Senior IT Support Specialist — Mac/iOS & Windows

Diamond Assets

Town of Milton (WI)

On-site

USD 55,000 - 75,000

Full time

14 days+

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Job summary

Diamond Assets in Wisconsin is seeking an experienced IT Support Specialist 2 to serve internal and external clients, own complex problems, and drive high‑quality end‑user experiences while shaping support standards and documentation.

You will collaborate with the CIO on priorities, install and deploy hardware/software, perform advanced MDM and device configuration, mentor Level 1 staff, and maintain the IT knowledge base and ticketing workflows to ensure reliable service.

Qualifications

Technical College degree in Information Technology or equivalent experience is mandatory; certifications such as CompTIA A+ and ACSP are required.
3+ years of hands-on end-user support and device repair experience or equivalent at Level 1.
Advanced proficiency supporting macOS, iOS, iPadOS, and Windows end-users.
Deep MDM and client deployment experience including configuration profiles, policy management, software distribution, and Apple Business/Apple School workflows.
Demonstrated ability to diagnose and repair electronic devices with good repair-versus-disposition judgment.
Proven track record supporting productivity software, email, collaboration systems, and end-user networking concerns.
Ability to mentor or train less experienced staff and lead by example.
Exceptional customer service aptitude, including with escalated or sensitive client interactions.
Strong problem-solving abilities with minimal supervision and meticulous documentation across systems.

Responsibilities

Serve as the escalation point for Level 1 staff, resolving complex end-user and client issues.
Install, configure, and deploy hardware and software, including imaging and provisioning workflows.
Perform advanced MDM and device configuration, policy management, and software distribution.
Define, document, and enforce technical standards across deployed systems.
Mentor, train, and review Level 1 specialists and grow the team.
Own and maintain the IT knowledge base and IT Help Desk ticketing system.
Lead small-to-medium projects and support larger initiatives under the IT Operations Manager.
Handle escalated client-facing technical situations with professionalism and clear communication.