Financial Services

Mike Massaro | Flywire

Mike Massaro, CEO
Boston, MA
Founded: 2009

Focus pays

At Flywire, Mike Massaro is relentlessly committed to taking the hassle out of international payment processing.

oon after joining Flywire as VP of Sales and Marketing, Mike Massaro could sense that the company’s business model held potential — but it also lacked focus.

Founded in 2009 to provide overseas payment solutions for international students, Flywire was struggling to gain scale and was considering additional direct-to-consumer offerings for students studying abroad, such as arranging air travel.

“Either you have a business in which you are the best in what you do, or you pivot to something else,” Massaro says. “We were in between, and everything else looked easier than what we were doing.”

Once Flywire resolved to focus on the company’s original mission, it found itself squarely on the path to becoming the leading provider of overseas payment solutions for international students. 


Simplifying and streamlining

Some 4.6 million international students were enrolled in overseas colleges in 2017, with nearly one-quarter of those attending universities in the US. While large corporations and financial services firms have the infrastructure for global payments, payment processing was not as straightforward for educational institutions and health care providers, often requiring multiple steps and approvals before a payment issued in one country could be accepted in another. In fact, Flywire founder Iker Marcaide started the company after his tuition payment to the Massachusetts Institute of Technology was held up in an overseas funds transfer for more than two months.

Once Flywire removed the distraction of entering the direct-to-consumer market, the company devoted its energy to signing up large education institutions in the US, including New York University, the University of Virginia and the University of Pittsburgh.

“We knew they would be reluctant to invest in a long relationship off the bat, so we had to get them to try our service first,” says Massaro, who became CEO in 2013.  “So we offered our subscription-based service at no cost to the school or their students.” The approach paid off, helping Flywire secure a leading share of the market for international payment processing. Today, the company solves complex global and local payment and receivables problems for more than 2,000 businesses and institutions, processing over $6 billion annually from 240 countries and territories in 125 different local currencies.

Flywire has also emphasized rolling out new features and functionalities that meet the needs of the market. “We have been consumed by a single focus: to improve our product and process payments more efficiently,” Massaro says. “We are relentless on innovation — how can we make it better for the payor?”

To make bill payments as seamless as possible, when international students receive an online invoice from the educational institution, they click on a button that directs them to the Flywire payment processing system. “We make it easy for them,” Massaro says. “The student and college don’t have to worry about international approval forms or currency rates.”

Either you have a business in which you are the best in what you do, or you pivot to something else.
Mike Massaro

Bringing expertise to new markets

With a solid foothold in the international college payments market in the US, Massaro has led the company’s expansion into education markets in Europe and Asia-Pacific, acquiring two companies in the UK and Australia. Soon after Flywire had established itself in the overseas educational payments market, Massaro realized that Flywire’s business model could be scaled readily for other markets, such as international health care payments.

Relying on its expertise in the payments industry has helped Flywire expand its horizon. “Too many companies take a Silicon Valley approach when they try to disrupt an industry,” he says, adding that in the payments space, “if you don’t understand how payments flow from one bank to another in different countries, then you can’t solve the problem. People don’t want to buy from people who don’t understand their space.”

He put that philosophy to work providing health care payments for patients from China and India. For example, someone from China seeking medical treatment in the US needs to provide proper documentation or the funds won’t be released. Patient data laws in the US make that difficult, so Flywire created a process in which the hospital would issue a redacted invoice to Chinese authorities so the funds could be made available.

As Flywire has expanded from a small company into a worldwide operation with 400 employees based in 10 offices globally, representing 32 nationalities, Massaro has focused on trying to maintain the corporate culture. He continues to play a key role in bringing new people on board, interviewing every new management hire and observing how they interact with current staff.

Massaro says he looks for people who are curious about the world and ready to speak up when they see that something is not working right. “We don’t get it right every day,” he says. “We all make mistakes. I want people who are ready to call you out on that.”

To keep everyone in the company pulling in the same direction, he holds company-wide meetings every six to eight weeks both in the morning and at night so that the offices in Asia can participate. This helps keep everyone in Flywire on the same page as they work to make life easier for clients.