and Copilot) to improve productivity.
• Bachelor's degree in Information Technology, Software Development, or a related field.