I work for a small business, which currently has 4 PCs, and everyone else uses laptops (about 10 other people). Some of us use Mac, but the vast majority of us are on Windows 8.

We are currently expanding, and are about to hire out another 40 or so contractors, who will each need their own laptop. They will all need Windows, Office, a Trend Micro antivirus subscription and an Office 365 $8 Mail user subscription (we use office 365 for our mail)

Here is a rundown of the current costs for each person

  • Laptop - ~$500
  • Laptop Accessories (bag, mouse etc) - ~$90
  • Windows 8 - $0 (comes with the laptop)
  • Office 2013 Home and Business - $278
  • Trend Micro License - $25 (We buy these in clusters of 6)
  • Office 365 email account - $8 per month

Of course, the laptop and licenses can be retrieved once a person leaves, so replacing people is effectively free.

Some users also occasionally need Visio and a few other tools (Me and my direct boss have Visual Studio for example)

Unfortunately things are becoming hard to manage. Installing everything on a new laptop is a real hassle, and if we forget something for a contractor (like Visio) then we have to manually go out onsite and give it to them, or if its a downloadable (usually free) application, we have to take them through the install process over the phone.

It is a total mess to support and manage all these laptops.

I have been tasked with coming up with a solution, but because I am not an IT guy (I am a programmer) I have probably done something wrong.

Anyway, here is an overview of what I am proposing. Keep in mind we have no Domain Controllers (and my boss doesnt want to spend money on a server or any of the MS server products) and we have no interest in setting up Linux servers on anything.

My current idea is to buy laptops in bulk from a company like Dell, where we can get them cheap, then purchase a Microsoft Open License for ~50 machines for Windows 7 Pro. After creating a basic image (which contains the basic OS, Office and the Intune Client), I plan to image all the machines. I am considering recommending Office 365 for our office licensing, although a Volume License for Office 2013 could also work.

Then we use Microsoft Intune to manage all the machines so that software installation can be done easily and remotely, and we can enforce things like Windows Updates and Virus Scans are actually occurring.

I guess the biggest problem I have is license management. What is the best way to make sure everything is licensed correctly and we have a proper, secure, accessible (to administrators) list of product keys? The good thing about Office 365 if is provides good quality License management via an online interface.

Am I doing something fundamentally wrong? Am I going to run into huge issues down the line? Are there things I haven't considered? I am not a sysadmin and this is the first such project I am undertaking.

Also, at what point should I recommend to the business that we get a proper domain setup, especially since we almost always use laptops (and the vast majority of employees are onsite at various clients almost all the time)?

Are there any god ways to save money and make organisation here easier? Even with this current system that I have proposed, it still means we have to manage licenses for Windows, Office 357 and Trend Micro separately. And I have to manually store product keys somewhere.

Is there an easy way to simplify all this?

migrated from superuser.com Nov 19 '14 at 3:46

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    It sounds like you are on the right track to me. You are employing a good tool for your system management. I advise you to stick with this approach and learn to use it really well. Good luck! – mcsilvio Nov 19 '14 at 1:28
  • Well the biggest problem I find is that I have to manage licenses in 3 different places (Office 365, Trend Micro, and have to locally store keys for other things like Microsoft products). As far as I can tell, while Intune does a good job of managing things like Volume Licenses, it doesn't actually manage product keys, which some products enforce. Also, I have no idea how Windows activates on a volume license – PlausibleSarge Nov 19 '14 at 1:30
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    Are data files stored on the laptops? Do they need to be backed-up? What's the sensitivity of the data on the laptops? How will you handle a user damaging the software environment (assuming they have Administrator rights)? Are you planning to have spares ready to ship out? How are you planning to handle OS and application updates? How long will these contractors be engaged (is this seasonal or permanent)? – Evan Anderson Nov 19 '14 at 5:06
  • Data files are stored on the laptops sometimes, however important documents can be stored in the cloud, especially if we go with Office 365. Laptops don't really need to be backed up, and workers are responsible for their own data files so they may need to back them up by themselves. The data is corporat data and it would be bad if it were leaked, however it's not data which is likely to destroy the company - its not financial or personal documents, it's more project requirements, test data, that kind of stuff. The worst would probably be code, which we really don't want stolen – PlausibleSarge Nov 20 '14 at 3:50
  • Intune has a remote management system in place to prevent users from damaging the software environment themselves (plus they wont have admin) so we can remote in if they have problems. Intune also handles OS and application updates easily. Windows updates can be scheduled (and forced) and we can push out new versions of applications. These contractors are going to be engaged for ~6 months, however they will pass on their computers as they leave so the laptops will be used in perpetuity – PlausibleSarge Nov 20 '14 at 3:51

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