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Remote Windows Systems Administrator Jobs in Florida

RIFLE LLC

Senior Systems Administrator

Winter Park, FL · On-site +1

$125K - $145K/yr

Support a hybrid Windows, macOS, iOS, and mobile device environment. * Monitor system performance ... Administer Windows Server, Active Directory, Azure Active Directory, Microsoft 365, and related ...

Lee Health

Advanced Imprivata Administrator

Fort Myers, FL · Remote

$43.59 - $56.66/hr

Remote - Florida Department: IS Information Technology Svcs Work Type: Full Time Shift: Shift 1/8 ... Lee Health, one of the largest not-for-profit health systems in Florida, is seeking an experienced ...

Lee Health

Advanced Imprivata Administrator

Fort Myers, FL · On-site +1

$43.59 - $56.66/hr

Remote - Florida Department: IS Information Technology Svcs Work Type: Full Time Shift: Shift 1/8 ... Lee Health, one of the largest not-for-profit health systems in Florida, is seeking an experienced ...

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All JobsWindows Systems Administrator JobsRemote Windows Systems Administrator JobsRemote Windows Systems Administrator Jobs in Florida

Remote Windows Systems Administrator information

What does a remote Windows systems administrator do?

A Remote Windows Systems Administrator manages and supports Windows-based servers, networks, and systems from a remote location. Their responsibilities include installing, configuring, and maintaining Windows servers, monitoring system performance, troubleshooting issues, and ensuring security compliance. They also handle tasks such as user account management, backup and recovery, and software updates. Communication with onsite teams and end-users is often required to resolve problems and ensure smooth IT operations.

How does a remote Windows systems administrator typically collaborate with on-site IT teams and end users?

As a Remote Windows Systems Administrator, you will frequently collaborate with on-site IT staff and end users through a combination of communication tools such as email, instant messaging, and video conferencing. You may assist with troubleshooting, deploying updates, and managing user permissions, often requiring clear documentation and effective remote support skills. Building strong relationships and maintaining timely communication are essential for resolving issues efficiently and ensuring system reliability, despite not being physically present. This role often involves participating in team meetings, coordinating on projects, and sometimes working outside standard hours to accommodate system maintenance or urgent incidents.

What are the key skills and qualifications needed to thrive as a remote Windows systems administrator, and why are they important?

To thrive as a Remote Windows Systems Administrator, you need expertise in Windows Server administration, network management, troubleshooting, and a solid understanding of security best practices, usually backed by a degree in IT or related certifications like Microsoft Certified: Windows Server or Azure Administrator. Familiarity with tools such as Active Directory, PowerShell, virtualization platforms, and remote monitoring systems is essential. Strong problem-solving skills, attention to detail, and effective communication are crucial soft skills for managing systems and collaborating with remote teams. These skills ensure reliable system performance, secure network environments, and timely resolution of technical issues in a distributed work setting.

What is the difference between Remote Windows Systems Administrator vs Remote Network Administrator?

AspectRemote Windows Systems AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and system securityManaging network infrastructure, routers, switches, and connectivity
Employer & Industry UsageIT departments, data centers, cloud servicesTelecommunications, enterprise networks, ISPs

Remote Windows Systems Administrators focus on managing and maintaining Windows server environments, ensuring system security and performance. In contrast, Remote Network Administrators oversee network infrastructure, troubleshooting connectivity issues and configuring network devices. While both roles require networking knowledge, the Windows Systems Administrator specializes in server OS and related services, making their skills more aligned with server management and security.

What are popular job titles related to Remote Windows Systems Administrator jobs in Florida?

For Remote Windows Systems Administrator jobs in Florida, the most frequently searched job titles are:

What job categories do people searching Remote Windows Systems Administrator jobs in Florida look for?

The top searched job categories for Remote Windows Systems Administrator jobs in Florida are:

Remote Windows Systems Administrator jobs near you
Infographic showing various Remote Windows Systems Administrator job openings in Florida as of July 2026, with employment types broken down into 1% As Needed, 84% Full Time, 12% Part Time, 1% Temporary, and 2% Contract. Highlights an 93% Physical, 3% Hybrid, and 4% Remote job distribution.

System Administrator

Tampa, FL • Remote

Bridgeway Benefit Technologies
See more jobs at Bridgeway Benefit Technologiesexternal

Full-time

Posted 4 days ago

Job description

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.

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