How Remote Working Makes Startups Better

Glen Yi
6 min readMar 10, 2015

Lessons learned from one month as a digital nomad

There’s a term that gets thrown around a lot lately that made me cringe a little every time I heard it. “Digital nomad”… shudder… But it has grown on me since and the concept even more so.

Now more than ever it’s easier to just pack your bags and choose a destination to work. Building a product while living in cities such as San Francisco, Seattle, New York or Toronto is expensive and most of all, unnecessary. There are a wealth of products out there that make it easier than ever for the modern entrepreneur to build their dreams from anywhere in the world.

But what about startups? What if you’re building a dream together as a team? Members can’t just pack-up and work in a foreign country leaving everything behind, can they?

#DigitalNomad

This is exactly what my coworker Ian and I decided to do for a month in Chiang Mai, and it was one of the greatest work experiences of my life. At Tab Payments we don’t have an official work policy per se, and it wasn’t without some justified reservations, but it made us all better in the end.

Doi Suthep, Chiang Mai, Thailand

What We Gained

Improved communication

Because we couldn’t just start a conversation with the person across the desk, it created the need for different processes. Having part of the team on a different continent forced us to use our communication tools to the fullest. Whether it was posting a link in Slack, creating a task in Asana or liking a comment in Quip, our communication flow became more streamlined and transparent. It may seem counterintuitive, but having periods of remote working can open the lines of communication.

Distraction free time

This is important for any role but it’s particularly important for developers. While in Chiang Mai, I’ve had days with 6 hours straight uninterrupted development time. It felt more productive and more than I would accomplish in 8–10 hours in the office. Other days it was 2–3 hours at one co-space before hopping over to a coffee shop down the road for a change of scenery. It was refreshing and allowed us to work at our own pace, uninterrupted.

Timezones

People will use your product in different ways and at different times. Having employees spread out among several timezones is a benefit when problems arise. This is particularly helpful if you have an international product and customer service is a big focus of your startup (as it should always be). Admittedly, we only have 2 developers and both of us were in Chiang Mai, so any technical issues on off times could have been difficult to deal with… But luckily nothing major came up during our stay. I still see this as an advantage for most startups out there though. ;)

Stimulation

This last point is invaluable both to a startup and the individual. I worked in Korea for 5 years then came back to Toronto in 2012. Since coming back, working on my own startup and then joining Tab, I realized I had never taken a real vacation! I’ve gone away on road trips and weekend getaways, but I really needed to get away for a while. The result was that I was more relaxed, productive and creative than I’ve felt in a long while. My list of ideas and backlog of things to learn grew rapidly over the month and I couldn’t be any happier about it.

Our Tools

Of course, keeping everybody synced up would be rough without the right tools. Here’s some of the major ones we use at Tab and how they help us work better.

Slack

The hub through which all our communication flows. And I do mean everything. I’ve loved Slack from the start and it’s a product that’s gotten better and better since launching. Whether it be for private 1 on 1 chats or a little team debate on product features, it’s the best tool out there for team chat. That’s not even getting into the extensive integrations Slack has with other products. While working overseas I would go to Slack first thing in the mornings to see what’s going on in Tab.

Asana

Keeps everyone informed and on the same track. I follow all the projects that are relevant to me or I’m interested in so that I can wakeup and check my Asana inbox to see what’s going on. New restaurant signups, internal dashboard requests or even fundraising progress. Asana can be more than just a project management tool and bring higher levels of transparency. I found myself ‘liking’ tasks and comments much more frequently than before to let everybody know that I dig what I see!

Quip

I’ll admit, I wasn’t sold on Quip at first. I thought it had a slick mobile interface with great notification and commenting tools. The problem for me was we already used Dropbox for storage and Google Drive for a variety of docs and spreadsheets. I argued that keeping documents consolidated into one place was simpler and hence better. My thoughts changed however once we were working remotely and the immense value of Quip came to light.

While Slack allows us real-time communication and Asana keeps us organized, Quip makes collaboration a breeze. I can see how our sales playbook is evolving, comment on product requirements and ‘like’ what other people have said. Just as in Asana, a ‘like’ provides strong feedback with the click of a button.

Notable Mentions

  • Invision. We’re very product and design driven. More opportunity for comments and likes.
  • Github. We try to keep our commits descriptive. Integrates nicely with Slack.
  • Heroku, Papertrails and Fabric/Crashlytics. Integrations with Slack let us know when things go wrong.
  • Mixpanel. While it’s not for communication, they do have good mobile tools so that I could schedule push notifications to our users in EST.

The Downsides

Yes, remote working is not without its drawbacks.

Product planning and strategy

At 5 people, Tab is a small team even for a startup. Our long term product roadmap is constantly changing and needs frequent updating. This is the nature of an early stage startup and requires constant communication with the entire team. Working remotely in different timezones makes it tough to keep everyone on the same page but is not impossible. Steer everyone at all times towards that north star.

Team building

One of the intangibles. Do anything fun on the weekend? What did you think of Birdman? Where should we go out for lunch? Let’s go out for a drink! A team that eats together stays together afterall. Yes we communicated daily through chat and calls, but it’s not quite the same. It’s why even a 100% remote company like Buffer has company retreats 3 times a year.

Serendipity

Another hard one to measure but cannot be underestimated. This was highlighted in Eric Schmidt and Jonathan Rosenberg’s book “How Google Works” when they claim that one of the ways to build a successful company is to “foster serendipitous conversations”. Design your work space so that there are as many interactions between employees as possible to just start random conversations. Innovative ideas can strike at anytime from these crossings which is extremely difficult (impossible?) to replicate with a distributed team.

Downside… not wanting to go back home.

How to start?

Talk with the team and make sure everybody sees the benefits. Set guidelines on how you’ll keep the lines of communication open and clear. Chat with your team often and hop on calls whenever needed because miscommunications can quickly cause rifts and set backs.

To know more about remote working, read about Buffer’s distributed team culture. Not many have built a startup with remote working from the ground up and there’s nobody else doing it quite as right.

In the end, I’d suggest either throwing darts at a map or head on over to Nomad List and pick a spot. The world awaits.

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