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Remote Windows Migration Technician Jobs in Mount Prospect, IL

Connection

Lead Field Technician

Schaumburg, IL · Remote

$40 - $42/hr

This is a full-time permanent position working remote with benefits. The Lead Field Technician ... imaging, Windows device configuration, and endpoint deployment · Ability to walk into a site ...

AtHoc

AtHoc - Senior Implementation Engineer

Chicago, IL · Remote

$112K - $157.50K/yr

Regular This is a fully remote position requires strong internet connection and access to major ... Maintain expert-level configuration and troubleshooting of Windows Server, IIS, and SQL Server

Software Technology Inc

DevOps Engineer

Chicago, IL · On-site +1

$54.50 - $74.50/hr

The ideal candidate would have Code Migration / Release Automation experience within a medium to ... Windows & Linux Server Administration * General networking/internet communication protocols ...

Clayco

Field Support Technician

Chicago, IL · On-site +1

$20.25 - $27.75/hr

Provide day to day support to our remote Jobsites * Prioritize problems and incidents and escalate to internal teams * Basic knowledge of Microsoft products (Windows, Office) * Physical Installation ...

Clayco

Field Support Technician

Chicago, IL · On-site +1

$20.25 - $27.75/hr

Provide day to day support to our remote Jobsites * Prioritize problems and incidents and escalate to internal teams * Basic knowledge of Microsoft products (Windows, Office) * Physical Installation ...

Clayco

Field Support Technician

Chicago, IL · On-site +1

$20.25 - $27.75/hr

Provide day to day support to our remote Jobsites * Prioritize problems and incidents and escalate to internal teams * Basic knowledge of Microsoft products (Windows, Office) * Physical Installation ...

Clayco

Field Support Technician

Chicago, IL · On-site +1

$20.25 - $27.75/hr

Provide day to day support to our remote Jobsites * Prioritize problems and incidents and escalate to internal teams * Basic knowledge of Microsoft products (Windows, Office) * Physical Installation ...

Clayco

Field Support Technician

Chicago, IL · On-site +1

$20.25 - $27.75/hr

Provide day to day support to our remote Jobsites * Prioritize problems and incidents and escalate to internal teams * Basic knowledge of Microsoft products (Windows, Office) * Physical Installation ...

Clayco

Field Support Technician

Chicago, IL · On-site +1

$20.25 - $27.75/hr

Provide day to day support to our remote Jobsites * Prioritize problems and incidents and escalate to internal teams * Basic knowledge of Microsoft products (Windows, Office) * Physical Installation ...

Sentinel

System Engineer, Senior

Downers Grove, IL · On-site +1

$120K - $140K/yr

This position can be work remote within the United States but must travel to Downers Grove, IL as ... Planning, executing, and overseeing the successful migration of data center infrastructure ...

Sentinel

System Engineer, Senior

Downers Grove, IL · On-site +1

$120K - $140K/yr

This position can be work remote within the United States but must travel to Downers Grove, IL as ... Planning, executing, and overseeing the successful migration of data center infrastructure ...

WithumSmith+Brown

IT Service Analyst I

Chicago, IL · On-site +1

$65K - $70K/yr

Withum is seeking a Service Technician to support the IT Team in our Lincolnshire , IL office ... Delivering remote support to users throughout the Firm via phone, email, chat or our remote support ...

Sentinel

System Engineer, Senior

Downers Grove, IL · On-site +1

$120K - $140K/yr

This position can be work remote within the United States but must travel to Downers Grove, IL as ... Planning, executing, and overseeing the successful migration of data center infrastructure ...

Withum

IT Service Analyst I

Chicago, IL · On-site +1

$65K - $70K/yr

Withum is seeking a Service Technician to support the IT Team in our Lincolnshire , IL office ... Delivering remote support to users throughout the Firm via phone, email, chat or our remote support ...

Ampcus

ServiceNow S2P Developer

Chicago, IL · Remote

Chicago, IL (Remote) The ServiceNow Source-to-Pay (S2P) Developer is responsible for designing ... Support development teams migration to other lower environments Documentation & Knowledge Transfer:

New

Kobie Marketing

Director, Technology Delivery

Chicago, IL · Remote

$218.40K/yr

Join a National Top Workplace Named a Top Workplace in the USA and Top Remote Workplace, Kobie is ... Coordinate change windows and release trains to minimize client impact and validate operational ...

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Remote Windows Migration Technician information

See Mount Prospect, IL salary details

$15

$19

$26

How much do remote windows migration technician jobs pay per hour?

As of May 27, 2026, the average hourly pay for remote windows migration technician in Mount Prospect, IL is $19.74, according to ZipRecruiter salary data. Most workers in this role earn between $17.45 and $21.49 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Windows Migration Technician, and why are they important?

To thrive as a Remote Windows Migration Technician, you need strong expertise in Windows operating systems, system administration, and troubleshooting, usually backed by relevant IT certifications such as CompTIA A+ or Microsoft Certified: Modern Desktop Administrator Associate. Familiarity with migration tools like USMT, remote desktop software, and enterprise deployment systems is commonly required. Excellent problem-solving abilities, attention to detail, and effective communication are valuable soft skills for this role. These skills ensure seamless migrations, minimal user disruption, and high client satisfaction during complex remote upgrade or transition projects.

