


Employees at Flywire rank Mike Massaro in the Top 5% of CEOs in Boston. Comparatively, employees at Western Union rank Devin McGranahan in the Bottom 30% of CEOs in Denver. Employees rate their CEO differently based on the frequency of interaction, ability to affect company culture, and drive measurable results.

CEO of Flywire
BIO: As CEO of Flywire, Mike Massaro’s responsibilities include aligning the international team with the company’s strategic direction and increasing the visibility of Flywire globally. He brings to Flywire more than fifteen years of extensive experience in solution engineering, sales, and marketing and is noted for his ability to leverage technology to create solutions to gaps in existing consumer and business transactional experiences. Mike’s background spans global payments, mobile software and hardware, and e-billing at high growth technology companies, including Carrier IQ and edocs, Inc. Since assuming the role of CEO in 2014, Mike has grown the business from concept phase to a stable, growing global company. He has overseen the company’s expansion in North America, Europe, and the Asia-Pacific regions. Mike began his career as part of the technical risk services practice at PricewaterhouseCoopers, LLP and has a Bachelor of Science degree in Management Information Systems from Babson College.

CEO of Western Union
BIO: Devin McGranahan is President, Chief Executive Officer, and Director of The Western Union Company, a global leader in cross-border, cross-currency money movement. After more than 25 years of business and leadership experience, McGranahan joined Western Union as its CEO in late 2021. Previously, he was Senior Group President, Global Business Solutions at Fiserv, Inc. In that role, McGranahan oversaw the company’s global merchant acquiring and processing businesses. During his tenure he was responsible for the launch of the Carat enterprise merchant omni-commerce platform, the development and launch of the Clover Connect integrated software vendor (ISV) platform, and the launch and acceleration of Clover Business Solutions, Fiserv’s digital-direct merchant platform. These capabilities propelled Clover to become the largest cloud-based SMB merchant platform in the market and grew the omni-channel business to over $1 billion in revenue. McGranahan previously spent 20+ years at McKinsey & Co., where he served as a Senior Partner, engaging with leading financial services companies on a broad range of strategy, payments, and business-building opportunities. McGranahan also held a variety of other senior management roles at the firm, including co-leading the North America Financial Services Practice and being a co-chair of the senior partner selection committee. McGranahan holds a Master of Business Administration from Harvard Business School, a Bachelor of Science in Mechanical Engineering from the University of Pennsylvania, and a Bachelor of Science in Economics from the Wharton School at the University of Pennsylvania.

Women at Flywire rated their CEO an A+

Women at Western Union rated their CEO a C-

Diverse Employees at Flywire rated their CEO an A+

Diverse Employees at Western Union rated their CEO a C-



At Flywire, employees in the Marketing department rate Mike Massaro the highest. According to employees, Mike Massaro's ability to drive business results is Excellent. At Western Union, the Operations department's employees rate their CEO highest. And, 40% of Western Union's employees approve of their CEO's management style.