IT Technical Lead

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.