Automattic’s Sonal Gupta on Communication and Chaos

Howdy, howdy. I'm Matt Mullenweg, the CEO of Automattic and the co-founder of WordPress. Automattic is a company that makes WordPress.com and a bunch of other cool 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 such a person. Sonal's been with the company for coming up on 3 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. Alrighty, let's get started with Sonal. Today we're going to go inside a company I know a little bit more about, Automatic, which is a company I founded in 2005. Today, Automatic has over 850 employees working from 68 countries. So to understand better how Automatic works, I'm joined by one of my colleagues, Sonal Gupta. Thank you so much for joining today, Sonal.

Thanks for having me.

She's the lead for what we call the Other Bets division, a name we borrowed a little shamelessly from Alphabet. Which oversees kind of a number of different emerging businesses, including our latest bet, which is focused on tools that power our distributed work model, Happy.Tools. Sona was both a tech founder and a lawyer. She joined Automatic 2 years ago as a legal counsel after a successful run as co-founder of Rank and Style. And Sona, you also been named as Fast Company's one of 100 most creative people. So when you joined Automatic, it was your first distributed work company. What made you want to apply for it?

Yeah, 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 in its employees. I had had really 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— 500 employees. Not, not huge, but for one office it was pretty big. You know, the office itself was nice, but the expectations around FaceTime 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've also had other different types of office experiences. I've worked in open plan offices, I've worked in a cubicle at a bank. I've also done the coworking space at WeWork. So my experience in offices really runs the gamut. My 2 years at Automatic is definitely— I mean, this is definitely the best fit in terms of the way that I work, the way that makes me most productive and overall life-work balance.

So one question that comes up sometimes is like, what's the first day? All right. There's no like desk you go to or computer. Like what was kind of your onboarding like?

Yeah, it's funny because, you know, you start your first day and you're sitting in your living room and it's like, you know, your friends or family say to you, do you really have a job? The first day at Automatic was great. Automatic requires every employee to do a 2-week support rotation so that everybody can really understand the product and, you know, how customers see our products.

So you log on that first day, you're in your living room, you got a laptop. What was your first impression?

I think my first day I thought that there would be more video chats, but all your onboarding is done.

All text.

All in text.

And so were you paired with someone or how's it work? I haven't been onboarded in, in a really long time.

Yeah, you're paired with a buddy mentor for your support rotation. You're just trained completely on Slack with a group of others who are also starting that day.

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

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

So one thing people get on the first day is internally to Automattic, we have something called a Field Guide, basically like our internal handbook, but it's a WordPress blog so anyone can edit it. Set of pages. There's a headline at the— on our Field Guide that says, Welcome to the Chaos. What'd you think when you saw that?

Seeing that just gives you comfort immediately because it is overwhelming. You're getting pinged in 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 Automatic's culture.

What's it mean to embrace the chaos?

To embrace the chaos to me means just surrendering to it and understanding that there's, that there's 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 it's, you know, you're not expected to just get it immediately.

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're 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 kind of helped you in that, or that you found made you better able to consume and produce written stuff?

Yeah, 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, 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.

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

Oh yeah, definitely. I had times when I was working, you know, overnight or till 4 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's just something that's really important to me.

What's an example of you using that?

Well, 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, you know, we're working with people in all different time zones around the world. And, you know, you might not be working the exact hours or maybe I take off 3 hours in the day and make it up later in the night. You know, however I want to make my schedule is sort of allowed.

You know, you joined as a legal counselor and you made the switch to running a division. Automatic has 4 divisions. You run one of them. Tell us about Other Bets, like how many people, what does it do, etc.?

So we develop or acquire products that fall into 3 categories: things that we need to exist for Automatic's operations, things that we build as experiments or that we 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 6 different teams.

Yeah, and I think part of the design goal of Other Bets is that we kind of want about 5% of the company always working on the future.

Yeah, exactly.

