Talking Remote Work with Automattic

camper home for cyber nomads

It’s getting latish here in Poland. I feel the adrenaline rush going as I’m waiting for some cool people to join me on a call. It’s the first time I’m doing this and it all feels pretty exciting. Michael and Maria are joining us from the States, Val from Spain, we’re also hoping for Hari to connect with us from the airport. It’s past midnight in India. But, he’s up traveling to Italy to meet Val and the rest of the team.

That’s only the beginning of the geography lesson. This is no surprise – we’re talking to Automattic – the company that takes pride in operating fully remotely as a distributed team.

We’ve already set the scene. Let’s go a bit deeper into the characters now 😉 :

A bearded man in sunglasses exposing his face to the sun.

Michael Arestad: A designer at Automattic. He didn’t buy into the whole remote work buzz easily, now a whole-hearted supporter and evangelist of the lifestyle. Before joining WordPress.com and Jetpack, he did some government and agency advertising work.  He tries to travel around as much as possible. Has traveled all the way up and down across Canada. This year’s plan: to head south-west, explore the areas in New Mexico. “Should be fun.” he sums up his plans for immediate future.

A lady is giving a talk in some conference

Valentina Thoerner: A minimalista pragmatica and a Happiness Team Lead at Woocommerce. 10 years ago, she fled from frosty Germany and found refuge in the Spanish sun. You can spot her running in ultramarathons – the longer the better. As a mother of 2-year-old twins, she has put traveling on hold, temporarily that is. She won’t get much sleep today as she still needs to pack before flying out to meet her team in Italy. If she gets there despite the strikes at Italian airports. In the worst case scenario, she’ll take a long power nap at the airport.

Maria from Automattic

Maria Scarpello: On the Woo team for 5 years, right now she runs customer research initiatives. She joins us from her compact camper that, apart from her, is a home for her husband, and her dog, Buddha. Having a follow-the-sun mentality, she’s been on the road for the past 7.5 years, even if she isn’t totally sure where they are right now, which can often be the case. She knows more or less where the motorhome is going to take her in the next couple of weeks. Knowing this entails taking into account all sorts of variables, like the events across the US worth attending with her running club, Burning Man, or music festivals.  

Hari Shanker: A silent hero of the play. Unconquered by time zones and the size of our globe, he got defeated by the airport operations and the sleep deprivation, probably. He’s on his way to Italy to engineer the happiness of WooCommerce users together with Val. We are soon to realize, he won’t be able to join our talk. ;( (We missed you greatly, Hari!)

Droplr logo

Droplr: A remote collaboration enhancer, a tool that does wonders ;). This time it’s Droplr who decides to ‘make a dent in the universe’ and gathers Automattic people living in three distant time zones to talk about remote work.

Why Automattic

Droplr: So, what brought you to Automattic?

Maria: Automattic chose us. (laughter) In terms of Woo. I came over with the acquisition 2 years ago. And why Woo? The remote culture appealed to me. I was already living on the road and I wasn’t really looking for a job. However, at the same time, I really admired Adii Pienaar’s leadership style. And I thought that working closely with him in an up-and-coming startup, in an industry that as a graphic designer I was comfortable and familiar with, would be a really awesome opportunity. I grabbed it and that’s what brought me to Woo.

Droplr: Does it mean that Woo was a remote company when you joined it?

Maria: Yes, the remote work culture was there right from the start. The three founders, actually, for the first year and half of business had never really seen each other face to face. Video conferencing wasn’t really a thing back then, so they communicated over texts. Then, they did start a small office in Cape Town, South Africa, hired a distributed team, and about a year after I joined the company they didn’t have to come to the office in Cape Town.

cyber nomad place to work

Sometimes users show you love by buying you a pint… 😉 Check out Maria’s Instagram for the full story!

D: Michael, do you have a similar story? You’re a graphic designer as well. Was it the remote work culture that lured you to Woo?

Michael: No! It’s a very different story with me. I worked with WordPress a lot in my freelancing years and working with all those agencies and just over the place. I was one of the few people back then who could make CSS work and make the WordPress pages look halfway decent compared to everybody else at those agencies. That was a hugely valuable skill that I grew. Then I got back to school.

One of the people I met there, Kevin Conboy, worked for this bizarre company called Automattic that I guessed made WordPress.com. At the time, it was just crazy to me: He would disappear for like two weeks to go to Iceland, which didn’t make any sense.  He didn’t do a good job explaining the reason for those trips to me. (laughter) I was like: “Why are you going there?” He was: “What? Why? To meet my team” as if it was totally obvious. And I was: “Ok… Cool.” I didn’t have much clue what it was all about. He encouraged me to apply. I was hesitant.

