1

Weekend Msp System Engineer Jobs in Chicago, IL (NOW HIRING)

MSP Tier 2

Elgin, IL · On-site

$75K/yr

Tier 2 IT Support Engineer (MSP Environment - In Office + Field Work) Location: Elgin, IL Salary ... Monitor client systems and respond to alerts via RMM tools. * Participate in client projects such ...

Tier 2 IT Support Engineer (MSP Environment - In Office + Field Work) Location: Elgin, IL Salary ... Monitor client systems and respond to alerts via RMM tools. * Participate in client projects such ...

Systems Engineer - Hybrid

Oak Forest, IL · On-site

$110K - $120K/yr

A Tech company is looking for a Sr Systems Engineer with 5+ years of experience. In this role you ... MSP experience ideal) Interviews are being conducted immediately so feel free to apply or contact ...

Troubleshoot system and application issues using documented procedures, available tools, and ... MSP experience preferred. Relevant internships, technical training, certifications, or equivalent ...

Troubleshoot system and application issues using documented procedures, available tools, and ... MSP experience preferred. Relevant internships, technical training, certifications, or equivalent ...

next page

Showing results 1-20

Weekend Msp System Engineer information

See Chicago, IL salary details

$55.1K

$131.1K

$172K

How much do weekend msp system engineer jobs pay per year?

As of Jul 31, 2026, the average yearly pay for weekend msp system engineer in Chicago, IL is $131,050.00, according to ZipRecruiter salary data. Most workers in this role earn between $101,000.00 and $161,700.00 per year, depending on experience, location, and employer.

What are the typical challenges faced by a Weekend MSP System Engineer, and how can I prepare for them?

Weekend MSP System Engineers often encounter challenges such as handling urgent client issues with limited on-site support, managing multiple clients’ systems simultaneously, and troubleshooting critical incidents outside of regular business hours. To prepare, it’s important to develop strong remote problem-solving skills, be comfortable with a wide range of technologies, and communicate proactively with both clients and team members. Familiarity with documentation and escalation procedures can also help ensure smooth operations when unexpected situations arise.

What is a Weekend MSP System Engineer?

A Weekend MSP System Engineer is an IT professional who works for a Managed Service Provider (MSP), focusing on maintaining and supporting clients' IT systems specifically during weekends. Their responsibilities typically include monitoring servers and networks, troubleshooting issues, applying updates, and responding to client requests outside regular business hours. This role is vital for ensuring continuous IT support and minimizing downtime for clients who operate or require support over the weekend. Weekend MSP System Engineers often work remotely or in shifts to provide round-the-clock coverage. They must have strong technical skills, problem-solving abilities, and experience with various IT systems and platforms.

What is the difference between Weekend Msp System Engineer vs Network Support Specialist?

AspectWeekend Msp System EngineerNetwork Support Specialist
CertificationsCompTIA A+, Network+, Microsoft CertifiedCompTIA Network+, Cisco CCNA, Microsoft certifications
Work EnvironmentManaged Service Provider (MSP) settings, remote and on-site supportCorporate IT departments, help desks, remote troubleshooting
Industry UsageCommon in MSPs providing 24/7 IT supportCommon in enterprise and small business networks

The Weekend MSP System Engineer primarily focuses on maintaining and supporting client systems within MSP environments, often working remotely or on-site during weekends. In contrast, a Network Support Specialist typically works within corporate IT teams, providing network troubleshooting and support during regular hours. Both roles require similar certifications and technical skills but differ mainly in work setting and scheduling.

What are the key skills and qualifications needed to thrive as a Weekend MSP System Engineer, and why are they important?

To thrive as a Weekend MSP System Engineer, you need strong expertise in network administration, troubleshooting, and server management, typically supported by a degree in IT or related certifications such as CompTIA, Microsoft, or Cisco. Proficiency with remote monitoring and management (RMM) tools, ticketing systems, and cloud platforms like Azure or AWS is crucial. Excellent problem-solving skills, effective communication, and the ability to work independently during off-hours are key soft skills for this role. These skills ensure timely resolution of client issues and reliable IT infrastructure support during critical weekend hours.
What are the most commonly searched types of Msp System Engineer jobs in Chicago, IL? The most popular types of Msp System Engineer jobs in Chicago, IL are:
Infographic showing various Weekend Msp System Engineer job openings in Chicago, IL as of July 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 93% In-person, and 7% Remote job distribution, with an average salary of $131,050 per year, or $63 per hour.

MSP System Administrator, Support Engineer - IL

Leapfrog Technology Group

Oakbrook Terrace, IL • On-site

$60K - $80K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 9 days ago


Job description

In a nutshell... we're looking for an energetic and organized engineer that has impeccable communication and customer service skills who enjoys variety as that is what an MSP offers more than anything. Our relationships are our livelihood...

  • Must have experience working for an MSP or managing a full environment relatively on your own
  • Must have server and cloud (O365, Azure) experience.

If you have both of those - GREAT, read on, because we certainly want to talk with you!

You would be part of the escalation team that focuses on escalated support issues (level II, III), project work and on site solutions. This results in a combination of work from home and visits to local IL customers, due to this you need to be in the local IL area & able to get to all customers across Chicagoland.

