Reed Albergotti has a great article titled Latest Amenity for Startups: No Office. You can put in your email to read I believe but it's behind a paywall otherwise. The Information is a pretty excellent site that alongside (former Automattician) Ben Thompson's Stratechery I recommend subscribing to. Here are some quotes from the parts of the article that quote me or talk about Automattic:

So it’s no coincidence that one of the first companies to operate with a distributed workforce has roots in the open source movement. Automattic, the company behind open source software tools like WordPress, was founded in 2005 and has always allowed its employees to work from anywhere. The company’s 680 employees are based in 63 countries and speak 79 languages. Last year, it closed its San Francisco office, a converted warehouse — because so few employees were using it. It still has a few coworking spaces scattered around the globe.

Matt Mullenweg, Automattic’s founder and CEO, said that when the company first started, its employees communicated via IRC, an early form of instant messaging. Now it uses a whole host of software that’s tailor-made for remote work, and as the technology evolves, Automattic adopts what they need.

Mr. Mullenweg said Automattic only started having regular meetings, for instance, after it started using Zoom, a video conferencing tool that works even on slow internet connections.

He’s become a proponent of office-less companies and shares what he’s learned with other founders who are attempting it. Mr. Mullenweg said he believes the distributed approach has led to employees who are even more loyal to the company and that his employees especially appreciate that they don’t need to spend a chunk of their day on a commute.

“Our retention is off the charts,” he said.

And:

“Where it goes wrong is if they don’t have a strong network outside of work—they can become isolated and fall into bad habits,” Mr. Mullenweg said. He said he encourages employees to join groups, play sports and have friends outside of work. That kind of thing wouldn’t be a risk at big tech companies, where employees are encouraged to socialize and spend a lot of time with colleagues.

But for those who ask him about the negatives, Mr. Mullenweg offers anecdotal proof of a workaround.

For example, he said he has 14 employees in Seattle who wanted to beat the isolation by meeting up for work once a week. So they found a local bar that didn’t open until 5 p.m., pooled together the $250 per month co-working stipends that Automattic provides and convinced the bar’s owner to let them rent out the place every Friday.

They didn't need to pool all their co-working allowance to get the bar, I recall it was pretty cheap! Finally:

For Automattic, flying 700 employees to places like Whistler, British Columbia or Orlando, Florida, has turned into a seven-figure expense.

“I used to joke that we save it on office space and blow it on travel. But the reality is that in-person is really important. That’s a worthwhile investment,” Mr. Mullenweg said.It might take a while, but some people are convinced that a distributed workforce is the way of the future.

“Facebook is never going to work like this. Google is never going to work like this. But whatever replaces them will look more like a distributed company than a centralized one,” Mr. Mullenweg said.