E3 to E5

As a ten-year veteran of Microsoft, I have recently moved into the Partner space as the Cloud and Collaboration Practice Manager at Insentra. This transition has been both rewarding and challenging. Thankfully my time at Microsoft allowed me to experience the big changes their sales model went through as they adapted to new market trends.

Traditionally vendors have been focused on having the licensing discussion and for good reason. It made sense, if you were selling a physical machine, software and other products it should come in a box for an up-front fee. However, times have changed and people are consuming technology in a different way – they want it available on demand. Whilst at Insentra we don’t transact any tier one software licenses, we are regularly engaged to assist our Partner’s clients in making the best licensing decision based on their business requirements.

With the rise of ‘consumption economics’, the conversation needs to change. If you’re anything like me and love a good tangent, I would recommend reading “Consumption Economics: The New Rules of Tech by  by J.B. Wood,‎ Todd Hewlin,‎ and Thomas Lah which outlines the significant impact megatrends like cloud computing, managed services, and the rise of consumer technology have on business and the way technology is consumed… but I digress.

How do you talk to a customer about Microsoft 365 E3 – v’s – E5?


Consumers are now smarter. Rather than being bamboozled by a hard to understand licensing construct, they are now making informed decisions based on perceived value driven by their usage of technology.

Accordingly,  we have to move to discussing the pain they are experiencing and the actual benefits they can realise. Let’s face it licensing discussions are boring at the best of times (E3 versus E5, P1 versus P2, BLAH versus Acronym BLAH Blah … are you asleep yet?…)  and invariably they result in a cost discussion – a place you don’t want to go if the value hasn’t been articulated.


So remember, don’t bore your customers with scripts like:

“E3 licensing costs $x. You get licenses to O365 which includes; EXO, SPO, Basic MDM (more acronyms I know)…and all the features you can read from a list.

“E5 is better because for $y you get not only E3 but you get CAS, ATP, AADP, AIP…BLAH, insert three letter acronym here…”

If you take this approach, watch as your audience slowly but surely nods off to sleep. Most of us have heard that broken record play since, well FOREVER!


If you want to make a difference, you need to consider what’s important to your customer. Sounds simple? Yes! Often though we have one pitch and don’t remember THE ‘customer’ could be a combination of people within an organisation, each with their own needs and desires.

Here are a few angles to consider;

CFO – Do I own it? If so, why am I not using it? Get rid of it then!

  • You’d be amazed how many companies are in this situation. Either they don’t know what they have, or no one has told the IT guys how to turn it on!

CTO – I have the basics (E3), why do I need the Rolls Royce solution?

  • Valid question, keep in mind that there two types of enterprises – those who have been hacked and those who don’t know they have? Do you really want to be in the last category?

CIO – We are a leading company, and proud that we are BYOD! We support any device.

  • Hmmm really? Great, what freedom your employees have! What great thought leadership! BTW, how are you managing the devices and ensuring that you are protecting your company data? BYOD typically means personal devices, doesn’t it?

CHRO – We give our teams choices, they can work from on the road, from home, etc.

  • Once again, good on you, you have embraced the mobile workplace. How are you protecting company data from being stolen, or user credentials being inadvertently being breached? Identifying logins happening from suspicious countries?

CSIO – Microsoft isn’t a security company. I have been using BLAH for X number of years. By the way, our enterprise security is second to none and we use; Product X for this scenario, we use Product Y for this mobile solution which is better than your integrated solution, we use Product Z for information protection.

  • Awesome, rock on! Is the CFO is going to be excited that you are paying for three products, the SIs to run the integration and time spent transforming three reports into one
  • Is your CIO is going to be excited about supporting three solutions
  • Best of all the CSIO is going to love having to manage the risk across three different identity and security models


Customers like to hear they are reducing complexity and gaining value from a solution. As I’ve said, Microsoft provides a single pane of glass for security.

Whilst the E3 license of provides the basics to secure your online experience, the step up to E5 helps to answer these questions:

  1. Is it possible to be in Melbourne, Seattle, and Beijing at the same time?

I think not, well unless you have a teleportation device! Whilst cool, not possible…yet! Protect identities and intrusion with Azure Active Directory Identity Protection

  1. What happens when I been out for the night and leave the laptop in the club or accidentally email the company files to my contacts?

Track where files go and who opens them and revoke access as well with Azure Information Protection.

  1. How can I stay across Shadow IT? What are my users installing, what are they doing in the environment, what IP or files are they sharing to unauthorised cloud storage?

Identify and protect the business with Office365 Cloud App Security.

  1. How can I Detonate links and attachments before they get hit my users and safeguard your network?

Exchange Online Advance Thread protection make this possible.

In many organisations, complexity breeds fear, inhibits productivity and is typically less cost-effective. Choosing an integrated solution reduces costs, complexity, and risk whilst increasing the overall security posture of your organisation.

There are other security platforms, most of the time made of several disparate solutions loosely coupled to work as an “integrated” platform.

Whilst there are other platformed security solutions, the One Microsoft Security solution provides a truly integrated, single point of management, monitoring and built on trust.


Confused a bit?  Let me break it down with an example I use to help me explain security in my discussions with customers and partners.

Think about how you and your neighbors secure your homes.

Your neighbor has chosen to buy their home security from multiple vendors. It comes with products that are the best in the market, albeit not fully integrated. Not a bad choice by any means but is it the right choice?

Their mailbox is made and monitored by Mailboxes-R-us, their gate and fence is monitored by Richo’s Gates, their front yard is monitored and maintained by Hunky Hambo’s Handy Home Services, their porch is looked after by Pirate Pete’s SecuraPorch and finally, their house is secured and monitored by Arun’s All-Up Security Solutions.

Yep best in the breed, but how do they manage the security system. They receive mail but how do they validate it is for them? What happens when someone breaks in; who do they call, how do they work out where the intrusion came from, what has been taken and how do they take preventive action. Last, of all how do they remove the intrusion.

Now going one door down, your house. You made a different choice by buying a fully integrated system. Whilst each component may not have been considered the best in the breed for every situation, as a package, not only was it more cost-effective but easier to deploy, manage, and maintain.  Importantly, you know the components solution will ultimately become contenders for best of the breed over time.


Remember, understand your customers pain in the present and how can you bring them not only value, but pleasure in the future.

Microsoft has a heap of content out there, as a partner take advantage of it. Take time to check out Security Practice Playbook and the Enterprise Mobility & Security Playbooks.

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