Executive Leadership

Michael Massaro has served as our Chief Executive Officer and a member of our board of directors since December 2013.  A passionate leader deeply committed to enhancing the value Flywire provides to its employees, clients, payers, partners, shareholders and more, Mike has led the growth of the business from a concept into a world-leading payments enablement and software company. He has overseen Flywire’s expansion into new regions while aligning Flywire’s global team with the company’s strategic direction, including the company's Initial Public Offering (IPO) in May of 2021 and multiple strategic and value-enhancing acquisitions. His background spans global payments, mobile software and hardware, and e-billing at high-growth technology companies, including Carrier IQ and edocs, Inc.

Mike has been named Entrepreneur of the Year by Ernst & Young, one of the 100 Most Intriguing Entrepreneurs by Goldman Sachs, and a CEO of the Year by Comparably, among other distinctions. Under his leadership, Flywire has been rated one of the World’s Top FinTech companies by CNBC, voted a Most Loved Workplace and been named a top place to work by the U.S. News & World Report, Fortune, INC and more.  He earned his Bachelor of Science degree in Management Information Systems from Babson College.

Rob Orgel has served as our President and Chief Operating Officer since November 2019. Mr. Orgel leads Flywire’s global payment network, business operations, finance, legal, compliance, and corporate strategy functions. He brings extensive experience with 20 years in the technology/payments ecosystem to Flywire, including hands-on experience in legal, compliance, finance, go-to-market, business development and global operations. Prior to Flywire, Mr. Orgel served in various roles at Apple Inc. from 2010 to 2019 where he was part of the leadership team that developed, launched and grew the Apple Pay business and global expansion as well as the launch of the Apple Card. Prior to his time at Apple Inc., Mr. Orgel served as Chief Operating Officer at Quattro Wireless, Inc. from 2008 until it was acquired by Apple Inc. in 2010. Mr. Orgel has also played key leadership roles at m-Qube, Inc., a carrier billing and payment platform which was acquired by Verisign Inc., and edocs Inc., an e-billing and payment solution which was acquired by Siebel Systems (subsequently acquired by Oracle Corporation). Mr. Orgel holds Bachelor of Arts and Master of Arts degrees in International Relations from Stanford University and a Juris Doctor degree from Harvard Law School.

Cosmin Pitigoi has served as our Chief Financial Officer since March 2024.  Mr. Pitigoi has over 25 years of experience in finance leadership roles.  Prior to Flywire, Mr. Pitigoi was SVP of finance at PayPal, leading a global cross-functional team across FP&A, operational finance and pricing, along with serving on the board of directors at Paidy and the audit committee chair of the PayPal Giving Fund. Prior to PayPal, Mr. Pitigoi held leadership roles at eBay across investor relations, business unit FP&A and treasury.  He began his career in operational and finance roles at E*Trade and Barclays. He holds a B.Comm. from Stellenbosch University in South Africa and an M.B.A. from Santa Clara University.

Peter Butterfield has served as our General Counsel and Chief Compliance Officer since March 2015. Prior to joining Flywire, Mr. Butterfield held various senior management roles within Devonshire Investors, the private equity arm of Fidelity Investments, and its operating companies from 2001 to 2015. During that time, Mr. Butterfield lived and worked for over a decade in Tokyo and Singapore managing legal, risk, and compliance functions, and leading the ex-Japan APAC operations for KVH Co., Ltd. Mr. Butterfield holds a Bachelor of Arts in History and Government from Bowdoin College and a Juris Doctor degree from Columbia University.

David King has served as our Chief Technology Officer since June 2019 and is responsible for oversight of our global technology and solutions development. Mr. King joined Flywire as its Vice President of Engineering in January 2018, following our acquisition of OnPlan Holdings where he was a co-founder and leveraged his background in payments, analytics and billing to develop innovative payment plan solutions for the healthcare and education sectors. Before co-founding OnPlan in May 2014, Mr. King founded other companies including infiNET Solutions, Inc., which delivered SaaS solutions to higher education and was subsequently acquired by Nelnet, Inc. in 2006. Mr. King served as president of Nelnet’s higher education division and led its transformation to become an online medical education program. He also led data security at Nelnet. Mr. King holds a Bachelor of Science in Mathematics and Physics from Westminster College, and a Master of Science in Physics from Miami University.

Sharon Butler has served as our Executive Vice President of Global Education since May 2016 Prior to serving as our Executive Vice President of Global Education, Ms. Butler served as our Vice President of Global Sales from June 2014 to May 2015 and as our Global Sales Director from December 2010 to June 2014. Ms. Butler has a degree in Communications with a minor in Business from Bridgewater State University.

John Talaga has served as our Executive Vice President of Healthcare since January 2018, following our acquisition of OnPlan Holdings where he was a co-founder and leveraged his background in payments, analytics and billing to develop innovative payment plan solutions for the healthcare and education sectors. Before co-founding OnPlan in May 2014, Mr. Talaga led the healthcare vertical for doxo inc., a multi-biller payment network. Mr. Talaga co-founded HealthCom Partners in 2001, which launched healthcare billing online account management solutions. After HealthCom sold to McKesson (to form RelayHealth, Mr. Talaga led the patient billing and payment business at RelayHealth for five years before joining doxo in 2011. Mr. Talaga holds a Bachelor’s degree from the University of Dayton.