Job Description
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.
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.
💡 Quick Summary
Seeking a career-building opportunity? The IT Technical Lead position is now open for candidates interested in the IT Engineer & Developer Jobs sector. This role in Chicago offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in IT Engineer & Developer Jobs is a plus.
