Remote Windows System Administrator Jobs in Florida

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 (root-cause content owned by the accountable engineering teams).
• 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 the Linux servers supporting these 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 - serving both corporate and customer access, including AVD host pool and session host lifecycle, session host image build and update cycles, application group and workspace assignment, FSLogix profile management, capacity and autoscale 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 configuration (Entra, Auth0, FusionAuth), and MFA and Conditional Access - under established security policy and least privilege.
• Own onboarding/offboarding provisioning (including HR-to-directory sync) and internal access requests for applications, shares, mail groups, and licenses; run periodic dormant-account and access reviews that produce SOC 2 and HIPAA audit evidence.
• Administer privileged credentials and vaults (1Password), and manage the service-account and API-key lifecycle to Security-owned standards.
• Execute patching for workstations, Windows and Linux servers, and third-party applications, and perform backup validation, restore testing, restore requests, and backup-failure alert response following pre-defined playbooks against Security-owned standards, handle backup validation, restore testing and requests, and backup-failure alerts per Security-owned playbooks and schedules.
• Track ticket volume, response times, and resolution times to spot trends and recommend self-service or automation that reduces volume.
• Create and maintain end-user knowledge base articles, FAQs, and troubleshooting guides that enable self-service and consistent support quality (product and hosting triage runbooks are owned by Platform Engineering).
• Communicate with end users in plain language, setting clear expectations on resolution.  
• Collaborate cross-functionally to align support processes with organizational goals and technology changes, staying current on our systems, tools, and common issues to improve first-contact resolution.
• Share the team's Tier 1 on-call/on-shift rotation for end-user and infrastructure support, escalating to Platform Engineering (Tier 2) per defined criteria.
• Write and maintain shell scripts (Bash, PowerShell) and scheduled jobs that automate routine administration, monitoring checks, and reporting across Windows and Linux estates. 

Requirements

• 2+ years in IT support or system administration, including hands-on Linux server administration in a production environment 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 and renewals.
• Endpoint management experience - device deployment, MDM, software packaging, and patching.
• Experience working an ITSM ticket queue to defined SLAs, with the written communication skills to explain technical issues to non-technical users and document them clearly.
• Comfort operating in a SOC 2 / HIPAA-regulated environment, executing access reviews and producing audit evidence, and willingness to share a Tier 1 on-call rotation.
• Experience using generative AI tools such as Claude and Copilot to improve productivity and deliver high-quality outcomes
• Bachelor's degree in Information Technology, Software Development, or a related field. 

Bridgeway is an equal opportunity employer.