Working Remotely: South America & Cuba

Online in eight countries.

Glenn Rogers
Float
5 min readAug 31, 2016

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We always encourage our team at Float to work wherever they like. Home or office, San Francisco or Portugal, as long as there’s great internet and a couple of hours cross-over with the team, they can live, work and travel wherever it suits them. Earlier this year, I took the opportunity to put this to test, traveling from New York to South America and Cuba. 9 weeks, 8 countries, 15,000 kilometers.

Medellín, Columbia

Setting your team up for working remotely

Working remotely across countries and time zones requires good preparation and expectation setting with your team.

At Float we have team members across five time zones. To ensure we have time for discussion and problem-solving we all agree on a mutual time to be online and available. For us, this is between the hours of 5pm and 7pm EST Monday to Friday. We’re all accessible at this time. The other times we set our communication channels to ‘Do Not Disturb’, where responses are optional. (Our customer support team are the exception, working 9am — 6pm EST). This gives our team long blocks of uninterrupted time where we can be at our most productive. The odd exception is important sprint releases or emergencies, but we try to keep this to a minimum.

Float is now in use in more than one hundred countries, so at any time, day or night, there is someone relying on us for their team scheduling. A stable, performant system is our top priority, so we spend a lot of time refining our process in case of emergencies. We have an escalation process for our Customer Support team, a Slack channel setup to notify our engineers, and in the case of major outages, management are automatically notified via phone, SMS and email (via Pagerduty). Customers can receive live updates via a dedicated system status page (using Statuspage).

Setting yourself up for working remotely

Here’s a list of the battle-tested items I use for working remotely:

  • Google Nexus 6P phone on Project Fi network: With Project Fi, Google have managed to do the unthinkable. They support data, messaging and voice in almost every South American country and you pay the same price as in the U.S.A. ($10 for 1/G of data). The only areas not covered in my travels were Cuba and Galapagos Islands.
  • Battery pack: Google sent me a pack with the 6P that supports the higher output 2.1A faster charging.
  • Priority Pass: A Priority Pass gets you into airport lounges in almost every country you visit in South America. From a small Santa Marta room, to the high-end lounges of Lima, you’ll get great WiFi, food of varying quality and a comfortable environment to get work done.
  • Macbook Pro: Rock solid.
  • Sennheiser Momentum headphones w/Android cable: I went with the wired model. In hindsight, I would go with the latest model, which has noise cancellation, bluetooth and most important, it’s foldable. I needed everything to be compact and these were a little too bulky for my liking.
  • Moleskin notepad and Retro 1951 pen: Two classics I swear by on the road and at home.
  • Travel adaptor: There’s a few different variations of power outlet across South American countries, with a split of US-based 120V, 60Hz and the 220V, 50Hz. Even within countries like Brazil, it can vary. You’ll get by most of the trip with a simple two prong adapter, which will cover your phone and laptop charging. In countries where this isn’t supported, there’s plenty of street vendors and hotel lobbies that can help.
  • Brooks backpack: Brooks are renowned for their high-quality, waterproof cycle bags. These also turn out to be fantastic day bags for traveling. There’s a separate layer for your laptop, plenty of pockets for devices, and you’re able to secure the main compartment, while using the side pocket around the back for easy access to cash or your passport. This last feature is important when you’re walking the busy markets of La Paz or peak traffic times in Rio.

The route:

Colombia (Cartagena, Tayrona National Park, Medellin), Cuba (Havana, Vinales), Ecuador (Quito, Galapogas Islands), Peru (Lima, Cusco, Inka Trail / Machu Pichu, Puno), Bolvia (La Paz, Uyuni Salt Flats), Chile (Atacama Desert), Argentina (Mendoza, Buenos Aires, Iguazu Falls), Brazil (Ilha Grande, Paratay, Rio De Janeiro).

What I learnt working remotely across South America & Cuba

  • Internet is *almost* everywhere: In 62 days of travel only 5 days were completely without internet: 3 days in the Galapagos Islands, and the first 2 days of the Inca Trail in Peru. Every other day, from Cuba to the peaks of the Andes Mountains, it was possible to connect with the team and our customers.
  • No internet is not your enemy, slow internet is: Slow internet is a productivity killer, and it was a common occurrence throughout the trip. Outside of major cities, in transit and yes, still in hotels, it was common to be communicating at dial-up speeds. I made a point of confirming accommodation had high-speed internet ahead of time and found Airbnb’s the most reliable.
  • Video conferencing suffers: With poor internet speeds, video conferencing becomes difficult. We reverted to audio-only meetings on several occasions and it wasn’t the same as being able to engage with the team and see their progress. This is one of the key reasons for taking time to find great internet.
  • Be prepared: In the famous words of Badden-Powell: Be Prepared. Do your research ahead of time and bring the right tools for the job. WikiTravel is a fantastic, free resource. Don’t assume you can pick up the right technology on the road, I spent hours in search of a USB-C cable, only to realize these are virtually non existent in South America.

The world is an amazing place. It feels infinitely large and yet paradoxically small with today’s technology. Taking the time to experience it, the people, places and cultures, is good for the mind and recommended to anyone who works for a global business.

Galapagos Islands

Float is the resource scheduling solution of choice for teams from South America to South Australia and South Africa. Start a free trial at www.float.com

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Glenn Rogers
Float
Editor for

CEO of @float. Building the best resource scheduling app on the planet. www.float.com