M365 & Windows Systems Engineer: Automation

LegalSight LLC; United States; Hybrid; USD 110,000 - 140,000; Full time

Benefits offered by this job

Hybrid work: 2 in-office days/week

Commutable to Ocean City, NJ

Job summary

LegalSight LLC seeks a high-energy IT Systems Engineer to own and modernize our Microsoft 365 and Windows environment. You’ll build automation to replace repetitive tasks, script complex workflows, and ensure governance across Entra ID, Purview, SharePoint Online, and Intune.

You will lead by doing, mentor peers, and drive changes with minimal supervision, while collaborating with engineering, security, and operations to align systems with business needs.

Qualifications

• 4+ years administering Windows and Microsoft 365 environments with real ownership.
• Ability to lead by doing and mentor teammates.
• Strong automation mindset to reduce repetitive manual work and enable self-service.
• Proficient with PowerShell and, ideally, Microsoft Graph API for automation.
• Hands-on experience with Microsoft Purview information protection, retention/DLP, and encryption concepts.
• SharePoint Online administration, architecture, and governance responsibilities.
• Solid Entra ID / Azure AD fundamentals including conditional access and MFA.
• Windows endpoint/server administration: Intune/MDM, GPO, patching, OS troubleshooting.
• High energy, ownership mindset, bias for action, and strong documentation habits.
• Excellent written communication and ability to document configurations.

Responsibilities

• Administer and harden the Microsoft 365 tenant end to end: Entra ID, Exchange Online, SharePoint Online, OneDrive, Teams, and Intune.
• Own data governance and compliance tooling in Microsoft Purview: retention, DLP, eDiscovery, and information protection configuration.
• Automate recurring admin tasks and create hands-off workflows using PowerShell, Microsoft Graph, Power Automate, and runbooks.
• Manage Windows systems across the fleet: endpoint configuration, imaging, provisioning, and OS-level troubleshooting.
• Investigate cross-system issues such as label/policy conflicts and identity/access edge cases.
• Administer SharePoint Online: site architecture, permissions, sharing governance, and lifecycle.
• Build and maintain identity/access workflows: provisioning/deprovisioning, conditional access, MFA, and least-privilege design.
• Support the company-wide helpdesk by identifying automatable patterns.
• Monitor tenant/endpoint health and drive remediation to closure.
• Document configurations and runbooks for team-wide maintainability.
• Partner with engineering, security, and operations for integrations and alignment.

Skills

Windows & Microsoft 365

Automation mindset

PowerShell

Microsoft Graph API

Entra ID / Azure AD

SharePoint Online administration

Intune/MDM admin

Documentation

Ownership & accountability

Written communication

Education

Microsoft 365/MS-102 certification (optional)

Tools

PowerShell

Microsoft Graph API

SharePoint Online admin tooling

Job description

LegalSight LLC seeks a high-energy IT Systems Engineer to own and modernize our Microsoft 365 and Windows environment. You’ll build automation to replace repetitive tasks, script complex workflows, and ensure governance across Entra ID, Purview, SharePoint Online, and Intune.

You will lead by doing, mentor peers, and drive changes with minimal supervision, while collaborating with engineering, security, and operations to align systems with business needs.