Demo

Windows 11 Upgrade & Migration Specialist

RSM Solutions, Inc
Chicago, IL Contractor
POSTED ON 4/16/2025
AVAILABLE BEFORE 5/15/2025

Thank you for stopping by to take a look at the Windows 11 Upgrade & Migration Specialist role I posted here on LinkedIN, I appreciate it.


If you have seen my Job Descriptions before, welcome back. If you are new to my JD's, welcome. I am a real human writing this (no bots, no AI)...I like to add a human touch to these things. I know that looking for work is about as fun as being poked in the eye, so if I can make it a little easier and - perhaps even with a little humor - I am going to be glad to do that.


As with just about every role I work on, social fit is almost as important as the technical fit. For this role, we are seeking that true 'lead'. Someone that has that mix of technical skills to do the work, but also that ability to be that point person in a meeting or discussion and be that 'if it is to be, it is up to me' person. This requires a relatively nifty mix of both EQ and IQ. So, if you are that person with EQ as well as IQ, you will be spot on with regards to what we are seeking for this role.


This is a contract role that will last for about 12-15 weeks. This one is being done remotely. However, I am only able to work with candidates that already reside in the US. In addition, I can only work with US Citizens or Green Card Holders. I cannot work with H1, H4, OPT, EAD, F1, STEM or anyone who is not already a US Citizen or Green Card Holder.


In addition, I am not working with external vendors for this role.


Here is what we are seeking. We are looking for that combination of a lead that can also do the work for this role. You will be working on an end-to-end Windows 11 Upgrade for about 4,000 endpoints.


This role will include Solution Architecture & Planning; Development of your Plan (including configuring and deploying Intune); and the PC Refresh and Autopilot Deployment (this will include a Pilot as well).


Here are some of the main tasks for this role:

  • Conduct current environment review and planning sessions
  • Review project goals, customer technical pain points, challenges, and future technical requirements
  • Detailed technical review of the existing O365/Azure infrastructure. Review existing design documents (if available) to ensure proposed solutions meet business objectives and design best practices – keeping in mind that the Windows 11 solution should be designed for Windows 11 best practices with respect to AD, user, object and group policies
  • Review O365/Azure licensing assignments and requirements
  • Identify current license assignments
  • Discuss future M365/Azure requirements and capabilities (this will include O365/Azure Security Best Practices)
  • Review of new feature requirements for: Intune, Autopilot, MDM
  • Review and define Win10/11 Deployment Profile requirements: OS Build, Embedded Apps, required plug-ins, Default settings/policies, and SaaS Bookmarks
  • Create and present Findings & Recommendations Report for both onsite and automated deployment
  • Documentation of Intune requirements (including updates & patches)
  • Develop your plan for this migration / upgrade. This will include device security policies, encryption polices, authentication, VPN support, configuration of MDM authority as well as all the other things that someone who has completed more than a few of these migrations probably already know like the back of their hand.
  • White Glove deployment for specific user groups.
  • Creation of development profiles
  • Creation of AutoPilot device groups
  • Determination of enrollment types
  • Determine requirements to deploy PowerShell scripts for new & existing machines.
  • Execution of that deployment


Here are the main requirements:

  • At least 1-2 Windows 11 upgrades or migrations. You should have a few other Windows upgrades or migrations in your past (version isn't that important) where you led that upgrade from start to finish. The Windows 11 experience is an absolute must 'gotta have'...without that experience with Windows 11 (at least 1 upgrade from start to finish) we wont have a fit.
  • Experience with environments of 4,000 endpoints or greater
  • PowerShell Scripting experience
  • Prior to your Windows 11 experience, you should have at least 4-5 years of experience as either a Systems Administrator or Network Administrator.

Salary : $60 - $90

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