You know, taking the thing that could be the next WordPress, could be the next Jetpack, could be the next WooCommerce. Going from 0 to 1 is really, really hard. And it's different from growing from, you know, $100 million to $120 million. And we don't disclose revenue, but we can say that Other Bets is about 10% of the revenue in Automattic, which is now starting to be quite substantial. Absolutely. Tell us about some of the products.

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

Competes with like a SurveyMonkey, maybe?

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

One of my favorites is actually SimpleNote, and it is a simple notes app, and it runs on Android, iOS, Mac desktop, Windows, everything. And it's just ultra-fast synchronization of super clean notes. And, you know, a lot of other notes apps become not that simple over time, but we've managed to keep this one pretty lean and mean.

That's correct. So SimpleNote is one that we're constantly building and improving it.

So let's talk about communication. So you have, you said 40 people. How many time zones does that generally span?

We work with people on both coasts in the US, a ton of people in Europe, and a couple people in Asia.

One of the things that's interesting is like people think of distributed as about being location-based. What do you think is the key to synchronous versus asynchronous communication? And like what can make that asynchronous collaboration productive?

The fact that we're in so many different time zones and people are working at different hours, you can sort of pass the baton to the next person, especially on the development side. So if you have somebody working in the US and then, you know, they go to bed at night and somebody in Asia works— wakes up. It's— it makes it very easy and seamless to just keep continuous work on different projects.

The teams have like regular meetings. How do— how do they generally work?

The teams do have regular meetings. Usually they use video chat using Zoom. And 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's generally very seamless communication.

So when do you use a Zoom, a Slack, a P2? Like, what do you use each for?

For Slack, I think is great for conversations with one or a small group of people where you're just trying to stay on the same page in real-time sort of 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, you know, 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.

So like if you met with a partner, you would post notes from that to P2 or to Slack or—

Yeah, so if I met with a partner, I would post notes to a P2 and just kind of make sure that everybody at Automattic who needs that information can easily access it. If I'm making a quick decision about something, I just need somebody's input. I'd 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.

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

That's, that's true.

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?

So most of the teams meet up at least once or twice a year on their own. And then there's 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, I'm generally on the road.

You have 6 teams meeting twice a year. That's 12 meetups. So do you go to a lot of those or—

I wouldn't say I go to every single meetup, but I try to make sure that I get some time with every one of 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.

What makes a great meetup?

If a team comes up with a meetup project that is something they can complete in a week, I think that always feels very satisfying. Or if they're just in the middle of developing a product and they can kind of come together and really make some progress on that, I think that always feels really fulfilling. And then the team bonding, I think, is a really big part of it too. They're all working together every day, all year long, and they get about 2 to 3 weeks of in-person time together. So I think most people find it really valuable that, you know, catching up over dinner and really getting to know each other is an important part.

You know, a common question that managers in distributed companies could ask is, how do you know your teams are working?

I'd say that posting on our internal P2s is one way that we do kind of, you can kind of have a sense of how much people are working, how much, 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, I'm not a micromanager. I like to trust people and give them autonomy. But I think, you know, I keep in touch with them very regularly and I think it becomes clear pretty quickly if somebody's not doing work. We look at, you know, performance. We look at communication at a distributed company. Communication is oxygen. So it's just really important that people are constantly communicating. And I mean, I think we probably veer closer to overcommunication. You know, in some ways you have to make sure you, you know, how to sift through all the, all the different communications coming your way. But I think it's an effective way of really understanding what people are working on.

Think of like your, your best team. You don't have to tell me which one it is, but like, what are some things that they do that you think makes them very effective?

So 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 and, or if not, updating me.

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

So it's very unique. So basically the benefit of hiring at a distributed company is you basically 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 the distributed culture works for them.

It's like a two-way evaluation.

Exactly.

Thank you very much, Shonal, for joining us today on the Distributed Podcast. If you want to learn more about HappyTools, you can sign up for a demo of HappySchedule at happy.tools.

Thank you so much for having me. It's been great to be here.

That was Sonal Gupta. Automatic has grown so much these past few years, and 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.