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

Description

Onsite Support Engineer II

Location: Chicago, IL

Ready to work hands-on and make a real impact every day? 

If you enjoy troubleshooting, working face-to-face with end users, and being the go-to expert when things go wrong, this role is for you. We're looking for someone who thrives on solving technical issues and providing high-quality support with a personal touch. If this sounds like what you're looking for, it could be a great fit, for you and for us. 

About the Role 

As an Onsite Support Engineer II, you'll be the front line of support for our clients, working 100% onsite at assigned customer locations. Your job is to resolve technical issues that come in through our ticketing system or phone queue, often escalating from our Level I team. You'll handle everything from system and network troubleshooting to vendor coordination and customer walk-throughs, bringing both tech skill and a friendly, professional presence. Your days will be a mix of hands-on fixes, remote diagnostics, and documentation. You'll manage support tickets, uphold service level agreements (SLAs), and ensure clients receive timely, effective solutions. This role relies on your ability to work independently while staying tightly aligned with internal procedures and escalation paths. Your success helps ensure business continuity for our clients and builds long-term trust in our IT services. 

What You'll Support 

• Troubleshoot network, server, and endpoint issues (virtual or physical environments) 
• Handle escalations from Level I engineers and follow escalation paths as defined in documentation 
• Maintain and document IT environments in IT Glue, updating or creating new articles 
• Remotely access systems to push scripts or run actions as needed 
• Manage and resolve Microsoft 365, AzureAD, DHCP/DNS, and Active Directory-related issues 
• Work with vendors to help restore service during outages 

Requirements 

• Ability to document work and progress in a ticketing system as tasks are completed 
• Strong communication skills for both remote and in-person support 
• Willingness to work entirely onsite and travel between client buildings as needed 

Recommended Skills 

• Proficiency in VMware or Hyper-V environments 
• Knowledge of Microsoft Windows Server environments, patching, and print server drivers 
• Familiarity with networking concepts such as VLANs, ISP troubleshooting, and firewall equipment 
• Experience using centralized documentation systems (e.g., IT Glue) 
• Comfortable working in support escalation and on-call rotations 

Schedule & Benefits 

• Location: 100% onsite at assigned client sites (travel between buildings required) 
• Hours: Full-time; must be available for on-call weeks and emergency outages 
• Benefits: Standard benefits package available (details provided during interview process) 

Why Join Path Forward IT? 

Path Forward IT, a Blue Alliance company, is a nationally recognized managed services provider (MSP) that exclusively supports the healthcare industry. Ranked among the top 15% of MSPs nationwide, we deliver world-class IT services that ensure technology never stands in the way of patients receiving the care they need. Our work is driven by urgency, empathy, and a patient-centered mindset. We understand the critical nature of healthcare operations and prioritize our work to empower providers to focus on what matters most: delivering exceptional care. Founded in 2002, Path Forward IT has grown to a team of over 100 professionals located across 40+ states. We foster a collaborative, career-focused culture where team members thrive. Many of our employees have been with us for years, and we regularly celebrate 5- and 10-year milestones. 

A Team Environment Built for Growth 

Joining Path Forward IT means working alongside IT specialists supporting complex, enterprise environments. As part of the Blue Alliance network, you gain access to a community of hundreds of peers and experts across the country. This means more opportunities for learning, professional development, and career advancement without losing the close-knit feel of a smaller team. 

You'll enjoy the best of both worlds: 

• The autonomy and client engagement typical of a local MSP 
• The resources, support, and structure of a leading national IT services organization 

A Unique Opportunity Through Blue Alliance 

As a Blue Alliance partner company, Path Forward IT provides team members with unmatched opportunities to learn, lead, and succeed. Each company in the network maintains its unique identity while working toward shared goals. If you're looking to make a meaningful impact and grow your career in a supportive, future-focused environment, this is the place for you. 

Benefits of working at Path Forward IT: 

• Be part of a fun, awesome team 
• 9 paid holidays 
• 401K Retirement with matching contributions 
• Excellent medical, vision and dental insurance 
• Life insurance and disability insurance 
• Cell phone stipend 
• 3 weeks PTO 

Top Reasons our Employees Love Being Part of the Blue Alliance Family: 

1. Entrepreneurial Culture 
2. Fast-paced Flow, with a Variety of Projects 
3. Collaborative Work Environment 
4. Training & Certifications  
5. Career Growth Opportunities 

Ready for the next step?  

The greatest rewards are reserved for those who want to be better and then put in the hard work, to be their best version of themselves. Interested applicants should click to submit their resume and application above.  

Please be advised we, Path Forward IT, participate in E-Verify. 

Requirements

186