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How to License Your Organization

For most organizations, determining the right license structure is not a cut and dry process. Not only are there quite a few plans to choose from, but you can mix and match however you need in order to meet your unique business requirements.

There are three considerations when researching plan options:

  1. Business vs Enterprise
  2. Office 365 vs Microsoft 365
  3. E3 vs E5

Let’s take it from the top.


The first step is to determine your company size. Luckily, this one is pretty straightforward – all Microsoft Business plans cap at 300 users.

If you plan to license more than 300, you’ll (almost always) fall into Enterprise plans. Done.

Now it starts to get complicated.

In July of 2017, Microsoft announced Microsoft 365, a “new” licensing model that bundles Office 365, Enterprise Mobility + Security, and Windows 10 Enterprise. I say “new” because, to the enterprise, Microsoft 365 is not a new concept, it’s just a different name.

Larger organizations have had a few years to benefit from the bundle, first as Enterprise Cloud Suite (ECS), then as Secure Productive Enterprise (SPE). The big news with Microsoft 365 is that this bundle is now available to small businesses (under 300 seats).

So it may be old news to some, but the bundle offers some significant advantages:

  • You have one simple cost to maintain for your licenses, operating system and security applications
  • You’re paying per user vs per device
  • Windows 10 Enterprise includes add-ons like BitLocker, AppLocker and Windows To Go that help eliminate the need for additional third-party applications
  • Identity, device and data management are available from day one with Enterprise Mobility + Security

There’s a chance you’re thinking you already have security applications available and Windows 8 works just fine, but consider the cost savings. Microsoft 365 costs as little as $31.67/user/month, even less for Business plans. How much do all of your applications add up to?

In addition to incredible cost-saving opportunities, Microsoft 365 also offers small businesses:

  • Microsoft Connections – a simple to use email marketing service
  • Microsoft Listing – an easy way to publish business information on top sites
  • Microsoft Invoicing – a new way to create invoices and get paid faster

Next step is to determine plan options.

FeaturesApplicationsMicrosoft 365 E3Microsoft 365 E5
Office applicationsWord, Excel, PowerPoint
Email and calendarOutlook, Exchange
Chat-based workspaceMicrosoft Teams
Voice, video and meetingsSkype for Business
PSTN Conferencing, Cloud BPX
Social and intranetSharePoint, Yammer
Threat protectionMicrosoft Advanced Threat Analytics, Windows Defender Analytics, Device Guard
Windows Defender Advanced Threat Protection, Office 365 Advanced Threat Protection, Office 365 Threat Intelligence
Identity and access managementAzure Active Directory P1, Windows Hello and Credential Guard
Azure Active Direcory P2
Device and application managementMicrosoft Intune
Information protectionOffice 365 Data Loss Prevention, Windows Information Protection and BitLocker, Azure Information Protection P1
Azure Information Protection P2, Microsoft Cloud App Security, Office 365 Advanced Security Management
Advanced complianceAdvanced eDiscovery, Curtomer Lockbox, Advanced Data Governance
PowerBI Pro, MyAnalytics

Not sold on the bundle? Office 365 plans remain tried and true, offering Office Pro Plus programs with an ever-growing list of applications to boost productivity and collaboration.

Click through to learn more about Office 365 plans and pricing

and Microsoft 365 Business plans

Or check out our Office 365 ROI Calculator.

Different employees, different plans

Now that you understand the plan options available to you, you need to consider which plan types work for each employee, department and/or business unit.

If you’re licensing a 1,000 user company, generally speaking, it’s not as cut and dry as purchasing 1,000 Microsoft E5 licenses. Luckily, Microsoft makes it easy to mix and match plans to fit your unique business needs.

Let’s say you’re a 1,000 user retail company with 10% of users in affiliate subsidiaries.

The employees in your headquarters within marketing, purchasing, finance, etc. are the employees you may want to provide with Microsoft 365. These employees are working with sensitive data, working on company and personal devices, and need effective security measures and productivity tools to perform on a day to day. These users would benefit from Office 365, Enterprise Mobility + Security and Windows 10 Enterprise.

Then you have your storefronts – hundreds of employees who don’t need all the bells and whistles of full licensing, just a small inbox, maybe SharePoint for intranet access, and who likely utilize shared workspaces. Retail workers can easily get by with Office 365 licensing.

Now let’s assume that you recently brought on three affiliate organizations – much smaller shops, but with users that you want kept in the loop. In this scenario you may even consider combining Enterprise and Business plans.

The point is, the choice is entirely up to you. It’s important to understand your business needs and goals and develop a plan. Remember, too, that you aren’t stuck and you can always scale up or down where needed later on.

Ready to get started?

For more information on licensing options and how to switch from Office 365 to Microsoft 365, fill out the form below. If you’re ready to get started with Office 365 (no matter the plan), click here.


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