IT Technical Lead

EVERGREEN REAL ESTATE SERVICES LLC • Chicago, IL

1d • $110,000 - $120,000 • Hybrid

About The Position

The IT Technical Lead serves as the primary translator between IT strategy and daily execution for Evergreen Real Estate Group, an affordable housing organization managing 130+ properties serving 15,000+ residents nationwide. This senior individual contributor role owns project delivery, MSP coordination, process documentation, and technical oversight-enabling the Director of IT to focus on strategic initiatives while ensuring operational excellence. The ideal candidate combines strong technical skills with a business process engineering mindset, understanding that technology serves mission outcomes: transforming communities and improving lives.

Requirements

• 5+ years of progressive IT experience with demonstrated project leadership
• Experience coordinating with managed service providers or external IT vendors
• Track record of translating business requirements into technical solutions
• Microsoft 365 administration (Exchange, SharePoint, Teams, OneDrive)
• PowerShell scripting for automation and administration
• SQL query writing and basic database management
• IT project management and documentation practices
• Strong documentation habits and attention to procedural detail
• Ability to translate technical concepts for non-technical stakeholders
• Proactive problem identification and resolution
• Comfortable working with ambiguity; creates clarity for others
• Vendor management and relationship building
• Collaboration across departments with varying technical literacy
• Results orientation-focus on business outcomes, not just technical elegance

Nice To Haves

• Property management, real estate, or affordable housing industry experience a plus
• MS-102: Microsoft 365 Administrator Expert
• AZ-104: Azure Administrator Associate
• SC-300: Identity and Access Administrator
• ITIL 4 Foundation
• CompTIA Security+ or equivalent
• Entra ID (Azure AD) identity and access management
• Python scripting for automation and integrations
• RealPage OneSite or similar property management software
• Microsoft Intune and Defender for endpoint management and security
• Power Platform (Power Automate, Power BI, Power Apps)
• Azure SQL database querying and basic administration
• API integration experience (REST, webhooks)

Responsibilities

• Lead technology implementations, migrations, and system upgrades from planning through completion
• Serve as primary escalation point for MSP (managed service provider) coordination, ensuring SLA compliance and quality delivery
• Develop and maintain IT policies, standard operating procedures, and technical runbooks
• Track project status, dependencies, and milestones; provide regular updates to IT Director and stakeholders
• Identify process inefficiencies and implement technology-enabled improvements across business units
• Coordinate cross-functional technology initiatives with Property Management, HR, Accounting, Development, and Construction teams
• Develop and maintain automation scripts (PowerShell, Python, SQL) to improve operational efficiency and reduce manual work
• Provide technical oversight for Microsoft 365, Entra ID, and Azure environments
• Support security posture through compliance monitoring, policy enforcement, and incident response coordination
• Serve as backup for Data Engineer on EREG-BIX database operations and reporting platform
• Evaluate emerging technologies and make recommendations aligned with business objectives
• Provide Tier 2/3 escalation support for complex technical issues beyond MSP scope
• Mentor and provide technical guidance to Systems Administrator and other IT team members

Benefits

• This role offers end-to-end ownership of meaningful projects, opportunities to shape technology strategy, and a clear path to management as our team grows.
• Your work directly impacts 15,000+ residents and enables our mission: providing safe, quality affordable housing for everyone.
• Evergreen Real Estate Group is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level