Desktop Support Technician II

Jackson Dawson • Dearborn, MI

3h • $27 - $32 • Onsite

About The Position

Jackson Dawson is hiring an experienced Desktop Support Technician II to join our IT team. This is a hands-on, senior-level individual contributor role for someone who thrives on solving the tough tickets, owning end-to-end device lifecycle work, and being the go-to technical presence both in our offices and out in the field at client events.

You'll operate with a high degree of autonomy — handling escalations from our Level I technician, leading imaging and provisioning workflows, and serving as the senior on-site IT presence at experiential marketing activations. You'll also act as an informal technical mentor to our Level I technician, sharing your knowledge and helping raise the bar for the whole team.

If you like variety — one day tuning up an Intune policy, the next day making sure a fleet of show computers is production-ready for a client activation — this role will keep you engaged.

Requirements

• 2–4 years of hands-on experience in a desktop support or IT technician role.
• Demonstrated proficiency supporting both Windows 10/11 and macOS in a business environment.
• Solid working knowledge of Microsoft 365, including advanced troubleshooting of Outlook, Teams, SharePoint, and OneDrive.
• Hands-on experience with MDM platforms — Microsoft Intune and/or Apple Business Manager.
• Experience with computer imaging and device provisioning for both Windows and Mac.
• Working knowledge of networking fundamentals: TCP/IP, DNS, DHCP, wireless, and VPN client troubleshooting.
• Familiarity with Active Directory or Microsoft Entra ID for basic user and device management.
• Experience supporting iOS devices (iPad/iPhone), including MDM enrollment and configuration.
• Proven ability to work independently, manage a ticket queue, and resolve complex issues without close supervision.
• Strong written communication skills — you can produce documentation that others can actually follow and build on.

Nice To Haves

• CompTIA A+, Network+, or Microsoft 365 Certified: Modern Desktop Administrator (MD-102).
• Experience supporting technology at live events, activations, or other fast-paced client-facing environments.
• Basic scripting for automating repetitive tasks (PowerShell preferred).
• Familiarity with Microsoft Defender for Endpoint or similar EDR at the end-user/device level.
• Experience coordinating with vendors for hardware warranty, repair, or replacement.

Responsibilities

• Serve as the escalation point for complex issues from the Level I technician and drive them to resolution with minimal direction.
• Diagnose and resolve advanced hardware issues on Windows PCs, Macs, laptops, displays, and peripherals, including component-level troubleshooting and vendor warranty coordination.
• Install, configure, and optimize business software on Windows and macOS, including conflict and compatibility resolution.
• Provide advanced Microsoft 365 support — mailbox configuration, Teams administration, SharePoint permissions, and OneDrive sync troubleshooting.
• Spot recurring patterns and recommend process or tooling improvements to the IT Administration & Help Desk Manager.
• Own the end-to-end imaging and provisioning process for Windows and Mac devices, including build configuration, software packaging, and security baselines.
• Prepare and validate show computers for client events, ensuring software, branding assets, and client-specific configurations are production-ready.
• Manage device enrollment, configuration profiles, and policies in Microsoft Intune and Apple Business Manager.
• Lead hardware refresh cycles: scheduling, data migration, decommissioning, and asset record accuracy.
• Maintain and improve imaging templates and provisioning runbooks, and keep the Level I technician up to speed on changes.
• Configure, manage, and troubleshoot iPads and iOS devices for both employee and client event use — MDM enrollment, app deployment, and configuration profiles.
• Support Android devices where applicable.
• Resolve advanced connectivity, application, and MDM policy issues across office and event environments.
• Diagnose and resolve end-user and device-level network issues across wired and wireless environments; escalate infrastructure-layer issues to IT Operations with clear documentation.
• Deploy, configure, and troubleshoot VPN clients for remote and traveling employees.
• Assist IT Operations with basic network tasks — switch port configuration, VLAN assignments, and access point provisioning — as directed.
• Set up and troubleshoot AV and presentation technology in conference rooms and event spaces.
• Lead the technology side of new hire onboarding: workspace build, account provisioning coordination, device handoff, and IT orientation.
• Travel to client events and experiential activations as the senior on-site IT presence.
• Plan, set up, test, and tear down show computers, displays, and supporting hardware; validate full technology readiness before go-live.
• Own on-site issue resolution during events and make sound judgment calls under time pressure in client-facing environments.
• Brief the Level I technician on event-specific configurations when deployed together.
• Provide pre- and post-event status reporting to the IT Administration & Help Desk Manager.
• Serve as the informal technical lead and day-to-day resource for the Level I technician — answering questions, reviewing work, and coaching through complex issues. (This is a mentoring relationship, not a management one.)
• Contribute to and maintain the IT knowledge base; document new solutions, update outdated procedures, and flag gaps.
• Log all support requests and resolutions in the ticketing system with thorough, KB-quality descriptions.
• Set the documentation standard for the team by reviewing and validating quality on escalated tickets.
• Maintain accurate records of device inventory, loaner equipment, and asset assignments.
• Surface systemic issues, recurring failures, and process gaps — with recommended solutions — to the IT Administration & Help Desk Manager.

Benefits

• You'll work at the intersection of enterprise IT and experiential marketing — supporting the technology behind live client activations for some of the most recognizable brands in the industry. It's a role where technical depth, calm judgment under pressure, and a client-ready presence all matter.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed