MSP Level 2 Help Desk Engineer, Chicagoland (3+ Yrs MSP Exp Required)

This isn’t your typical Level 2 help desk role - beyond answering emails and phones, you’ll take on occasional on-site client visits and project work as part of the team.

Are you an experienced MSP professional looking to join a company that values initiative, continuous improvement, and strong technical execution?

We are a well-established (21 years) and growing Managed Service Provider delivering comprehensive IT consulting and support to small and mid-sized businesses throughout the Chicago area. Our clients typically range from 10-100 users, and we standardize environments using mainstream, best-practice solutions to ensure predictable, secure, and reliable networks.

Due to growth, we are looking for a Level 2 Help Desk Engineer who can hit the ground running, take ownership of Level 1 and Level 2 requests, and grow with our team.

Location & Schedule

• Hybrid role: you’ll work the help desk queue remotely and travel to client sites in Chicago or surrounding suburbs on a regular basis
• On-site visits include both scheduled work (which may span multiple consecutive days) and on-demand visits when a client needs someone in person, sometimes with limited notice
• Must live within the Chicago or the surrounding suburbs
• Full-time, Monday-Friday, 8:00 AM - 5:00 PM
• Participate in the after-hours on-call rotation, covering approximately one week of nights and weekends every six weeks. While on call, you’ll cover the phones and handle Level 1 and Level 2 requests, and occasionally issues that fall between Level 2 and Level 3.
• Valid driver’s license and reliable transportation required

What You’ll Do

• Handle Level 1 and Level 2 requests and troubleshooting
• Support multiple client environments and switch contexts efficiently
• Assist with client onboarding and infrastructure projects
• Lead and audit endpoint deployments to ensure full coverage
• Perform entry-level network administration tasks: apply firewall firmware and rule updates, configure and troubleshoot wireless access points, and back up firewall/network device configurations
• Support Microsoft 365 tenant administration, including SharePoint site administration and OneDrive management (user provisioning, permissions, sharing/security settings, and file recovery)
• Maintain and update technical documentation in IT Glue (documentation-first mindset required)
• Manage hardware/software vendor relationships on behalf of clients
• Provide on-site consulting and hardware support as needed

• 5+ years of IT support experience
• At least 3 years of IT MSP experience (required) - this means providing outsourced IT support to multiple external client businesses, not an internal IT role at a single employer/customer, even one where you personally handled many different services or tasks
• Strong troubleshooting methodology and root-cause analysis skills
• Experience with RMM tools and ticketing systems
• Excellent phone presence and professional communication skills
• Comfortable supporting users at all levels, from executives to non-technical staff
• Willing and able to participate in the after-hours on-call rotation (approximately one week every six weeks)

Technical Experience Required

• Windows Server support (not full server administration) Active Directory, Group Policy, DNS, DHCP, domains, and server patching: 3 years (required)
• Microsoft 365 tenant administration, including SharePoint, OneDrive, and Entra ID: 2 years (required)
• Microsoft Intune experience is a plus but not required
• Entry-level networking: firewall administration (applying updates, configuration backups) and wireless access point configuration/troubleshooting (required)
• Apple/macOS support experience is a plus but not required

The Environment You’ll Support

You don’t need experience with our exact tools. If you’ve worked in a comparable MSP tool stack, you’re a strong fit.

In general, our environment includes:

• Windows Server and Windows desktop environments across a range of client sizes
• Microsoft 365 / cloud productivity (Exchange Online, SharePoint, OneDrive, Teams)
• Network equipment including routers, switches, firewalls, and wireless access points from HP, Ubiquiti, Meraki, and SonicWall
• Endpoint detection and response (EDR) / endpoint security platforms
• Email security and anti-phishing filtering
• VoIP / cloud phone systems
• PSA/RMM and remote support tooling
• A dedicated documentation platform (IT Glue), * * This is a hybrid role. You’ll work the help desk remotely and travel to client locations in Chicago or the surrounding suburbs on a regular basis - including scheduled visits (which may span multiple consecutive days) and on-demand visits when a client needs someone in person, sometimes with limited notice. Are you able to do this, and comfortable working independently on-site? (Required)
• • Do not apply if you do not have at least 5 years of IT support experience. How many years of IT support experience do you have? (Required)
• • Do not apply without 3+ years of IT MSP experience - supporting multiple external clients, not internal IT at one employer. How many years do you have? (Required)
• • How many years of hands-on Microsoft 365 administration (SharePoint, OneDrive, Exchange Online, Entra ID, licensing/tenant administration) experience do you have? Intune experience is a plus but not required. (Required)
• • How many years of hands-on experience do you have with basic network administration tasks such as firewall updates, wireless AP configuration, or backing up device configurations? (Required)
• • This role includes an on-call rotation covering nights and weekends approximately one week every six weeks. Are you available and willing to participate? (Required)

Work Location: Hybrid remote in Buffalo Grove, IL 60089

This Role Is:

• Independent, hands-on MSP support
• A critical part of a small technical team
• A growth opportunity toward higher-level technical responsibilities

This Role Is Not:

• Entry-level help desk
• A call-center style position
• A senior architect/engineering role

About Netsphere Technologies

Netsphere Technologies is a stable and growing MSP serving small and mid-sized businesses across the Chicago area. Many of our clients rely on us as their fully outsourced IT department. We support networking, security, internet services, VoIP, email, hardware procurement, and day-to-day IT operations.

Compensation & Benefits

• Pay: $58,000.00 - $80,000.00 per year
• 401(k) with 3% match
• Health insurance
• Dental insurance
• Paid time off
• Bonus pay
• Retirement plan

If you are an experienced MSP professional who values ownership, accountability, and technical excellence, we encourage you to apply.

Pay: $58,000.00 - $80,000.00 per year, * 401(k)

• 401(k) matching
• Dental insurance
• Health insurance
• Paid time off
• Retirement plan