The CEO of a $700 million startup explains why he's ditched the normal rules of hiring by leaving candidates with his assistant and taking them on team lunches

Mike Massaro Flywire CEO

  • Flywire is a Boston-based payments company which has
    raised more than $143 million in VC funding.
  • The company makes international payments across
    healthcare and education simpler and recently raised $100 million
    to give it a valuation of around $700 million, according to
  • CEO Mike Massaro claims that changing his hiring
    approach has helped bring in better talent to the

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Hiring the best staff is one of the toughest parts of running a
succesful business. Getting the right people with the best culture
fit is a major cause of stress for founders. 

Beyond asking a set of generic questions to get responses, how
do you get people who are the right culture fit for your company,
particularly at an executive level?

Mike Massaro, CEO of Boston-based payments company Flywire, has
his own way of dong things. “When I’m looking at working with an
investor or trying to hire an executive I have a set of little
tricks and tests I like to employ,” he told Business Insider in an

“Such as, how do they treat the wait staff if you’re at a
dinner? Sometimes, I leave prospective candidates alone with my
assistant in the meeting room and say i’m going to be late to see
how they react to that and interact with her in that period.”

For Massaro, it’s important to ensure that potential staff
behave as they would in a professional environment at that time.
Unsurprisingly, a head of sales will probably sell themselves well
at interview, but how do they interact with other staff

“Sometimes in the middle of a four hour interview session, I’ll
say we’re having lunch with the team and then watch them to see
whether they go first or last in line, whether they speak to people
and interact with staff,” Massaro added. “It’s important that you
have a culture fit.”

Massaro told Business Insider that his approach has helped hire
team members who have been instrumental to the company’s recent

Flywire was founded in 2009 by Spanish entrepreneur Iker
Marcaide, and was originally called peerTransfer. Massaro took over
in 2013. The company handles billions in payments each year, having
provided software to universities and healthcare providers to
aggregate their payments processes.

While Massaro declined to give details on the firm’s valuation,
data-firm PitchBook has
said that the company secured $100 million in funding earlier this
year to be valued at approximately $700 million with around $143
million in total financing.

This need for culture fit extends to getting the right investors
on board too, according to Massaro. “It helps when boards
understand the business because you need those people to be there
when things are going wrong, not going well, and it’s the same with
investors,” he said. 

CEO has a pitch-deck slide titled ‘Why you shouldn’t invest in us’
that he says was a key draw for $140 million in VC

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Source: FS – All Tech News
The CEO of a 0 million startup explains why he's ditched the normal rules of hiring by leaving candidates with his assistant and taking them on team lunches