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Windows 11 Migration Jobs (NOW HIRING)

... with Windows 11 administration and troubleshooting 2. Laptop/desktop deployment, imaging ... backup, and data migration (OneDrive/SharePoint) 7. Ability to perform basic network ...

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... data migration, and customer communication. This is not an entry-level IT position. Applicants ... Diagnose and resolve Windows 10 and Windows 11 operating system issues * Remove malware, viruses ...

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Windows 11 Migration information

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$15

$19

$27

How much do windows 11 migration jobs pay per hour?

As of Jun 26, 2026, the average hourly pay for windows 11 migration in the United States is $19.87, according to ZipRecruiter salary data. Most workers in this role earn between $17.55 and $21.63 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in the Windows 11 Migration position, and why are they important?

To thrive in a Windows 11 Migration role, you need strong expertise in Windows operating systems, experience with system deployment and imaging tools, and a solid understanding of enterprise IT infrastructures. Familiarity with tools like Microsoft Endpoint Configuration Manager (SCCM), Active Directory, and certifications such as Microsoft Certified: Modern Desktop Administrator Associate are highly valued. Excellent problem-solving, project management, and communication skills are crucial for coordinating with stakeholders and addressing user concerns. These abilities ensure smooth, efficient migration processes with minimal disruption to business operations.

What is a Windows 11 Migration job?

A Windows 11 Migration job involves upgrading an organization's computers from an older operating system, such as Windows 10, to Windows 11. This process includes assessing hardware compatibility, backing up data, deploying the new OS, updating drivers, and ensuring software compatibility. IT professionals in this role also provide user support, troubleshoot issues, and optimize system performance post-migration. The goal is to ensure a smooth transition with minimal downtime for users.

What are some typical challenges faced during a Windows 11 migration, and how does the team address them?

A common challenge in Windows 11 migration projects is ensuring compatibility between existing applications and the new operating system, which may require thorough testing and troubleshooting. Teams often face tight deadlines and must work to minimize downtime for end users, sometimes coordinating after-hours deployments or providing rapid support. Successful Windows 11 migration professionals collaborate closely with IT, end users, and management to resolve issues quickly and maintain clear communication throughout the process. Proactive planning and continuous feedback help the team address obstacles effectively and keep the migration on track.

More about Windows 11 Migration jobs
What cities are hiring for Windows 11 Migration jobs? Cities with the most Windows 11 Migration job openings:
What states have the most Windows 11 Migration jobs? States with the most job openings for Windows 11 Migration jobs include:
Infographic showing various Windows 11 Migration job openings in the United States as of June 2026, with employment types broken down into 41% Full Time, 5% Part Time, and 54% Contract. Highlights an 100% In-person job distribution, with an average salary of $41,333 per year, or $19.9 per hour.
IT Systems and Infrastructure Manager

IT Systems and Infrastructure Manager

Sentinel

Chicago, IL โ€ข On-site

Contractor

Medical, Dental, Vision, Retirement

Posted 22 days ago


Sentinel Real Estate rating

6.2

Company rating: 6.2 out of 10

Based on 5 frontline employees who took The Breakroom Quiz

138th of 210 rated facilities management


Job description

Responsibilities
Sentinel is seeking an IT Systems and Infrastructure Manager for a Chicago-based partner. This role leads execution across cybersecurity, infrastructure, endpoint management, and enterprise IT operations. Responsibilities include driving initiatives such as email security, Intune/Autopilot deployments, Windows 11 migration, and incident response readiness, while ensuring network reliability, outage recovery, and failover planning. The manager partners with key vendors and oversees identity management, onboarding/offboarding, and cross-functional support across office, plant, and executive teams. Additionally, the role promotes continuous improvement through automation, documentation, user training, and standardized processes, while monitoring operational performance and high-volume support. This position ensures secure, scalable, and efficient IT operations aligned with business goals.
This is a contract-to-hire hybrid position that requires onsite work 4 of 5 days a week at the client location in Chicago, IL.
Qualifications
  • Strong expertise in cybersecurity, email security, and compliance frameworks
  • Deep knowledge of Microsoft 365, Intune, Autopilot, and Windows endpoint management
  • Proven ability to manage network infrastructure, incident response, and outage recovery
  • Experience supporting enterprise environments across office, plant, and executive functions
  • Proficiency in identity and access management (Active Directory, MFA, user lifecycle)
  • Ability to lead vendor relationships and coordinate with external partners (e.g., Cisco, AT&T, Sentinel)
  • Strong process improvement mindset, including automation, documentation, and standardization.
  • Excellent troubleshooting skills with capacity to manage high-volume IT support operations.
  • Relevant IT certifications (e.g., Microsoft, Cisco, CompTIA, or cybersecurity-focused credentials) preferred
  • Demonstrated experience in IT roadmap development and execution to support organizational growth and scalability
  • A valid driver's license and proof of vehicle insurance will be required
  • Legally authorized to work in the US without sponsorship
  • Must demonstrate a "can-do" attitude

We focus on candidates that display our "ACE" factor - Attitude, Compassion, and Enthusiasm to deliver quality solutions with exceptional customer service.
Compensation Range:
$90,000-$125,000
What you get:
We offer weekly competitive pay, medical, dental, vision, 401K and more.
Overview
MOTIVATED.....make IT happen!
Sentinel Technologies, Inc. has been rated a top workplace every year since 2012!
About Us:
Sentinel delivers solutions that can efficiently address a range of IT needs - from security, to communications, to systems & networks, to software applications, to cloud and managed services; all of which include our staffing solutions for our clients. Since 1982, Sentinel has grown from providing technology maintenance services to our current standing as one of the leading IT services and solutions provider in the US. We have aligned with many of today's global technology leaders including Cisco, Dell, VMware and Microsoft. Sentinel services customers both nationally and internationally with primary support operating centers in Downers Grove (HQ), Chicago, and Springfield, IL; Phoenix, AZ.; Lansing, and Grand Rapids, MI; Milwaukee, WI; and Denver, CO.
If you are MOTIVATED... you can make IT happen at Sentinel. Our commitment to our employees is to create a work environment that encourages creativity, an entrepreneurial spirit, fosters growth through certification and hands-on training, and values a team-oriented culture with rewards based on impact!
If you share our passion about what technology can do and want to be part of a top workplace environment - we'd like to have you join our team. Learn more at www.sentinel.com/careers.
As part of Sentinel's employment process, candidates will be required to complete a background check. Only those who meet the minimum requirements will be contacted. No phone calls please.
Sentinel is proud to be an equal opportunity employer including disability and veterans. In accordance with Title VII and state regulations, all qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, marital status, pregnancy, genetics, disability, military, veteran status or any other basis protected by law.
If you are an individual with a disability and need assistance in applying for a position, please contact SentinelHR1@sentinel.com.
The "Know Your Rights" Poster is available here
https://www.eeoc.gov/sites/default/files/2023-06/22-088_EEOC_KnowYourRights6.12ScreenRdr.pdf
Sentinel EEO Policy Statement is available here.
https://www.sentinel.com/about/diversity
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