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Entry Level Windows Systems Administrator Jobs in Boston, MA

The System Administrator will collaborate with other members of the IT Infrastructure Team, maintaining and administering Linux, Windows, and VMware computer environments and related computing ...

The System Administrator will collaborate with other members of the IT Infrastructure Team, maintaining and administering Linux, Windows, and VMware computer environments and related computing ...

... Administrator, capable of providing information technology support to groups performing cutting ... Provide Tier 2 and Tier 3 support to Windows and Linux based operating systems across Riverside ...

In-depth knowledge of Linux and Windows Operating systems including administration, configuration, and troubleshooting. * Strong Linux command line skills * Experience hardening systems to CMMC and ...

Windows Patching (PCI Compliance a big Plus). Environment Monitoring & Troubleshooting. Environment Build ( .NET, SQL Server, IIS, Middleware). Hands on experience with implementation, system ...

Windows Patching (PCI Compliance a big Plus). Environment Monitoring & Troubleshooting. Environment Build ( .NET, SQL Server, IIS, Middleware). Hands on experience with implementation, system ...

Windows Patching (PCI Compliance a big Plus). Environment Monitoring & Troubleshooting. Environment Build ( .NET, SQL Server, IIS, Middleware). Hands on experience with implementation, system ...

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Entry Level Windows Systems Administrator information

See Boston, MA salary details

$58.7K

$104.2K

$141.8K

How much do entry level windows systems administrator jobs pay per year?

As of Aug 29, 2026, the average yearly pay for entry level windows systems administrator in Boston, MA is $104,247.00, according to ZipRecruiter salary data. Most workers in this role earn between $85,800.00 and $120,000.00 per year, depending on experience, location, and employer.

What does an entry level Windows Systems Administrator do?

An Entry Level Windows Systems Administrator is responsible for assisting with the setup, configuration, and maintenance of Windows-based servers and workstations within an organization. Their duties often include monitoring system performance, installing updates, troubleshooting basic technical issues, and helping ensure the security of the IT environment. They usually work under the supervision of more experienced administrators and provide support to end-users as needed. This role is ideal for those starting a career in IT and looking to build foundational skills in system administration.

What are the key skills and qualifications needed to thrive as an entry level Windows Systems Administrator?

To excel as an Entry Level Windows Systems Administrator, a solid understanding of Windows operating systems, basic networking concepts, and troubleshooting skills—often supported by a relevant degree or coursework—is essential. Familiarity with Active Directory, PowerShell scripting, and foundational certifications like CompTIA A+ or Microsoft Certified: Windows Server Fundamentals is highly beneficial. Strong problem-solving abilities, attention to detail, and effective communication are standout soft skills for this role. These skills and qualifications are crucial for ensuring reliable system performance, quick issue resolution, and seamless collaboration within IT teams.

What are some common challenges faced by entry level Windows Systems Administrators during their first year on the job?

Entry level Windows Systems Administrators often encounter challenges such as learning to efficiently troubleshoot unfamiliar system errors, managing time while juggling multiple support tickets, and adapting to the organization's specific network and security protocols. Balancing day-to-day maintenance tasks with urgent support requests can be demanding, especially when prioritizing issues for minimal disruption. However, most teams foster a collaborative environment, so asking questions and seeking guidance from more experienced admins is encouraged and can help build confidence and technical proficiency.

What is the difference between Entry Level Windows Systems Administrator vs Network Support Technician?

AspectEntry Level Windows Systems AdministratorNetwork Support Technician
CertificationsCompTIA A+, Microsoft Certified: Windows Server FundamentalsCompTIA A+, Cisco CCNA
Work EnvironmentServer rooms, data centers, IT departmentsHelp desks, client sites, network operations centers
Primary ResponsibilitiesManaging Windows servers, user accounts, system updatesTroubleshooting network issues, configuring routers/switches

Entry Level Windows Systems Administrators focus on managing and maintaining Windows server environments, while Network Support Technicians primarily troubleshoot and support network infrastructure. Both roles require foundational certifications and are common entry points in IT, but they differ in daily tasks and work settings.

What are popular job titles related to Entry Level Windows Systems Administrator jobs in Boston, MA?

For Entry Level Windows Systems Administrator jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Entry Level Windows Systems Administrator jobs in Boston, MA look for?

The top searched job categories for Entry Level Windows Systems Administrator jobs in Boston, MA are:

Infographic showing various Entry Level Windows Systems Administrator job openings in Boston, MA as of July 2026, with employment types broken down into 100% Full Time. Highlights an 92% In-person, and 8% Hybrid job distribution, with an average salary of $104,247 per year, or $50.1 per hour.

Systems Administrator

Boston, MA • On-site

Massachusetts Trial Court
Public Safety Administration • 5 - 10K employees

$137K/yr

Full-time

Posted 4 days ago


Job description

Systems Administrator

Apply now Job no: 501607
Work type: Full-time
Location: Boston
Categories: Administrative, Information Technology

Official Title: Systems Administrator

Pay Grade: Management

Salary Range: MGT Entry Level Pay $93,183.22 to Pay Range Maximum $137,488.26

Starting Pay: $93,183.22

Salary Notes: This position is designated as Management. Starting Salary will be based on a review of qualifications and experience.

Departmental Mission Statement:

Enhance access to justice through the effective use of technology. Partner with Judges and all Court Staff to use technology to speed the delivery of justice.  Build a culture that values transparency, collaboration, inclusivity, and continuous improvement. 

