Why?
Because the consequences of getting this wrong can be far more expensive than whatever productivity gains you, the individual employee, claim to be achieving.
Docker, for example: we had absolutely no interest in individual users directly accessing their online features (we took a bit of trouble to block them, in fact), so theoretically, the free Personal licenses should have been fine. No.
Ok, so just have each Docker user pay that $5 themselves. How do we make sure every person who has Docker installed on their PC really is paying for a license? Even if we gave them all corporate cards, and Docker was going to be cool with several hundred accounts (or more) from the same domain not being on the "Business" plan, we then get to set up a process with Accounting to make sure the PC scans match the payments.
This might all sound ridiculous to start-up/boutique employees, but is a basic fact of life in corporate IT... which Docker was hoping to get a lot of money out of.
But why do we know what users have installed on the PCs assigned to them, aside from the licensing? When your product has a security hole (and unless your product never, ever talks to the Internet or other devices, it will someday), we need to know exactly who has it so that we can force them to patch. Again, tens of thousands of users with potentially thousands of products that need to have security issues tracked. Nightmare.
So if your custom software house** doesn't want to sell us your product in a way and provide management mechanisms that we feel comfortable with, then we'll find one of the many that does, or is happy to work with our preferred resellers. Or we will help departments redesign their processes to not need it.
Corporate IT cares deeply about what managers want, as they pay the bills. If they want your product for their subordinates, we will work to make that happen in a way that keeps our legal department and IT security management happy. Corporate IT cares deeply about users being able to use the products and services their managers are paying for. Corporate IT does not give a fig what individual users want, if they can't get their managers to pay for the cost of us dealing with that new product.
Negotiating license agreements and tracking usage, as I said before, is a full time job for several people. I am fortunately not one of them, but I've worked with them when supporting products within the company. Large companies do not employ these folks out of charity.
Corporate IT and corporate life is certainly not for everyone. Corporate IT doesn't work this way because we're humorless prigs; it works this way because there are billions in sensitive data and intricate production processes to protect, and tens of thousands of well-meaning folks who are competent in things other than infosec potentially providing network access to people who are not well-meaning.
If you want that sweet sweet corporate cash, figure out how to accommodate their purchase and IT management processes. Software resellers may be a good compromise. If you don't want to deal with corporate purchasing, don't be upset when a lot of your potential users end up with someone else's product.
** Anything smaller and more niche than SAP may as well be a "custom software house".
Legal is often still involved when it comes to new software products, because, among other things, there's GDPR. Oh, and Works Council.
My main point remains unchanged: relying on tens of thousands of end users to manage their licenses is something that large enterprises just can't do, so we end up with rules that seem draconian, and you, the hopeful seller of software/services to be used in corporate environments, will benefit from understanding how we work, even if you think it's stupid.
