The Gatehouse Blog

Flying high…with your people in tow


We sat down with Kelly Hartman, Flywire’s new Chief People Officer, to find out more about this growing company’s working culture, with a particular focus on how they drive their unique employee experience. 

Flywire is a fintech company that offers streamlined international payment solutions for institutions and their international payers. Founded in 2011 as a fledgling start-up, the company has grown to become a prominent player in its industry through a mix of organic growth and acquisitions around the globe.

Headquartered in Boston, it currently employs 320 employees spread across North America, Australia, Asia and Europe and plans to grow its teams at an even faster pace in the coming months.

From take-off to cruise control

After such a colossal metamorphosis in just seven years, there was a pressing need to implement a robust people strategy. It became a company priority to focus on talent acquisition and retention – and to provide a supportive and productive working environment consistently across all locations.

That’s when Kelly Hartman was brought in. Recruited as Chief People Officer by CEO Mike Massaro himself, Kelly recalls their initial conversations. “I was impressed by how passionate he felt about the business and the culture. He was clear that he wanted someone who would help shape the employee experience and drive that alongside him”.

Since taking on the role, Hartman has rejected a traditional corporate HR approach: “I never used to like the way HR was run in my previous roles. I didn’t believe they understood the business. They were making decisions and hiring for a business they didn’t understand.  It was all about being reactive rather than proactive.” For this reason, Kelly has turned this approach on its head and embraced proactivity, reaping major rewards with regards to the culture at Flywire.

“After such a colossal metamorphosis in just seven years, there was a pressing need to implement a robust people strategy.”


Flying in tandem

Flywire’s employee experience strategy is shaped around direct feedback from employees – ‘Flymates’. Since joining the business under a year ago, Kelly has embarked on no fewer than 25 trips, running workshops and roundtables with employees in an attempt to get to grips with their needs and their wants, and most importantly, taking time to actively listen to their comments and concerns. As Kelly puts it, “Why would you invest time and budget into something that is not adding value to your employees? Our ambition is to deliver exactly what our Flymates want”. This is a fundamental part of the framework used by her team to ensure Flymates are treated as well as clients are:

  1. Operating in partnership – Flymates have to be worked with, respected and listened to rather than just spoken to/at.
  2. Customisation – There can be no ‘one size fits all’ policy. Flymates, like clients, have different needs and no blanket strategy will work for everybody.
  3. Diversity – Given Flywire’s international presence, national and cultural sensitivities need to be acknowledged. Legal and regulatory differences must be recognised also.
  4. Going above and beyond for your people – So that employees will do the same!
  5. Create ways to bring people together – A united team is infinitely stronger and more productive.

Avoiding turbulence

Beyond the traditional internal communication channels such as e-newsletters, leadership email updates, and executive roundtables, Flywire has adopted a number of unconventional ‘techniques’ where the corporate model of hierarchy plays a very minor role.

“We’re not like other organisations, where just the executives go out to the different locations, or where only the senior leadership team may be taken out for a luxury dinner. Here, everybody goes – no matter what level you are, no matter what you do.”

Often, motivating employees takes place out of the confines of the office – in day trips and excursions and even exercise classes, which Kelly describes as ‘organic’ and essentially ingrained in the company culture, rather than forced or prescribed occasions.

Cascading in order to soar…

Office managers are an integral part of Kelly’s extended team as employee experience can’t sit in any single team. They help them cascade the messages, ensuring that employees are and stay informed, and support the roll out of initiatives that echo and reinforce the company’s values.

Initiatives so far have included partnering with client universities to give students an opportunity to pitch a business idea and be rewarded as innovators; or organising round tables where employees can hear clients’ feedback and understand the positive impact of their work.

Flywire’s distinct culture has become its main selling argument, and the company strongly encourages clients and partners to come and visit their offices to get a sense of how they foster innovation. It is also the company’s main challenge – to maintain its culture as it faces an ever-faster growth.

“Here, everybody goes – no matter what level you are, no matter what you do.”


Biography: Kelly Hartman

With more than two decades experience in organisation development, cultural change, talent
acquisition, succession planning, and employee relations, Kelly Hartman is a bona fide authority in the sphere of human relations. Her weighty resumé includes a myriad of senior and executive positions held in prominent multinational companies in offices across the globe.