Senior IT Engineer

Extreme Reach

Extreme Reach

IT

Chicago, IL, USA

USD 105k-115k / year

Posted on Apr 22, 2026

The Senior IT Engineer plays a critical role in ensuring the stability, security, and scalability of the organization’s global IT environment. This position sits at the intersection of end-user support and enterprise infrastructure, providing hands-on technical expertise across Microsoft 365, cloud platforms, and core systems while delivering a seamless experience for both onsite and remote employees.

Acting as a senior escalation point, this individual is responsible for managing and optimizing Microsoft 365 services, overseeing identity and access management, and maintaining endpoint and infrastructure health across a complex, fast-paced environment. The role combines operational excellence with strategic input—driving automation, improving system performance, and implementing governance and security best practices.

In addition to day-to-day support and troubleshooting, the Senior IT Engineer partners cross-functionally on projects, contributes to continuous improvement initiatives, and helps elevate team capability through documentation and knowledge sharing. This is a highly collaborative, hands-on role suited for someone who thrives in a dynamic environment, takes ownership of challenges, and is motivated to enhance both systems and user experience at scale.

Responsibilities

  • Manage and maintain the overall M365 tenant configuration and health.
  • Support hybrid identity and authentication (Azure AD, SSO, MFA).
  • Administer mail flow, mailbox management, and email security.
  • Configure transport rules, retention policies, and hybrid Exchange setups.
  • Manage site collections, permissions, and sharing settings.
  • Support OneDrive sync issues and implement DLP policies.
  • Configure Teams policies, lifecycle management, and integrations.
  • Support Teams voice, calling plans, and meeting configurations.
  • Implement and monitor Microsoft Defender for Office 365 and Purview.
  • Manage Conditional Access, audit logs, and compliance features.
  • Deploy and manage devices using Microsoft Intune.
  • Configure compliance policies, app protection, and Autopilot.
  • Provide insights and recommendations to improve M365 usage.
  • Develop PowerShell scripts for automation and reporting.
  • Utilize Power Automate and Graph API for workflow automation.
  • Act as Tier 3 support for M365-related issues.
  • Extensive knowledge of Windows OS’s & MAC OS's
  • Administer and support global active directory domain including but not limited to DHCP, DNS, Group Policy, Sites & Services.
  • Undertake additional duties and special projects as assigned.

Pursuant to Chicago's Pay Transparency Laws, the base pay range for this position is $105,000-$115,000 per year; base pay offered may vary depending on job-related knowledge, skills, and experience.

  • 5+ years of experience managing Microsoft 365 environments.
  • Strong expertise in Exchange Online, SharePoint Online, Microsoft Teams, and Intune.
  • Deep understanding of Active Directory (AD) and Azure Active Directory (Azure AD), including:
    • Group Policy Objects (GPOs), OU structure, and domain trust relationships.
    • User and group management, permissions, and access control.
    • AD replication, DNS, and troubleshooting domain-related issues.
  • Experience with hybrid identity environments, including Azure AD Connect and synchronization troubleshooting.
  • Proficiency in PowerShell scripting for automation, reporting, and bulk operations.
  • Solid grasp of Conditional Access, MFA, and identity protection strategies.
  • Familiarity with compliance tools such as eDiscovery, DLP, and audit logging.
  • Excellent troubleshooting, documentation, and communication skills.
  • End point management systems (Jamf, Intune, Endpoint Central).
  • Troubleshooting remote and onsite user issues across multiple different endpoint types and OSs.
  • In-depth understanding of Microsoft Active Directory.
  • VMware/vSphere experience (installation, configuration, maintenance and troubleshooting).
  • Experience with Linux & Windows Servers.
  • Domain trusts, AD replication, AD Connect, GPO, OU structure management.
  • Storage skills, Fibre channel, ISCSI, SAN and NAS.
  • Experience with cloud technologies, especially Azure, AWS, EC2, WorkSpaces .
  • Technical proficiency and knowledge of IT infrastructure, networks, and systems to effectively manage and troubleshoot issues.