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3 ways executives can strengthen company culture in a hybrid workplace

People meeting in a remote working space with cafe

Sourcing good local office and meeting space is vital for hybrid-first companies. Image: Pexels/Helena Lopes

Mike Massaro
CEO, Flywire
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Davos Agenda

  • A CEO explains his company's hybrid-first approach to working and the leadership changes required to manage it.
  • Here, he shares three insights from his experience that may help other leaders and organizations navigate their global cultures.
  • These include prioritizing social interaction and staying engaged with day-to-day business concerns via messaging apps.

In the past three weeks, I’ve traveled to the UK, Singapore, and Vietnam. All were for different purposes—from an annual user conference to an office opening to a strategic offsite. While international travel isn’t anything new to me, my approach to how I spend my time on the road has evolved since we’ve become a more hybrid-first workplace. I am more intentional about where I go, why I’m going, and how I decide to spend my time.

Work for most people looks very different inside and outside the office, and our leadership styles need to flex in response. I have heard from more than a few CEOs, executives, and people-leaders that our job needs to have two sides now: one for remote and one for in-person.

As the CEO of Flywire, a payments company with more than 14 global offices and nearly 1,000 FlyMates (employees) that collectively speak more than 35 languages worldwide, managing a global workforce that embraces remote and hybrid working styles have required a specific leadership approach. I have learned critical success factors to ensure that we maintain the right level of connectivity and cohesion no matter where we are in the world. Here are three insights from my experience that may help other leaders and organizations navigate their global cultures.

Prioritize social interaction while on the road

For days executives plan to be in the office, they need to create a new experience for employees that highlights the cross-border, communal nature of the company.

I have found that the worst thing I can do when visiting one of our offices is duck into a conference room all day and sit on Zoom. This behavior was more common pre-covid, when executives traveled more frequently and face-to-face time was more regular. But now that we are being more strategic about when and where we travel, it’s important that my presence is more pronounced and that I structure my visits to socialize and get to know FlyMates - not just get down to business.

Post-covid, we’re much more deliberate about scheduling. On every trip, we build in an all-hands or an ask-me-anything-type meeting with FlyMates in those regions. Then, I make sure that the remainder of the days there (typically, I spend between two and four days when I visit offices) are relevant to the needs of the people in those places.


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Lean on local office support to tailor each visit

In this same way, unifying a global culture requires being hyper-local. A visit by me or any executive team member to Singapore looks different than one to our office in Valencia, Spain, or Tel Aviv, Israel. These visits must be tailored to our employees’ expectations, roles, and priorities. You cannot try to replicate one schedule from one part of the world to use it for another.

Experience managers, who work in every office at Flywire, are our culture ambassadors. Their job goes beyond planning in-person lunches or remote cooking classes to becoming in tune with those working in and around that region. Our experience managers get together regularly on Google Meets to share learnings and then enhance the entire firm’s culture. Similarly, global travel wouldn’t work for us without our strong executive business partners. When executives take trips to offices, our executive business partners work very closely with the experience managers to plan the entire day and activities outside the office, tailored to the needs of the region but still in line with Flywire’s personality.

Embrace authenticity to create cross-border connections

Global culture building cannot rest on a few in-person trips a year. Authenticity is paramount in ensuring that culture remains strong when we’re back to our day-to-day rhythms.

Slack gives me a great pulse check on how our FlyMates are feeling. I have a few channels in my high-priority section that help me zero in on culture, such as our local channels for our global offices and channels for specific interest groups—like moms and dads, travel, and more.

It’s important that I stay engaged in these channels, so I never lose sight of what makes up the whole person of each of our FlyMates. It’s a mistake to think that our employees only find fulfillment at work, so I like to celebrate every picture I see of new babies, weddings, trips around the world, and all the other achievements they choose to share.

FlyMates anywhere in the world can join any office channel, and you don’t have to be a parent or a global traveler to join those channels, either. It’s all a great way to share and learn about things outside of their own familiar experiences, see the personality of each region around the world, and celebrate one another. Remember that global collaboration is driven top-down, but execution happens from the bottom up. Life is richer when you can work and learn from people who are different from you.

Have you read?

Fostering global collaboration amongst colleagues

Maximizing social interaction, creating new experiences, and being authentic are three ways we continue to foster global collaboration and ensure it remains a strong core value at Flywire. And as usual, our employees speak more eloquently about these things than we as executives can.

Let’s look at two FlyMates we connected on video—Yuan in Shanghai and Andrei in Cluj, Romania. They didn’t know or work regularly with one another. They were not in the same room when the video was filmed. Yet their conversation appears as if it is between two old friends. When asked what global collaboration meant to them, Andrei summed it up quite nicely: “Wherever we are, we can execute whatever mission we have with success and, in the end, become friends.”


Mike Massaro is the CEO of Flywire.

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