IT Support Specialist

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 SLAs.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 FORRoughly 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 HAVECompTIA 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 HEREYou 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. BENEFITSPaid time off, holidaysIT Certification support and reimbursementAccess to experts and resources for your Learning & Development journeyOpportunity for internal mobilityEmployee referral bonus program
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