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Distinguished Alumnus

Mike Massaro ’96 P’23 ’25 ’28, CEO of Flywire

Each year, St. John's Prep proudly recognizes an alumnus whose life personifies the spirit and values of the Xaverian Brothers and the extraordinary commitment of our faculty and staff. In all endeavors, this individual models for fellow alumni what it means to be a Prep graduate and inspires current students to be change makers and forces for good in the world.

In keeping with a tradition that's now in its fourth decade, St. John's Prep is proud to recognize Mike Massaro ’96 P’23 ’25 ’28 as the School's Distinguished Alumnus for the 2023-24 academic year. Mike serves as CEO of Flywire, a global payments enablement and software company supporting the global education, healthcare, travel, and b2b industries. The Distinguished Alumnus award honors a St. John's graduate whose life exemplifies the spirit and values of the Xaverian Brothers and inspires current students to be change-makers and forces for good in the world.

Five years ago, Flywire was a private Fintech company. As CEO, Mike oversaw 300 employees (aka FlyMates) for the global payments-enablement and software firm, which at that time boasted 2,000 global clients and supported 100-plus local currencies across 220 countries and territories. Mike took the company public in 2021 (NASDAQ-FLYW) with a mission to successfully and seamlessly deliver the world’s most important and complex payments. Today, Flywire has grown to employ more than 1,200 FlyMates, with 3,700-plus global clients, and supports 140-plus local currencies across 240 countries and territories.

“Public market investors want to talk about revenue and growth and profitability, but scaling a company is an art as much as it is science and math,” says Massaro. “That’s the people side of it. You can have the numbers, but if you don't have the other stuff, at some point, it’s going to break. Sometimes, you have to be willing to do something that the numbers don’t indicate is the right answer. Because there’s some other data point, some other kind of art that you see something in a person that makes you think they deserve an opportunity.”

The tempo Massaro is setting and the level of disruption and innovation he’s churning through is noteworthy given that it’s happening in the intensely regulated financial services industry within a payments business moving tens of billions of dollars every quarter. We’re talking high stakes. Yet, Massaro doesn’t fit the mold of the archetypal play-caller so often sought after by investors: transgressive, breakneck, iconoclastic.

“That’s very different from the way Mike’s built,” says Matt Harris, a partner at Bain Capital Ventures and a board member at Flywire. “He is fundamentally a measure twice, cut once type of person. But even with great care as a foundational value, he’s somehow retained a commitment to constant reinvention, challenging the organization to keep growing at a high pace even if it means doing things very differently tomorrow than they did them yesterday.”

Mike is focused on people, and the authenticity he brings to his role as a CEO resonates deeply with St. John’s commitment to build healthy, positive, and enduring personal relationships within our community and beyond. Sharon Butler, Flywire’s Executive VP of Global Education, stresses the fact Massaro excels at the soft skills that drive human relations.

“Mike brings people together, he builds a lot of confidence around the business, he’s super accountable, and displays tons of humility,” she says. “To me, the core of Mike is his integrity. It’s very unusual to be business-minded and analytical, but remain well-balanced and possess the emotional intelligence to understand that to lead a great company, you need people that feel fulfilled and happy.”

Mike's commitment to modeling servant leadership as Flywire’s CEO is also laudable. The company is heavily invested in a charity called School The World, an international nonprofit solving extreme poverty through the power of education.

“As we were gearing up to go public, everybody said our culture would change,” he says. “If you’re not careful, all you talk about is the financial results, where we need to go, and how to get there. That starts to overshadow some of the other things that we’ve always held really important, including being a company that impacts its community. In that regard, we’ve really focused on the areas in which we work: education and healthcare from a global perspective.”

The Prep’s Distinguished Alumnus Award was established in 1993 to celebrate individuals who demonstrate a commitment to faith, family, and service; who have achieved professional success; and who have made significant contributions to society as volunteers, mentors, or benefactors. Mike Massaro joins an impressive group of change-makers and forces for good in the world who have earned the honor. Please join us in celebrating Mike’s extraordinary leadership and service to humanity as we congratulate him on this honor as our 2023-24 St. John’s Prep Distinguished Alumnus.

