Behind The Scenes: Culture and Tools of Remote Work at Automattic

Thanks to my teammate Nabs who snapped this photo!

Last week, I gave a presentation on remote work at the Online News Association’s Women’s Leadership Accelerator. Tran Ha, my former boss at the Chicago Tribune’s RedEye, was the workshop’s facilitator and asked me to bring Automattic’s culture to the cohort.

In assembling the presentation, I thought to myself – “Is this way too obvious?” As someone who has worked remotely for 6 years, all of this feels intuitive. But, the positive feedback from attendees made me realize just how valuable this information could be to newsrooms.

So, I thought it was worth blogging about. Below is my presentation, written loosely in transcript style, with slides embedded. It’s broken down into 3 sections: About Me, Culture, and Tools.

How I Got To Automattic…


Hello! I’m Steph Yiu and I lead support at VIP. I’ve been working remotely for 6 years at a completely distributed company. Yes, we have no headquarters. In fact, we kind of had headquarters for a while but then we closed it because no one wanted to commute in.


I haven’t always been a remote worker. In fact, I loved working in an office. For a few years I sat in the bustling newsroom at the Chicago Tribune’s RedEye. And after that, I worked in a real-life test kitchen leading digital strategy at America’s Test Kitchen. That was an awesome job. I gained a lot of weight. They should have given us a gym membership.

In 2012, while in NYC promoting our latest round of cookbooks, I stumbled upon the WordPress booth. I had just helped our team launch our blogs on WordPress, and I wanted a sticker for my laptop. I walked up. I said hi!

The guy on the other side of the booth said, “I’ll give you a sticker if you’ll fill out a survey.”

The guy turned out to be Mo Jangda, who is now our Head of Platform. I really liked him. He was smart and we had a lot in common — an international background and an interest in journalism. I told him that I worked at the intersection of journalism and technology. Hmmm, he said. We might have an opening for someone like you.


WordPress is a company with salaried jobs?! I wondered. I had always thought it was an open source platform. So I went online, did some research, and learned about the company. It seemed too good to be true. As someone who spent her early career in publishing, I had never seen job perks like this before.

But, I was passionate about working with journalists. And, I could see that at the core, this company cared about its employees and wanted to create an environment where people could thrive.

Remote Work 101

Turns out, the company wasn’t too good to be true. I joined VIP as an account engineer 6 years ago, when our team was 15 people and our company was 140. Today, the VIP team is 80 people and our company is nearly 900. When I became a manager about a year into the job, I led a team of 8. I now manage a team of 50.



I’m uniquely qualified to talk to you about remote work because it is the most difficult part of my job, and I have to stretch myself every single day. Why?

  • I am an extrovert. I love being around people and get my energy from groups. When I am forced to work by myself on a daily basis, I am completely exhausted and drained at the end of each week. More on that here.
  • I am an auditory learner. My retention rate for podcasts, presentations, and conversations is 90 percent. My retention rate for written materials is probably 50 percent. I am a slow reader. To force myself to absorb information in a written-format daily is taxing.
  • Interpersonal communication is one of my greatest strengths. I thrive working with people face-to-face. This is not an option the majority of the time.

For me, remote work is like having me manage a team with both hands tied behind my back. Because it’s so taxing for me, I employ a lot of strategies to help me function.


But… for all the things that are difficult about remote work, there’s freedom. Freedom to set your schedule, create your environment, design your commute (mine’s a 20 minute walk), and build your everyday work experience.

But, being productive as an individual contributor is one thing. Creating a productive and collaborative team is another.


Automattic has been a distributed company since the very beginning. That means remote work is baked into our core beliefs. There are lots of core beliefs across the company, but here are five that I believe contribute to our ability to work in a distributed manner.

Let’s Talk About Culture



The VIP team deals with high pressure situations all day, every day. Demanding clients. Election night. Security protocols. Breaking news. In order for our team to handle the stress, we have to be in the trenches together. Teamwork is core to how we operate – it’s the first thing new hires will say when describing our culture.


As a fully remote company, everyone must understand and embody this belief on a daily basis. A great example of this belief is how we don’t use email internally. Email is a black box. Email locks things away from other teammates, and when someone leaves, all their knowledge disappears. I’ll talk about this a little later, but we use an internal system called P2 that allows us to transparently communicate to each other. And boy, do we communicate. Our internal channels are bustling, and that’s a great thing.


You’ll hear me repeat this again and again in meetings — when we assign someone a project, are we setting them up for success? And, are we inclusive of all work styles? A good example of how we handle this is our team calls. There’s an agenda posted ahead of time, so that if you need more time to prepare to speak up, if you don’t speak English as your first language, or if you prefer to post your comments in text ahead of time — this gives you the opportunity. We rotate our call host and note takers so that each member of the team gets a go at it. And, when the host is someone in a different timezone, we shift the call to accommodate their workday.

