IT Support Specialist II

Diamond Assets; Town of Milton (WI); On-site; USD 55,000 - 75,000; Full time

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.

Skills

End-user support

macOS

iOS/iPadOS

Windows

MDM deployment

Troubleshooting

Customer service

Documentation

Mentoring/leadership

Project coordination

Education

Technical College degree in Information Technology

CompTIA A+

Apple Certified Support Professional (ACSP)

Tools

Apple Business / Apple School

MDM tools

Deployment imaging workflows

IT Help Desk ticketing system

Job description

Company Overview

It’s not enough to have the right technology today, you must have a plan for tomorrow. At Diamond Assets we service schools, businesses, and governments by creating sustainable technology plans that ensure equitable access to technology for their current fleet but also well into the future. In addition, we take pride in delivering the highest-quality, refurbished Apple products at an affordable price. With our “lifecycle through upcycle” approach, we strive to meet our mission of providing equitable and affordable access to technology.

Job Title: IT Support Specialist 2

The IT Support Specialist 2 is an experienced technical resource who serves both internal and external clients and acts as the primary escalation point for first-line support staff. Building on the foundation of the Support Specialist 1 role, this position takes ownership of complex problems and troubleshooting, delivers high-quality technology experiences for end-users, and helps set the standards, workflows, and documentation the support team relies on day to day.

Expect to work closely with the CIO on prioritization, issue resolution, projects. This role embodies all of Diamond Assets’ Core Values: Teamwork, Flexibility, Service, Integrity, and Innovation.

Responsibilities:

• Serve as the escalation point for IT Support Specialist 1 staff, independently resolving complex end-user, department, and client issues.
• Install, configure, and deploy hardware and software, including building and maintaining standard deployment configurations and imaging/provisioning workflows.
• Perform advanced MDM and client deployment work — device configuration, policy management, software setup and distribution — and refine deployment standards over time.
• Define, document, and enforce technical standards and specifications across deployed systems, ensuring consistency and repeatability.
• Mentor, train, and review the work of Level 1 specialists, helping them grow their technical and customer service skills.
• Own and maintain the IT knowledge base, documentation standards, and administer the IT Help Desk Ticketing System (queue health, categorization, SLA adherence).
• Lead small-to-medium projects and contribute to larger initiatives under the IT Operations Manager.
• Handle escalated, client-facing technical situations with professionalism and clear communication.

Qualifications:

• Technical College degree in Information Technology, end-user devices, a related field, or equivalent experience is mandatory; certifications such as CompTIA A+, Apple Certified Support Professional, are required.
• 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-users.
• Deep, hands‑on MDM and client‑deployment experience, including configuration profiles, policy management, software distribution, and Apple Business / Apple School ecosystem workflows.
• Demonstrated ability to diagnose and repair electronic devices, with strong judgment on repair‑versus‑disposition outcomes.
• Proven track record supporting productivity software, email, collaborative systems, and end‑user networking concerns.
• Demonstrated ability to mentor or train less experienced staff and to lead by example.
• Exceptional customer service aptitude, including with 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 proficiency, including the ability to prioritize across competing demands.

Beyond:

The person in this position is expected to continue to learn, grow and contribute in a fast‑changing and highly productive work environment. In addition, there are high expectations for excellent communication, teamwork, and problem‑solving abilities.