Skip to content
MetropolisMetropolisChicago, IL

Technical Support Technician, Tier 2

Serve as Tier 2 escalation support for complex technical issues in a macOS/enterprise environment. Mentor Tier 1 staff, manage hardware lifecycle, administer Jamf Pro MDM and Google Workspace, lead IT projects, and participate in on-call rotation. Requires 3+ years progressive technical support experience.

64k – 89k
On-site3+ YOESupport Engineering

About the role

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
  • Expert proficiency in troubleshooting and resolving issues within a macOS enterprise environment
  • Experience with Jamf Pro, IRU or other MDM system for Apple device management, deployment, and policy enforcement
  • Proficiency with Mac hardware, network printers, peripherals, and advanced network connectivity concepts like TCP/IP, DNS, DHCP, and VPN clients
  • Experience with Google Workspace administration and enterprise mobile device support for iOS and Android
  • Proficiency in IT ticketing systems like Jira, ServiceNow, or Zendesk
  • Exceptional multitasking, analytical, and problem-solving skills in complex support environments
  • Strong communication and interpersonal skills with a customer-focused mindset and experience in fast-paced, high-growth tech environments
  • Able to lift 25 lbs unassisted, bending, kneeling, crouching, reaching, and spending extended periods standing or walking during deployments

Nice-to-haves

  • Familiarity with scripting tools like Bash or Zsh to automate routine IT tasks on macOS
  • Industry certifications such as Jamf Certified Tech/Admin, CompTIA Network+, or Security+

Skills

macOSJamf ProMDMGoogle WorkspaceTCP/IPDNSDhcpVpniOSAndroidJiraServicenowZendeskBashZsh
Ontic

Client Support Specialist

OnticUnited States

Client Support Specialist providing technical support and issue resolution for Ontic's AI-powered security platform. Serves as liaison between clients, success, and product teams; manages tickets, documentation, metrics, and cross-functional collaboration in a remote SaaS environment.

65k – 75k
Remote3+ YOESupport Engineering
Motive

Installations Specialist

MotiveUnited States

Install, maintain, and repair telematics devices, AI cameras, and IoT equipment in customer vehicles. Travel 50-75% for on-site installations, quality checks, customer training, and technical support.

65k – 75k
RemoteSupport Engineering
Intercom

Technical Support Specialist

IntercomChicago, IL

Technical Support Specialist owns complex technical queries, debugs issues, escalates investigations, and collaborates with product teams to improve the platform. Requires 3-4+ years technical support experience, API knowledge, and strong problem-solving in a hybrid Chicago role.

62k – 74k
Hybrid3+ YOESupport Engineering
Tabs

Technical Support Analyst

TabsNew York

Technical Support Analyst troubleshoots complex issues with invoicing, payments, and integrations like NetSuite, QuickBooks, and Stripe for SaaS customers. Requires 3-5 years experience in support, technical aptitude, and strong problem-solving in fast-paced fintech environment.

60k – 83k
Hybrid3+ YOESupport Engineering
Skydio

Technical Support Specialist - West Coast

SkydioUnited States

Provide premier technical support for Skydio's autonomous UAS drone products to commercial customers in utilities, public safety, and infrastructure. Troubleshoot hardware, software, and cloud issues while driving customer satisfaction and retention.

60k – 100k
Remote5+ YOESupport Engineering