Stripe would almost certainly prefer to outsource this for places where they have a small handful of employees, and dealing with one company has a big opportunity cost buried in it that they almost certainly would be willing to pay.
If that was true then they would be, but they aren't. Companies that big can easily afford one or many full-time employees focused on office and resource management which is more than enough to figure out a few leases.
Remember this is a company that already has a major international business in one of the most regulation industries. Adding in a few real-estate deals is unlikely to be a major source of friction.
Isn't that We's end goal though? To get billion dollar companies like Microsoft, Stripe, etc. as tenants. People that don't really want to deal with running an entire building when they can just pay someone else to do it.
Counterpoint: Google now outrights owns a absurd amount of buildings outright on Manhattan's West Side near SoHo.
These big companies have so much money, that they stand to make even more money just holding the damn real estate for all they care if they end up not using it.
It's the same as a individuals buy vs. rent scenario for a house. Sure, rent may be cheaper, but there are long term pros just holding the property yourself if you can afford it.
Which makes sense If you run your own investments / pensions your going to want to have some commercial property investments (normally by having a certain % in funds / REITS)
No. Companies that big have the resources and stability do it themselves, and want control over their space as well. They have no need for a middleman other than real-estate brokers or construction companies to actually get the space.
'Affording flexibility' means accepting higher costs in order to get short-term leases, which is exactly what companies like We offer. Going the normal office rental route has longer-term leases and thus much less flexibility.