Remote Work 101(1)

In a culture where everyone prides themselves on being a continuous learner, feedback is a key way of improving. If you’re not getting constructive feedback from your manager, demand it. If you’re a manager, continue to improve your feedback skills, and ask how other managers do feedback. It is an art. We have a few ways of giving feedback at the company: a tool to request for anonymous feedback from your teammates, and, a regular cadence of development feedback twice a year.


In a little bit, I’ll talk about our documentation, and I’ll tell you how everyone at our company can update our documentation. Our guidelines and processes start from a place of trust, not the lowest common denominator. If we’ve hired you, we expect that you always strive for a higher standard.


So, that’s just five core beliefs I distilled for the purposes of this presentation. But, there are many, many others throughout Automattic and VIP. It all starts from our creed, which we post publicly.

Let’s Talk About Strategies


Alright, so those beliefs are nice and warm and cozy, but, how do we translate that into our day-to-day?


We include a trial in our hiring process. It’s as much a trial for us as it is a trial for the applicant. While we are looking for how well the applicant performs in the trial, we’re also looking for excellent collaboration in a remote environment. Even if you are highly skilled, if you aren’t able to communicate well, you most likely are not a good fit for our team. We aren’t looking for heroes (i.e. people who can temporarily solve a problem in the short term), we’re looking for team players.


This is the Automattic Field Guide, our company’s internal documentation. Anyone can update the pages on this site. It’s one of the first things you see when you join the company, and you’re encouraged to update it before your onboarding ends. If you see a mistake, fix it. If you discover a new process, create a page for it. It the central knowledge repository for our company’s processes.


We don’t use email internally at Automattic. We use P2. This is a WordPress theme that converts WordPress into a message board that allows for posting, tagging, commenting, and liking. Each team and project typically has their own P2, and any major event, idea, client meeting, or decision gets posted.

Yes, we use Slack (and before that, we used IRC). But, we treat chat as ephemeral and don’t require our teammates to read backscroll. The phrase we use around our company: “P2 or it didn’t happen.”

For about five years, I was the primary account engineer for Fritz Enterprises (not real name). For every meeting or decision with the client over the years, I would post to P2 with the tag #vip-client-fritz-enterprises. When I went on sabbatical, I wrote up a client summary and linked to historical posts. The new account engineer had all the information at their fingertips, which made onboarding them much easier (and a smoother experience for the client).


Each manager on my team has a 1:1 with their teammates every two weeks. It is one of the most important and valuable tools a manager has to support their team. For every 1:1, we have a shared Google Doc with the teammate. Agenda items can be added throughout the week. Then, notes are taken during the call and action items are posted. The document is organized in reverse chron, so the latest call notes are at the top.


As our team has doubled in size over the last year, we’ve been working on establishing clearer expectations about what it means to work on our team. It gives our teammates freedom to focus on what’s important to their job, and clear guidelines for what overwork looks like (and when it’s time to ask for help). We’ve also been nudging our managers towards creating agreements (or commitment conversations) with their teammates. With every assignment, do both sides understand what is being asked of them, and, are all questions and resource needs addressed?


Here’s a photo of the VIP team’s call on Halloween :) Each team has their call once a week, and we have an all-VIP call every month. There’s always a bit of room made for social interactions (some teams call it banter, other teams call it ice breakers). Team calls are a great opportunity for folks to surface problems they need help with, and for the lead to help build alignment across the team. We use Zoom for our team calls – it has been the most stable and reliable video conferencing platform by a long shot.


If there’s one thing I want you to remember from this presentation, it’s that in-person time is critical to your remote team’s success. We are humans, not robots. You must make the time for your team to gather at least twice a year. I cannot tell you what a huge difference it makes to building alignment across your team and smoothing out communication issues. Time and again I have new employees tell me how much their work life has improved after attending a meetup.

When you design your meetup, schedule lots of room for downtime. Have activities. Dinner. A walk outside. Get out of the conference room and spend some time with your colleagues. The most meaningful conversations come from these pockets of downtime.

You also can’t be fuzzy about the social stuff at a meetup — make it a priority. Two ice breakers I’ve seen work very well:

  • Tell the story of how you joined the company, and share your one “Work Superpower.” What’s one thing folks should come to you for help with?
  • Have folks write down their own personal readme (i.e. how I operate at work), and share parts of it out with the rest of the team.

When I helped organize our division’s 80-person gathering, I set four goals for the meetup. Here they are, in case you want to borrow them for your own meetups:

  • Was attending this meetup beneficial to your day-to-day work after you returned home?
  • Did the meetup help you better understand different aspects of our business?
  • Did you have meaningful conversations or discussions with your colleagues?
  • Did you leave the meetup with a feeling of excitement for the year ahead?

In Conclusion

Let’s take a moment to recap.





Thank you!

More reading…

Also, in 2016 I spoke at the first-ever ONA-Poynter Leadership Academy for Women in Digital Media. Attending was a powerful experience, and here’s my recap.