In our office, we'd definitely need the enterprise version for compliance reasons, not because of the features. That's about 14/user/month.
At a workforce of roughly 2500, that's a 4million+ yearly cost for something that is comparable to something you can get without that pricetag. It's no competition at all at that point. Think about it, would you be willing to ask your boss to pay 4 million so you can have a different chat app? No matter how much more ergonomic and friendly and intuitive it is.
The question is: "are staffers $14 / mo more productive with it, than the free version?"
The answer may also boil down to satisfaction, support calls, other things, aka 'total cost of ownership' as well.
Not 'But it costs $X million!'.
Companies will spend a fortune giving staff the right monitor, or chair, but literally don't think they're smart enough to know the dam tool they use all day?
Let them pick their chat software, like they pick their monitors.
The person responsible for picking our work laptops asked me for advice selecting our new Macs since our old model was being replaced:
"Do we really need to spend an extra $1000 for 64GB of RAM instead of 24GB?"
"That'd save us $300 per year, or about a dollar a day, over the deprecation schedule, and it'd make our devs slower. We spend more than this to have lunch catered."
"You know... good point. 64GB it is, then."
And that's how we opted for beefy machines on this hardware cycle. The guy I talked to is extremely smart and competent, but just hadn't looked at it from that angle. Once he saw it, he instantly bought in. There are dumb ways to save money with massive negative ROI, and cheaping out on basic equipment and resources is one of them.
I, living in Germany, rather wonder myself quite often why US-American tech startups don't act much more frugally: this would give them so much more leeway/runway to make their startups succeed.
Note that you don't hear so much about the many, many startups doing slow growth things in less glamorous fields. I know a few companies making agricultural products for small farmers. Yes, frugality makes perfect sense for them. They're not going to have a hockey stick growth curve where they go from $0 to $10M to $1B over the course of 2 years. Their revenue graph will look more like a traditional manufacturer. They're doing things the way you describe, but they're not all over tech and non-tech news sites.
Better to go bust quick, than to eke out a tiny profit by being super frugal. The latter is a waste of everybody's time.
You’re actually giving that same venture capitalist $4m of their own money back, in a way that makes their investment more valuable.
"It’s one banana, Michael, how much could it cost? 10 dollars?"
Also yes, volume licensees generally get massive discounts.
(I don't love Slack by any means. Still, I'd pay $9/mo out of my own pocket not to use Teams.)