Service Desk Technical Lead

Illinois Housing Development • Chicago, IL

53d • $81,117 - $101,397 • Hybrid

About The Position

The Service Desk Technical Lead serves as a critical liaison between end users, service desk agents, and IT support teams, providing expert guidance and hands-on support for both first- and second-level technical issues. This role functions as the primary escalation point for complex or unresolved incidents, ensuring timely and effective resolution to minimize disruption to business operations. Departments across the organization rely on this individual to address technical challenges that hinder productivity. The Technical Lead is expected to respond swiftly and efficiently, while also collaborating with the team to implement sustainable solutions that prevent recurring issues. Through proactive leadership, technical expertise, and a commitment to continuous improvement, this role helps elevate the overall performance and reliability of IT support services.

Requirements

• Minimum of 10 years of hands-on experience supporting and administering Microsoft Windows environments.
• At least 5 years of experience in a call center or service desk support setting.
• Proven track record with 7–10 years in Tier 2/Tier 3 technical support, including leadership responsibilities within a service desk team.
• Deep understanding of computer systems, hardware, software, and audio-visual equipment in enterprise environments.
• Strong analytical and troubleshooting skills, with the ability to resolve complex technical issues efficiently.
• Excellent interpersonal and communication skills, with the ability to collaborate across teams and engage with users at all levels.

Nice To Haves

• Experience with creating and deploying PC images is preferred.
• Proficiency in Microsoft 365 cloud services, Office Suite, System Center Configuration Manager (SCCM), Azure, Intune, and SharePoint is preferred.
• Proficiency with Automation technologies such as Powershell, Power Automate, or similar is highly preferred.
• Functional knowledge and in-depth understanding of ITIL framework is highly preferred.

Responsibilities

• Serve as the primary escalation point for service desk agents when technical issues exceed first-level resolution capabilities, ensuring timely and effective support for end users.
• Foster cross-functional collaboration by working closely with internal departments and broader workgroups to maintain ownership of user-reported issues, driving resolution within established service-level expectations.
• Provide technical leadership and oversight by evaluating the effectiveness of current support methodologies, identifying gaps, and implementing innovative solutions to enhance service desk performance and user satisfaction.
• Assess training needs and deliver targeted learning sessions to strengthen the technical proficiency of service desk staff, ensuring the team remains current with evolving technologies, tools, and best practices.
• Perform all other duties as assigned.

Benefits

• Paid time off, plus paid holidays
• Currently in a hybrid work arrangement, but candidates must reside in Illinois at time of hire
• Medical/dental/vision insurance plan
• Life insurance
• Short/long term disability
• Tuition reimbursement
• Flex spending
• 401K plan – immediate vesting
• IHDA employees may be eligible for federal loan forgiveness programs

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 251-500 employees