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Remote Windows System Administrator Jobs in Florida

Cabanas Law Firm

System Administrator

Pembroke Pines, FL · On-site +1

$85K/yr

... systems, and solving problems before anyone notices them? Are you the person people call when they ... Remote staff. More locations coming fast. We're bringing IT in-house to fuel rapid expansion. We ...

New

Carrier

DCIM Support Specialist

FL · On-site +1

$79K - $158K/yr

... remote operations. Preferred Qualifications * Windows System Administration skills. * Knowledge of Linux. * Experience with Web technologies (Web Services, IIS, XML, etc.). * Application Sys Admin.

Hard Rock Digital

Senior Systems Administrator

Hollywood, FL · On-site +1

$78K - $106K/yr

This role will maintain system security, user access and roles, integrations, workflows, and ... Act as a supporting administrator for the financial systems, including user access, security roles ...

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 ...

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 ...

CFS

Coupa Administrator/AP

Sarasota, FL · Remote

$55K - $65K/yr

Remote Salary: $55,000 - $65,000 DOE Why This Opportunity Stands Out: * Fully remote role with ... Blend of systems administration and hands-on AP exposure * Ability to make process improvements and ...

CFS

Coupa Administrator/AP

Sarasota, FL · Remote

$55K - $65K/yr

Remote Salary: $55,000 - $65,000 DOE Why This Opportunity Stands Out: * Fully remote role with ... Blend of systems administration and hands-on AP exposure * Ability to make process improvements and ...

Usagenesiscare

Services Administrator

Fort Myers, FL · Remote

The Remote Services Administrator (RSA) is responsible for the operational leadership, performance ... Proficiency in EMR/EHR systems and call center technology platforms. Core Competencies

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Remote Windows System Administrator information

What are the key skills and qualifications needed to thrive as a Remote Windows System Administrator, and why are they important?

To thrive as a Remote Windows System Administrator, you need expertise in Windows Server administration, Active Directory, network protocols, and typically a degree in IT or related certifications like Microsoft Certified: Windows Server or Azure Administrator. Familiarity with tools such as PowerShell, Remote Desktop Services, VMware, and monitoring platforms is essential for managing and troubleshooting systems remotely. Excellent problem-solving, communication, and time-management skills help you to efficiently address issues and collaborate with distributed teams. These competencies ensure system reliability, security, and fast resolution of technical challenges in a remote environment.

What is a Remote Windows System Administrator?

A Remote Windows System Administrator is an IT professional responsible for managing, configuring, and maintaining Windows-based servers and systems from a remote location. Their duties include monitoring system performance, applying updates and patches, troubleshooting technical issues, and ensuring the security and reliability of Windows environments across an organization. They often use remote access tools to perform their tasks, helping organizations maintain efficient and secure IT operations without being physically present on-site.

What are some common challenges faced by Remote Windows System Administrators and how can they be addressed?

Remote Windows System Administrators often face challenges such as ensuring secure remote access, coordinating with geographically dispersed teams, and promptly resolving issues without on-site presence. To address these, effective communication tools, robust security protocols (like VPNs and multi-factor authentication), and proactive monitoring solutions are essential. Building strong documentation practices and maintaining regular updates with team members can also help manage tasks efficiently and ensure smooth operations.

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

AspectRemote Windows System AdministratorRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, Active Directory, and server infrastructureManaging network hardware, routers, switches, and network security
Employer & Industry UsageIT departments across various industries focusing on Windows environmentsOrganizations needing network infrastructure management across industries

Remote Windows System Administrators primarily focus on managing Windows server environments, Active Directory, and related infrastructure. In contrast, Remote Network Administrators concentrate on network hardware, routing, switching, and network security. While both roles require networking certifications like CompTIA Network+ or Cisco CCNA, their daily tasks and focus areas differ significantly, catering to different aspects of IT infrastructure management.

What are the most commonly searched types of Windows System Administrator jobs in Florida? The most popular types of Windows System Administrator jobs in Florida are:
What cities in Florida are hiring for Remote Windows System Administrator jobs? Cities in Florida with the most Remote Windows System Administrator job openings:
Remote Windows System Administrator jobs near you
Infographic showing various Remote Windows System Administrator job openings in Florida as of July 2026, with employment types broken down into 81% Full Time, 3% Part Time, 3% Temporary, and 13% Contract. Highlights an 6% In-person, and 94% Remote job distribution.
System Administrator

System Administrator

Cabanas Law Firm

Pembroke Pines, FL • On-site, Remote

$85K/yr

Full-time

Posted yesterday

Job description

Build the Tech Backbone of America’s Fastest-Growing Divorce Law Firm

Do you love fast growth, tight systems, and solving problems before anyone notices them?

Are you the person people call when they want something fixed right the first time?

Can you support a team spread across multiple offices AND remote locations without missing a beat?

If yes, this is your lane.

We are a fast-growing South Florida family law firm, recognized on the 2025 Inc. 5000 list.

Ten offices now. Remote staff. More locations coming fast.

We’re bringing IT in-house to fuel rapid expansion.

We need an IT Specialist who can keep systems strong, secure, and smooth — anywhere the team works.

This is not a ticket-taker role.

This is a build-it-better, eliminate bottlenecks, protect the firm's role.

We Offer

  • Competitive pay
  • A high-performance culture that moves fast
  • Leadership that values tech and invests in it
  • Growth as we expand across the state
  • A chance to build the internal IT function from scratch
  • Stability from a firm recognized on the 2025 Inc. 5000 list

This is an in-house role for someone who wants ownership, not red tape.

Why This Rocks

  • You build the tech backbone of a rapidly expanding business
  • Your work impacts every attorney, paralegal, and remote staff member
  • You shape an IT system that supports statewide growth
  • You eliminate friction and build speed into the company
  • You become the go-to expert inside a no-excuses culture

If you take pride in making everything run smoother…

If you want ownership…

If you want to support a winning team…

We want you here.

Compensation:

$65,000 - $85,000 DOE


Responsibilities:

You Will Handle

  • Desktop, laptop, and device setup for office and remote employees
  • Remote troubleshooting via screen share, remote access, and secure admin tools
  • Network troubleshooting and optimization
  • VoIP, conference rooms, and office tech
  • Cloud systems, drives, VPNs, permissions, and access control
  • Cybersecurity monitoring and best practices
  • Backup systems and disaster recovery
  • Software installs, updates, and integrations
  • Support across 10+ offices and remote locations
  • Rapid setup and deployment for new sites and new remote hires

If it logs in, connects, syncs, or boots up — you own it.


Qualifications:

You Are

  • A high-energy problem solver
  • Fast, calm, and confident under pressure
  • Obsessed with uptime, speed, and reliability
  • Comfortable supporting remote teams using VPNs, cloud systems, and remote tools
  • Experienced with multi-office and distributed work environments
  • A strong communicator who explains tech in simple words
  • A no-excuses professional who owns resolutions
  • A builder who embraces growth, change, and challenges

You prevent chaos.

You create stability.

You make remote and office teams feel like they’re in the same room.


About Company

At Cabanas Law Firm, our mission is to guide clients through life's most challenging family law matters with compassion, integrity, and excellence. As one of Florida's fastest-growing family law firms, we are committed to building a culture of accountability, teamwork, innovation, and continuous professional growth.

We invest in our employees by providing opportunities for career advancement, ongoing training, and leadership development. Our team members play an essential role in delivering exceptional service while helping families navigate difficult transitions with confidence.

If you're looking to join a collaborative, high-performing legal team where your work truly makes an impact, we'd love to hear from you.