The Remote X is a series by the Planetary team to feature the experiences of remote teams across the world (literally!). Every week, we interview people leading or working in remote teams and share their knowledge with others in the hopes that we can all grow and benefit from their experiences.

Art by Vince Joy.

Lauren Proctor is the Head of Marketing at Jobbatical, a marketplace that connects companies to talented tech and business employees across the world. For this week’s Remote X post, she tells us about her experience working in a cross-cultural team, and managing her own team remotely.

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Hey Lauren, where are you based in right now?

I’m living half-time between New York and Tallinn, Estonia! That’s right next to Russia.

Cool! Could you tell me more about yourself and your role in Jobbatical?

My name is Lauren Proctor, and I’m the Head of Marketing at Jobbatical. I was working remotely in New York when I kind of signed up for Jobbatical on a whim. They contacted me directly and said “Hey, wanna go on a jobbatical working for Jobbatical?” and that was it!

I have also been running my own company for about 9 years! I still run it on the side, but I mainly do marketing for Jobbatical, and it’s such a cool company.

Are you guys totally remote?

So we have an office in Tallinn, Estonia, and we also have an entity in Malaysia. Right now there’s no one working right there, but we plan to go back to somewhere in Southeast Asia and have offices there as well.

Our headquarters are here, but we have people working all the time from Hong Kong, Malaysia, Singapore, the UK, San Francisco and New York.

How big is Jobbatical?

There are about 27 of us now, and from 11 different nationalities!

On a personal basis, how do you structure your day while working remotely? Do you find it a challenge to keep yourself focused?

The biggest thing for me is time zones — I’m most creative between 4pm to 2am, so that makes it hard if I’m in the wrong time zone. I’m really trying to figure out the “when are you on and when are you off” thing!

I’m one of those people that won’t do something if I don’t want to, but fortunately, I love my work. If I get to choose what I want to do right now, 80% of the time, it’s to be working. So that’s lucky for me, and makes working remotely very easy. Well, easy for me, but not my girlfriend!

Why did you guys choose to grow a remote team?

I think travel and the inspiration that you get from being where you wanna be is so, so integral to the DNA of our company. The idea of flexibility and working where you’re happy is so important to us, that in some ways, we have no choice but to figure out remote work.

“The idea of flexibility and working where you’re happy is so important to us, that in some ways, we have no choice but to figure out remote work.”

It’s certainly been a struggle to figure out the logistics of such an asynchronous communication style. However, we also believe that it doesn’t matter if you’re from India or South America — if you’re good at design or if you’re a great web developer, it doesn’t matter your passport, those skills are going to the best. So we wanted to think about hiring the best people we possibly can, and it doesn’t matter to us where they are.

Do you guys do video conference calls often?

ALL THE TIME. We’re on Hangouts every day. Well not the whole team, but basically every day, we’ll see each other in some form.

As the head of marketing, how do you manage your team and keep them organized/productive?

We try to keep really definitive goals, and track not only what we’re doing, but also how much time we’re spending on them — for example, this takes 5 hours and produced these results. So I think we try to really be data-based.

We also use Asana, Slack and Hangouts a lot.

How much of an emphasis do you put on keeping your team members emotionally connected?

I do try to do that. I think one of the biggest or hardest things when you’re remote is knowing if people feel lost, or if they’re like “I don’t quite understand the goal of this”. We have a thing called Donut, where even if you’re remote, we ask you to at least have tea with the person.

Like… virtual tea?

Yeah! Like, I’ve had virtual tea when we both went to teahouses! And we were like “oh, what teas do you have!” (laughs)

As marketers, I think we’re a funny bunch. People say that in the office, we’re always the loudest. And I think that applies to on Slack — we’re always the jokesters, telling legends about wherever we are and stuff like that.

What’s the biggest challenge you’ve faced while managing your remote team, and how did you solve it?

I think the asynchronous communication of when someone asks a question, and figuring out how to get on the same page — that’s a really difficult thing. You need to be a good writer who can communicate concisely, and understand what the other person’s asking you and what the end goal is. And that is very very difficult, especially in a cross-cultural team where we’re working with people who english is their second or seventh language.

Have you had any like frustrating experiences?

We’ve had some frustrations where projects take much much longer because one person’s on one side of the world, and they give like a two-word answer, and the other person wakes up, and that’s one asleep, and you know, your frustrations build because that’s a bottleneck.

We set a rule where if we couldn’t get it figured out, people wouldn’t be allowed to work remotely.

So did it come into play — did you have to enforce it?

No, we didn’t have to enforce it hard, or in a definitive way. I think it was more like having the clear realization that we need to work on this. ’Cause even know, it’s hard — it requires a constant effort.

What’s the best thing/your favorite thing about your team?

I love working with so many people from so many different countries. We have a #random Slack channel and anytime anything political happens in the world, people will say stuff like “Guess what, this just happened in Egypt and this is what the news is saying about it, but this is how me and my friends feel”. Or we’d joke with each other, like “Hey so-and-so, here’s what the pizza looks like over here, you from Italy!”

One time, someone kept leaving the toilet seat up. So finally, someone said something in Slack and they said, “Why? My mother taught me in Hong Kong that means that it’s clean and ready for the next person.” So finding out about these cross-cultural differences are really cool.

Describe your remote working experience in 5 words or less!

Thriving on freedom!

Any last advice for anyone out there working remotely, or thinking of doing so?

Someone told me that if you’re gonna build a remote company, it’s going to be much easier to start with remote in your DNA from day 1. That’s because you figure out how to communicate in the beginning as opposed to having 50 people in the office by the water cooler and one person sitting halfway around the world. I think that’s a really big thing. (Of course, not to say that you can’t do it ever.)

“If you’re gonna build a remote company, it’s going to be much easier to start with remote in your DNA from day 1.”

Another thing — maybe this comes from how I believe in humans, but I think everyone’s actually really trying to do their best and sometimes that’s lost in remote arrangements. I always take an extra second — and I don’t always do it successfully — to try and understand who this person is, where they’re coming from, what they’re trying to do and what we’re trying to do together.

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Shout out to Lauren for the awesome interview, and for sharing her invaluable experiences with us! Find her on Twitter at @LaurenProctor32 and at laurenproctor32.com.

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