So I have worked on Office 365 with a number of companies and they all want to get on the bandwagon, but is that a good thing?
Many times a CEO, senior IT or business person will get a demo of what Office 365 can do for their business and decide it is right for the company. But the problem is often when it comes to selling it to the business. If the business can see the benefit and become engaged then Office 365 will fly....if not then IT will have yet another under-utilized system to support.
The key to success for Office 365 is to carefully plan what services are key and how you can enable all functionality for each component as quickly as possible. Providing services such as Teams with only the "Team Site" capability and no 1:1 chat, OneDrive or meeting functionality will quickly switch users off. It quickly becomes too constrained with users unable to utilise the service as designed.
Office 365 is intended to be mobile so should be deployed as such with it being available on mobile devices for all colleagues. There is little requirement for invasive Mobile Device Management for personal devices with Mobile Application Management giving a secure offering with limited impact on users. The ability to take notes on the go, save to OneDrive or share through Teams is what makes Office 365 work.
BUT....you need to think differently and not tailor these solutions for your existing services and deployment processes. Use them out-of-the-box and you will be rewarded. Throw away SharePoint designer and embrace PowerApps and Flows. Allow Teams to drive other systems and services and invest in BoTs, they will reduce repetition and help to streamline processes.
The only way you will achieve this is to empower your users and the business. Office 365 is intended to open up functionality for the business, not just IT as is often the case. Yes you need controls, but why can't business users develop SharePoint communication sites with Flows and PowerApps? They are often the people who know what they want and can drive integration and help with investment.
So, I guess what I'm saying is that Office 365 is worth it, but only if you fully utilise and embrace the services across the business. There are other options out there, but the tight integration into Office apps such as Word and OneNote make it a compelling option.