IT Support Specialist

IT Support Specialist

IT  •  Hireology  •  Chicago, IL  •  Hybrid

Hireology’s technology empowers businesses to build great teams. Over the last decade, we’ve grown from a scrappy startup into a market-leader, and we’ve built an award-winning culture that makes this an amazing place to work. We’re headquartered in Chicago and support a hybrid workforce across the country.

We are seeking an IT Support Specialist to join the Hireology IT team. In this role, you’ll report directly to the IT Manager and serve as a key partner for both our in-office and remote employees — handling everything from hardware and software troubleshooting to SaaS account management, identity and access controls, and endpoint security.

We run a lean IT team — you’ll get real, day-one ownership, building skills and tackling problems that would take years to reach in a larger department. You’ll work closely with our IT Manager to define and continuously improve the processes that keep Hireology running smoothly.

• Provide day-to-day technical support to employees across hardware, software, networking, and SaaS platforms
• Maintain and support our macOS-only environment, including device setup, configuration, and lifecycle management
• Administer and support core SaaS tools including Jamf, Okta, Google Workspace, Slack, Zoom, Zendesk, and Glean
• Support endpoint security and compliance initiatives, including SOC 2
• Test and coordinate software upgrades and OS deployments prior to company-wide rollout
• Develop and maintain IT documentation and inventory
• Obtain and maintain certifications in core platforms (Jamf, Okta, and others as the stack evolves)

In Your First 90 Days

• Get hands-on with our full tech stack — learn how we provision devices, manage access, and support the business day to day
• Take ownership of the helpdesk queue and start resolving tickets independently
• Own your first full employee onboarding or offboarding end to end
• Identify one process or gap you want to improve and bring a proposal to the team
• Complete your Jamf 200 course and certification

This is a hybrid role based out of our Chicago office four days a week — Monday, Tuesday, Wednesday, and Thursday are in-office days. That said, there will be times (company events, team sprints, etc.) that call for a full week on-site, and we ask that you’re able to accommodate that when needed.

Required

• 1–3 years in an IT support role
• Experience with Jamf or another macOS MDM tool
• Experience with an identity and access management platform (Okta, Entra, or similar)
• Solid understanding of networking fundamentals including Ethernet, TCP/IP, Wi-Fi, and VPN
• Strong communication skills — you can explain technical concepts clearly to a non-technical audience
• A self-starter mindset with the ability to manage and prioritize multiple open issues simultaneously

Preferred Qualifications

• Experience supporting users in a SaaS or tech-forward environment
• Google Workspace administration experience
• Shell scripting, Bash, or other automation experience
• Familiarity with compliance frameworks like SOC 2 & ISO 27001
• Experience with Zendesk or a similar helpdesk ticketing platform
• Exposure to AI and productivity tools at scale (Glean, Claude, Copilot, etc.)

• Base Salary: $65,000–$70,000 (Plus 10% Bonus)
• Health, Dental, and Vision coverage from day one
• 401(k) with company match
• Unlimited PTO and mental health days
• A dedicated budget for certs, courses, and conferences
• Real career advancement — we promote from within

Must be authorized to work in the United States. We are not able to provide Visa sponsorship. Agency and/or Third Party inquiries will not be accepted.

Hireology is committed to equal employment opportunities regardless of race, color, genetic information, creed, religion, sex, sexual orientation, gender identity, national origin, age, marital status, disability status or protected veteran status, or any other category protected under the law. All employment decisions are solely based on business needs, job requirements, and individual qualifications. We support an inclusive workplace where Hireologists excel based on personal merit, qualifications, experience, ability, and job performance.