Two Flywire employees became CEO for the day. Find out what they learned.

Have you ever wondered what’s it like to be Flywire’s CEO Mike Massaro for the day? Two of our FlyMates were able to find out by spending a whole day working alongside Mike! Amiel Howell, Cash Management & Treasury Senior Associate and Isadora Coelho, Payment Experience Specialist got to live a day in the life of Mike. They were able to join every meeting and eat lunch together in our Boston office.

We caught up with Amiel and Isadora to find out exactly what this experience was like for them.

What made you want to enter for the “CEO for the day” experience?

Amiel: I thought it would be an opportunity to experience Mike’s day. It would also allow me to learn more about Flywire and what goes on in the company beyond my scope in global payments.

Isadora Coehlo with Flywire CEO Mike Massaro
Isadora Coelho with Flywire CEO Mike Massaro

Isadora: When I saw the opportunity to enter to be “CEO for the Day”, I knew I wanted to throw my name into the ring. Seeing what a positive experience Anne-Sophie had previously, I was curious to see if Mike’s day-to-day would be similar to or different from when she was “CEO for the day” in 2021. To my surprise, I was selected to be one of the “CEO’s” and was excited to not only spend the day with Mike but also interact with other FlyMates I normally wouldn’t connect with on a regular basis.

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

Amiel: I knew that Mike was busy but- wow! It felt like he was constantly shuttling from one meeting to another. He thought quite quickly on his feet regarding every question or situation thrown at him. Generally, I need to stop and think before any calls or meetings and he simply did not.

Isadora: Going into the experience, I knew a little bit about what to expect but still had so many questions. When Mike showed me the agenda for the day, I knew it would be a long one. Our day specifically was packed with external meetings with a lot of different meetings. What truly surprised me was how quick and natural Mike had to switch up. Each meeting was so different from one another and it was impressive to see him cover so many different aspects of the business throughout the day with little to no time in between each meeting to essentially prep. After each meeting, we would talk about what was discussed and he ensured that I had all my questions answered. It was also interesting to see how Mike works and how he manages his workload and schedule.

What was your favorite part of the day?

Amiel: My favorite part of the day was listening to Mike discuss his thoughts on our EDU offsite and how he was able to quickly disseminate all of the information being thrown around in that meeting. Whereas I would only be able to quickly break down a few key points Mike had an entire page worth of notes and comments and was very easily able to break down everything he heard even though he is not involved in those actions on a day to day basis. It was really cool to see how he thought about things.

Isadora: I would say overall my favorite part of the day was being able to sit in conversations that I would likely never be able to participate first hand. I also really enjoyed learning more about Mike’s hobbies and passions!

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

Amiel: I have been at Flywire for almost 3 years now and I have seen so much change happen at this company and it was cool to see how those changes start from the top and filter down. I’m sure when I look back at this experience, I will see some more of these start to filter down.

Amiel Howell with Flywire CEO Mike Massaro
Amiel Howell with Flywire CEO Mike Massaro

Isadora: I ended the day understanding how the smallest decisions can ultimately impact the company and FlyMates as a whole. Decisions that wouldn't even occur to me that Mike would need to make. It was also so interesting to hear what non-FlyMates thought of Flywire and their understanding of what we do. It definitely provided a different perspective on Flywire.

Do you think we should do the CEO experience again for other FlyMates and why?

Amiel: Yes, I think it is wonderful for our FlyMates to get to spend a day with our C-level executives and learn from them. Just seeing how they communicate and break down loads of information into very transferable bits can be an invaluable lesson. I think the soft skills you can learn from this experience are extremely valuable and can allow you to really grow in your career.

Isadora: I definitely think other FlyMates should consider participating in this experience. Not only is it a chance to have 1 on 1 time with Mike, it allows you to be exposed to other aspects of the company you probably wouldn’t access on a day to day. It is also a good opportunity to network with other FlyMates and do something different!

Anything else you would like to share?

Amiel: I would just like to thank Mike, and all the other people I got to interact with. It was a pleasure. Also can we get some heat in Peter’s office?

Isadora: I was definitely nervous going into it at first. I remember thinking what we would talk about and who we would meet but seeing how excited Mike was to share what his day would look like, I knew it would be a great day. I would like to thank Mike for the opportunity to follow him around all day and learn so much in such a short amount of time and also my FlyMates who made the day even more special!

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