IT Support Specialist acting as the front line of our service desk and keep client environments and internal operations running smoothly.
ABOUT THE ROLE
This is an early-career, growth-oriented role. We are looking for aptitude, reliability, critical thinking and strong client communication more than a long resume. We will train the right person on our tools and, over time into reporting, automation, and security work. It is the anchor operational seat in a small, high-standards shop, so ownership, coachability and adaptability matter as much as what you already know.
WHAT YOU'LL DO
- Act as first responder for client and internal support tickets in our PSA (ticketing) system: triage, resolve, document, and escalate within the SLA’s.
- Support and maintain endpoints through our remote monitoring and management (RMM) platform: patching, deployments, monitoring, and basic remediation.
- Administer Microsoft 365: user setup, mailboxes, licensing, MFA, and common Entra ID, SharePoint, and OneDrive support.
- Work within our security stack under guidance: endpoint allowlisting, managed detection and response (MDR/XDR) alerts, privileged access management, and a password manager.
- Handle everyday Windows, Active Directory, and basic networking support.
- Document your work in our knowledge base to company standards and keep client records current.
- Provide on-site support at Chicago-area client locations as needed.
- Keep the service desk running independently.
AS YOU RAMP (GROWTH WORK)
- Learn to build and maintain reporting dashboards (Power BI).
- Extend internal low-code tools and light automation and scripting (PowerShell).
- Contribute knowledgebase articles and runbooks.
- Identify areas for improvement including, but not limited to: internal efficiencies, process automations, client relationship development and product growth.
- Potential for leadership and oversight of others as the business grows.
WHAT WE'RE LOOKING FOR
- Roughly 2 to 3 years of IT support experience: help desk, desktop support, internship, or equivalent hands-on or home-lab experience.
- Working comfort with Windows and Microsoft 365, and a willingness to learn Active Directory and our support tools on the job.
- Genuine customer-service instinct with clear written and verbal communication and a strong desire to help customers solve problems.
- A clear ability to apply critical thinking skills to solve unique problems day in and day out without escalation support.
- Reliable, in-office presence in Chicago and willingness to travel locally to client sites.
- Able to pass a background check (our clients operate under regulated frameworks).
- Valid driver's license and reliable transportation for on-site visits.
NICE TO HAVE
- CompTIA A+ or Network+ (or actively pursuing).
- Any prior MSP or IT services exposure.
- Curiosity about security, reporting (Power BI, SQL), or low-code tools.
- Exposure to CMMC, NIST 800-171, or HIPAA environments.
- Experience leading a team.
WHO THRIVES HERE
You take ownership without being chased, communicate clearly with non-technical clients, and are comfortable being the on-site point person on a small team. You document as you go, and you want to grow toward automation, reporting, and security work overtime. You thrive working with a small team and take accountability seriously, but enjoy a fun atmosphere. You see the possibility and potential of helping a small business grow into something great.
BENEFITS
- Paid time off, holidays
- IT Certification support and reimbursement
- Access to experts and resources for your Learning & Development journey
- Opportunity for internal mobility
- Employee referral bonus program