Automattic’s Sonal Gupta on Communication and Chaos

Read more about Sonal Gupta in “Welcome to the Chaos.”

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Sonal Gupta leads Automattic’s Other Bets division, a team that builds products that aren’t yet core to Automattic’s business, but keep the company innovating and pushing it to explore new territory. In this episode, Sonal and our host Matt Mullenweg talk about how important communication is in the organized chaos of a fully distributed company.

The full episode transcript is below.


MATT MULLENWEG: Howdy howdy. I’m Matt Mullenweg, the CEO of Automattic, and the co-founder of WordPress. Automattic is the company that makes and a bunch of other things. At Automattic we have a division called Other Bets, which encompasses a host of experimental projects that aren’t directly related to our core business. When we started thinking about this department, I knew we needed a renaissance person to lead it — with a background in legal, finance, and entrepreneurship, Sonal Gupta is just such a person.

Sonal’s been with the company for coming up on three years, and I wanted to get some time on the calendar to talk to her about what made her want to work for a distributed company, what she likes about it, and what she finds challenging. 

Alright, let’s get started with Sonal. 

MATT: Today we’re going to go inside a company I know a little bit more about — Automattic, which is a company I founded in 2005. Today, Automattic has over 850 employees working from 68 countries. 

So to understand better how Automattic works, I’m joined by one of my colleagues, Sonal Gupta. Thank you so much for joining today, Sonal.

SONAL GUPTA: Thanks for having me.

MATT: She is the lead for what we call the Other Bets Division, a name we borrowed a little shamelessly from Alphabet, which oversees a number of different emerging businesses, including our latest bet, which is focused on tools that power our distributed work model, 

Sonal is both a tech founder and a lawyer. She joined Automattic two years ago as a legal counsel after a successful run as cofounder of Rank & Style. And Sonal, you’ve also been named as one of Fast Company’s 100 Most Creative People. So when you joined Automattic, it was your first distributed work company. What made you want to apply for it?

SONAL: Yes, actually the distributed nature and culture of Automattic was one of the things that really drew me to it in the first place. I was really intrigued and loved how open and transparent everything was and the amount of autonomy Automattic places on its employees. 

I had had all sorts of experiences with different offices as a corporate lawyer for a big part of my career. I worked in a big corporate office here in New York City where I had my own —  

MATT: How big?

SONAL: 500 employees.

MATT: Wow.

SONAL: Not huge but for one office it was pretty big. The office itself was nice, but the expectations around face time and just being in the office just in case a client might need you, those types of expectations made it a little bit difficult to keep up that kind of lifestyle. 

I have also had other different types of office experiences. I have worked in open plan offices, I have worked in a cubicle at a bank, I have also done the co-working space at WeWork. So my experience in offices really runs the gamut. My two years at Automattic [has been] definitely the best fit in terms of the way that I work, the way that makes me most productive, and overall life/work balance. 

MATT: So one question that comes up sometimes is, “What’s the first day?” There’s no desk you go to or computer. What was your onboarding like?

SONAL: Well it’s funny because you start your first day and you’re sitting in your living room and your friends or family say to you, “Do you really have a job?” [laughter] The first day at Automattic was great. Automattic requires every employee to do a two-week support rotation so that everybody can understand the product and how customers see our products.

MATT: You log on that first day, you’re in your living room, you’ve got a laptop. What was your first impression?

SONAL: I think my first day I thought that there would be more video chats but all your onboarding is done — 

MATT: All text.

SONAL: All in text. So that’s — 

MATT: Were you paired with someone? How does it work? I haven’t been onboarded in a really long time.

SONAL: Yes you’re paired with a buddy — mentor — for your support rotation. You’re trained completely on Slack with a group of others who are also starting that day.

MATT: And going from law to doing customer support, what was that like?

SONAL: It was interesting. I did interact with our customers. I hadn’t really experienced anything like that. 

MATT: One thing people get on the first day is — internally to Automattic we have something called the Field Guide, basically our internal handbook, but it’s a WordPress blog so anyone can edit a set of pages. There is a headline on the Field Guide that says “Welcome To the Chaos.” What did you think when you saw that?

SONAL: Seeing that just gives you comfort, immediately. Because it is overwhelming. You’re getting pinged from every direction. But as soon as you learn to embrace the chaos rather than resisting it, it makes it so much easier to understand Automattic’s culture.

