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Technical Support Technician, Tier 2

Metropolis · Chicago, Illinois, United States · Posted Jul 6, 2026

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Who we are

The real world is the next frontier, and at Metropolis, we are creating the artificial intelligence to make it responsive. We are pioneering the Recognition Economy — a future where mundane repetition disappears and being known unlocks access, comfort and belonging everywhere you go. From transforming parking into a seamless drive-in, drive-out experience for millions of Members to expanding our intelligence layer across retail and hospitality, we are building a world that feels instinctive and magical. The future isn’t coming; it’s here, and we need builders, innovators and problem solvers to help us create it.

Who you are

Metropolis is seeking a seasoned, proactive, and solution-oriented IT Support Technician, Tier 2 to provide advanced IT support and contribute to strategic IT initiatives for our internal teams. This role moves beyond foundational support, requiring deeper technical expertise to diagnose and resolve complex issues, mentor Tier 1 staff, and actively participate in IT projects. You will play a critical part in maintaining robust IT infrastructure and ensuring smooth, efficient business operations as Metropolis continues to scale. This position is ideal for a highly capable problem-solver eager to take on greater responsibility and leadership within a dynamic IT environment.

What you'll do

Serve as an escalation point for Tier 1 support, resolving complex technical issues using advanced troubleshooting techniques

Mentor Tier 1 technicians and support knowledge transfer through best practices and guidance

Lead and contribute to IT projects including system upgrades, software rollouts, and infrastructure improvements

Manage IT hardware lifecycle: procurement, inventory, configuration, deployment, and decommissioning

Administer and troubleshoot macOS, Jamf Pro (MDM), Google Workspace, basic server/network functions, and enterprise applications

Enforce IT security best practices, support policy implementation, and assist in incident response

Document complex technical issues, configurations, and processes for the internal knowledge base

Collaborate with Tier 3 and other IT teams to resolve systemic issues and maintain operational continuity

Communicate proactively with end-users and stakeholders, ensuring transparency and professionalism

Participate in a rotating on-call schedule to provide after-hours and weekend support as required, while building technical skills and providing backup coverage as needed

What we're looking for

3+ years of progressive technical support experience, including 1–2 years in a Tier 2 or escalation role

Demonstrate expert proficiency in troubleshooting and resolving issues within a macOS enterprise environment

Possess experience with Jamf Pro, IRU or other MDM system for Apple device management, deployment, and policy enforcement

Demonstrate proficiency with Mac hardware, network printers, peripherals, and advanced network connectivity concepts like TCP/IP, DNS, DHCP, and VPN clients

Possess experience with Google Workspace administration and enterprise mobile device support for iOS and Android

Demonstrate proficiency in IT ticketing systems like Jira, ServiceNow, or Zendesk

Apply exceptional multitasking, analytical, and problem-solving skills in complex support environments

Exhibit strong communication and interpersonal skills with a customer-focused mindset and experience in fast-paced, high-growth tech environments

Able to lift 25 lbs un-assistated, bending, kneeling, crouching, reaching, and spending extended periods standing or walking during deployments

While not required, these are a plus:

Possess familiarity with scripting tools like Bash or Zsh to automate routine IT tasks on macOS

Possess industry certifications such as Jamf Certified Tech/Admin, CompTIA Network+, or Security+

4 Days in Office: Metropolis values in-person collaboration to drive innovation, strengthen culture, and enhance the Member experience. Our corporate team members hold to our office-first model, which requires employees to be on-site at least four days a week, fostering organic interactions that spark creativity and connection

When you join Metropolis, you'll join a team of world-class product leaders and engineers, building an ecosystem of technologies at the intersection of parking, mobility, and real estate. Our goal is to build an inclusive culture where everyone has a voice and the best idea wins. You will play a key role in building and maintaining this culture as our organization grows. The anticipated base pay for this position is $31.00 USD to 43.00 USD hourly. The actual base salary offered is determined by a number of variables, including, as appropriate, the applicant's qualifications for the position, years of relevant experience, distinctive skills, level of education attained, certifications or other professional licenses held, and the location of residence and/or place of employment. Base salary is one component of Metropolis' …

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