Position Title:  IT Technical Lead 

Department: Information Technology 

Reports To: Director of IT 

Location: Hybrid - Chicago Corporate Office (3 days/week) 

FLSA Status: Exempt 

Salary Range:  $110,000 - $120,000 annually

Job Summary 

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. 

Key Responsibilities 

Project Delivery & Coordination (60%) 

• 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 

Technical Responsibilities (30%) 

• 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 

Support & Collaboration (10%) 

• 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 

Technology Environment 

You'll work with enterprise platforms across our business units: 

• Microsoft 365 Ecosystem: Exchange, SharePoint, Teams, OneDrive, Entra ID, Intune, Defender 

• RealPage: Property management platform (130+ properties) 

• Autodesk Construction Cloud: Construction management for GCDC 

• Paycom: HRIS, payroll, expense management 

• Microsoft Power Platform: Power Automate, Power BI for workflow automation and reporting 

• Azure SQL: Internal database and reporting platform 

Education & Experience 

• Bachelor's degree in Information Technology, Computer Science, or related field preferred; equivalent combination of education and experience considered 

• 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 

• Property management, real estate, or affordable housing industry experience a plus 

Licenses & Certifications 

Preferred (not required): 

• MS-102: Microsoft 365 Administrator Expert 

• AZ-104: Azure Administrator Associate 

• SC-300: Identity and Access Administrator 

• ITIL 4 Foundation 

• CompTIA Security+ or equivalent 

Technical Skills  

Required: 

• 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 

Preferred: 

• 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) 

General Skills 

• 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 

Work Environment & Physical Demands  

• Hybrid work schedule: 3 days in Chicago corporate office (Monday, Wednesday, Thursday), 2 days remote 

• Primarily desk-based computer work in climate-controlled office environment 

• Occasional travel to properties for technology implementations or troubleshooting (less than 10%) 

• Ability to lift and carry IT equipment up to 35 pounds 

• Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions 

Why Join Evergreen?  

Join Evergreen Real Estate Group at a pivotal moment as we professionalize IT operations to support growth from 130 to 260 properties by 2030. 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.