Flywire Reimagines Remote Work

Samantha Mackowitz
Samantha Mackowitz is Senior Communications and Social Media Specialist

In the Fall of 2020, Flywire experimented with a regional, socially-distanced gathering for a small group of FlyMates (Flywire employees) that I was lucky enough to be part of. During this time COVID-19 cases were under control in the state of Maine and our executive team had previously reserved a ski lodge for an offsite which was no longer happening. So instead, myself and 11 FlyMates from different departments in our Boston office took advantage of the space. We worked remotely together for a week which provided collaboration and some much needed socializing after months apart. We followed all regulations in Maine at the time, and each person was tested for COVID-19 in advance of the trip. We lucked out with amazing weather and there was plenty of indoor and outdoor space to work.

Take a look at what our experience was like!

In our eyes, the experiment was a huge success and had a big impact on us all. For us and our leadership team at Flywire, it was a huge wake-up call about the value of having people together. We had not seen one another live in over six months. One of our newer FlyMates had been hired after quarantine and was meeting some of us in person for the first time!

There are aspects of work that happen when people are physically together that you just can’t replace on screen. It builds stronger connections that carry people through tough times.

Based on our feedback from the experience our CEO Mike Massao said, “When the time is right, Flywire is looking for ways to replicate this type of gathering for our other offices around the world. We need to be careful, follow guidance in each region, and make sure people feel completely safe, but it’s an important part of who we are as a company. We won’t be crossing international borders anytime soon, but at Flywire we believe even small group gatherings will deliver big benefits in both the short and long term.”

Flywire has hired 70 new FlyMates since March 2020. Like others who have started a new job since COVID started, most people only know their fellow colleagues as someone on the computer screen.

Flywire is expecting to add another 100 FlyMates to our team this next year and our CEO Mike Massaro commented, “I would very much like these people to get to know some of their colleagues in person. We are not sure things will ever return to the way they were, but at Flywire we want to retain some aspects of what we had pre-COVID. I’m curious how others are approaching this and what successes or lessons learned you might have to share.”