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Windows Rollout Jobs (NOW HIRING)

$66.56K - $85.28K/yr

ABOUT US Rollout Systems works with a wide spectrum of talent to establish an atmosphere that ... A working knowledge of the M365 office suite, MS Teams, and the windows operating system ...

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Windows Rollout information

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$10

$55

$67

How much do windows rollout jobs pay per hour?

As of Jun 3, 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 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 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.

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 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:
Windows System Engineer

Other

Medical, Dental, Life, Retirement, PTO

Posted 18 days ago


Job description

Description

Company Description

The Vertex Companies, LLC (VERTEX) is a $180M global consulting firm that integrates strategic advisory, project management, and dispute resolution services for organizations facing complex challenges in a world of risk. We embody our core values of embracing lifelong learning, operating with urgency, maximizing value, and driving collaboration to better outcomes for our clients, colleagues, and communities. Join us if you are looking for a career that offers you a chance to love what you do and deliver meaningful impact. 

Job Description

Vertex is seeking a highly experienced Windows System Engineer to support our IT operations. This role is responsible for IT support and administration, from hands-on helpdesk and end-user assistance to the administration of enterprise-grade systems including Microsoft 365 E5, network infrastructure, security tooling, and backup solutions. The ideal candidate brings deep technical expertise, a service-oriented mindset, and a proven track record of supporting day-to-day business operations. 

