Technical Support Technician, Tier 2 Chicago, Illinois, United States

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‑assisted, 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’ total compensation package, which may also include access to or eligibility for healthcare benefits, a 401(k) plan, short‑term and long‑term disability coverage, basic life insurance, a lucrative stock option plan, bonus plans, and more. Metropolis may utilize an automated employment decision tool (AEDT) to assess or evaluate your candidacy for employment or promotion. AEDTs are used to assist in assessing a candidate’s application relative to the required job qualifications and responsibilities listed in the job posting. As part of this process, Metropolis retains data relevant to your candidacy, including personal information, for a period that is reasonably necessary for the use of the tool. If you are hired for the position, your data may become part of your employee records. Metropolis Technologies is an equal opportunity employer. We make all hiring decisions based on merit, qualifications, and business needs, without regard to race, color, religion, sex (including gender identity, sexual orientation, or pregnancy), national origin, disability, veteran status, or any other protected characteristic under federal, state, or local law. #J-18808-Ljbffr metropolis.io