Broadly, there are tradeoffs, including organizational risk tolerance, and which margins one is permitted or not permitted to take which risks on.

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.)

A lot of smaller companies elect to onboard international employees as the employee’s country’s equivalent of a 1099 rather than setting up the local infrastructure. I am not sure at what point this no longer becomes viable because it’s obviously not a practice followed by larger corporations for the most part.

Its certainly a lot harder to hire someone in a country that you don't have a presence in, usually this means setting up things like employer tax arrangements, pensions, health benifits etc. Some companies get around this by having their remote employees in countries where they don't have a legal entity become independent contractors, and there's a couple of startups looking to solve this problem as a service.

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

I think GitLab does a decent job of that. I think There is a list of countries and how you could work with them. I.e. employed vs contracted vs not-at-all

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.

I am sure there are legal reasons but if I had to set up a remote company I would probably try to restrict the timezones. My current company has dev teams in South America and India. They are all good people but dealing with India [13 hours) is a big pain because somebody has to make calls during his personal time instead of work time. It’s a real burden. And in my view you absolutely have to make direct calls from time to time. You can’t resolve all issues with asynchronous communication.

> You can’t resolve all issues with asynchronous communication.

Name one?

An example is custom hardware not working as expected. To debug this you may need five different people on the line at the same time. If you do this in an async manner it will take days or weeks to resolve.

But can be resolved...

Pair programming!

This is the only one that actually is valid. Good point!

1:1 career conversations

You can't have these in slack async? (because I have)

I don't believe you can have that conversation effectively if each person gets to send one message per day due to timezone-induced lack of workday overlap.

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> ...

It can work if you're not in a rush. If you need to wait overnight to get help with something that slows you down.

So its a trade off? But still can't name one..

I work at Stripe, in the remote hub, from Tokyo. Stripe has a large and growing workforce outside of North America and so far it seems to be going OK.

The biggest challenge (from a trenches perspective) is timezones, so teams end up being either NA+APAC or NA+EU.

There are two issues at least. First is working in a country whose government could demand or seize your company-issued equipment, jeopardizing privacy and corporate secrets. Second is tax regulation. If you are an working in a country where your company doesn’t have a presence, suddenly the government can make the case that now there is a reason to tax the company because your working there can constitute presence. So not only would you be potentially liable for taxed earnings but so too your employer. Also some companies have announced that they would adjust compensation in accordance with cost of living, so moving from the Bay Area to Idaho or Belize would no longer be as favorable (I’m sure it would still afford a very comfortable standard of living regardless).

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.

Another challenge is time zone differences.

This is definitely true for most orgs, but in some case it can actually be a benefit, with work following the sun".

I worked at a mostly remote company for 5 years. It works very well with on-call rotations but it's a big problem for product work.

In ideal world yes, but reality is that it requires significantly more effort, e.g.: "anywhere in the world" would really mean "anywhere in the world except Iran, Crimea, and other countries/regions that US thinks you should not do business with". Sometimes a company may not be even allowed to have non-US citizen employees.

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.

Yes and no, depending on jurisdiction and the compromises you’re willing to make.

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.

The article says they have people in "Australia, Brazil, Canada, France, Germany, India, Indonesia, Ireland, Japan, Mexico, Netherlands, Singapore, Sweden, UK, and the U.S."

Definitely - see GitLab and hundreds of others.