MATT: What does it mean to embrace the chaos?

SONAL: To embrace the chaos to me means just surrendering to it and understanding that there is just going to be a barrage of information coming at you from all angles and it will take a little time to have a process in place, but you’re not expected to just get it immediately.

MATT: One of the things that I’ve always thought is —  recovering lawyers or attorneys — you write a lot in school, you read a lot, you are consuming and writing massive amounts compared to almost any other modern-day trade or industry. Automattic has a basis of a lot of written communication. Were there any things that you learned as you were training to be a lawyer that helped you in that, or that you found made you better able to consume and produce written stuff?

SONAL:  Yes, absolutely. Being successful at a company like Automattic — you have to be able to communicate effectively via text. As you said, we’re using all different kinds of messaging and internal blogs in order to communicate with the entire company. So I think my legal background was really helpful in being able to convey messages and information to people in a very clear and succinct way.

MATT: How many hours did you work in a given week before versus now? Did you burn the midnight oil in the corporate job?

SONAL: Oh yeah, definitely. I had times where I was working overnight or till four in the morning, but there are times at a law firm where you have downtime too. I think at Automattic, I wouldn’t say that overall I work that much less but I just work in a way that really works with my schedule and my life. So that is just something that is really important to me.

MATT: What’s an example of you using that?

SONAL: We use Slack and internal blogs for communication and it’s all async. While I try to get back to my colleagues or external partners as soon as I can, there is an understanding that we’re working with people in all different time zones around the world and you might not be working the exact hours, or maybe I take off three hours in the day and make it up later in the night. However I want to make my schedule is allowed.

MATT: You joined as a legal counsel and you made the switch to running a division. Automattic has four divisions; you run one of them. Tell us about Other Bets. How many people, what does it do, etcetera?

SONAL: We develop or acquire products that fall into three categories — things that we need to exist for Automattic’s operations, things that we build as experiments or that are useful tools for our community, and things that have the potential for substantial revenue growth. A lot of our products cross multiple categories. We are currently 40 people in the division, spread across six different teams.

MATT: And I think part of the design goal of Other Bets is that we want about five percent of the company always working on the future.

SONAL: Yes, exactly.

MATT: Taking the thing that could be the next WordPress, could be the next Jetpack, could be the next WooCommerce, going from zero to one is really, really hard, and it’s different than going from 100 million to 120 million. We don’t disclose revenue, but we can say that Other Bets is about 10% of the revenue at Automattic, which is now starting to be quite substantial.

SONAL: Absolutely.

MATT: Tell us about some of the products.

SONAL: Well we’ve got about 20 products in the portfolio, not all actively developed at the moment. Some of our products are Crowdsignal, which is a poll and surveys platform.

MATT: Competes with Survey Monkey maybe?

SONAL: Exactly. And we’ve got our new suite of products, Happy Tools. Our ads business is also part of the portfolio.

MATT: One of my favorites is actually Simplenote. It is a simple notes app, and it runs on Android, iOS, Mac desktop, Windows, everything. It’s just ultra- fast synchronization of super clean notes. A lot of other notes apps become not that simple over time but we have managed to keep this one pretty lean and mean.

SONAL: That’s correct. So Simplenote is one that we’re constantly building and improving.

MATT: Let’s talk about communication. You have 40 people, how many time zones does that generally span?

SONAL: We work with people on both coasts in the U.S., a ton of people in Europe, and a couple people in Asia.

MATT: One of the things that’s interesting is, people think of distributed as being location-based. What do you think is the key to synchronous versus asynchronous communication? What can make that asynchronous collaboration productive?

SONAL: The fact that we’re in so many different time zones and people are working at different hours, you can pass the baton to the next person, especially on the development side. So if you have somebody working in the U.S. and then they go to bed at night when somebody in Asia wakes up, it makes it very easy and seamless to just keep continuous work on different projects.

MATT: Do the teams have regular meetings? How do they work?

SONAL: The teams do have regular meetings. Usually they use video chat, using Zoom. For teams with people in different time zones, they just try to find a time that really works for everyone. Sometimes they also communicate via Slack. We also communicate via our internal blogs, which we call P2s. Between the three, there is generally very seamless communication.

MATT: When do you use a Zoom, a Slack, a P2, what do you use these for?

