For example, some software companies are regulated in some jurisdictions. A not-too-hypothetical regulation is "regulatee understands and enthusiastically consents to unannounced site inspections by regulator at any time of our choosing." Thankfully, this doesn't apply to most software companies, but ones who it does apply to have hopefully long-since had a chat with their competent legal professionals about precisely what the definition of a "site" is.
There are many, many issues like this, and they're fractally complicated. Even the basics of "How do I hire a full-time white collar employee with the standard package plus equity?" vary substantially between jurisdictions. Setting up the infrastructure for it in a jurisdiction can take the better part of a year. (It would be an excellent thing, for everyone, if jurisdictions decided to compete on ease to employ their residents.)
However seeing as Stripe are advertising office based Roles in 6 different countries having all the remote roles as "North America Only" just seems plain lazy. I get that timezones might be an issue for some roles, although its better to then advertise a remote role as "GMT-8 to GMT-5" or whatever rather than a geographic location
From a legal perspective I get the limitations to local countries. I considered hiring remote (currently not easily possible due to company policies on eg in presence card pickup and activation) and would’ve scoped to the EU only in that case.
There are great people available outside of the EU, but the additional legal hassle makes the trade-off not worth it unless you expect a large amount of remote employees in that country.
Name one?
Day 1 M> So, what do you think your next career move would be?
Day 2 E> I don't know. I really enjoy software engineering, but I think I'm ready to take on some kind of leadership role.
Day 2 M> OK, that's great. Do you need any kind of support before taking that on?
Day 3 E> I'm not sure what you mean.
Day 3 M> ...
The biggest challenge (from a trenches perspective) is timezones, so teams end up being either NA+APAC or NA+EU.
Note that I am not a tax attorney nor an expert on international affairs. These are some things I’ve gathered for why I can’t sit on a beachfront property in Thailand or South America and work.
Then, you have to make sure you can handle payroll, taxes, and overall operations.
It doesn't have to be all or nothing: expanding from an office-centric to all-US is a good start - baby steps.
Hotjar, for instance, use contractor arrangements for most countries, then setup employment infrastructure in countries where there’s enough hires (or potential hires) to make the investment in overhead worthwhile.