IT Support and Operations Specialist

Kelly Scott Madison—KSM—is a leading, independent media and advertising agency that futureproofs brands and fuels business growth. Our team of strategists, solutionists, technologists, and data analysts work united alongside incredible brand partners, helping them connect with customers in more meaningful ways today and positioning them to move with the customers of tomorrow. It’s always an amazing and transformative time at our growing media agency.

At KSM, it’s about more than just a passion for our industry and craft. It’s about the impact we make on the lives and livelihoods of those around us, and the highly personal experience we have here. Being an independent, mid-size agency—not too big, not too small, and proudly entrepreneurial—you’ll be empowered, recognized, and challenged to grow here. We’re adding new Bold Builders and uncommon perspectives to our community and can’t wait to learn more about you. But first, let’s explore the opportunity...

We’re looking for a part-time IT Support and Operations Specialist who is excited to build their IT career while making an immediate impact. You will help employees solve everyday technology challenges, prepare laptops and equipment, support onboarding and offboarding, and assist with device, account, access, and Microsoft 365 requests. You will also gain valuable experience across endpoint management, systems, networking, infrastructure, security, and cloud technologies.

This part-time opportunity is ideal for someone seeking meaningful, hands-on experience, a flexible schedule, and the chance to grow their IT skills while making a visible impact across the agency. For the right person, the role may have the potential to grow into a full-time opportunity based on exceptional performance, evolving business needs, and mutual interest.

The ways you will make an impact:

· 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.

Experience you should bring:

· 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 escalate 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

Who you are:

· A practical problem-solver who enjoys troubleshooting hardware, software, devices, and peripherals

· Organized, dependable, and committed to following requests through to resolution

· Comfortable working independently, following documented procedures, and escalating complex issues when appropriate

· A clear and patient communicator who enjoys helping others navigate technology

· Curious and committed to continuous learning across endpoint management, systems, networking, infrastructure, security, and cloud technologies

Benefits we offer:

As a part-time employee, you will not be eligible for KSM’s benefits package; however, upon a successful transition to full-time employment, here is what you can look forward to. We’ve got you covered—and we’re not just referring to robust health insurance. To us, coverage is about supporting your full experience and whole self, from inclusive benefits, flexibility, and an appreciation for time away to recognition, professional development, and growth opportunities. We’ve got you.

· Talent Enablement: Career pathing, integrated learning ecosystem, mentorship, and employee recognition

· Financial: Competitive compensation, 401(k) with company match, profit sharing subject to company performance, pre-tax programs, referral rewards, and a remote work reimbursement

· Wellness: Comprehensive health insurance (medical, dental, vision, pet, and life), onsite fitness center covered 100%, discounted membership rates at partner gyms and access to virtual fitness classes, Employee Assistance Program (EAP), and curated opportunities to nurture your breaktime

· Balance: Personalized Paid Time Off (i.e., “Unlimited PTO”), remote work flexibility, paid parental leave (maternity, paternity, and adoption), and a variety of Employee Resource Groups

· Giving Back: Volunteer opportunities and corporate donation matching through KSM Cares Outreach, our Corporate Social Responsibility program