Hudson Sky LLC IT Support Specialist Chicago, IL · Full time Company website

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Hudson Sky is a Chicago-based managed security services provider. We run IT and cybersecurity for companies that can't afford to get it wrong: defense contractors, law firms, healthcare practices, and logistics operators working under CMMC, HIPAA, and CIS. We're a small, senior team with high standards, which means the work here is hands-on, the impact is visible, and there's real room to grow into security and automation.

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