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
- 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.