Part-Time IT Support & Operations Specialist - Remote & Flexible

Kelly Scott Madison; Chicago (IL); On-site; USD 28,000 - 41,000; Part time

Benefits offered by this job

Talent Enablement

Remote work reimbursement

Profit sharing

401(k) with company match

Comprehensive health insurance (if/as

Job summary

Kelly Scott Madison (KSM) invites an entry-level IT Support and Operations Specialist to join our Chicago office on a part-time basis. You will prepare laptops, support onboarding and offboarding, and handle routine help desk requests, while gaining hands-on experience across endpoint management, systems, networking, and cloud technologies.

You will work with Windows 11, macOS, and Microsoft 365, using documented procedures and remote tools to troubleshoot issues and escalate when needed.

Qualifications

• Working knowledge of Windows 11 and familiarity supporting macOS and Microsoft 365.
• Basic hardware, peripheral, and end-user troubleshooting skills.
• Strong communication, organization, follow-through, and practical problem-solving skills.
• Ability to work independently on routine requests, follow documented procedures, and elevate when needed.
• Early career candidate with up to two years of relevant experience through employment, internship, school IT, lab work, or similar hands-on experience.
• Ability to provide onsite support in the Chicago office as required.
• Experience working with Intune or Autopilot, Entra ID or Active Directory, Apple device management, SharePoint, remote support tools, networking, or PowerShell preferred.
• Entry-level IT certification preferred.

Responsibilities

• Prepare Windows and Mac laptops for new hires, replacements, and swaps.
• Support onboarding, equipment handoffs, and routine offboarding tasks.
• Handle basic help desk requests and follow up with users through resolution.
• Troubleshoot common device, Microsoft 365, application, printer, dock, monitor, and peripheral issues.
• Complete routine account, access, group, distribution list, and SharePoint requests using documented procedures.
• Assist with device enrollment, application deployment, inventory, and equipment organization.
• Document recurring support tasks and procedures.

Skills

Windows support

macOS familiarity

Microsoft 365

End-user troubleshooting

Communication

Independent work

Onsite support

Education

IT certification

Tools

Intune/Autopilot

Entra ID/Active Directory

SharePoint

PowerShell

Job description

Kelly Scott Madison (KSM) invites an entry-level IT Support and Operations Specialist to join our Chicago office on a part-time basis. You will prepare laptops, support onboarding and offboarding, and handle routine help desk requests, while gaining hands-on experience across endpoint management, systems, networking, and cloud technologies.

You will work with Windows 11, macOS, and Microsoft 365, using documented procedures and remote tools to troubleshoot issues and escalate when needed.