Help Desk Manager — US-Based MSP

We are a Managed Service Provider (MSP) based in the Chicago suburbs (Illinois, USA). We provide IT support, Microsoft 365 management, cybersecurity, and backup/disaster recovery to small and mid-sized businesses across the Chicagoland area, including some clients in regulated industries.

We're a tight-knit, growing team and we're looking for a Help Desk Manager to help us deliver great service to our clients every day. You'll work closely with the owner and be a key part of our leadership as we grow.

This is a hands-on leadership role. You'll manage the ticket queue, but just as importantly, you'll actively mentor and develop our technicians, handle the more complex technical issues they escalate to you, and continuously raise the quality of our service. Our current technicians are capable and self-sufficient on day-to-day work — we're looking for someone who can take them to the next level while owning the harder problems and keeping our whole operation running smoothly.

WHAT YOU'LL DO:

Service Desk Operations:

• Manage the daily ticket queue in Autotask — prioritize, assign, and keep work moving
• Make sure tickets are resolved on time and clients are kept in the loop
• Spot recurring problems and work with the team to fix them for good
• Keep an eye on monitoring alerts and make sure nothing slips through

Team Development and Mentorship:

• Coach and mentor our technicians, actively helping them build new skills and grow into more complex work
• Identify skill gaps on the team and create clear paths to close them
• Review resolved tickets to find learning and improvement opportunities
• Run knowledge-sharing sessions and document best practices for the team
• Set technical standards and help the team consistently meet them
• Take our capable technicians and make them great

Client Relationships:

• Be a friendly, reliable point of contact for our clients
• Keep clients updated on their open issues
• Help resolve concerns before they become bigger problems
• Work alongside the owner on client reviews and building strong relationships

Technical Escalations and Higher-Tier Work:

• Serve as the escalation point for issues the L1/L2 team can't resolve
• Handle complex work involving Microsoft 365, Exchange, Intune, Conditional Access, Azure/Entra ID, and Active Directory
• Own root-cause analysis so recurring problems get fixed permanently, not just patched over
• Guide our field technician during onsite visits over Microsoft Teams
• Coordinate with vendors on tougher technical issues

Documentation, Process, and Quality:

• Keep IT Glue documentation accurate, complete, and useful
• Build and maintain SOPs so common issues get resolved consistently across the team
• Review ticket quality and documentation standards, and coach the team to improve
• Identify automation and efficiency opportunities to reduce repetitive work
• Contribute ideas to make our service better as we grow

The Partnership:
The owner is actively involved in the business every day — working with clients, driving growth, and supporting the team. You won't be left on an island. This role is about working together to build something great. As we grow, this role grows too, with real opportunity to shape how our service delivery works and to lead a larger team over time.

OUR TOOL STACK (experience with these is a big plus):

• Autotask PSA (ticketing and time tracking)
• Datto RMM
• NinjaOne (remote monitoring and management)
• IT Glue (documentation)
• Microsoft 365 Business Premium (Intune, Conditional Access, Exchange, Azure/Entra ID)
• Datto BCDR and SaaS Protection (backup)
• Huntress (managed EDR / security)
• Auvik (network monitoring)
• Fortinet firewalls & switches
• Cisco Merkaki hardware

WHAT WE'RE LOOKING FOR:

• At least 4 years working in a Managed Service Provider (MSP) environment
• Some experience leading or coordinating a helpdesk/service desk team
• Hands-on experience with a PSA tool (Autotask, ConnectWise, Halo, or similar)
• Hands-on experience with an RMM tool (NinjaOne, Datto RMM, ConnectWise Automate, N-able, or similar)
• Experience with a documentation platform (IT Glue, Hudu, or similar)
• Solid Microsoft 365 administration skills
• Excellent written and spoken English — you'll talk with US clients by email , phone, and Teams
• Able to work US Central Time business hours
• Reliable high-speed internet and a professional home office setup

NICE TO HAVE:

• Experience specifically with Autotask, NinjaOne, and IT Glue
• Microsoft certifications (MS-900, AZ-900, SC-900, or higher)
• Experience with Datto BCDR, Huntress, or FortiGate
• Experience supporting clients in regulated industries (healthcare, finance, etc.)
• PowerShell scripting
• ITIL familiarity

HOW TO APPLY:

To show us you've read this posting, please start your application with the word "MANAGED" and answer these three questions:

1. Which PSA and RMM tools have you used, and for how long?
2. Tell us about your experience in an MSP and any team you've supported or led.
3. What is your expected monthly salary in USD?

We read every application that follows these steps. We'll share more about our company, clients, and team during the interview process. We're excited to find the right person to grow with us.

We look forward to hearing from you.