I was CEO of Flywire for a day. This is what I learned.

Recently, Flywire held an auction during “Spring cleaning” season for veteran FlyMates to go through their gently used Flywire branded gear that may be better utilized or appreciated by other FlyMates. After work one day, a group of FlyMates held a live auction where employees could bid on items and proceeds would be donated to the FlywireForGood initiative which sits under the Flywire Charitable Foundation.

As part of this, our CEO Mike Massaro came up with the idea of auctioning off an experience: be the CEO for the day! The winning bidder could join every meeting Mike has that day, have a 1:1 lunch in Boston, and dinner after work with a group of FlyMates.

Anne-Sophie Kadjo, a Sales & Operations Associate on our travel team, had the winning bid! We caught up with Anne-Sophie to hear more about what this unique experience was like tagging along for a day with Flywire’s CEO, Mike Massaro.

What made you want to bid on this “CEO for the day” experience?

Sitting in the Boston office for my third time, I was wondering which swag I was going to bid on during the Flywire Swag Auction. I was considering a hat or maybe a T-shirt that was gifted to FlyMates before I joined in November 2020. I was still indecisive when I heard other FlyMates announce that they were also offering experiences as part of the auction. The first one they proposed was becoming the “CEO for the day.” I was intrigued. What does the day of a CEO truly look like? Who does Mike interact with day-to-day? What types of questions is he expected to have the answer to?

I decided to find the answer to my questions and bid on the “CEO for the day” experience. Luckily, I had the winning bid! Beyond answering my questions, I was hoping that this experience would allow me to learn more about Flywire as a new FlyMate and learn from Mike.

What was the most surprising part of your day with the CEO? What was your favorite part of the day?

One question that I had set out to answer was “who does Mike interact with day-to-day?” I was surprised to see how many FlyMates from different teams, countries and in different roles Mike interacts with in a single day.

To name a few, we started the day discussing an initiative that the Education team is working on with FlyMates from the Global Payments, Agents, Marketing and Product teams from the US, Australia, India and more. We discussed data culture at Flywire with the Data Analytics Team. I also sat in on a market research interview with the B2B team and even had the opportunity to join external meetings on various topics.

It was a full day of global collaboration! Interacting with FlyMates I do not directly collaborate with on a day-to-day basis in my role, Mike included, was definitely the highlight of my day!

Can you share something new that you learned from this experience?

As a recent graduate, I had previously only been in the interviewee seat during interviews. As part of the meetings I attended with Mike, I had the opportunity to sit in on an interview. For the first time, I was among the ones on the other side of the conversation.

Before the start of the interview, Mike shared with me more details on his interview process. I learned how he makes sure the candidate is comfortable by letting them know exactly what to expect during the interview and encouraging them to ask any questions. We also talked about how to pay attention and derive insights from how a candidate introduces themselves, from the experiences they decide to highlight to the words they choose.

During the interview, I got to see the theory put in practice. The interview flowed naturally like a conversation, yet every point discussed earlier was covered. After the interview, we got time to debrief. I hope to use these lessons to be helpful with interviews in the future as we grow the travel team.

Anything else you would like to share?

Another great part of my day was seeing how much FlyMates played into the “CEO for the day” concept. I heard great jokes and it was fun to pretend to be the CEO as FlyMates asked me for my final thoughts after a meeting. Sadly… I did not get a chance to review any of the requests for promotions.

I enjoyed ending the day spending time with FlyMates at dinner after work. Thank you for being part of my day. I would like to thank Mike for his time and choosing a day with so many interesting meetings. Finally, I would like to thank our FlyMates for organizing the Flywire Swag Auction. I am glad to see how much money we raised for the Flywire Foundation!