Any bundle with the word “Business” in it will pretty much get you started on the Office 365 platform, if you are a small or mid-sized business of less than 300 users. In fact, if you have or have had “Small Business Server” (SBS) or Windows Server Essentials (WSE) in the past, then you are probably shopping in this bracket. Especially if you are mostly cloud-based, or are headed in that direction, away from on-premises based Windows Servers of yore.
Office 365 Business Essentials – For access to Email via Exchange Online, document sharing via SharePoint Online, OneDrive, Teams and other “online” apps, you can stick with this very modestly priced subscription at only USD $5/user/month. Not a lot of extra bells and whistles here, folks–that’s why it’s called “Essentials.”
Office 365 Business Premium – Everything that Essentials includes, as well as subscriptions to the Microsoft Office desktop applications (for Windows, Mac, etc.), this is USD $12.50/user/month. NOTE: This is also the most popular plan in the SMB space, and is the recommended minimum starting place if you plan to use Microsoft Office software with your 365 cloud-based services, since Microsoft will restrict support for current and older “Open/volume” licensed software in 2020.
Microsoft 365 Business – Everything in Business Premium plus a whole lot more for managing your users, data and devices: applying Security & Compliance settings, Information Protection (Encryption), Data Loss Prevention (DLP), Advanced Threat Protection (ATP), Windows 10 licensing, and more–all for USD $20.00/user/month (FANTASTIC value). The idea with this subscription is that you do not need a Windows Server on-premises–everything can be managed in the cloud (or you are at least well on your way down that path–this can help get you the rest of the way there). I recommend Office 365 Business Premium customers look toward this upgrade, and this or the E3 plan should be your starting point if you are in an industry such as medical or financial services, due to all of the included security & compliance features.
And the “Enterprise” track?
If your organization has more than 300 users, and/or, if you are still heavily reliant on Windows Servers that run in your own data-center or in a co-location (and they won’t be going anywhere in the next 5+ years), then consider looking toward the Enterprise track, which is targeted more toward “hybrid” organizations–or larger companies with data and applications both on-premises and in the cloud.
Office 365 Enterprise:
E1 – Similar to the Business Essentials bundle above–this SKU would be applied to a “cloud only” user, with no applications on the desktop; USD $8.00/user/month.
E3 – Includes the Office 365 Pro Plus software for Mac and PC, as well as several nice Security & Compliance upgrades: Exchange Online Archiving, DLP, Information Protection (Encryption), and more! USD $20.00/user/month (NOTE: this is the most commonly deployed subscription in the Enterprise space)
E5 – Includes everything in E3, but adds fancier “cloud-based phone system” and audio conferencing capabilities to Skype/Teams, as well as even more security features including Advanced Threat Protection (ATP), for USD $35.00/user/month
Enterprise Mobility + Security:
E3 – A bundle of tools for managing user identity, devices and data across cloud and premises-based locations: Intune, Azure AD Premium P1, Information Protection P1, Advanced Threat Analytics (ATA) and more, for USD $8.74/user/month; another bonus here is that the subscription includes Windows Server CAL’s, so you do not need to purchase those for Windows Server 2019 if you have this subscription.
E5 – Everything in the EMS E3 bundle, plus Cloud app security, Azure Advanced Threat Protection, and “P2” versions of Azure AD Premium and Information Protection plans, for USD $14.80/user/month
Microsoft 365 Enterprise:
E3 – A bundle of bundles including: Office 365 E3, Enterprise Mobility + Security E3, and Windows 10 Enterprise E3, USD $32.00/user/month
E5 – The fullest boat of bundles: Office 365 E5, Enterprise Mobility + Security E5, and Windows 10 Enterprise E5 (including top-end security features like Windows Defender ATP), for USD $57.50/user/month
Last, be mindful of this important fact: moving from the “Business” to the “Enterprise” track or “Enterprise” to “Business” will usually mean re-installing software for the end users, since Office 365 Business edition is literally a different software package than Office 365 Pro Plus, which is included with Enterprise. Same is true of Windows 10: the “Pro” or “Business” version of Windows 10 is different from “Enterprise,” and requires a wipe/reload of the OS. So best to start off in the “right track” and upgrade as needed down that path, rather than switch between them. The exception here is that EMS E3 or E5 can be tagged on top of a Business subscription–there is no reinstall of software required for that–the rule only applies if you are switching either the operating system or Office software.
Azure Active Directory Seamless Single Sign-On (Azure AD Seamless SSO) automatically signs users in when they are on their corporate devices connected to your corporate network. When enabled, users don't need to type in their passwords to sign in to Azure AD, and usually, even type in their usernames. This feature provides your users easy access to your cloud-based applications without needing any additional on-premises components.