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Remote Pos Technical Support Jobs in Chicago, IL

Carefeed

Support Engineer

Chicago, IL · On-site +1

You must be able to convey complex technical concepts clearly, both verbally and in writing, to ... You will regularly need to collate information from SQL databases, remote server logs and client ...

Carefeed

Support Engineer

Chicago, IL · Remote

You must be able to convey complex technical concepts clearly, both verbally and in writing, to ... You will regularly need to collate information from SQL databases, remote server logs and client ...

Addison Group

Service Desk Analyst

Chicago, IL · Remote

$20 - $25/hr

Information Technology / Technical Support Location (City, State): Chicago, IL (Remote with preference for local candidates) Assignment Type: Long-Term Contract Pay: $20 - 25 / hr Work Schedule:

Avidity Science LLC

Sales Coordinator

Evanston, IL · Remote

$55K - $70K/yr

... supports the Life Sciences sales team while also providing technical guidance and coordination across internal teams. The salary range for this role is $55,000 - $70,000/ year. Location: Remote, but ...

Zortech Solutions

SAP S/4 Consultant

Chicago, IL · Remote

$64.50 - $88/hr

... Applications,Technical Support,SAP As an SAP Consultant Contractor, you will be responsible for ... not required. -Remote contractors are acceptable if they agree to work CT hours. -Remote ...

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Showing results 21-40

All JobsPos Technical Support JobsRemote Pos Technical Support JobsRemote Pos Technical Support Jobs in Chicago, IL

Remote Pos Technical Support information

See Chicago, IL salary details

$14

$26

$46

How much do remote pos technical support jobs pay per hour?

As of Aug 7, 2026, the average hourly pay for remote pos technical support in Chicago, IL is $26.83, according to ZipRecruiter salary data. Most workers in this role earn between $19.81 and $29.23 per hour, depending on experience, location, and employer.

What is the difference between Remote Pos Technical Support vs Remote IT Help Desk Support?

AspectRemote Pos Technical SupportRemote IT Help Desk Support
Required CredentialsCompTIA A+, Network+, relevant certificationsCompTIA A+, Microsoft Certified, relevant certifications
Work EnvironmentCustomer-facing, troubleshooting hardware/software issuesHelp desk, remote troubleshooting, user support
Employer & Industry UsageRetail, POS system providers, hospitalityIT service providers, corporate support centers
Search & Comparison IntentUnderstanding POS-specific support rolesGeneral IT support roles

Remote Pos Technical Support focuses on troubleshooting and maintaining point-of-sale systems, often requiring specific POS certifications. Remote IT Help Desk Support covers broader IT issues, assisting users with various hardware and software problems. Both roles involve remote work and customer interaction but differ in technical scope and industry focus.

What is a remote POS technical support specialist?

Remote POS (Point of Sale) Technical Support specialists are professionals who assist businesses and individuals with troubleshooting, maintaining, and optimizing POS systems from a remote location. They handle issues such as software glitches, hardware malfunctions, network connectivity problems, and user errors. These specialists communicate with clients via phone, email, or chat to diagnose problems, provide step-by-step solutions, and sometimes remotely access systems to resolve complex issues. Their goal is to ensure that POS systems operate efficiently, minimizing downtime and disruptions for businesses.

What are the key skills and qualifications needed to thrive as a remote POS technical support specialist?

To thrive as a Remote POS Technical Support Specialist, you need strong troubleshooting abilities, knowledge of point-of-sale systems, and experience in customer service, often supported by relevant IT certifications or technical training. Familiarity with remote support tools, ticketing systems, and POS software such as Square, Toast, or Lightspeed is typically required. Excellent communication, patience, and problem-solving skills help you effectively assist clients and resolve issues remotely. These competencies are crucial for minimizing downtime, ensuring customer satisfaction, and maintaining smooth business operations for clients.

What are the most common challenges faced by remote POS technical support professionals, and how can they effectively address them?

Remote POS Technical Support professionals often encounter challenges such as troubleshooting complex hardware or software issues without physical access to the equipment, communicating effectively with non-technical users, and managing multiple support requests simultaneously. To address these challenges, it’s important to develop strong diagnostic skills, use remote access tools efficiently, and maintain clear, patient communication with clients. Staying organized and collaborating with team members or on-site technicians can also help resolve issues more efficiently and ensure high customer satisfaction.
What are the most commonly searched types of Pos Technical Support jobs in Chicago, IL? The most popular types of Pos Technical Support jobs in Chicago, IL are:
What are popular job titles related to Remote Pos Technical Support jobs in Chicago, IL? For Remote Pos Technical Support jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Pos Technical Support jobs in Chicago, IL look for? The top searched job categories for Remote Pos Technical Support jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Pos Technical Support jobs? Cities near Chicago, IL with the most Remote Pos Technical Support job openings:
Remote Pos Technical Support jobs near you

Technical IT Support Specialist - Chicago, IL

Buckeye Mountain

Chicago, IL • Remote

Full-time

Posted 9 days ago

Job description

The Role

We are looking for a technically minded IT support professional who can bridge the gap between end-user helpdesk and senior engineering. You are not a traditional help desk — you understand systems well enough to triage a network issue, interpret a monitoring alert, and know whether to resolve it yourself or get the right engineer involved. You will own monitoring across our network, cloud, and NaaS environments, serve as the first-level escalation for technical issues, and support endpoint and device management operations. When something is wrong somewhere in our environment, you will often be the first to know.

What You'll Own

Monitoring & Observability

• Monitor network, cloud, and NaaS environments using observability and alerting platforms — Splunk, cloud monitoring consoles, and remote management tools

• Own NaaS site monitoring — track link health, power telemetry, and connectivity status for all active remote sites

• Respond to and triage monitoring alerts; resolve within your scope or escalate with full context to the appropriate engineer

• Manage NaaS firmware and configuration changes for live sites in coordination with the Field Engineering team

Technical First-Level Support

• Serve as the first technical escalation point for issues routed up from the helpdesk — network connectivity, application access, system performance

• Perform first-level network troubleshooting — diagnosing issues before escalating to the Senior Network Engineer

• Own the technical ticket queue for infrastructure-adjacent issues, ensuring nothing sits unrouted

• Contribute to SLA compliance by maintaining response time discipline and clear ticket documentation

Endpoint & Device Support

• Assist the Identity & Endpoint Systems Administrator with device enrollment (Intune, Apple Business Manager), compliance policy deployment, and device imaging

• Support OS patching cycles for Windows and Linux systems under direction of the Systems & Application Engineer

• Contribute to knowledge base and troubleshooting documentation for recurring issues

What We're Looking For

Required

• 3+ years in an IT support, NOC, or junior systems administration role

• Working knowledge of networking concepts — TCP/IP, DNS, VLANs, subnetting, basic firewall behavior

• Experience with monitoring and alerting platforms — Splunk, PRTG, Datadog, Zabbix, or equivalent

• Familiarity with Microsoft Intune or another MDM platform for device enrollment and policy deployment

• Experience supporting Windows environments at a systems level — not just end-user troubleshooting

• Strong communication skills — ability to escalate clearly, document concisely, and keep stakeholders informed during incidents

• Experience with a ticketing platform (Jira Service Management preferred)

Preferred

• Experience monitoring or supporting remote or field-deployed network infrastructure

• NaaS, managed connectivity, ISP, or telecom support background

• Splunk experience — dashboards, searches, alert configuration

• Basic scripting ability — PowerShell or Python for automation or log parsing

• Linux command-line proficiency at a support level

Details

• Location: Remote — must be available during core US business hours

• Travel: Minimal

• Employment type: Full-time