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      Flywire

      Engaged Employer

      Flywire reviews

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      3.4

      57% would recommend to a friend

      (221 total reviews)
      avatar

      Mike Massaro

      70% approve of CEO

      48% positive business outlook

      Ratings by category

      3.8

      Work/Life balance

      3.7

      Diversity & inclusion

      3.4

      Culture & values

      3.4

      Compensation and benefits

      3.1

      Senior management

      3.1

      Career opportunities

      Flywire has an employee rating of 3.4 out of 5 stars, based on 221 company reviews on Glassdoor which indicates that most employees have a good working experience there. The Flywire employee rating is in line with the average (within 1 standard deviation) for employers within the Financial Services industry (3.7 stars).

      Ratings by demographic groups

      Reviews by job title

      221 reviews
      1.0
      Jul 25, 2025

      Management very misleading and dishonest

      Manager
      Recommend
      CEO approval
      Business Outlook

      Pros

      -Selling the dream of stock options and great healthcare but then....

      Cons

      Acquired our company after laying off 10% of their workforce and stated that their would be no layoffs related to the acquisition. Was asked repeatedly during the overview of the acquisition and clearly stated that no more layoffs would be forthcoming directly from the COO and SVP of Travel in our corporate office to the company. Then proceeded to layoff employees right before the cutover date. Wanted the customers and not the employees.

      avatar
      Flywire Response
      10mo
      Thank you for sharing your thoughts. We truly value all feedback. Our strategy for acquisitions is to grow and strengthen the combined company and teams, enabling us to deliver even greater value to our clients. We are proud of our consistently high multi-year employee retention rate, which reflects our commitment to our team and culture. While integrating companies can naturally involve difficult, strategic decisions to align our teams with evolving objectives and needs, and we recognize that this can mean changes for some individuals, these decisions are always made thoughtfully for the long-term success of the organization. We are truly grateful for the dedication and hard work of every individual who has been a part of our journey, and we are excited about the future of Flywire. We wish you all the best in your next professional endeavors. -Rob Orgel
      3.0
      Jan 21, 2025

      Good, not Great

      Anonymous employee
      Recommend
      CEO approval
      Business Outlook

      Pros

      -Great colleagues, some of the most talented individuals I've ever met -Plenty of opportunity to travel -Hybrid flexibility, not forced to go into the office -Generous PTO policy

      Cons

      Overall, Flywire is a decent place to work. However, several factors ultimately contributed to my decision to leave. The HR department—referred to internally as the "People Team"—has significant room for improvement. A considerable portion of employees, around 90%, have expressed concerns about the Chief People Officer, noting a culture of fear surrounding them. Despite the Executive Team being aware of this, no meaningful action has been taken to address the issue. Additionally, I found the People Team to be largely difficult to connect with. Upon my departure, I encountered several problems, including the premature cancellation of my benefits, which were supposed to remain active until the end of the month. Resolving this issue required three weeks of persistent follow-ups, which was frustrating and disheartening. After years of enjoying my time at the company, it was disappointing to experience such challenges at the end of my journey with Flywire.

      avatar
      Flywire Response
      1y
      Appreciate you taking time to provide feedback, as always we welcome it, work to learn from it. Few comments based on your specific feedback: (1) Ensuring we have a great off-boarding process for FlyMates is important, it sounds like your experience was not great and that does not meet our expectations...will work to figure out why and improve. (2) In relation to your comments on our annual FlyOver survey, we are constantly working to review feedback and take action. I realize it can be frustrating if you may not see the direct actions being taken as the company has grown, but it is important to know it is happening. Ultimately, building a global technology company is never easy, it is a complex/difficult Journey, but I do want to thank you for your contributions and wish you all the best. As always, please feel free to reach out directly to me with any additional feedback. ~ M. Mike Massaro CEO @ Flywire
      1.0
      Feb 26, 2025

      Terrible Sr Management

      Anonymous employee
      Recommend
      CEO approval
      Business Outlook

      Pros

      International with over ten countries

      Cons

      Flywire is run by two people: Mike Massaro (CEO) and Rob Orgel (President). They have way too much power and are the source of constant bottlenecks which lead to a stale and non performative culture.

      avatar
      Flywire Response
      1y
      Appreciate you sharing your thoughts on this. At Flywire, we encourage our leaders to trust their teams to own their work and run with new and different ideas. While leaders and management ultimately make the final call on big decisions, we work hard to set up our teams to move quickly without getting stuck waiting for approvals. We want FlyMates to try new things, even if they don't always work out - that's how we learn and get better. We're always looking for ways to cut through red tape and work faster and more efficiently together as a global team. If something's holding you back or you see room for improvement, please talk to us directly. Your perspective matters, and we genuinely want to hear how we can make things better. -The People Team
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      Glassdoor has 259 Flywire reviews submitted anonymously by Flywire employees. Read employee reviews and ratings on Glassdoor to decide if Flywire is right for you.