Senior Systems Administrator

Gills Point S Tire and Auto Service

• $95K — $115K *
Boston, MA 02115In-Person
Information Technology
Less than 5 years of experience
Today
Be an Early Applicant
Job Overview by Ladders

Qualifications

  • 4+ years of experience in systems administration, infrastructure, networking, or cloud environments.
  • Hands-on experience with Microsoft 365, Entra ID, and Intune.
  • Microsoft 365 administration certification (MS-102 preferred).
  • Strong PowerShell scripting and automation abilities.
  • Proficiency in troubleshooting complex technical issues.
  • Solid understanding of networking, security, and infrastructure best practices.

Responsibilities

  • Administer Microsoft 365 services such as Exchange Online, SharePoint, and Teams.
  • Manage identity services through Microsoft Entra ID, including Conditional Access and MFA.
  • Support endpoint management and software deployment using Intune.
  • Maintain hybrid cloud infrastructure in Azure and AWS environments.
  • Develop automation scripts in PowerShell to enhance efficiency and reporting.
  • Support network infrastructure, including firewalls, switches, and VPNs.
  • Administer enterprise VoIP systems and monitor system performance.

Benefits

  • Competitive pay and comprehensive benefits package
  • 401(k) plan with company match
  • Support for professional development and certifications
  • Exposure to cloud, automation, and AI technologies
  • Opportunities for career growth in a rapidly expanding company
  • Collaborative and family-oriented work culture that fosters innovation.
Full Job Description
Job Type

Full-time

Description

What You'll Do

Cloud & Systems Administration:
  • Administer Microsoft 365, including Exchange Online, SharePoint, OneDrive, Teams, licensing, and tenant management.
  • Manage Microsoft Entra ID, Conditional Access, MFA, and identity governance.
  • Support Intune, endpoint management, software deployment, patching, and asset lifecycle processes.
  • Maintain hybrid cloud infrastructure across Azure and AWS environments.
  • Develop PowerShell automation to improve efficiency, consistency, and reporting.

Network, VoIP & Security:
  • Support network infrastructure across multiple locations, including firewalls, switches, wireless networks, VPNs, and DNS.
  • Administer and troubleshoot enterprise VoIP systems.
  • Monitor system performance, reliability, and availability.
  • Support cybersecurity operations, endpoint protection, vulnerability remediation, audits, and security frameworks such as NIST and ITIL.

Automation & AI Solutions:
  • Administer Microsoft Copilot and other approved AI platforms.
  • Build workflow automation using Power Automate, PowerShell, and RMM tools.
  • Identify manual processes and implement solutions that improve productivity and scalability.
  • Support future integration, orchestration, and data connectivity initiatives.

Technical Leadership & Projects:
  • Serve as a Tier 2/3 escalation resource for complex technical issues.
  • Mentor junior IT team members and contribute to documentation and process improvement.
  • Lead infrastructure projects, technology rollouts, and acquisition integrations.
  • Help establish standards that support organizational growth and operational excellence.


Requirements

What We're Looking For:

Required Qualifications:
  • 4+ years of progressive experience in systems administration, infrastructure, networking, or cloud environments.
  • Hands-on experience with Microsoft 365, Entra ID, and Intune.
  • Microsoft 365 administration certification (MS-102 preferred or equivalent).
  • Strong PowerShell scripting and automation skills.
  • Experience troubleshooting complex technical issues independently.
  • Solid understanding of networking, security, and infrastructure best practices.

Preferred Qualifications:
  • Azure and/or AWS administration experience.
  • CCNA, Network+, Security+, or related certifications.
  • Experience with NIST or ITIL frameworks.
  • VoIP administration experience.
  • Experience with Microsoft Copilot, enterprise AI platforms, or workflow automation tools.
  • Experience supporting multi-site organizations and technology integrations related to growth or acquisitions.

Why Join Gills Point S?
  • Competitive pay and comprehensive benefits
  • 401(k) with company match
  • Professional development and certification support
  • Opportunities to work with cloud, automation, and AI technologies
  • Career growth within a rapidly expanding organization
  • Collaborative, family-oriented culture that values innovation and new ideas

At Gills Point S, you'll help build the technology foundation that supports our future growth. If you're ready to make a meaningful impact through automation, cloud technologies, and technical leadership, we'd love to hear from you.
* Ladders Estimates

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