IT Technician (Mid & Senior Level)

Syscon • Scottsdale, AZ

1d • Hybrid

About The Position

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.

Requirements

• 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
• 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
• 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)

Nice To Haves

• Prior MSP experience strongly preferred
• PowerShell scripting experience (basic to moderate) a plus

Responsibilities

• 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
• 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
• onsite work may include light on-prem networking and hands-on support in generally simple client environments.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed