When you run your own company, you make the rules. You decide how you spend your money. You decide the structure of your company and where and when you do work.

The default option is to get an office in a city like New York (where we are) and work normal business hours. John and I have both been curious to flip that requirement on its head and build a remote team.

We recently had the opportunity to run an experiment for two months where everyone would be in a different place.

Why try to become a remote company?

2.5 billion people in the world have internet access. Statistically speaking, the chances that the best person for us to hire for any position is among the 0.023 billion people in the New York metro area is unlikely.

We want to hire the best people regardless of location

I don’t want to tie myself (or the company) to New York City. It has a ridiculous cost of living, but it’s a great place.

We could give employees the opportunity to be nomadic and work while exploring the world. What if you wanted to spend 2 months in Asia, and didn’t want to quit your job or wait until retirement?

There’s a tremendous feeling of freedom when you abandon the shackles of a specific location.

The question we were trying to answer:

Could we work from different places just as effectively as in the office in New York?

How did we go from knowing nothing to learning the answer to that question?

Work like a remote team before you need to

John and I have been chatting about remote work for a while. We started our company with remote being a possibility from day 1.

Campfire has been our primary way to communicate in and out of the office for as long as I can remember. When it was just me and John, we used to work late in to the night from home leaving messages for each other on campfire.

If you’re next to someone and they have their headphones on, messaging them in chat is a more respectful (and productive) way to ask them a question.

Communicating asynchronously even when you aren’t forced to gives you the discipline to work remotely and makes it much easier to make the transition to being anywhere.

Start by working remote in the same city

I started working 2 days a week from home in Brooklyn rather than doing the 1/2 hour (each way) commute in to the office in Manhattan.

This was a low-risk way to test remote working. If it was terrible, I could always just come in to the office. It wasn’t. My productivity skyrocketed on the days I worked from home. I did find myself a little stir crazy at the end of the day though and realized I need to get out more on those days.

This let us know that at least in small stints of remote work, the sky didn’t fall. But it wasn’t enough to truly give us confidence to build a remote company.

A 2 month trial where we were physically remote

We had to up the ante to learn more about working remotely. For September and October, team Customer.io worked almost entirely remotely.

At it’s peak of our team travel people were all over the place:

Henry in LA

Michael in NY

John in Florida

Asha in Brazil

Colin in London

Our daily standup done over Google hangout was 8am for Henry in LA and 4pm for me in London. This was a bit challenging but we made it work. Beyond the daily standup, we used a bunch of other tools.

How we collaborate when working remote

Google Hangout - for daily standup and face to face conversations.

Campfire - for persistent chat throughout the day

Screenhero - for screensharing / working on code together

Balsamiq - Planning UI to build

Asana - Managing tasks

Google Docs - Communicating in longer written docs / stats in spreadsheet form

Email - Everything else

What did the team have to say about our remote experiment?

Overall, it was a success (but not without trade-offs). Understanding those negatives gave us the confidence to go forward with building a remote company.

Bad things about remote teams

No casual socialization

Everyone on the team missed socialization like getting lunch together, grabbing a quick game of ping pong, going on a coffee run, and the off the cuff conversations where you end up talking about product ideas.

Communication challenges

We realized how important it is to be a good communicator (and responsive). It feels a lot easier to talk something through when you can just grab a conference room and talk face to face. Communicating over chat / email requires more discipline when hashing things out. Google Hangouts with screensharing are a pretty great substitute.

With time differences, if you get blocked on work, you sometimes have to wait for business hours for the person who has the answer.

In Remote, Jason Fried and DHH advocate for 4 hours of overlap for people working together. This might mean adjusting schedules to make sure you’re online at the same time.

You need control over your work environment

If you’re traveling, you don’t always have access to a great place to work. Coffee shops can be noisy for a video chat. Being around family if they are on vacation (and you’re working) can be distracting. It’s important to have the discipline to find a good place to do work and a great internet connection.

If you can work around the issues above, then it’s all up from there.

Good things about remote teams

No commuting!

Cutting out the commute means that if you’re working from home, you can spend the time you would be commuting exercising, gardening, cooking, or whatever it is you’d rather be doing than sitting on a train, bus or driving in a car.

Freedom to travel

When your company is set up for people to work anywhere, you can do just that – work anywhere. Going for a wedding? Why not spend a week instead of just the weekend when you can just work from there?

You can tune-out your coworkers

When you switch to asynchronous communication, if you REALLY need to do work, you can just turn off all possible distractions and focus. If people can’t tap you on the shoulder, those interruptions either get solved on their own, or handled by email / chat.

Can we build a remote company?

We’re going for it. I’m planning for 1/2 of our team to be full-time remote on January 1st, 2014.

There are still some things we’re going to learn and tweak along the way but I have a lot of confidence that now is a great time to build a globally remote company.

Here’s what we’re planning to do going forward:

Hire the best people regardless of location (keeping in mind the 4 hour work overlap).

Bring everyone in the company together once or twice a year (probably on a retreat).

Have new hires spend time face-to-face with the people they’ll be working with (still figuring out how this will work).

Have a daily check-in over google hangout.

I’d like to experiment with adding idonethis to our workflow as a way to keep up with things especially as the team grows.

I’m optimistic about the future of remote working for Customer.io. If you have questions about what we’re doing, or advice for us, let me know.

More reading on remote teams