What are some common challenges faced by Remote Windows Migration Technicians during large-scale migrations?

Remote Windows Migration Technicians often encounter challenges such as coordinating schedules with end-users across different time zones, ensuring minimal disruption to daily operations, and troubleshooting unexpected compatibility or connectivity issues. Effective communication and strong problem-solving skills are essential for addressing user concerns and resolving technical setbacks promptly. Additionally, maintaining data integrity and security during migrations is a top priority, requiring careful planning and adherence to organizational protocols.

What is a Remote Windows Migration Technician?

A Remote Windows Migration Technician is an IT professional who specializes in assisting businesses or individuals with transitioning their computers and data from older versions of the Windows operating system to newer ones, all done remotely. This role involves tasks such as planning migrations, transferring files and settings, ensuring application compatibility, and troubleshooting issues during the process. Technicians use remote access tools to securely connect to client systems, minimizing downtime and disruption. They also provide support and guidance before, during, and after the migration to ensure a smooth transition.

What is the difference between Remote Windows Migration Technician vs Remote Network Support Specialist?

AspectRemote Windows Migration TechnicianRemote Network Support Specialist
CertificationsCompTIA A+, Microsoft Certified: Windows Server FundamentalsCompTIA Network+, Cisco CCNA
Work EnvironmentClient sites, remote support for OS migrationsNetwork infrastructure, troubleshooting network issues remotely
Industry UsageIT services, system administrationIT support, network management

The Remote Windows Migration Technician primarily focuses on migrating and upgrading Windows operating systems remotely, requiring certifications like CompTIA A+ and Microsoft certifications. In contrast, the Remote Network Support Specialist handles network-related issues, often with certifications like CompTIA Network+ or Cisco CCNA. Both roles operate in remote environments within the IT industry but differ in their technical focus and daily tasks.

What job categories do people searching Remote Windows Migration Technician jobs in Mount Prospect, IL look for? The top searched job categories for Remote Windows Migration Technician jobs in Mount Prospect, IL are:
What cities near Mount Prospect, IL are hiring for Remote Windows Migration Technician jobs? Cities near Mount Prospect, IL with the most Remote Windows Migration Technician job openings:
Remote Windows Migration Technician jobs near you
Lead Field Technician

Lead Field Technician

Connection

Schaumburg, IL • Remote

$40 - $42/hr

Full-time

Medical, Dental, Vision, Life, PTO

This job post has expired today. Applications are no longer accepted.

Job description

Connection has a fantastic opportunity for a Lead Field Technician. This is a full-time permanent position working remote with benefits. The Lead Field Technician serves as the senior technical resource for field operations, responsible for performing complex installations, deployments, troubleshooting technical issues, and leading field technicians to ensure projects are completed safely, efficiently, and to quality standards.

This role combines hands-on technical work with field leadership, coordinating daily activities, mentoring technicians, and acting as the primary on-site liaison between customers, project managers, and internal teams. There is typically travel to different client sites.

Must be a U.S. Citizen. We are unable to sponsor or take over sponsorship of an employment visa at this time.

Key Responsibilities

· Lead and support multi-site device deployments across healthcare and enterprise client environments

· Perform and oversee:

o SCCM imaging and device provisioning

o Laptop and desktop refreshes, swaps, installs, and upgrades

o Monitor, dock, scanner, RFID, and other peripheral setup and integration

o Device validation with end users prior to completion

· Direct field technicians onsite and keep teams aligned to daily install targets, quality standards, and client expectations

· Coordinate with site contacts on access, schedule, readiness, and execution

· Troubleshoot and resolve issues in real time to avoid delays and rework

· Ensure installs are completed cleanly, consistently, and according to defined standards

· Provide field feedback to program and operations leadership to improve execution and repeatability

What We’re Looking For

· Strong hands-on experience with field services, hardware deployments, and multi-site rollouts

· Experience leading technicians or serving as the senior technical resource in the field

· Solid working knowledge of SCCM imaging, Windows device configuration, and endpoint deployment

· Ability to walk into a site, assess what is needed, and take control of execution

· Comfortable operating in fast-paced, high-visibility environments

· Strong communication skills with both technicians and client-facing site contacts

· Professional presence, sound judgment, and ability to work independently

Environment

· Work will take place across a mix of healthcare and enterprise settings

· Travel is required based on deployment needs

· Flexibility to support varying schedules, including off-hours work, is important

Company Description

Connection, a Fortune 1000 Global Solutions Provider, drives customer growth by calming the confusion of IT, guiding the connection between people and technology. The Connection brand includes Connection® Business Solutions, Connection® Enterprise Solutions, and Connection® Public Sector Solutions, which provide IT solutions and services to SMB, enterprise, and public sector markets. Connection holds hundreds of certifications with top vendors and offers expertise across multiple technology areas, delivering solutions to customers in over 174 countries.