


Employees at Flywire rank Mike Massaro in the Top 5% of CEOs in Boston. Comparatively, employees at TransferWise rank Kristo Kaarmann in the Bottom 15% of similar sized companies. 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 TransferWise
BIO: Kristo lived and breathed the world of finance from the inside. At PwC and Deloitte, he helped banks and insurers bring their processes and systems into the 21st century. But stunned by the inefficiency of financial institutions, he wanted to do more. At TransferWise, he is in charge of all operations activities, technology, development, compliance and regulatory issues.

Women at Flywire rated their CEO an A+

Women at TransferWise rated their CEO a C-

Diverse Employees at Flywire rated their CEO an A+

Diverse Employees at TransferWise rated their CEO a F


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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.

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