IT Technician (Mid–Senior) – Chicago Western Suburbs / Chicagoland

Chicago, IL

Full Time

Mid Level

IT Technician – Mid-Level or Senior

Chicago Western Suburbs / Chicagoland | Work From Home with Onsite Client Visits
Location: Chicago Western Suburbs / Chicagoland Area (local residency required)

Syscon is a Managed Services Provider (MSP) supporting small and mid-sized businesses with reliable, practical IT solutions. We are a cloud-first IT services company, focused on Microsoft 365, security, and simplifying client environments while delivering consistent, high-quality support.

We are hiring an IT Technician (Mid-Level or Senior) based in the Chicago Western Suburbs / Chicagoland area.

This is a home-based role supporting clients throughout the Chicago Western Suburbs and greater Chicagoland area. Most support is delivered remotely, with onsite visits to client locations as business needs require. Candidates must reside within reasonable driving distance of the Western Suburbs to support onsite responsibilities.

Level (Mid-Level or Senior) will be determined based on experience, judgment, and ability to work independently.

About the Role

Work-from-home, client-facing IT support role
Onsite client visits within the Chicago Western Suburbs / Chicagoland area as needed
Hands-on onsite work involving simple networks, installs, and troubleshooting
Primarily cloud-based environments with minimal on-prem infrastructure

What You’ll Do

Provide remote and onsite technical support with professionalism and sound judgment
Support Microsoft 365 environments (Exchange Online, SharePoint, OneDrive, Azure AD / Entra ID)
Troubleshoot endpoint, security, and networking issues
Perform hardware and software installations, updates, and maintenance
Document work and time clearly to support accurate billing and client trust
Communicate clearly with clients, explaining impact and next steps before acting
Identify opportunities to prevent repeat issues and improve environment stability

Project Work May Include

Migrating file shares to SharePoint Online
Supporting cloud virtual desktop environments
Azure AD / Entra ID configuration and identity management
Security improvements (MFA, endpoint protection, best practices)
Client onboarding and environment cleanup
Backup and disaster recovery support

What We’re Looking For

Mid-Level Candidates Typically Have:

Strong Tier 2 experience
Solid Microsoft 365 and endpoint support skills
Ability to resolve most issues independently
Good judgment and willingness to ask clarifying questions
Comfort working in a fast-paced MSP or similar environment

Senior-Level Candidates Typically Have:

Advanced troubleshooting and decision-making skills
Ability to work independently with minimal oversight
Strong client communication and professional maturity
Experience identifying root causes and preventing repeat issues
MSP experience strongly preferred

Technical Experience

Microsoft 365 (Exchange Online, SharePoint, OneDrive, Azure AD / Entra ID, Intune)
Endpoint management and RMM tools
Security fundamentals (MFA, EDR/AV)
Networking basics (DNS, DHCP, VPNs, firewalls)
Light on-prem and hands-on networking experience

Why Join Syscon

Meaningful work supporting real client environments
Growth-focused, collaborative team culture
Clear structure and accountability (EOS framework)
Opportunity to expand technical depth, ownership, and impact
Small team where your contributions genuinely matter

Benefits & Perks

Competitive salary based on experience
Unlimited PTO based on tenure
Medical, dental, and vision insurance
Retirement plan with company participation
Paid holidays
Mileage reimbursement for onsite client visits
Supportive, people-first team environment

Role Details

Full-time
Monday–Friday, 8:00 AM–5:00 PM (local time)
Occasional local travel to client sites
Chicago Western Suburbs / Chicagoland residency required

Note: Please do not call or email regarding this position. All applications must be submitted through the application process.

Syscon is an Equal Opportunity Employer (EOE).

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Cover Letter

Do you have a valid driver's license?*

What's your citizenship / employment eligibility?*

What's your highest level of education completed?

College or University

What languages do you speak fluently?*

Earliest start date?

How many years of experience do you have as a Senior Technician or in a similar senior IT support role?*

How many years of hands-on experience do you have working in an MSP (Managed Services Provider) or outsourced IT environment supporting multiple clients concurrently?*

This role requires onsite support for clients in the Chicago Western Suburbs / Chicagoland area. Do you currently reside within 60 miles of the Chicago Western Suburbs and able to commute to client sites as needed?* Yes- I currently live within 60 miles and can reliably commute.Yes - I live currently within approximately 45-60 miles of the Western Suburbs or Chicagoland area.No- I do not currently live in the area, but I am willing and able to relocateNo- I live outside the area (more than 60 miles away)No - I currently reside outside 60 miles and am not planning to relocate.

Are you able to travel to client sites in the Western Chicago Suburbs and greater Chicagoland area as needed?*

What is your minimum base salary requirement to consider this role?*

When was the last time you personally performed hands-on technical work in a production environment?*

Indicate your hands-on experience level : Microsoft 365 Experience

0 = No experience
1 = Basic exposure (end-user or assisted support)
2 = Regular hands-on support
3 = Advanced configuration / administration
4 = Expert-level design, implementation, and troubleshooting*

Indicate your hands-on experience level : Azure AD / Entra ID
0 = No experience
1 = Basic exposure (end-user or assisted support)
2 = Regular hands-on support
3 = Advanced configuration / administration
4 = Expert-level design, implementation, and troubleshooting*

Indicate your hands-on experience level : Intune

0 = No experience
1 = Basic exposure (end-user or assisted support)
2 = Regular hands-on support
3 = Advanced configuration / administration
4 = Expert-level design, implementation, and troubleshooting*

What is your experience level using an RMM tool to manage endpoints?
0 = No experience
1 = Used dashboards / alerts only
2 = Regular monitoring and basic remediation
3 = Automation, scripting, and policy management
4 = Platform ownership, tuning, and optimization*

Indicate your working knowledge and application for the following questions using the scale:
0 = No experience
1 = Conceptual understanding only
2 = Basic troubleshooting
3 = Regular configuration and support
4 = Advanced design and troubleshooting

Use the scale above to indicate your working knowledge of - DNS/DHCP*

Use the scale above to indicate your working knowledge of - Firewall rules*

When was the last time you personally configured or troubleshot Microsoft 365 or Entra ID?*

Describe one environment you personally owned or significantly influenced. What decisions were yours?*

When was the last time you personally configured or troubleshot the following in a production environment? Microsoft 365, Entra ID / Azure AD, Endpoint management (Intune, MDM, Etc.) Choices are in the next set of questions.

Microsoft 365 (Exchange, SharePoint, Teams, identity, security settings)*

Entra ID / Azure AD (identity, access, conditional access, directory services)*

Endpoint management (Intune, MDM, device policies, compliance, app deployment)*

Have you previously applied to any role with Syscon, Inc?*

Which level do you most confidently see yourself operating at in this role?*

What state do you currently reside in?*

Human Check*

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