Desktop Support Technician II

About the Role

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.

Work environment: On-site (Dearborn, MI)

What You'll Do

Advanced End-User Support

• 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.

Device Imaging, Provisioning & Lifecycle

• 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.

Mobile Device Management

• 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.

Connectivity & Workspace Support

• 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.

Event & Show Site Support

• 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.

Mentorship & Knowledge Sharing

• 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.

Documentation & Help Desk Operations

• 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.

What You Bring

Qualifications

• 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.

Preferred

• 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.

Why Jackson Dawson

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.

Jackson Dawson is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, or protected veteran status.