Work and Travel

Remote & Ready Since Day One - The Pilot Way

Updated on:  
May 25, 2022
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Taarika Rajani
Taarika Rajani
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Here's how the Pilot team started 100% remote and is building an amazing team culture. Learn about the different tools we use to make remote working effective and engaging!

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Today’s global health climate is truly unprecedented. With the onset of the current global pandemic, many companies have been forced to fundamentally change the way they conduct business. The Digital Nomad lifestyles that many pursuit were also in jeopardy as many countries went into lockdown. Moving online has proven to be challenging for even the most innovative and established of organizations.

Along with the obvious technical challenges of transitioning to remote work, companies also have to figure out how to keep employees engaged while they are miles away from their colleagues. Fortunately, unlike most businesses, Pilot did not have to deal with transitioning to a new working style. Our team has always been 100% remote.

Our team of passionate individuals truly live and breathe Pilot’s goal of helping people live happier lives through shared experiences. Whether it’s our collaborative work calls or our supportive Slack channels, sharing our experiences and ideas is key to creating something extraordinary. Working from locations all across Canada, our B2C SaaS startup began and remains, to this day, completely remote.

This may make you wonder how we can work together efficiently, and what our team dynamic looks like. How can we be friends, care about each other’s lives, and make working fun without having a traditional team foundation to build upon?

Well, there are many strategies our team has been using to stay close to each other although we may be in different physical spaces. Setting aside collaborative work time has helped us have remote discussions, optimizing our use of Slack has been hugely beneficial for team communication and creating virtual bonding experiences has strengthened our personal relationships!

Creating A Culture Of Collaboration

Because we are working toward tons of fast approaching goals, it is really important for us to bounce ideas off each other. Each day, we have a chunk of time booked in our calendars for “collaborative work”. This means that we post a Zoom link in our team’s general Slack channel, and anyone can join or leave that Zoom call at any time over several hours. Remote working means we have to be respectful and flexible towards everyone’s time zones and schedules, so there is no obligation to be working during those times. However, if someone does happen to be working during a collaborative session, we simply jump on the Zoom call to answer each others’ questions and complete tasks together. This strategy has helped our team move fast and work together efficiently.

Our team also has weekly all-hands and department specific meetings to keep everyone in the loop about what each team member is working on. We host these meetings via video chat so we can check in with everyone face to face.

Pilot team Zoom meeting snapshot
The Pilot team after another collaborative Zoom call where we discussed growth strategies.

Making Remote Connections Meaningful

Aside from ensuring that our team works efficiently, we also recognize the importance of establishing strong relationships between everyone on the Pilot team. So while some departments naturally work more closely than others, we use a Slack application called Donut to randomly connect each employee with another member of the team for a casual conversation. This has allowed us to get to know each other on a more personal level, which definitely makes working together more enjoyable. Since we all work remotely, the chance to connect with someone with diverse and unique experiences is incredibly valuable and helps us feel closer to each other even when we are apart.

A real donut held in front of Donut, the slack app
Here is how Donut appears on Slack -real donut not included but definitely adds to the experience!

Fun Stuff!

Apart from working, we also like to have fun! We have a  Pilot Spotify playlist that we add songs to via a bot on Slack called Jukebot - feel free to give it a follow :) Our bi-weekly virtual happy hours where we play team games are another great way for us to relax and bond together even if we can’t do so in person. During our last team Pilot Abi, our People and Experience expert, put together a challenging travel themed trivia competition for the team. See if you can answer one of Abi’s trivia questions from our game night below :)

Trivia travel-related pop quiz from Pilot
The answer is a) Wellington, New Zealand. Did you get it right?

We want to hear from you!

As daunting as remote work can seem, at Pilot, we are always finding new and creative ways to develop a fantastic team culture. We love learning about how other companies are maintaining their tight knit bonds while working remotely - let us know how you and your teams are getting closer and more creative in quarantine!

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Originally published on:  
July 15, 2020

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