IT Operations Lead

29th Street • Chicago, IL

4d • $90,000 - $100,000

About The Position

Are you a detail-driven Systems Administrator who thrives on ownership, structure, and continuous improvement? At 29th Street, you will play a critical role supporting a growing real estate investment and property management environment — with corporate users and distributed property locations nationwide. This is an operational role where your expertise ensures technology is secure, aligned, and reliable across the organization. You’ll establish and enforce standards, monitor compliance, and drive execution in partnership with internal teams and our co-managed MSP. If you’re energized by making IT systems predictable, secure, and well-governed, you’ll thrive here.

Requirements

• Hands-on administration of Microsoft 365 + Entra ID
• Intune compliance & Conditional Access experience
• Co-managed MSP operations + vendor coordination
• Strong documentation and operational discipline
• Excellent communication and collaboration skills

Nice To Haves

• PowerShell / Graph scripting
• Autotask and/or Jira Service Management experience
• Experience supporting distributed user environments

Responsibilities

• Manage Intune compliance, device lifecycle, and Autopilot standards
• Enforce Conditional Access and MFA requirements
• Audit identity posture and remediate configuration drift
• Govern Microsoft Teams, SharePoint, OneDrive, and M365 Groups
• Maintain secure and well-organized collaboration environments
• Support cross-tenant access for multiple business units
• Lead daily support operations in Autotask with MSP delivery partners
• Improve workflows and visibility through Jira Service Management
• Track SLAs and ensure accountability through evidence and cadence
• Maintain accurate hardware/software inventory for reporting and audits
• Oversee secure onboarding/offboarding and timely access removal
• Develop and enforce system configuration and operational standards
• Produce operational metrics and drive compliance improvements
• Execute small/medium projects with clear plans and outcomes

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: High school or GED