ORGANIZATIONAL PROFILE:

https://www.mass.gov/info-details/about-the-trial-court-information-technology-it-department

Notes: This position is designated as Management and is covered by the Personnel Policies and Procedures Manual. Compensation commensurate with experience. You must upload a resume to your profile to be considered for this position, in addition to completing all the application steps. First consideration will be given to those applicants that apply within the first 14 days.

Position Summary: The Systems Administrator will work with the Application, Database, Network, Information Security, and End User teams along with vendors to design, evaluate and implement computer systems and associated applications. Maintains Trial Court computer systems and server infrastructure. Performs updates, diagnostics, backups, and other technical functions on Trial Court technology platforms to ensure employee access to data and applications. This position requires the Systems Administrator to focus on operational, project, and user support tasks as part of their workday.

Supervision Received: The Systems Administrator position reports to the Server Operations Manager, receiving general direction in performing duties in accordance with established guidelines.

Essential Functions and Responsibilities: 

  • Install, configure, and support the Judiciary's infrastructure systems, including new and existing servers, cloud-based systems, storage systems, and other enterprise systems;
  • Responsible for the day-to-day support of services by performing server administration for physical and virtual server operating systems and configuring, maintaining, and troubleshooting physical and virtual hardware and network interfaces;
  • Manage and maintain Microsoft 365 tenant;
  • Proactively collaborate with peer teams and vendors to coordinate solutions;
  • Configure, maintain, monitor, upgrade and support both Linux and Windows servers;
  • Responsible for vulnerability identification, analysis, resolution, and reporting, including Center of Information Security (CIS) control compliance;
  • Partner with the Information Security team to provide secure, auditable Linux and Windows systems;
  • Responsible for planning, developing, maintaining, supporting, and optimizing the assigned application environments as well as implementing best practice methodologies;
  • Research and troubleshoot server technical issues and communicate status to Server Team and stakeholders;
  • Resolve complex enterprise system hardware and software problems;
  • Ensure complete and accurate backups of supported systems and associated data on a regular schedule;
  • Create and maintain documentation of systems, policies, and procedures;
  • Effectively provide and support standard lifecycle/system management processes including Configuration/Change management, Vendor/Supplier management, Resource/Capacity plans, and related processes as needed to implement forward-looking planning and management, using the ITIL Framework;
  • Contribute and implement plans, designs, and configurations to ensure compliance with backup and disaster recovery policies and procedures for IT infrastructure;
  • Interact with internal project teams, user support, application, network and database teams, as well as external vendors; 
  • Support recovery, performance and tuning of Linux and Windows Server systems;
  • Participate in on-call rotation; and
  • Additional tasks as required.

Job Competencies: All applicants must be able, through the interview process, to prove efficiency in the following areas:
Ethics and Values: Communicates and demonstrates the ethics and values of the Judicial Branch.
Mission: Understands, upholds, and communicates the Judicial Branch and Information Services missions.
Applied Knowledge: Understands information services operations, specialized tools, applications, and software, with knowledge of policy development and appropriate expertise in project planning methodologies.
Continuous Learning: Demonstrates a commitment to continuously improve their knowledge of fast-changing computer systems and practices.
Commitment to Diversity: Promotes an environment of diversity through understanding, respect, and positive communication with persons of varies racial, ethnic, economic and cultural backgrounds.
Customer Service: Conducts oneself in a courteous and professional manner when assisting all employees of the Judiciary, regardless of their position in the Judiciary.
Collaboration: Works with others cooperatively, demonstrating a willingness to be a team player, and contributing to a work environment that focuses on shared departmental goals.
Problem Solving: Is comfortable identifying additional outside resources that can contribute to best practice approaches to problem solving and conflict resolution.

Minimum Requirements:

Education and Experience:
Bachelor's degree in Computer Science, Engineering, or a related technical discipline, and 3 years of work experience in IT in a comparable size organization; equivalent combinations of education and experience will be considered for meeting the minimum requirements.
Experience of Linux platforms (Red Hat Enterprise Linux or a related derivative) including configuring network, syslog, storage, etc.
Experience administering Windows Server platforms.
Demonstrated knowledge of infrastructure services and networking topologies.
Knowledge of VMware ESXi and NSX.
Working knowledge of Microsoft 365 administration.
Experience with storage systems (NAS, SAN, object storage) and network hardware.
Understanding of backup systems and their replication and recovery methods.
Experience with Linux and Windows security, including SSL/TLS, certificates, encryption, key stores, firewalls, PAM, and system auditing.
Knowledge of server design, documentation, and change management processes.
Experience writing automation and/or custom scripts in one or more languages (Bash, Perl, PowerShell, and/or Python).
Required Skills:
Excellent verbal and written communication skills.
Ability to understand and document complex technical processes and procedures.
Ability to maintain confidential information and communications.
Ability to work effectively, both alone and as a member of a team.
Strong problem-solving skills, critical thinking, and analytical ability.
Strong task-oriented, organizational, and planning skills.
Ability to work well under pressure with various levels of Management.
Knowledge of ITIL Change and Configuration Management.
Certification Requirements:
ITIL 3 or 4 Certification is a plus.
Red Hat Certified Systems Administrator or Red Hat Certified Engineer is a plus.
Microsoft Certified: Windows Server Hybrid Administrator Associate is a plus.
Microsoft 365 Certified: Administrator Expert is a plus.
VMware Certified Professional is a plus.

Advertised: 25 Aug 2026 Eastern Daylight Time
Applications close: 25 Sep 2026 Eastern Daylight Time

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