"There is substantial organizational, legal, and financial infrastructure required to support each new jurisdiction we hire in, so we have to be measured in how quickly we expand."

Each country you want to pay salary in comes with legal aspects. Therefore they have to be a bit tactical with where they try to hire people.

As remote guy I see potential for disruption in this area. So far umbrella subsidiaries or agencies and invoice-based contracting does the job, but stuff like IP rights and liability is quite complex. We would need some Stripe-like service for employment matters.

In the US there are PEOs (professional employer organizations) that function as virtual co-employers that allow companies to hire in all 50 states without establishing a physical presence, handles payroll, state taxes, health insurance and benefits in all the states etc.

Something like that, but on a global scale, would be amazing for remote hiring. What unfortunately now seems to happen is that remote foreign employees get classified as contractors (which probably wouldn't stand up to any real scrutiny), which isn't great for either party.

This is spot on. People who've never had to deal with the administrative overhead of having to accommodate a new locale per employee don't realize how difficult it can be. There is substantial tooling on the front office side with respect to remote work, but the back office is sorely lacking and one of the key inhibiters of more companies doing this at sufficient scale.

I wonder if there are additional restrictions based on being in financial services. It may require different licenses, registrations, insurance and employer regulations (e.g. different collective bargaining agreement) compared to traditional industries.

I work remotely for a U.S. based company from South Africa. I don't think they do anything special for each different territory. The IRS stuff just has two categories - U.S. and outside U.S.

I'd love to apply for an engineering job at Stripe.

If you don't care about the laws in South Africa that's fine but they are too big to risk that.

You're acting like hiring a local firm for a few hours to advise on this is somehow constricting. Its not.

Hiring in other locales is a perceived difficulty. Not a reality.

Establishing a registered entity to employ in a foreign country is not a few hours advice. It is difficult, expensive and time consuming.