Senior Systems Administrator

Reposted 9 Days Ago
Be an Early Applicant
Boston, MA, USA
In-Office
90K-115K
Senior level
Automotive • Professional Services • Retail • Transportation
The Role
Administer Microsoft 365, Entra ID, Intune, Azure, AWS, networks, VoIP, and security infrastructure. Develop PowerShell and Power Automate solutions, support AI platforms, troubleshoot escalated technical issues, mentor junior staff, and lead infrastructure projects, technology rollouts, and acquisition integrations across a multi-site organization.
Summary Generated by Built In

Description

  

Join a Team Built on Growth, Innovation, and Technology

Are you an experienced IT professional who enjoys solving complex technical challenges, automating business processes, and building scalable technology solutions?

At Gills Point S, technology is a key driver of our continued growth. We're looking for a Senior Systems Administrator to help manage and modernize the infrastructure supporting our multi-state organization. This role combines cloud administration, networking, security, automation, AI technologies, and technical leadership within a fast-paced environment where your ideas and expertise can make a real impact.

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.

Skills Required

  • 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, preferably MS-102 or equivalent
  • Strong PowerShell scripting and automation skills
  • Experience troubleshooting complex technical issues independently
  • Solid understanding of networking, security, and infrastructure best practices
  • 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
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The Company
HQ: Bend, OR

What We Do

Gills Point S Tire & Auto Service is a family-operated network of tire and auto service centers offering tire sales, express installations, maintenance, and vehicle repairs across the United States. With over 135 locations in 17 states and membership in the Point S co‑op, it combines local hometown service with national buying power, warranty coverage, financing options, and a loyalty program to deliver convenient, transparent auto care.

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