Senior IT Technician

We’re Hiring: Senior IT Technician (Remote – Chicagoland Area)

Location: Remote (Based in Chicagoland Area) | Type: Full-Time

Syscon, Inc. is a Managed Services Provider (MSP) and technology consulting firm that’s passionate about helping businesses thrive through smart, reliable 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’re looking for a Senior IT Technician who enjoys problem-solving, building trusted client relationships, and taking ownership of their work. This is a great opportunity for an experienced and highly detailed IT professional to join a small but rapidly growing team where your input truly matters.

Why Join Syscon?

• Work-life balance – Fully remote position based in Chicagoland, with occasional local client visits.
• Comprehensive benefits – Competitive salary, travel reimbursement, and participation in team meetings held in Phoenix or the Chicago area.
• Supportive culture – A collaborative team that values respect, growth, and accountability.
• Growth opportunity – Expand your technical depth and troubleshooting expertise in a growing company.
• Meaningful work – Empower clients to use technology effectively and make a tangible difference in their daily operations.
• Collaborative structure – Your input will have real influence in shaping team priorities and processes. We operate under the EOS framework (from Traction by Gino Wickman), ensuring clarity, transparency, and shared ownership.

What You’ll Do

• Provide remote senior-level technical support to clients with professionalism and precision.
• Perform hardware and software installations, updates, and proactive maintenance.
• Troubleshoot complex issues involving Microsoft 365, networking, security, and endpoint management.
• Document all client issues and time to maintain an accurate audit trail.
• Ensure all work aligns with Syscon’s best practices and quality standards.
• Maintain a positive, professional attitude to promote strong client relationships and teamwork.

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.
• Implementing security features and best practices.
• Supporting client onboarding and integrations.
• Backup and disaster recovery implementation and testing.
• Standardization and automation of recurring tasks and configurations.

What We’re Looking For

• Located in the Chicagoland area (required).
• Experience with Microsoft 365, including advanced functionality (Exchange Online, OneDrive, SharePoint Online, Azure AD, Conditional Access Policies, Intune, Autopilot).
• Experience implementing proactive solutions to prevent recurring support issues.
• Experience with virtual environments (Terminal Servers, RDS Farms, Azure Virtual Desktop).
• Experience working with an RMM tool to manage endpoints.
• Experience with enterprise security tools such as MFA, EDR/AV, or MDM.
• Strong understanding of basic networking concepts (DNS, DHCP, VPN, VLANs, firewall rules).
• PowerShell scripting experience (basic to moderate) is a plus.
• Prior MSP experience strongly preferred.

Skills & Competencies

• Strong written and verbal communication skills.
• Excellent documentation habits and client-facing communication.
• Advanced troubleshooting and problem-solving abilities.
• Ability to work with ticket queues, SLAs, and prioritization.
• Strong interpersonal skills and effective time management.
• Self-driven, organized, and able to prioritize in a dynamic environment.

About the Role

• Remote position based in the Chicagoland area, with occasional on-site client visits.
• Typical schedule: 8:00 AM – 5:00 PM CST, Monday–Friday.
• Travel reimbursement provided.
• Participation in team meetings a few times per year (Phoenix or Chicago area).

Ready to Apply?

If this sounds like a great fit, submit your application today. Selected candidates may be contacted for additional questions about their experience.

Please, no phone calls regarding this position.

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