Mike Massaro became Flywire’s CEO in late 2013. He has more than fifteen years of extensive experience in solution engineering, sales, and marketing and leveraging technology to create solutions to address gaps in existing consumer and business transactional experiences. His background spans global payments, mobile software and hardware, and e-billing at high growth technology companies, including Carrier IQ and edocs, Inc.
Though Mike’s involvement with Flywire came a few years after the startup’s participation with MassChallenge in 2010, he has over the years become increasingly involved in the startup Accelerator, from being a mentor to a judge, to recently beocming a member of MassChallenge’s Board of Advisors.
We were able to catchup with Mike and get some great insights about how he thinks about startup ecosystems and why he has continuously increased his involvement with MassChallenge over the years.
How has your involvement with MassChallenge evolved over the years?
Personally, over the past 6+ years, I have been an active judge, mentor, guest speaker, and now advisory board member.
What’s led you to expand your involvement in MassChallenge?
I believe that the leadership team is evaluating and exploring so many important ways to improve and grow the program. As a leading tech player in Boston, we at Flywire have an opportunity to give back and help other entrepreneurs, while also growing a robust innovation ecosystem. It’s important to me to give back to the program and ecosystem that helped Flywire.
What has been valuable to you in your experience volunteering as a judge and mentor?
Once your startup begins to take off some, you start to realize how much of what you learned was during the journey, when you were exposed to new challenges and different relationships. So, in addition to wanting to give back to the community that helped me, I also wanted to stay up to speed on the types of companies that the ecosystem is creating. Being a mentor was a great fit for being able to both help and learn.
Do you think there’s an advantage, broadly speaking, to being involved in supporting MassChallenge?
There’s a level of participation within the business community that MassChallenge helps foster. The level of corporate engagement is very unique. There’s been relationships that I’ve built from being a mentor and being present at various events that I definitely wouldn’t have gotten without MassChallenge. And other accelerators or incubators, that I’ve seen, don’t seem to have that level of participation.
Why do you think a startup should join MassChallenge?
The ability to get mentorship and get connected to some of the top venture capital investors and large companies that support MassChallenge is huge benefit that can really make a difference for young startups.
When Flywire was in MassChallenge, the connections we made were critical to ensuring the company found the right balance of strategy and focused execution. This has been an important part of our success.
What do you think MassChallenge’s opportunities are in 2020 and beyond?
The ability to connect early-stage companies with large corporations looking to innovate and partner is a cornerstone of MassChallenge strategy in 2020 and beyond. This helps significantly differentiate it from other incubator-type programs and I believe it is the largest opportunity for MassChallenge going forward.
I think the approach MassChallenge has taken in collaborative efforts between startups and established businesses to solve complex and important problems is unique and exciting. One thing that happens with a lot of startups and tech companies in accelerators is that they are looking to find their first big deal, a big partner deal. But there are so many things that could go wrong in those conversations between big corporations and small startups that can derail the initial mission. MassChallenge’s efforts towards a more mutual and advanced structure has great potential.