A man climbing up a steep mountain wall

Work hard and catch the day. See more on Mike’s Instagram.

It took me a couple of years but, eventually, I applied and got in. I loved the open source aspect of it. That was the first reason why I applied. I was kind of iffy about the whole remote work thing.  I’d done some freelance work before but I wasn’t sure about how it would be as a full-time gig.

I started getting involved in contributing to WordPress because I felt I could help improve the product. 😀 After a while, things started to fall into a place. All of a sudden a few of my interests were coming together on one project.

D: Why did you hesitate for so long?

Michael: The whole nomad thing looked cool but kind of scary.  I liked my friends at home, my apartment. But then I decided to give it a go. I put my things in a storage and I started traveling. I headed to the east coast, all the way up the coast, drove a little across Canada with a friend, and all the way down the west coast. I have done a couple similar loops since then. It’s super fun.

Seven hundred people work for Automattic. So basically, wherever I go, chances are there’s somebody I know. Folks always love showing off the cool places near their home so we always have a good time. Because of this travel, I see co-workers more often than not.

automattic meetups

D:  Ok. Tell us some more about Kevin disappearing to Iceland. Is it something that simply happens to you when you join Automattic? 😉 

Michael: At Automattic, we do meetups with our team once in a while – simply to hang out, really bond a bit. We don’t see each other in person very often. We, of course, do video calls like the one we’re having now, but that’s not enough to create a strong bond. So, every now and again, we go somewhere to talk shop for a week and really get to know our co-workers. We usually do some odds and ends activities while we’re there. Like go on a hike or go to a movie.

D:  So, you don’t work during this time…

Michael: We used to do projects a few years ago. We would work on something that the team had been thinking about working on for a while. We would meet to hammer it out, prototype, test or whatever, in just a week. It used to be like a hack week. Now it has progressed in a good way. Most of the time, we focus on bigger picture changes, like fixing flows. It varies from team to team based of their expertise and product focus. There’s definitely a lot of work during the meetup.

people over a bowl of rice dish, eating together

Valentina with her team, The Woo Team 😉 You’ll find more pics at her Insta!

Val: In our case, in Italy, it’ll be 40% of socializing and 60% of work. Unfortunately, my team has a German lead, so they don’t get away with too much of free time. (laughter)

We’re going to do 2 to 3 hours ticket work. And then, in the afternoons, we will be working on refining onboarding for the new employees and sorting out the Github snippets. On Saturday we’re going to Rome to have a walking tour and pizza until we can’t walk anymore. We’ll just have fun.

By Monday we’ll gonna know one another much better and so we’ll know who works best at what. So, we’ll break up into pairs, one person does the tickets, and the other one will be shadowing them to see what their workflow is and learn.

Remote work and having family

Maria:  Val, you weren’t on the Woo team. You came in after the acquisition. What’s your answer to what brought you to Automattic?  

Val: I was headhunted. When the hiring agency contacted me, I had just had the twins, so I thought there was no way I could do it. But the girl, who contacted me, Pam, went: “Listen, I have triplets. You can do it!”  So, when I started the trial my kids were 3 months old and I was working full time running my own support company. After 6 weeks of the trial, I simply told Karen (my trial lead) that I needed a decision sometime soon. I couldn’t maintain that rhythm for another month.

a young woman by her laptop in a coffee shop

Maria: Yes, but even if you were headhunted there must have been something that appealed to you and made you want to work for Automattic.

Val is thinking for a while…

Val: If you’re the founder of the company, you’re most likely the most experienced person in the room. I think I wanted to work with somebody I could learn from. And also, if you’re at the top of the company and something goes wrong, you’re the one who jumps in, no matter it’s Sunday morning or not. This doesn’t really mesh well with young children. Not being the founder and working remotely, I can have more predictable working hours. So it was a very pragmatic decision for me.

time organization while work remotely

D: What does the whole time-management look like when you work remotely? Is it easy to separate private and work life?

Val: I organize my time according to the rhythm of my family, which basically means getting up really early so that now I get to work when the kids are still asleep. Then they go to a nursery and I get back to work. The third shift for me is when the kids are in bed. What’s cool about this is that I can bridge Asia and US.

D: How do you make sure the job doesn’t encroach on your private life?

Val: I’m very conscious about tracking my work hours. Otherwise, it would be very easy to work 10 hours a day, which is not the idea. I track the time and look what exactly what I’m doing and analyze where my time goes. Otherwise, the work would take over.

posters with canoes, jeep and tractor

Always be moving, whatever it takes. (Michael traveling, again.)

