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Windows Rollout Jobs (NOW HIRING)

Description Windows Automation Engineer- The Windows Automation Engineer is responsible for ... phased rollout strategies (pilot, canary, regional, enterprise‑wide) Deployment & Release ...

Desktop Support Technician

Wilmington, OH · On-site

$18 - $23/hr

With the impending rollout of Windows 11 and the subsequent relocation of the Desktop Services team to the Tech Center building, there is an urgent need to hire a new IMT-Desktop Support Person. This ...

Desktop Support Technician

Wilmington, OH · On-site

$18 - $23/hr

With the impending rollout of Windows 11 and the subsequent relocation of the Desktop Services team to the Tech Center building, there is an urgent need to hire a new IMT-Desktop Support Person. This ...

Windows Sales Specialist

Tucker, GA · On-site

$21.25 - $28.75/hr

A Brief Overview The Windows Sales Specialist generates and secures new sales within a specific ... Assists Company's Sales and Product Line Manager team in developing a timeline for rollout of ...

Windows Sales Specialist

Tucker, GA

$21.25 - $28.75/hr

A Brief Overview The Windows Sales Specialist generates and secures new sales within a specific ... Assists Company's Sales and Product Line Manager team in developing a timeline for rollout of ...

Senior VDI Admin/Engineer (WFH, C2C)

Houston, TX · On-site

$48.50 - $60.75/hr

... Windows Server and VMware * 6 years of experience supporting Microsoft Active Directory domains ... Manager • Provide rollout and production support to end users • Document as-built ...

Desktop Support

Melbourne, FL · Remote

$20.75 - $26.25/hr

Prepare requests for rollout * Prioritize change requests * Create roll implementation process ... Windows Operating systems * Clients: Windows7, Windows Vista, Windows XP, Windows 2000 * Servers:

... and rollouts. * Participate in security risk assessments and compliance reviews. Requirements * Strong system administration and troubleshooting experience * Proficiency in Linux and Windows ...

... and rollouts. * Participate in security risk assessments and compliance reviews. Requirements * Strong system administration and troubleshooting experience * Proficiency in Linux and Windows ...

IT Support Eng. Intern

Tempe, AZ · On-site

$14.50 - $19.50/hr

... Windows 10 End-of-Life (EOL) hardware replacement initiative. This is a long-term temporary ... rollout activities across multiple business units nationwide. The ideal candidate is hands-on ...

... and rollouts. * Participate in security risk assessments and compliance reviews. Requirements * Strong system administration and troubleshooting experience * Proficiency in Linux and Windows ...

IT Support Eng. Intern

Tempe, AZ

$14.50 - $19.50/hr

... Windows 10 End-of-Life (EOL) hardware replacement initiative. This is a long-term temporary ... rollout activities across multiple business units nationwide. The ideal candidate is hands-on ...

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Windows Rollout information

See salary details

$10

$55

$67

How much do windows rollout jobs pay per hour?

As of Jul 1, 2026, the average hourly pay for windows rollout in the United States is $55.87, according to ZipRecruiter salary data. Most workers in this role earn between $48.08 and $61.54 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Windows Rollout Specialist, and why are they important?

To thrive as a Windows Rollout Specialist, you need expertise in operating system deployment, system imaging, and troubleshooting, often supported by a degree in IT or related certifications like Microsoft Certified: Modern Desktop Administrator Associate. Familiarity with tools such as Microsoft Endpoint Configuration Manager (SCCM), Active Directory, and PowerShell scripting is commonly required. Excellent problem-solving, communication, and organizational skills help in coordinating with users and teams to minimize disruption during rollouts. These skills ensure smooth, efficient, and secure deployments, supporting business continuity and user productivity.

What is the fastest growing IT career?

The fastest growing IT careers include roles like cybersecurity analyst, cloud engineer, and data scientist. These positions are driven by increasing demand for security, cloud computing, and data analysis skills, often requiring certifications and familiarity with tools like AWS, Azure, or security protocols.

What is a Windows Rollout?

A Windows Rollout refers to the process of deploying a new version or update of the Microsoft Windows operating system across multiple computers within an organization. This process involves planning, testing, and systematically installing the operating system to ensure compatibility, security, and minimal disruption to users. IT teams often use specialized tools and strategies to automate and manage the rollout efficiently. Properly executed, a Windows Rollout helps keep systems up-to-date, secure, and standardized.

Why is Gen Z struggling to get jobs?

Gen Z faces challenges in securing jobs like Windows Rollout roles due to limited work experience, high competition, and evolving skill requirements such as proficiency with new operating systems and remote collaboration tools. Building relevant skills, certifications, and gaining practical experience can improve their employment prospects in this field.

