Windows Desktop OS Engineer

Job Tittle: Windows Desktop OS Engineer
Duration: 6 month rolling contract
Location: Onsite 5x/week - 130 Royall Street Canton Massachusetts 02021; transition to hybrid down the line
Minimum Requirements:

• 5yr+ Windows OS Admin experience
• Windows 10 & 11
• 2yr+ POS Device Image Building experience
• Very nice to have MCSE/MCSA (not required)

Job Summary We are seeking a skilled Windows OS Engineer to manage, configure, and troubleshoot our fleet of Windows-based point-of-sale (POS) devices. The ideal candidate will have strong technical skills in Windows operating systems, including windows 10 LTSC and LTSB, Windows 11, device imaging, and configuration management across multiple POS devices and Windows tablets. While server administration experience is relevant, this role is specific to in-store Windows clients or desktops, as Windows servers are not involved in our POS systems. Key Responsibilities

• Manage and maintain Windows-based POS devices across multiple locations
• Responsible for the build and maintenance of Windows OS images of the Dunkin and Baskin enterprise in-store POS desktop environments, ~70,000 POS Windows machines.
• Create, test, and deploy Windows images for POS devices
• Configure and optimize Group Policy and other Windows settings for POS applications and security
• Troubleshoot and resolve Windows-related issues on POS devices
• Evaluate and remediate Windows security vulnerabilities from periodic scans
• Develop and maintain documentation for POS device configurations and processes
• Collaborate with IT and operations teams to ensure POS device reliability and performance
• Manage wireless functionality for Windows tablets

Misc Information from HM:
Powershell and batch scripting is a nice to have skill, we use scripting to some degree, but if this person will rely on scripting, they ll need advanced level scripting skills. Myself personally, I would shy away from a candidate who still uses scripting as their mainstay, but someone who is extremely knowledgeable in the areas of vbs, powershell, or similar scripting would certainly be of interest. Any kind of scripting skill shows the candidate probably has a mindset that we re looking for, meaning a logical approach to building and following processes.

This person will be building new hardened images from clean Windows builds from our hardware vendor (Client). The supplied images are wide open so there is a lot of hardening to do so that these images meet our extreme security specifications. They will also be deploying these images to our labs as well as maintaining them in the field.
The overall main skillset is a deep knowledge level of Windows 10 (LTSB & LTSC) and Windows 11 (from a Windows client or desktop perspective), including Group Policy as we don t use Active Directory on our POS terminals. To take a clean Windows image from our vendors (mainly Client) and (following a documented process) apply strict security measures and policies to the image. This person should have the depth of knowledge to 1), understand these measures and policies as well as 2), know of ways within the OS where we can strategically better our security measures. This paragraph is probably the overall main thing we re looking for, along with an advanced ability to work as a team and raise their hand when they see something that can be improved.
Required Qualifications

• Bachelor s degree in computer science, Information Technology, or related field (or equivalent experience)
• 5+ years of experience managing Windows-based systems, preferably in a POS environment
• Strong knowledge of Windows client operating systems, particularly in enterprise environments
• Experience with imaging and deployment tools
• Familiarity with Group Policy
• Experience with remote management and monitoring tools
• Project planning, deployment, and documentation
• Experience with Windows Embedded Shell
• Experience with Windows DISM tool

Preferred Qualifications

• Microsoft certifications (e.g., MCSA, MCSE)
• Familiarity with POS hardware configurations, printers, etc...
• Knowledge of retail and/or hospitality IT operations
• Familiarity with networking concepts and troubleshooting
• Experience managing Windows tablets and their wireless functionality

Key Skills

• Windows OS administration
• System imaging and deployment
• Configuration management
• Troubleshooting and problem-solving
• Technical documentation
• Strong communication skills

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