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Remote Windows Systems Engineer Jobs in Gloucester, MA

YO AI Labs

AI Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

Nasuni

Senior Software Engineer - File System

Boston, MA · On-site +1

$133K - $175K/yr

Mentor engineers and raise the quality bar for systems design, code quality, testing, and ... Strong written communication skills for design docs, reviews, remote collaboration, and operational ...

YO AI Labs

Machine Learning Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

YO AI Labs

AI Software Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

YO AI Labs

RL Environment Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

YO AI Labs

Machine Learning Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

YO AI Labs

AI Software Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

YO AI Labs

RL Environment Engineer - Remote

Boston, MA · Remote

$80 - $120/hr

Remote Job Summary We are seeking experienced Senior Software Engineers to support an AI training ... Build deterministic verification systems and golden reference solutions. * Evaluate AI agents ...

YO AI Labs

AI Consulting Expert - Remote

Boston, MA · Remote

$100 - $200/hr

... AI systems. In this role, you will evaluate, review, and refine AI-generated business content ... Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical & Report Writing

YO AI Labs

AI Consulting Expert - Remote

Boston, MA · Remote

$100 - $200/hr

... AI systems. In this role, you will evaluate, review, and refine AI-generated business content ... Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical & Report Writing

YO AI Labs

AI Consulting Expert - Remote

Boston, MA · Remote

$100 - $200/hr

... AI systems. In this role, you will evaluate, review, and refine AI-generated business content ... Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical & Report Writing

Atlas Technica

Team Lead (Remote)

Boston, MA · Remote

... engineering, systems administration, or a related technical function. Additional qualifications include: * Experience providing end-user and desktop support for Microsoft Windows, Microsoft Office ...

YO AI Labs

DevOps Engineer - Remote

Boston, MA · Remote

$50 - $150/hr

Remote Job Overview We are seeking experienced DevOps Engineers to create and evaluate production-style infrastructure and automation tasks for next-generation AI systems. You will work on CI/CD ...

YO AI Labs

DevOps Engineer - Remote

Boston, MA · Remote

$50 - $150/hr

Remote Job Overview We are seeking experienced DevOps Engineers to create and evaluate production-style infrastructure and automation tasks for next-generation AI systems. You will work on CI/CD ...

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All JobsWindows Systems Engineer JobsRemote Windows Systems Engineer JobsRemote Windows Systems Engineer Jobs in Gloucester, MA

Remote Windows Systems Engineer information

See Gloucester, MA salary details

$11

$56

$83

How much do remote windows systems engineer jobs pay per hour?

As of Sep 8, 2026, the average hourly pay for remote windows systems engineer in Gloucester, MA is $56.86, according to ZipRecruiter salary data. Most workers in this role earn between $45.00 and $68.17 per hour, depending on experience, location, and employer.

What does a remote Windows systems engineer do?

A Remote Windows Systems Engineer is responsible for designing, implementing, and maintaining Windows-based server environments from a remote location. They manage tasks such as installing updates, configuring security settings, troubleshooting technical issues, and ensuring system performance and reliability. These engineers often work with cloud platforms, virtualization technologies, and collaborate with IT teams to support business operations. Their remote role allows them to provide support and maintenance without being physically present on-site.

What are the key skills and qualifications needed to thrive as a remote Windows systems engineer?

To thrive as a Remote Windows Systems Engineer, you need expertise in Windows Server administration, system troubleshooting, and network protocols, often backed by a degree in IT or computer science and certifications like Microsoft Certified: Windows Server Hybrid Administrator Associate. Familiarity with tools such as Active Directory, PowerShell, virtualization platforms, and remote management software is essential. Strong problem-solving abilities, effective communication, and self-motivation are critical soft skills for managing systems and collaborating virtually. These skills ensure secure, reliable system operations and efficient remote support in distributed IT environments.

What are some common challenges faced by remote Windows systems engineers, and how can they be effectively managed?

Remote Windows Systems Engineers often encounter challenges such as troubleshooting complex system issues without direct physical access, ensuring secure remote connectivity, and coordinating across distributed teams and time zones. Effective management of these challenges involves utilizing robust remote monitoring and management tools, maintaining clear and regular communication with colleagues, and following best practices for system security and documentation. Staying proactive with updates and leveraging collaboration platforms can significantly enhance productivity and reduce downtime.

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

AspectRemote Windows Systems EngineerRemote Network Administrator
CertificationsMicrosoft Certified: Windows Server, CompTIA Network+Cisco CCNA, CompTIA Network+
Work EnvironmentManaging Windows servers, troubleshooting OS issues, deploying updatesConfiguring and maintaining network infrastructure, monitoring network performance
Industry UsageIT, technology, enterprise environmentsIT, telecommunications, service providers
Search IntentFocus on Windows server management and supportFocus on network infrastructure and connectivity

The Remote Windows Systems Engineer primarily manages and supports Windows server environments, ensuring system stability and security. In contrast, the Remote Network Administrator focuses on maintaining network infrastructure, including routers, switches, and connectivity. While both roles require networking knowledge and certifications, their core responsibilities differ, with the Systems Engineer centered on Windows OS and server management, and the Network Administrator on network hardware and connectivity.

What job categories do people searching Remote Windows Systems Engineer jobs in Gloucester, MA look for?

The top searched job categories for Remote Windows Systems Engineer jobs in Gloucester, MA are:

What cities near Gloucester, MA are hiring for Remote Windows Systems Engineer jobs?

Cities near Gloucester, MA with the most Remote Windows Systems Engineer job openings:

Remote Windows Systems Engineer jobs near you

AI Engineer - Remote

YO AI Labs

Boston, MA • Remote

$80 - $120/hr

Full-time

Posted 12 days ago

Job description

Senior Software Engineer

Job Type: Contractor (~15 hours/week)
Location: Remote

Job Summary

We are seeking experienced Senior Software Engineers to support an AI training project by creating reinforcement learning environments that evaluate AI models on complex software engineering tasks using Model Context Protocol (MCP) tools.

You will design reproducible environments, deterministic verification, and reference solutions for tasks such as bug fixing, feature implementation, codebase refactoring, and performance optimization. No prior AI experience is required.

Key Responsibilities
  • Create reinforcement learning environments for software engineering tasks.
  • Design tasks involving bug fixing, feature development, refactoring, and performance optimization.
  • Build deterministic verification systems and golden reference solutions.
  • Evaluate AI agents' ability to reason through complex codebases and use MCP tools effectively.
  • Develop realistic, reproducible software engineering scenarios.
  • Ensure tasks accurately measure coding ability, problem-solving, and tool usage.
  • Document solutions and provide clear technical feedback.
Required Skills
  • Strong proficiency in Python 3, Java, Rust, C++, or TypeScript.
  • Strong understanding of algorithms and data structures.
  • Experience with bug fixing and debugging complex software issues.
  • Proven experience in feature implementation and codebase refactoring.
  • Strong knowledge of performance optimization and tuning.
  • Excellent written and verbal communication.
  • Strong attention to detail.
Preferred Qualifications
  • Experience working with large-scale or distributed codebases.
  • Familiarity with AI/ML systems is a plus but not required.
  • Experience with rigorous code reviews and software engineering best practices.
  • Experience working effectively in remote or cross-functional teams.
Hiring Process
  1. Submit an application and screening questions.
  2. Complete an AI interview (~30 minutes).
  3. Complete a technical assessment, if required.
  4. Hiring Manager review.
Compensation

Compensation is output-based, with payment provided per task that meets project specifications. Minimum weekly submission requirements may apply.

Availability

Selected experts should be prepared to begin their first tasks within 24–48 hours of completing onboarding.