Support Jobs in Milton, WI

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30d ago

IT Support Specialist - II

Diamond Assets Milton, WI

Milton, WI

30d ago Closed

Full time Apple Business Manager Computer Skills End User Support

This position is no longer accepting applications (closed Aug 12, 2026).

Job Description

Diamond Assets is seeking an IT Support Specialist II to provide advanced on-site technical support in Milton, WI.

Responsibilities

Act as the escalation point for Level 1 IT Support staff, independently resolving complex end-user, departmental, and client issues.
Install, configure, and roll out hardware and software, maintain standard deployment configurations, and manage imaging and provisioning workflows.
Execute advanced MDM and client deployments, handling device configuration, policy management, software setup and distribution, and iteratively refine deployment standards.
Define, document, and enforce technical standards across deployed systems to ensure consistency and repeatability.
Mentor and train Level 1 specialists, reviewing work to develop their technical and customer service skills.
Own and maintain the IT knowledge base and documentation standards; administer the IT Help Desk system, monitor queue health, categorization, and SLA adherence.
Handle escalated, client-facing technical situations professionally with clear communication.
Lead small to medium projects and contribute to larger initiatives under the IT Operations Manager.

Requirements

Mandatory: Technical College degree in Information Technology, end-user devices, or related field, or equivalent experience; required certifications include CompTIA A+ and Apple Certified Support Professional.
3+ years of hands-on end-user support and device repair experience or demonstrated equivalent capability at the Level 1 role.
Advanced proficiency supporting macOS, iOS, iPadOS, and Windows end-user environments.
Deep hands-on MDM and client deployment experience, including configuration profiles, policy management, software distribution, and Apple Business/Apple School workflows.
Proven ability to diagnose and repair electronic devices with sound judgment on repair versus disposition outcomes.
Track record of supporting productivity software, email, collaboration tools, and end-user networking concerns.
Ability to mentor or train less experienced staff and lead by example.
Exceptional customer service skills, including handling escalated or sensitive client interactions.
Strong problem-solving abilities: identifying, researching, troubleshooting, and resolving technical issues with minimal supervision.
Thorough documentation discipline for supported systems, procedures, and processes.
Robust organizational and task-management skills, with the ability to prioritize across competing demands.

Technologies

macOS
iOS
iPadOS
Windows
Apple Business Manager
Apple School Manager
Mobile Device Management (MDM)

Benefits

401(k)
401(k) matching
Dental insurance
Health insurance
Life insurance
Retirement plan
Tuition reimbursement
Vision insurance

Company overview

Diamond Assets partners with schools, businesses, and governments to design sustainable technology plans that extend equitable access to devices now and into the future. The company also delivers high-quality refurbished Apple products at affordable prices and follows a lifecycle through epicycle approach to meet its mission of affordable, equitable technology access.

Beyond

The role requires ongoing learning and contribution in a fast-moving, productive environment, with high expectations for communication, teamwork, and problem solving.

Ability to commute

Milton, WI 53563 (Required)

Work location

On site, in person

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