  Core Responsibilities Helpdesk & End User Support
  • Serve as the escalation point for all HelpDesk tickets, ensuring timely and effective resolution.
  • Provide hands-on and remote desktop support along with external MSP to end users across hardware, software, and connectivity issues.
  • Ensure to work with MSP to solve issues in timely manner and maintain SLAs and end-user satisfaction.
  • Document issues, resolutions, and procedures in the IT knowledge base.
  • Onboard and offboard employees, including device provisioning and account lifecycle management. 
Business Application Support
  • Support and troubleshoot line-of-business (LOB) applications used across departments.
  • Coordinate with software vendors, MSP and internal stakeholders for application updates, patches, and integrations.
  • Assist in deployment, testing, and validation of business application updates and new rollouts.
  • Develop and maintain documentation for application configurations and support processes. 
Network Administration
  • Work in close collaboration with the MSP to manage and maintain LAN/WAN infrastructure, encompassing switches, routers, firewalls, and access points. 
  • Monitor network performance, troubleshoot connectivity issues, and ensure uptime across all sites. 
  • Administer VPN solutions for remote access and virtual desktop applications.  
  • Support DHCP, DNS, and IP address management (IPAM) operations. 
  • Collaborate with MSP, ISPs and network vendors on circuit management and escalations. 
Microsoft 365 E5 Administration
  • Administer the full Microsoft 365 E5 suite including Exchange Online, Teams, SharePoint, OneDrive, and Intune. 
  • Manage user identities, licenses, and roles via Azure Active Directory / Entra ID. 
  • Configure and enforce Conditional Access policies, MFA, and identity protection features. 
  • Administer Microsoft Defender for Endpoint, Defender for Identity, and Defender for Office 365. 
  • Manage Compliance Center configurations including DLP policies, retention labels, and eDiscovery. 
  • Monitor Microsoft Secure Score and drive improvement initiatives across the tenant. 
Backup & Disaster Recovery
  • Administer and monitor enterprise backup solutions (e.g., Veeam, Azure Backup, or equivalent). 
  • Review and monitor regular backup validation, restoration tests, and ensure compliance with RPO/RTO objectives. 
  • Respond to and manage data recovery requests in a timely and accurate manner. 
Security Tools & Compliance
  • Manage endpoint security tools including EDR/XDR platforms, antivirus, and patch management solutions. 
  • Monitor security alerts, investigate incidents, and coordinate response efforts. 
  • Conduct regular vulnerability assessments and drive remediation activities. 
  • Enforce security baselines and hardening standards across all Windows endpoints and servers. 
  • Support internal and external compliance audits ( SOC 2, GDPR, or similar). 
Business Process Support
  • Work with business units to understand technology needs and translate them into IT solutions. 
  • Participate in IT project planning and execution, including system migrations and technology refreshes. 
  • Develop automation scripts (PowerShell, batch) to streamline repetitive tasks and improve efficiency. 
  • Maintain accurate asset inventory and lifecycle management for all hardware and software. 
  • Provide IT input into vendor evaluations, procurement decisions, and contract renewals. 
Qualifications & Competencies
  • Bachelor's degree and 5 years of related experience, a Master's degree and 3 years of related experience, or 8 years of related experience and no degree.
  • Demonstrated experience supporting Microsoft 365 environments at an enterprise level.  
Knowledge & Skills
  • Expert-level proficiency in Windows Server (2016/2019/2022) and Windows 10/11 desktop environments.
  • Deep knowledge of Microsoft 365 E5 services: Exchange Online, Teams, SharePoint, Intune, Defender suite.
  • Strong networking fundamentals: TCP/IP, DNS, DHCP, VLANs, VPN, firewalls (Cisco, Fortinet, or similar).
  • Hands-on experience with enterprise backup platforms (Veeam, Azure Backup, Acronis, etc.).
  • Proficiency in PowerShell scripting for automation and system administration.
  • Familiarity with ITSM platforms (ServiceNow, Jira Service Management, or similar).
  • Experience with Active Directory, Group Policy, and Azure AD / Entra ID management.
  • Knowledge of security frameworks and tools: SIEM, EDR, patch management, vulnerability scanning. 
  • Excellent communication skills with the ability to convey technical concepts to non-technical stakeholders.
  • Strong analytical and problem-solving capabilities with a proactive approach to issue resolution.
  • Customer-first mindset with a commitment to delivering a high-quality end-user experience.
  • Self-motivated team player who thrives in a collaborative environment. 
Preferred Certifications
  • Microsoft Certified: Azure Administrator Associate (AZ-104) 
  • Microsoft 365 Certified: Enterprise Administrator Expert (MS-102) 
  • Microsoft Certified: Security, Compliance, and Identity Fundamentals (SC-900) or higher 
  • CompTIA Security+ or equivalent security certification 
  • ITIL Foundation Certification 
  • Cisco CCNA  
Additional Information At VERTEX, we invest in top talent with a highly competitive total compensation package that rewards performance and supports long-term success. Total compensation includes a base salary and a discretionary variable bonus program, depending on your level. Our comprehensive benefits package offers multiple healthcare and dental plan options, as well as company-paid Life Insurance, Short-Term Disability, and Long-Term Disability coverage—ensuring peace of mind for you and your family.   We offer a 401(k) plan with immediate matching and full vesting, empowering employees to build financial security from day one. Additional benefits include Flexible Spending Accounts, a robust Employee Assistance Program, and a suite of exclusive perks that enhance everyday life.   At The Vertex Companies, our salary ranges are intentionally designed to support meaningful career growth over time. These ranges allow employees to develop, expand their impact, and increase their earnings as they progress within their job level. A new hire’s starting compensation is determined by their experience, geographical location, scope of the role at the time of hire, and Company affordability. Our ranges are structured to reward growth and performance, ensuring there is room for advancement and long-term opportunity.   The salary ranges for this role are as follows:  $86,000 - $234,000 USD annually (Geographical Tier AA - Sample Locations: NY Metro, San Franscisco, San Jose, Seattle)   $79,000 - $216,000 USD annually (Geographical Tier A - Sample Locations: Irvine CA, Middlesex NJ, Tacoma WA, Boston, Alexandria)    Time away matters—so we provide a generous paid time off program, including vacation, sick time, and paid holidays (with prorated options for eligible part-time employees).   At VERTEX, growth never stops. Our signature “Lifetime of Learning” program offers tuition reimbursement and personalized support for employees pursuing advanced education—helping you sharpen your skills and accelerate your career.    Notice to Third Party Agencies:


Please note that The Vertex Companies employs a fully staffed recruiting team. We do not accept unsolicited resumes from recruiters or employment agencies. In the absence of a signed Recruitment Agreement, VERTEX will not consider or agree to payment of any referral compensation or recruiter fee. In the event a recruiter or agency submits a resume or candidate without a previously signed agreement, VERTEX explicitly reserves the right to pursue and hire those candidate(s) without any financial obligation to the recruiter or agency. Any unsolicited resumes, including those submitted to hiring managers, are deemed to be the property of VERTEX.

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