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Distinguished Alum Mike Massaro '96 Masters ‘Teacher for a Day' Role at St. John's Prep

Distinguished Alum Mike Massaro '96 Masters ‘Teacher for a Day' Role at St. John's Prep

FinTech CEO’s immersion with student body zeros in on humility, teamwork, and faith as personal and professional ‘must-haves’

Photos from the Day

Mike Massaro ’96 P’23 ’25 ’28 spends his workweeks in sitdowns with C-Suite execs, conjuring operational efficiencies, and traveling the globe on BizOps/Biz Dev assignments—all while navigating the delicate realities of shareholders’ sensibilities. Throughout this past week’s visit to the Prep campus as the School’s 32nd Distinguished Alumnus, the CEO of Flywire artfully adjusted his technique to command the attention of sixth graders and seniors, alike. At a ceremony honoring Massaro that evening, a retired St. John’s faculty member offered a reason why Massaro, her former student, could captivate a classroom as well as he does a boardroom: “He’s comfortable in his own skin and he’s got a very big heart—and he was just like that as a teenager.”

Massaro was so relatable, in fact, that during three extended sessions with different student audiences throughout the day, he served as a genuine sounding board as opposed to a speaker at a lectern. Students kept him busy, peppering him with sophisticated questions about the social-emotional challenges of failure, pressure, doubt, starting over, and personal fulfillment. Just as often, he was asked to weigh in on nuanced entrepreneurial pinch-points like M&A, selling a company, cultivating investors, loss-making startups, facing headwinds, and how to stay outcome-oriented. 

Taken together, the lively exchange of ideas between Massaro and students of all ages coalesced into a doctrine of sorts. Intentional or not, the man who took over at Flywire in a period of uncertainty for the company and grew it into a $3 billion publicly traded company, sketched the broad strokes of a professional playbook that prioritizes faith, wellness, and enough individual stick-to-itiveness to overcome the inevitable “evolution of failure” that’s built in to the pursuit of excellence.


Massaro’s morning gathering with grades 7 and 8 in Kaneb Auditorium was part TED Talk, part fireside chat. The format and the level of student engagement allowed him to explore a number of themes and topics beyond a superficial treatment. In addressing the notion of professional pressure, he urged students to accept their limitations, to consider the individual demands they face in a broader human context, and to understand that how they measure up to challenges doesn’t define them.

“You’re not supposed to be great at everything,” he said. “I probably make a hundred decisions a day at my job. I don’t make good decisions every time. And so, first you have to be willing to say you’re going to make mistakes, right? The question is: What do you do about it? What do you learn from it? How do you do it better the next time? You’ve got to be comfortable with that dynamic, first and foremost.”

Massaro added that coping with pressure is a two-part equation in his view. Aside from accepting inevitable missteps, you have to find a way to offload pressure, which he believes is part and parcel of achieving fulfillment.

“For me, I have a strong faith and trust in a power greater than myself,” he said. “I think for me, that’s an important part. The world’s tricky. You can’t solve all the problems. And so if you’re trying to put that pressure on yourself to do it, you’ve just got to accept you’ll do the best you can. As a CEO, I’ve faced countless decisions, many impacting the livelihoods of my colleagues. It was an impossible burden for me to handle without my faith, which I was fortunate to be introduced to early in my life by my parents, and it was reinforced at St. John’s.”

Boston-based Flywire is a worldwide payments enablement and software company supporting the global education, healthcare, travel, and b2b industries. Massaro, who is the father of a Prep grad, two current students, and another entering sixth grade this fall, often returned to the vital role that team-building plays in professional success, including surrounding oneself with people ‘who are great at what you’re not great at,’ then openly, reciprocally, and creatively collaborating with them.

“Mike focuses on his integrity and his ability to both connect with and care about people,” said Head of School Ed Hardiman. P’19, ’21, ’26. “Whether or not he knew it from the start of his tenure as a CEO, he’s modeling the Xaverian values of humility, trust, zeal, compassion, and simplicity. He’s on the sidelines at his son’s sporting events, in attendance at academic ceremonies, in the drop-off line in the morning, and supporting his wife Meredith in all her endeavors as they lovingly model an incredible partnership and a tremendous family.” 


In the course of Massaro’s day on campus, multiple students asked him about achieving “work-life balance.” Interestingly, he pushed back on the validity of the concept. 

The FinTech exec sees the tension between personal and professional contentment as analogous to a flowing river. Massaro believes striving for a state of balance is a misguided endeavor. Rather, we should embrace the reality that different currents and tributaries of our work and life flow with different intensities at different times, and we must understand that we have some ability to modulate and influence the flow rates.

“I’m actually a big believer in fulfillment versus balance,” he said. “Striving for ‘balance’ assumes dynamics are equal, and that’s not necessarily the case. Plus, people have different needs to be fulfilled personally and professionally. I think finding that definition of what fulfills you is the tricky part because nobody can define that for you. The other thing that we try to remind our team about is that as you grow and change, what you need to be fulfilled is different.

“Sometimes for me, certain times of the year, I’ll have professional ‘out-balancing’ personal commitments, but to me that’s okay because for your whole life, personal stuff and work stuff are going to get mashed together,” he added. “Everybody wants to segment it and have this line between it. It isn’t that way. It’s just your life. To me, that’s more of a fluid experience, almost a moving river. The important part is to know yourself enough to figure out what you need and how to get back on track if you’re not getting enough of one or the other. It’s a constant learning exercise, and knowing that leads to greater fulfillment.” 


Massaro’s final student session of the day involved him rotating among small groups of high school students who were assigned C-Suite roles in solving a real-life business problem within a 40-minute timetable. The exercise, dubbed ‘A Masterclass,’ was designed by Computer Science teacher Lisa Standring and Shaw Family Director for Innovation and Design Claudia Wessner of the School’s Center for Mission and Research. 

Two themes emerged. First, it’s not practical or productive to second-guess or have remorse over the choice you didn’t make. Secondly, any job you take on ultimately has an end date.

“What I realized early on as a CEO is that if at a certain point I’m not the best person to do this thing, that’s okay,” he explained. “The Board will find someone else that will do it. But if I’m believed to be the best CEO to run the company today, then great. I’ll do the best I can in that role. But that doesn’t define me. I’m just trying to do the best I can with the information I’m given, and there’s a lot that’s outside of my control. I think having something other than putting all that pressure on yourself and having either trust or faith in something greater than yourself—I think that helps.”

Faith was also something he brought to the fore during his Distinguished Alumnus acceptance speech that evening.

“Faith is such a powerful gift. There are many great lessons I took away from my time at St. John’s which have had a significant impact on my personal and professional life. I’m deeply proud of this campus and (the people who help it) foster an environment that encourages young men to strive for excellence in their work while also ensuring they realize that faith, lifelong learning, community, and compassion are key ingredients to helping them achieve great things and becoming a force for good in the world.”