What are some common challenges faced during a Windows Rollout project, and how can they be mitigated?

During a Windows Rollout project, common challenges include compatibility issues with legacy applications, user resistance to change, and coordination across multiple departments. These can be mitigated by conducting thorough compatibility testing, establishing clear communication channels, and providing comprehensive end-user training. Additionally, working closely with stakeholders and IT support teams ensures smoother deployment and timely resolution of unforeseen issues.

What is the difference between Windows Rollout vs Windows Deployment Specialist?

AspectWindows RolloutWindows Deployment Specialist
Primary FocusPlanning and executing large-scale Windows OS deploymentsDesigning, implementing, and troubleshooting Windows deployment processes
CertificationsMicrosoft Certified: Modern Desktop Administrator, Windows certificationsMicrosoft Certified: Windows Server, Deployment certifications
Work EnvironmentIT departments, enterprise environments, project-basedTechnical support, deployment teams, consulting
ResponsibilitiesManaging rollout schedules, coordinating teamsCreating deployment images, troubleshooting deployment issues

While both roles involve Windows OS deployment, Windows Rollout focuses on managing large-scale deployment projects, whereas Windows Deployment Specialist emphasizes technical deployment tasks and troubleshooting. Understanding these differences helps organizations assign the right expertise for their Windows deployment needs.

What jobs in the US pay 300,000 a year?

In the context of Windows rollout and IT roles, senior positions such as IT directors, cloud architects, and cybersecurity executives can earn $300,000 or more annually. These roles typically require extensive experience, advanced certifications, and leadership responsibilities within large organizations or specialized consulting firms.

What jobs make $3,000 a day?

High-paying jobs that can earn $3,000 a day include specialized roles such as senior software engineers, IT project managers, and cybersecurity consultants, often requiring advanced skills, certifications, and experience. These roles typically involve complex problem-solving, leadership, and working in high-demand industries or consulting environments.
What states have the most Windows Rollout jobs? States with the most job openings for Windows Rollout jobs include:
What job categories do people searching Windows Rollout jobs look for? The top searched job categories for Windows Rollout jobs are:
Infographic showing various Windows Rollout job openings in the United States as of June 2026, with employment types broken down into 45% Full Time, 22% Part Time, 11% Temporary, and 22% Contract. Highlights an 100% In-person job distribution, with an average salary of $116,200 per year, or $55.9 per hour.
Windows Automation Engineer

Windows Automation Engineer

TEKsystems

Irving, TX • On-site

$60 - $75/hr

Contractor

Medical, Dental, Vision, Life, Retirement, PTO

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


Key responsibilities

  • Automate the end-to-end software update lifecycle for Windows operating systems and Windows-based applications.

  • Develop and execute automated testing including smoke, regression, and post-deployment health checks.

  • Standardize and optimize deployment workflows and support phased rollout strategies across development, test, and production environments.


Job description

Description

Windows Automation Engineer- The Windows Automation Engineer is responsible for automating the end‑to‑end software update lifecycle for Windows operating systems and Windows‑based applications. This role focuses on patching, certification, automated testing, and controlled deployments across development, test, and production environments, ensuring stability, security, and compliance in large‑scale enterprise platforms.

Skills

Automation, Python, Automated testing, Test automation, windows, linux

Top Skills Details

Automation,Python,Automated testing,Test automation,windows,linux

Additional Skills & Qualifications

Standardize and optimize deployment workflows across environments

Software Update Certification & Testing

Implement automated pre‑deployment certification checks

Patch validation

Application compatibility testing

Dependency and version checks

Develop and execute automated testing (smoke, regression, post‑deployment health checks)

Support phased rollout strategies (pilot, canary, regional, enterprise‑wide)

Deployment & Release Management

Experience Level

Intermediate Level

Job Type & Location

This is a Contract position based out of Irving, TX.

Pay and Benefits

The pay range for this position is $60.00 - $75.00/hr.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following:
• Medical, dental & vision
• Critical Illness, Accident, and Hospital
• 401(k) Retirement Plan – Pre-tax and Roth post-tax contributions available
• Life Insurance (Voluntary Life & AD&D for the employee and dependents)
• Short and long-term disability
• Health Spending Account (HSA)
• Transportation benefits
• Employee Assistance Program
• Time Off/Leave (PTO, Vacation or Sick Leave)

Workplace Type

This is a hybrid position in Irving,TX.

Application Deadline

This position is anticipated to close on Jun 30, 2026.

About TEKsystems

We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

About TEKsystems and TEKsystems Global Services

We’re a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We’re a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We’re strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We’re building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.