IT Technician (Mid & Senior Level)

Remote

Full Time

Experienced

We are hiring two positions: one Chicagoland-based and one Remote
Locations:

Chicagoland Area (local candidates required)
Remote (U.S.-based)

Syscon, Inc. is a Managed Services Provider (MSP) and technology consulting firm passionate about helping businesses thrive through reliable, well-designed IT solutions. We care deeply about our clients and foster a culture where our company, employees, and clients grow and succeed together.

As we continue to grow, we are hiring two IT Technicians - one local to the Chicagoland area and one remote to provide hands-on IT support in a managed services (MSP) environment, supporting Microsoft 365, Azure AD / Entra ID, networking, security, and endpoint management. Level (mid-level or senior) will be determined based on experience and ability to work independently.

About the Roles

Chicagoland-based role: Primarily work-from-home, with occasional same-day onsite client visits (roughly once per week, on average). Syscon does not maintain a local office; this role is home-based.
Remote role: Fully remote, supporting clients primarily through remote tools

Both roles are hands-on, client-facing positions within a fast-paced MSP environment.

Experience level: Mid-Level to Senior (based on experience)

Why Join Syscon

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

What You’ll Do

Provide remote and on-site technical support with professionalism and precision
Troubleshoot issues across Microsoft 365, networking, security, and endpoint environments
Perform hardware and software installations, updates, and proactive maintenance
Document all client issues and time thoroughly to maintain an accurate audit trail
Ensure work aligns with Syscon’s best practices and quality standards
Build trusted client relationships through clear communication and follow-through

Project Work May Include

Migrating clients to cloud virtual desktop environments
Moving file shares to SharePoint Online Document Libraries
Transitioning from Active Directory to Azure AD / Entra ID
Implementing security features and best practices
Supporting client onboarding and integrations
Backup and disaster recovery implementation and testing
Standardizing and automating recurring tasks and configurations
For Chicagoland-based technicians, onsite work may include light on-prem networking and hands-on support in generally simple client environments.

What We’re Looking For
Mid-Level Candidates Typically Bring:

Solid hands-on experience supporting Microsoft 365 environments
Ability to resolve most user issues independently and escalate appropriately
Comfort working in a fast-paced MSP or similar environment
Willingness to learn, accept feedback, and grow technical depth

Senior-Level Candidates Typically Bring:

Advanced troubleshooting skills and strong technical judgment
Experience implementing proactive solutions to prevent recurring issues
Ability to work independently and take ownership of complex environments
Prior MSP experience strongly preferred
PowerShell scripting experience (basic to moderate) a plus

Technical Experience

Microsoft 365 (Exchange Online, OneDrive, SharePoint Online, Azure AD / Entra ID, Intune, Autopilot)
Virtual environments (Terminal Servers, RDS Farms, Azure Virtual Desktop)
RMM tools and endpoint management
Security tools such as MFA, EDR/AV, or MDM
Networking fundamentals (DNS, DHCP, VPN, VLANs, firewall rules)

Benefits & Perks

Competitive salary based on experience
Medical, dental, and vision insurance
Unlimited PTO based on tenure
Paid holidays
Retirement plan with company participation
Travel reimbursement for Chicagoland-based role
Opportunity to grow your skills and career in a supportive, people-first environment

About the Role

Full-time positions
Typical schedule: Monday–Friday, 8:00 AM–5:00 PM (local time)
Chicagoland role includes same-day local travel as needed
Periodic team meetings held in Phoenix or the Chicago area

NOTE: Please NO phone calls.

Syscon, Inc. is an Equal Opportunity Employer (EOE) committed to fostering a diverse and inclusive workplace.

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Cover Letter

What's your citizenship / employment eligibility?*

What's your highest level of education completed?*

What languages do you speak fluently?*

Earliest start date?

This is a fully remote role supporting clients through remote tools only. Are you currently authorized to work in the United States without sponsorship?*

This role follows a Monday–Friday, 8:00 AM – 5:00 PM (local time) schedule. Are you able to consistently work these hours?*

This role requires fluent spoken and written English to communicate professionally with clients and teammates. Do you meet this requirement?*

How would you classify your current technical skill level?*

Have you worked in a Managed Services Provider (MSP) or outsourced IT environment supporting multiple client organizations concurrently?*

If you answered Yes, please list the MSP(s) you worked for, your role title, and dates of employment. (Example: ABC MSP – IT Technician – 2021–2023)

Recency of your MSP Experience*

Use the following scale for the next questions:
0 = No experience
1 = Basic exposure / assisted support
2 = Regular hands-on support
3 = Advanced configuration / administration
4 = Design, implementation, and troubleshooting ownership

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

Azure AD / Entra ID (users, groups, MFA, Conditional Access)*

Endpoint Management (Intune, MDM, policies, app deployment)*

In an MSP environment, which best describes you?*

DNS / DHCP*

Firewall rules / VPNs*

RMM Tools (monitoring, remediation, automation)*

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

What is your target base salary range for this role?*

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

If you are located in Illinois, are you within reasonable driving distance (approximately 60 miles) of the Chicagoland area?*

What state do you currently reside in?*

Human Check*

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IT Technician (Mid & Senior Level)

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