You will always be stepping in, resolving escalations, making sure the right thing is being done for the customer. We do have a heavy load of projects and you would be running the projects with a team as needed or just yourself on smaller projects.

You will be responsible for one thing - excellence in customer service - ensuring that our customers are delighted and wow'd by every interaction with you and your colleagues. We are a results driven organization and our quality of service tops all else. Customers can choose from thousands of IT firms. With that comes accountability for providing excellence.

How do you know if you fit? Well, some things about you:

  • You love doing a little bit of everything. You thrive with your hands in everything. You understand that even if you've never done it before, there's always a first.
  • You love getting involved with new projects. Something new? Never done it before? Bring it on! All I need is the vision and Google, and I'll get pretty far along on my own, and will gladly work with the team to learn anything else with pleasure.
  • You thrive in a fast-paced work environment. Boredom is your enemy. I want to work on many things, look up and realize hours have passed.
  • You're high energy. A powerhouse even without your afternoon espresso. You're vibrant and energetic in all that you do.
  • You're an owner. You take on a project from end-to-end with little guidance. You ask for help when necessary, but you don't drop the ball and assume the person you asked to help is suddenly the owner of that task.
  • You don't ask for permission, you just go for it and make things better within the guidelines you've been given. You are also intelligent enough to know when you SHOULD ask for permission.
  • You want to grow yourself and make an impact on the growth of those around you.
  • You realize the potential in everyone and everything.

Essential Duties and Responsibilities:

  • Ensure exceptional client satisfaction is consistently delivered and maintained.
  • Maintain highly effective project management for all projects, small or large, within the engineering team.
  • Implement and maintain processes to ensure we are proactively serving our customer base.
  • Active Directory, Azure, Office365, Exchange, Windows Server, System Center, Citrix, Windows deployments and other administration.
  • The role expects the Support Engineer to recommend industry best practice solutions to clients when on site and to observe and recommend solutions that address their business needs, whether the client recognizes the need or not.
  • Serve as the triage escalation point, overflow or otherwise for technical support issues or outages.
  • Serve as the escalation point for customers and customer needs.
  • Ensure all policies and procedures are consistently followed and updated as necessary.
  • Host daily team meetings to review, reprioritize and reassign service requests as well as project planning meetings.
  • Ensure the team responds to emergencies quickly and efficiently.

Knowledge, Skills, and/or Abilities Required:

  • Having worked for an MSP or managing a full environment relatively on your own is required.
  • Windows, Windows Server, Azure, AWS, Office 365, Proper Server Administration, Firewalls (Cisco, Fortinet, Sonicwall etc), Routers, Desktop Imaging, Networking, Outlook, Active Directory, Exchange Server, Group Policy, Teams, Microsoft Admin Center, Patching, Alerts & Monitoring all required
  • To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required.
  • The ability to routinely multitask in a fast paced environment.
  • Maintain expert knowledge of key products and services including Azure, Microsoft 365 products and offerings, Microsoft Server maintenance and issue resolution, EDR/MDR solutions, Office applications, network routing, anti-virus solutions, and other key technology offerings.
  • Effectively prioritize service requests, escalations along with other duties and tasks on a daily basis

Desired Technical Skills (IMPORTANT)

  • Windows, Windows Server, Azure, AWS, AVD, Defender, Terminal Server, Exchange, Office 365, Citrix, Firewalls (Cisco, Fortinet, Sonicwall), Routers, Desktop Imaging, Networking, Internet Explorer, Outlook, Remote Access, Remote Desktop, Active Directory, Exchange Server, Group Policy. Additional third party application skills and network infrastructure a plus..

Desired Soft Skills

  • Ability to manage your time and customer's expectations.
  • Excellent written and verbal skills, ability to understand business concepts and operations, independent worker, punctual, professional, asks detailed questions.
  • Must possess the drive to enhance skills as we need to stay current and relative as a company.

What do we offer?

  • Compensation will be offered based on experience, technical ability - and is flexible based on the candidate.
  • Opportunity to have an impact on the growth and path of both our organization and our client organizations.
  • You will learn more in this job than you've learned in your career - in just the first few months. Really - we have Master's Degree candidates who learn more in their first three months with us than they learned in the entire college and work history.
  • Bonuses
  • Commission
  • Unlimited Time Off
  • Free training
  • Certification Reimbursement
  • We give raises for each certification you obtain...

Company Description

Throughout the course of each day, our organization delivers the absolute highest quality and reliable technical support and network design-implementation to small and medium organizations between 20 to 1000 computers with multiple servers. We are a Microsoft Certified Partner, focusing on network infrastructure, advanced network infrastructure and managed services. Established in 2000, the company employs a diverse and elite group of highly capable senior engineers focused on providing IT strategy and ongoing operational support.
Our offices are located in Oakbrook Terrace, IL and Franklin, TN. Self-motivated, organized and being an outgoing person will work well in this environment. We are an energetic and busy group with a solid customer base and a growing need to add additional people to our team. This position requires heavy time management skills, use of technology software to ease the burden on the support specialist, and is extremely challenging. Even for seasoned professionals, a role in a service based firm is a challenging one. This is a position in which the staff is held to the highest standards and will be held accountable to use our proven methodologies.