Droplr: And how about you, Maria and Michael? Is it difficult to get down to work, having all day long to do that and no boss who breathes down your neck? I can imagine it’s very easy to procrastinate…

Maria: I tend to capitalize on my productivity hours. So, rather than saying you have to work 9-5. I can take a break, step away, I can take a drive to the next location. Then I can work for an hour or two.  I don’t know this for certain but it feels like everyone at the company works more than everyone at a regular company.

dog sleeping by a laptop open at Automattic's job ad

While some capitalize on their productivity, others recharge … 😉

Being forced to come to the same space every day, for the same hours every day, there’s no way you can be always on. And when my computer is open, I’m working full time. Fully focused, I get more things done.

Michael: I agree. Like you’re saying, we can skip these lame hours when we’re not productive. We can do errands then and get back to work in my productivity hours. 

Val: There’s a little caveat for Happiness Engineers, (for customer support). We schedule chat hours for 2 weeks in advance and you can’t change your mind, you need to be there when you promised.

Michael: Yeah, and even on the product design side there are just times when you have to be there. You gonna be there that day for launching a new thing or testing a new thing.

I’ve noticed that people who live in one location choose to have more fixed schedules, too. They prefer to work 9-5 because their friends are working in that time. This way they can hang around after hours together.

Droplr quote

D: OK. But… if you go to an office, you get the opportunity to learn from the people you work with.

Maria: We also have the possibility. Actually, we have the opposite problem. We have a saying here: “If you didn’t P2 it, it didn’t happen.” P2 is the code name for the internal blogs we use to blog about the work we do.  So, we actually have the opposite problem: We have so many knowledgeable, talented people share their experience that there’s no way you could ever keep up with all of the amazing knowledge that is there.

The nice thing about that is that if you ever wanted to research how we came to a decision or learn about a particular topic, we have tools that allow us to do this pretty quickly. I actually think that the knowledge sharing is greater than in the office.

Maria from automattic

D: Do you ever wish you had a different lifestyle?

Maria: And at this point, I don’t think I could ever go back to an office. I feel like Automattic might have ruined me on any other company ;).

I hear laughter – Michael has just shown :+1: printed.

Michael: Yeah. I don’t think I could ever go back either without some huge motivation. It would be a huge lifestyle change.

Maria: Aside from the benefit of being able to work from anywhere I have a cell phone connection, I think the second biggest perk is just being able to work when that works for me. And I know it’s especially helpful for parents in the company.

what personality fits to remote work

D: Is remote work for everyone? What types would thrive in this model of working?

Val: Entrepreneurial. Self-driven. Freelancer. There’s no one telling you that you need to be there at this time you need to do that at this time. We’re setting the goals to reach and it’s up to you how to get there.

Michael: There’s an edge for people who are able to figure things out for themselves. You cannot just sit and wait for a reply from a colleague to come. If you’re bad at Google search, it’s gonna be hard.

Maria: Yes, we’re professional Googlers. 😉  And, on top of being self-motivated and self-directed, you need to be great at communicating. We have a huge focus on diversity and inclusion in the company. We try to accommodate support in other languages not just English, but the primary internal communication is in English. Just being able to communicate what you’re working on is very important. When hiring we definitely look at this aspect to see if the person is going to be a good fit or not.

Droplr quote

D: Ok. This feels rather awkward to ask, but: What do you think of me? I get the feeling you use me a lot. 😉

Maria: The Woo team used Droplr from before the acquisition and still does to this day.

Val: The dot.com teams as well. We love the fact that you can make a screenshot and add text, arrows, boxes etc, right on the spot. That way we can not only send a screenshot to our customers, but we can highlight exactly where they have to click (pointing at the button with an arrow – you couldn’t be clearer).  That helps a lot.

Maria: I personally love it. I use it all the time to quickly share a screenshot with the team in Slack, to add to GitHub issues, to do a quick screencast, or to shorten a really long, ugly link. Anytime I’ve had a question or an issue I’ve found the support to be really helpful and responsive, which is always a huge plus for me with any company or service I work with.

man kiss a cat

D: In one word, what you like most about working remotely?

Maria: FLEXIBILTY

Val: INDEPENDENCE

Michael: #CulturalExposure 😉

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I'm a service designer and a digital marketer, passionate about human-centered design and storytelling. To my own surprise, I frequently find myself writing about motivation and organizational culture. Why? This could be the human factor at play...

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