“Public market investors want to talk about revenue and growth and profitability, but scaling a company is an art as much as it is science and math,” says Massaro. “That’s the people side of it. You can have the numbers, but if you don't have the other stuff, at some point, it’s going to break. Sometimes, you have to be willing to do something that the numbers don’t indicate is the right answer. Because there’s some other data point, some other kind of art that you see something in a person that makes you think they deserve an opportunity.”Mike Massaro '96 P'23 '25 '28

Established in 1993, the Distinguished Alumnus Award, allows the St. John's Prep community to present a living example of faith, brotherhood, and wisdom to our students. We continually strive for excellence in all that we do, and our Distinguished Alumnus is someone who has achieved professional success; has shown a commitment to lifelong learning; pursues enduring personal relationships; and serves as a model for servant leadership in the Catholic, Xaverian tradition.

Distinguished Alumni

St. John's graduates are leaders in every field, from medicine and education to religious life, sports, business, technology, the military and many more.

We are proud to recognize our distinguished alumni with an award presented annually to a graduate whose life personifies the spirit and values St. John's seeks to instill in students. St. John's established the Distinguished Alumnus Award in 1993 to honor individuals who demonstrate a commitment to faith, family and service; who have achieved professional success; and who have made significant contributions to society as volunteers, mentors or benefactors. We proudly list the recipient of the Distinguished Alumnus Award by the year in which they were honored:

  • 2024: Mike Massaro ’96 P’23 ’25 ’28, CEO of Flywire
  • 2023: Mike Niconchuk ’07, Program Director for Trauma & Violent Conflict (TVC) at Beyond Conflict 
  • 2022: Maj. Gen. Thomas H. Needham '60, retired U.S. Army General 
  • 2021: Art W. Coviello '71, Technology Investor and Advisor; Former CEO of RSA Security 
  • 2020: Paul F. Niehaus, Ph.D. '00, Co-Founder of GiveDirectly and Segovia; Associate Professor at University of California in San Diego
  • 2019: Thomas J. DeSimone '68, Executive Vice President and Member of the Executive Committee, WS Development
  • 2018: John Peter Frates III '03*, ALS Activist
  • 2017: Bishop Robert Reed '77, Auxiliary Bishop of Boston and President/CEO of the CatholicTV Network
  • 2016: Mike Kennealy '86, Secretary of Housing and Economic Development for the Commonwealth of Massachusetts
  • 2015: John A. Driscoll '90*, Educator
  • 2014: David E. Monahan, MD '62, Physician, Chula Vista, California
  • 2013: Bill O'Brien '88, Offensive Coordinator and Quarterbacks Coach, University of Alabama
  • 2012: Thomas W. Haas '74, Pilot, Flight Instructor, Trustee of Aircraft Owners and Pilots Association
  • 2011: Jude A. Curtis '77, Chief Ethics and Compliance Officer, PriceWaterhouseCoopers, LLP
  • 2010: John L. Dunlop '84, Program Officer, United States Agency for International Development
  • 2009: Samuel T. Byrne '83, Managing Partner and Co-Founder, CrossHarbor Capital Partners
  • 2008: The Rev. Gerard Dorgan '50*, Pastor, St. Mary of the Annunciation Church in Danvers
  • 2007: Peter R. Dolan '74, Board Chairman Tufts University, Allied Minds PLC, ChildObesity180
  • 2006: The Rev. Leo B. Shea, M.M. '56, Director of Development, Maryknoll Fathers and Brothers
  • 2005: The Rev. James J. Ronan '62, Pastor of Saint Catherine of Siena and Saint Mary's Parishes, Charlestown, Massachusetts. Founder, Rostro de Cristo, Duran, Ecuador
  • 2004: John C. Archer '68, President and CEO, Archer Insurance Agency, Inc.
  • 2003: David W. Ives '75, Vice Chairman and CEO, Northshore International Insurance Services, Inc.
  • 2002: Richard Iorio '77, Chief, Adult Reconstruction and Total Joint Arthroplasty Service, Brigham and Women's Hospital
  • 2001: James M. Sears '81, Attorney, Sears & Sears
  • 2000: Joseph R. Levis '60, Chief Executive Officer, Crusader Paper Company
  • 1999: James C. Zampell '71, President, Zampell Companies
  • 1998: John J. Studzinski '74, Managing Director and Vice Chairman, Pimco
  • 1997: David B. Perini '55, Retired Commissioner, Commonwealth of Massachusetts Division of Capital Asset Management
  • 1996: Brother James M. Boyle, CFX '48*, Retired Superior General, Xaverian Brothers
  • 1995: Joseph A. Milano '62, President, Union Oyster House and Honorary Consul General Thailand
  • 1994: Paul L. Hennessey '52*, Retired Partner, Boston Partners Asset Management
  • 1993: Thomas M. Leonard '54*, President, Essex National Heritage Commission

*Denotes deceased