SONAL: For Slack I think it’s great for conversations with one or a smaller group of people where you’re just trying to stay on the same page in real-time communication. Our internal blogs are really useful for keeping the entire company up to date on our progress or different updates. They’re really helpful for being able to search our entire database of P2 posts so anyone coming to the company in the future can always get all the backstory on a specific conversation or product.

MATT: If you met with a partner, you would post notes from that to P2 or to Slack?

SONAL: If I met with a partner, I would post notes to a P2 and just make sure that everybody at Automattic who needs that information can easily access it. If I’m making a quick decision about something and I just needed somebody’s input, I would probably use Slack. I have one-on-ones with each of my direct reports on a weekly basis and for those I generally use Zoom video chat. I really do value in-person or face-to-face communication so I think Zoom helps fill that gap.

MATT: It’s funny because you’ve used face-to-face and Zoom a little interchangeably and really that’s screen-to-screen, right?

SONAL: That’s true.

MATT: And video communication is obviously higher bandwidth. So you get a lot of value from that. When do you get together in person with people?

SONAL: Most of the teams meet up at least once or twice a year on their own and then there is also an all-company Grand Meetup every year where the entire company gets together. I, as a division lead, try to meet with each of the teams as much as I can. So I’m generally on the road.

MATT: So you have six teams meeting twice a year. That’s 12 meetups. Do you go to a lot of those?

SONAL: I wouldn’t say that I go to every single meetup but I try to make sure that I get some time with everyone on my teams at least once a year, and then at the Grand Meetup as well. So between team meetups and conferences, I’m probably on the road once a month.

MATT: What makes a great meetup?

SONAL: If a team comes up with a meetup project that is something they can complete in a week, I think that always feels really satisfying. Or if they’re just in the middle of developing a product and they can come together and make some progress on that, I think that always feels really fulfilling. And then the team bonding is a really big part of it too. They’re all working together, every day, all year long, and they get about two to three weeks of in-person time together. So most people find it really valuable. That catching up over dinner and really getting to know each other is an important part.

MATT: A common question that managers at distributed companies could ask is how do you know your teams are working?

SONAL: I’d say that posting on our internal P2s is one way that you can have a sense of how much people are working, how many ideas they’re sharing, what kind of meetings they’re having. So I think we do put some value on how much people are posting but other than that… 

Personally, I’m not a micromanager. I like to trust people and give them autonomy. But I keep in touch with them very regularly and I think it becomes clear pretty quickly if somebody is not doing work. We look at performance, and we look at communication at a distributed company. Communication is oxygen. So it’s just really important that people are constantly communicating. I think we probably veer closer to over-communication. In some ways you have to make sure you know how to sift through all the different communications coming your way but I think it’s an effective way of understanding what people are working on.

MATT: Think of your best team — you don’t have to tell me which one it is — but what are some things that they do that you think makes them very effective?

SONAL: I think my best teams are great at communicating via P2 and having roadmaps and plans in place, and making sure that they’re meeting their plans or, if not, updating me. 

MATT: So Sonal, you do a lot of recruiting and hiring for your division. How does that change when you’re hiring from everywhere in the world, versus when you’ve hired for startups or companies in the past, and how does that interview process work?

SONAL: It’s very unique. The benefit of hiring at a distributed company is you have access to a global pool of talent, which allows you to bring in the most diverse qualified candidates. As far as the interview process — it is quite unique. Some teams hire completely through text communication without ever hearing a candidate’s voice. I personally haven’t done that yet but I generally interview on the phone or via Zoom or sometimes if a candidate is local I’ll meet them in person.

Everybody we hire, we have them go through a trial project process first, which usually lasts about a month. That really helps us figure out if the candidate is a good fit and it also helps the candidate figure out if a distributed culture works for them.

MATT: So like a two-way evaluation?

SONAL: Exactly.

MATT: Thank you very much, Sonal, for joining us today on the Distributed podcast. If you want to learn more about Happy Tools you can sign up for a demo of Happy Schedule at

SONAL: Thank you so much for having me, it’s been great to be here.

MATT: That was Sonal Gupta. 

Automattic has grown so much these past few years, and at over 950 employees, it’s not always easy for me to get a ground-level perspective of what’s going on in the various parts of the company. It’s great to be able to catch up with people like Sonal, who keep me up-to-date about all the exciting projects going on, and about how our distributed work model complements those projects. Thank you for joining us, and see you next time.

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