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Remote Windows System Administrator Jobs in Massachusetts

CarGurus

Systems Administrator II

Boston, MA · Remote

... System Administrator II, you will help support and improve the core systems and services our employees use every day. You will work across identity, collaboration tools, office networking, and remote ...

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All JobsWindows System Administrator JobsRemote Windows System Administrator JobsRemote Windows System Administrator Jobs in Massachusetts

Remote Windows System Administrator information

See Massachusetts salary details

$59K

$104.8K

$142.5K

How much do remote windows system administrator jobs pay per year?

As of Aug 14, 2026, the average yearly pay for remote windows system administrator in Massachusetts is $104,797.00, according to ZipRecruiter salary data. Most workers in this role earn between $86,300.00 and $120,700.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote Windows system administrator?

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 Massachusetts?

The most popular types of Windows System Administrator jobs in Massachusetts are:

What are popular job titles related to Remote Windows System Administrator jobs in Massachusetts?

For Remote Windows System Administrator jobs in Massachusetts, the most frequently searched job titles are:

What job categories do people searching Remote Windows System Administrator jobs in Massachusetts look for?

The top searched job categories for Remote Windows System Administrator jobs in Massachusetts are:

What cities in Massachusetts are hiring for Remote Windows System Administrator jobs?

Cities in Massachusetts 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 Massachusetts as of August 2026, with employment types broken down into 1% As Needed, 86% Full Time, 11% Part Time, and 2% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $104,797 per year, or $50.4 per hour.

Systems Administrator Quality Assurance

Starfish Storage Corporation

Waltham, MA • On-site, Remote

$125K - $185K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 13 days ago

Job description

Location:
Remote, onshore in the USA
Salary:
$125k to $185k per year depending on experience and skills
How to Apply:
Please only apply to one open position. If you aren't a fit for it, we'll consider you for other positions automatically.
Please submit your resume and a cover letter (in .pdf) that a) highlights your relevant experience related to the qualifications listed below; b) explains your interest in Starfish in particular; and c) addresses the following questions:
  1. Describe the most creative test case you've ever written to uncover a bug. What was the bug, why was it difficult to find, and how did you identify it?
  2. Describe a time when your automation scripts passed, yet a bug was still released. What went wrong in the design of those tests? How did you change your processes going forward to prevent that kind of bug in the future?
  3. How do you resolve a situation where a developer insists a bug you found is a "limitation" or "intended behavior," particularly when user documentation does not yet exist?
  4. What is your superpower? Help us see the forest for the trees and tell us where you shine most and what you might uniquely contribute to our organization. This is important to us because it tells us what unique value you can bring to the organization.

Required Qualifications:
  • 7+ years of experience in Linux and Windows system administration
  • Strong experience with:
    • Linux server administration (RHEL/CentOS/Ubuntu)
    • Windows Server (2016/2019/2022)
    • Active Directory & Group Policy
    • Python and Powershell scripting
    • Large-scale unstructured data management
  • Experience implementing QA methodologies in infrastructure environments
  • Knowledge of CI/CD pipelines and automation tools (Ansible, Terraform, Jenkins, etc.)
  • Strong understanding of networking fundamentals (TCP/IP, firewalls, routing)
  • Excellent troubleshooting and root cause analysis skills
  • Flexibility
  • Excellent interpersonal skills
  • Independent worker with a strategic mindset and the ability to thrive in a collaborative, fast-paced environment.
  • University degree required; STEM (Science, Technology, Engineering, Mathematics) background preferred. An advanced degree is a plus.
  • Ability to work in the U.S. on a full-time basis.
  • Background check required.
Preferred Qualifications:
  • Cloud certifications (AWS, Azure, GCP)
  • Microsoft and Red Hat certifications
  • Experience in research environments
  • Bash scripting
Key Competencies
  • Strong analytical and problem-solving skills
  • Detail-oriented with a quality-first mindset
  • Excellent communication and documentation skills
  • Ability to manage multiple priorities in a fast-paced environment

Job Overview:
We are seeking a highly skilled Senior Linux & Windows System Administrator with strong Quality Assurance (QA) experience to join our growing technology team. This role requires deep systems expertise across both Linux and Windows environments, combined with a quality-driven mindset to ensure reliability, security, performance, and compliance across our infrastructure.
You will play a critical role in designing, maintaining, securing, automating, and validating the Starfish Storage product while integrating QA best practices to assure it's reliable and bulletproof.
QA & Reliability Engineering
  • Develop and execute infrastructure validation and testing plans
  • Build automated test scripts for system validation and deployment pipelines
  • Validate system updates, patches, and configuration changes before production rollout
  • Enforce documentation, change control, and release management processes
  • Collaborate with DevOps and development teams to improve CI/CD reliability

About Starfish Storage:
At Starfish Storage, we are revolutionizing the way organizations manage unstructured data at scale and across enterprises. With over a decade of experience, our innovative platform is designed to empower clients across various industries. Our clients include industry leaders in media & entertainment, research computing, biotech, higher education, and government sectors. You'll be working with visionary C-suite clients and the top-tier technical teams who make digital transformations happen. This is an opportunity to drive change in some of the most technically demanding environments in the world.
Benefits:
We recognize that satisfaction and well-being are integral components for long-term sustainability and business success. As such, employees are provided competitive compensation, options (potential), as well as the following benefits:
  • Competitive compensation and benefits
  • Multiple health insurance options
  • Dental insurance
  • Vision insurance
  • 401(k) savings plan with employer matching
  • Long-term disability insurance
  • Paid holidays and PTO that increase with tenure
  • Opportunities for growth!

Equal Opportunity Employer
Starfish Storage provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, marital status, amnesty, military service, or veteran status in accordance with applicable federal, state and local laws.

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