Flywire Taps Former Apple Pay Exec As COO

November 5, 2019

A relentless focus on customer experience and simplifying complexity are the defining characteristics of the most valuable companies in the world today. It’s a concept Rob Orgel, now the new president and chief operating officer at Flywire, told Karen Webster was foundational to his decade-long career at Apple — where he was part of the leadership team that developed, rolled out and grew the Apple Pay business. While there, Orgel was most recently involved in the launch of the new Apple Card.

Flywire announced his appointment Tuesday (Nov. 5) to the newly created position. As Boston-based Flywire's President and COO, Orgel will oversee its global payment network, business operations, finance, legal, compliance, and corporate strategy and development. He will report to CEO Mike Massaro, who will now focus his efforts on the long-term growth plans, go-to-market expansion, and strategic partnerships, according to an announcement.

Orgel told Webster shortly before the news broke that some of the “magic” of Apple and Apple Pay was the work that went into mapping the customer journey end to end, then prioritizing and designing an experience that was intuitive, clear and transparent — and focused on what matters most to the customer. It’s what he sees as the “incredible opportunity ahead for Flywire.”

Flywire is tackling that challenge in an even more complex space because it is business-to-business (B2B), global and high-ticket — “it’s all the things that add complexity to payments,” he said. For Orgel and Flywire, that will mean a continued focus on verticalized solutions, and an intense focus on the significant markets that are “worth winning and worth getting right.”

Massaro said that Orgel’s appointment comes at a time in the company’s history where “demonstrated leadership is necessary to scale, develop and shape Flywire for the future.” He added, “Rob brings all of that and more with a customer-first mindset from Apple that fits perfectly with our culture here.”

Massaro told PYMNTS in an interview just last month, that the lesson Flywire has learned in a decade of building its global platform is that when moving money between parties, neither the person paying or the party being paid is really all that interested in the technology or the mechanics. What they want is to trust their transactions are secure, understand the process in front of them and be free to choose the methods they want to use.

“To get payers to want to pay, it is more about acceptance and being able to use what they know and trust then it is about who we are and what we are doing. In some ways, they care more about the payment methods on the screen and they are things they were familiar with. The customer is telling us loud and clear, 'I already know what I want and need to do.’ ”

The value in offering up new payment methods and value-added services, Massaro told Webster, isn’t in trying to solve problems consumers and merchants don’t have and trying to sell them on it. It's solving the problems that they do have and better meeting their needs.

Massaro and Orgel are longtime colleagues, who first worked together at the eBilling and payment solution firm edocs which was acquired by Oracle/Siebel. He also previously held a leadership role at m-Qube, which was acquired by Verisign.

“I’ve had the opportunity to work with him before and know that he’ll add tremendous value to the business and the organization as we write our next chapter,” Massaro said.

Looking at what the firm has done across education, healthcare and travel as three of its principal markets, Orgel said, “we’re already well into that journey of verticalized and specialized solutions.”