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Level IV Systems Engineer

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Job DescriptionJob Descriptionn

We're Hiring: Level IV Systems Engineer
Location: Remote with periodic onsite visits (Chicago area) | Type: Full-Time

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Are you a seasoned IT professional with deep knowledge of network infrastructure, server management, and cloud transitions? Do you thrive on designing, maintaining, and improving complex systems that support small and mid-sized businesses across the country? Are you looking to join a supportive, skilled, and growing team?

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Syscon, Inc. , established in 1986, provides technology solutions and IT support services to small and medium-sized businesses throughout the U.S., with a strong emphasis on the construction industry. At Syscon, we care deeply about our clients—and about each other. We foster a culture where our company, employees, and clients grow and succeed together.

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As a successful member of our Syscon team, YOU:

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  • Take initiative, embrace feedback, and grow from experience.
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  • Show confidence without ego and pride in doing excellent work.
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  • Tackle technical issues creatively and thoroughly, with the end-user in mind.
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  • Communicate clearly with clients, teammates, and leadership.
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  • Collaborate with your team to share knowledge and contribute ideas.
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  • Own your time, tasks, and outcomes—with professionalism and integrity.
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  • Thrive in a fast-paced, collaborative environment with high expectations and strong support.
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We believe you will thrive in the Level IV Systems Engineer role if you possess:

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  • 6+ years of experience as a senior or Level IV IT technician.
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  • Strong background in Microsoft Windows Server (2012 R2 to 2019), including troubleshooting, patching, backups, and configuration.
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  • Experience working for an Outsourced IT company or Managed Services Provider (MSP).
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  • Familiarity with backup solutions such as Datto BDR , Solarwinds , and best-practice retention and monitoring strategies.
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  • Hands-on experience with VMware ESXi , vSphere, V-Center, and server provisioning.
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  • Knowledge of SonicWall firewalls and VPN configuration and troubleshooting.
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  • Solid grasp of LAN/WAN fundamentals, network segmentation, and Wi-Fi architecture (HP Aruba experience is a plus).
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  • Experience onboarding and managing Microsoft 365 accounts, as well as architecting SharePoint migrations and Exchange to M365 transitions.
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  • Exposure to Azure environments, including tenant migrations and administration.
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  • Familiarity with RMM tools such as N-Able/N-Central , and remote access tools like Take Control , Remote Desktop , or LogMeIn Rescue .
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  • Experience supporting HP servers, switches, and end-user hardware.
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As our Level IV Systems Engineer, your responsibilities will include:

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  • Maintaining our hosting infrastructure (ESXi, Datto, SonicWall HA firewalls, switches, and MSAs).
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  • Supporting remote and on-premise client environments across the U.S.
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  • Onboarding, maintaining, and supporting Microsoft 365 accounts, backups, and SharePoint transitions.
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  • Performing client migrations from Hosted Exchange and on-prem systems to M365 and Azure.
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  • Providing remote and on-site support, upgrades, and assessments for client infrastructure.
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  • Monitoring backups and infrastructure health using N-Central and Solarwinds.
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  • Participating in team meetings, Daily Stand Ups, and network design planning.
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  • Communicating with the Customer Support desk and clients to update status and document resolutions.
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  • Maintaining accurate and thorough documentation in our ticketing system, including time worked, steps taken, and outcomes.
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  • Protecting client confidentiality and meeting project timelines.
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Skills & Competencies for Success in This Role:

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  • Expert-level troubleshooting skills and diagnostic ability.
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  • Strong organizational and time management abilities.
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  • Excellent written and verbal communication—both technical and client-facing.
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  • Confidence working independently and collaboratively.
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  • Professionalism, punctuality, and attention to detail.
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  • Desire to grow within a high-performing team and take ownership of your work.
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Certifications ():

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  • Microsoft Certified: Windows Server or Azure
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  • VMware Certified Professional
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  • SonicWall Network Security certifications
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  • Datto Certified Advanced Technician
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  • Other related technical certifications
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Perks & Benefits

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  • A place to grow your skills and career.
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  • Work with a talented, committed, and supportive team.
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  • Excellent medical, dental, and vision benefits.
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  • Unlimited PTO
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  • Work remotely with occasional on-site client visits.
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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.

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Please, no phone calls regarding this position.

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

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