This pioneering tech company figured how to make work-from-home work

In this series, Perfect Company, we are examining pockets of excellence in the corporate world. No single company is perfect, but together they show what the corporate ideal could look like.

The platonic ideal

“We like to give people the freedom to work where they want, safe in the knowledge that they have the drive and expertise to perform excellently, whether they [are] at their desk or in their kitchen. Yours truly has never worked out of an office, and never will.”—Richard Branson, Virgin Group founder

The practice

The headquarters of Automattic, the maker of, is a bright and airy space in San Francisco’s South of Market district. Hawthorne, as it’s called after the small alley it sits on, is decidedly industrial with its concrete floors and exposed beams. Like many of its neighboring tech companies, there are ping pong tables, free snacks, and company swag. But something’s missing here. Where are all the employees?

 “I’ll keep shouting from the rooftop because everyone should do it.” 

With a staff of 450 spread over 45 countries, Automattic is often regarded as one of the largest and most successful examples of a fully distributed workforce. “I used to be very conflicted,” says CEO Matt Mullenweg. “All I hear from my friends in San Francisco is how hard it is to hire. Should I not tell them this secret? I decided it’s a great idea and everyone should do it. I’ll keep shouting from the rooftop because everyone should do it.”

For Mullenweg, it was only natural the company’s employees would work remotely given its roots in WordPress, an open-source blog publishing network with collaborators all over the world. (WordPress VIP, however, is a commercial product that powers many news organizations’ websites, including Quartz.) “We’ve never worked any other way,” he says. While the company does pay for employees’ coworking spaces, overall it’s saving on real estate and relocation costs, though it declined to say how much. The company insists that ultimately cost wasn’t a deciding factor.

To make the distributed model work, Automattic, which was founded in 2005, relies on technology to keep employees in sync. Even if team members are in the same location, the company encourages meetings to take place online in the spirit of transparency. “The worst possible thing when you’re working from home is that you feel you’re not in the loop,” says Toni Schneider, who served as CEO from 2006 to 2014. “We want everyone else who is remote to feel completely equal.” (Like many WordPress employees, Schneider likes to mix work with travel, as he did during a cross-country road trip with his family in the summer of 2008.)

 “The worst possible thing when you’re working from home is that you feel you’re not in the loop.” 

Automattic is a place with few hard and fast rules. In addition to letting staff work where and when they want, it has an open-vacation policy and urges employees to “use your best judgment” when it comes to expenses, according to Ingrid Miller, who works in human resources. The company is broken up into about 70 teams varying in size from two to about a dozen people. Mullenweg describes the setup as “a collection of small startups working in harmony with each other.” Teams are empowered to try new tools if they believe it can help them work more efficiently.

A decade-plus of experimentation has led Automattic to its current set of tools:

  • Slack, a business chat app used for day-to-day communication
  • P2, a WordPress theme modeled after Twitter’s stream with in-line replies for more in-depth discussions
  • Wikis, field guides with content that rarely changes
  • Zoom video conferencing

But there were many pain points before it arrived at this arrangement. Originally, Automattic used Internet Relay Chat (IRC), a text chat protocol that predates AOL Instant Messenger, for instant messaging. But with the proliferation of mobile devices, employees sought an easier way to chat from their phones. Skype was far from a perfect solution, but it had a mobile app, making it one of the better offerings in 2008. The main drawback was that conversations were siloed into individual groups, which “is terrible for distributed companies,” says Schneider.

There was an awkward transition period where employees were expected to be on both IRC and Skype. Eventually, the company migrated to Slack en masse, but even that came with its false starts, as various teams had used and abandoned the chat app before it finally stuck for good in 2014. “Our lifeblood today is Slack and [a WordPress theme] we created called P2,” says Mullenweg.

Slack checked off a number of boxes for Automattic. It had a mobile app, and it allowed employees to chat in public channels, privately in groups, and directly with colleagues. Still “there were some holdouts,” recalls software engineer Kat Hagan, who lives in Oakland. Some employees worried about trusting a third party with its chat logs. Plus, in an ideal world, all of Automattic’s tools would be open source. In this case, convenience won out.

As with all chat apps, Slack’s constant pings can be distracting, and it’s easy for conversations to get derailed. To keep important discussions from disappearing into the ether, the company has a specific WordPress theme that keeps conversations focused with threaded conversations. Created during a 2008 company gathering in Oracle, Arizona, P2 (originally called Prologue) is “like the WordPress equivalent of an activity stream,” says Davide Casali, a London-based designer whose team works on WordPress themes.

For all the thought that went into chat, there are gray areas. There are times when a discussion in Slack picks up so much chatter that it becomes better suited for P2. “We have an emoji for that—a P2,” says Casali. That usually prompts a person involved in the conversation to transcribe and summarize the discussion in a P2 post.

But subtlety can get lost in text transmission. “I would probably say the biggest breakthrough for us was really when [Google] Hangouts started to come along, and really the idea of group video conferencing all of a sudden became very doable,” says Schneider. In Automattic fashion, some teams later tried Zoom, a video conferencing chat app that displays participants in a Brady Bunch-like grid, and “now we’re all sort of hopping on the Zoom train,” says Hagan.

Of course, video is not a complete replacement for face-to-face interactions. Some within the organization, including Mullenweg, have contemplated the role virtual reality can play in collaboration, but that’s a faraway future. For now, it’s hard to beat the real thing—sitting across from a coworker, able to read his or her body language and facial ticks in person. This is why Automattic organizes a company-wide meetup once a year in an exotic locale for a week. Teams are also encouraged to plan their own outings, mixing work and play, two to three times a year with a budget of about $250 per person per day, excluding airfare.

“While it’s possible to work remotely, there’s a bonding and a familiarity that develops when you’re in person together that’s irreplaceable,” says Mullenweg.

The takeaways

For a fully distributed company to work, everybody needs to be on the same page. Automattic believes transparency is a key part of that, and that means making conversations, documents, meetings, and leadership training sessions open to the entire company. Furthermore, as Mullenweg wrote in a 2012 blog post, you “have to be really committed to keep the creative center and soul of the organization on the internet, and not in an office.”

 “If we make it look easy, it’s because we’re working incredibly hard at it.” 

Employees are drawn to Automattic because of the company’s flexibility, but that can also make it tough to maintain a work-life balance, something employees have to figure out for themselves. For example, Hagan, a night owl who says she works best from 9pm to 2am, will offset a particularly long workday with a shorter one. Ultimately, Automattic’s not the kind of company that feels the need to peer over employees’ shoulders. It’s less focused on setting rules as much as expectations that employees will get their work done.

When Automattic grew to 50 people and later to 150 people, Mullenweg had concerns around how the distributed model would scale. Much thought went into what tools to use and how to use them. Employees, who are in small, agile teams, are encouraged to experiment with different ways of working. Sometimes these experiments are adopted companywide (as was the case with Slack), and sometimes, they fail (like one team’s attempt at Holacracy).

“If we make it look easy, it’s because we’re working incredibly hard at it,” says Mullenweg. At this point, though, he doesn’t “see an upper bound to it” and says he “can imagine Automattic as a company with thousands” of remote employees.

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