Flywire
What's It Like to Work at Flywire?
Frequently Asked Questions
Flywire supports employee job satisfaction by giving employees the opportunity to solve complex global payment challenges while investing heavily in learning, collaboration, inclusion and long-term career development. Employees work on technology that helps organizations across education, healthcare, travel and B2B industries simplify high-value, cross-border payments in more than 240 countries and territories, connecting their work to meaningful outcomes for clients around the world. The company's culture is guided by six core values—Global Collaboration, Authenticity, Fulfillment, Execution, Ambitious Innovation and Evolved Learning—which shape hiring, performance and day-to-day decision-making.
- Mission-driven work with global impact: Flywire gives employees the opportunity to build software that solves complex international payment challenges at scale. Its global payments platform supports thousands of clients across education, healthcare, travel and B2B, enabling secure payments in more than 140 currencies and serving customers in over 240 countries and territories. Employees can see how their work helps institutions improve payment experiences while reducing administrative complexity for organizations and consumers worldwide.
- A culture built around ownership, collaboration and continuous learning: Flywire intentionally reinforces behaviors that encourage employees to collaborate across regions, take smart risks, share feedback and continuously improve. The company emphasizes learning as an ongoing process, encouraging employees to question, challenge and develop new skills throughout their careers. Employees reflect this culture, with one employee describing Flywire as having a "collaborative supportive environment," while another highlighted its "strong cultural values" and "lots of potential."
- Growth, development and employee support: Flywire invests in employee development through structured onboarding, internal mobility, leadership opportunities and continuous learning. Employees have access to professional development resources, mentorship opportunities and a culture that encourages growth as the company expands globally. Flywire also supports employees through comprehensive benefits that include medical, dental and vision coverage, retirement savings plans where applicable, paid parental leave, generous paid time off, employee assistance programs, wellness initiatives and programs that promote belonging through employee resource groups including Women of Flywire, Flywire Pride, FlyBLACK, API at Flywire, LatinX and Flywire Globals.
- External signals:
- Great Place To Work recognition: 95% of employees say Flywire is a great place to work, significantly above the typical U.S. company benchmark. (Great Place To Work)
- Strong workplace trust: 97% of employees say management is honest and ethical in its business practices, while 97% say people care about one another and 97% say they felt welcomed when joining the company. (Great Place To Work)
- National workplace recognition: Flywire was named one of the Fortune Best Workplaces in Financial Services & Insurance, recognizing its employee experience and workplace culture. (Great Place To Work/Fortune)
Bottom line: Flywire supports employee job satisfaction by combining meaningful global work with a collaborative, values-driven culture that encourages ownership, continuous learning and innovation. Employees also benefit from strong development opportunities, comprehensive wellbeing programs and an inclusive workplace designed to help people grow professionally while making an impact across global payments.
Many employees recommend Flywire because it offers the opportunity to work on meaningful global payment technology while fostering a culture centered on collaboration, learning and employee growth. As Flywire continues expanding its global payments platform across education, healthcare, travel and B2B, employees have opportunities to work on large-scale international products alongside colleagues from around the world. The company's emphasis on transparent leadership, continuous learning and strong cultural values helps create an environment where employees can build long-term careers while contributing to a fast-growing global business.
- Employees highlight the people and culture: Employees emphasize Flywire's collaborative environment and supportive colleagues. The company's values encourage employees to share ideas openly, work across teams and help one another succeed regardless of location or role. Employees similarly describe Flywire as a "great place to work" with a "collaborative supportive environment," while another employee highlighted the company's "good people, strong cultural values" and significant future potential.
- Opportunities to grow with an expanding global fintech: Flywire continues investing in new products, international expansion and strategic acquisitions, giving employees opportunities to work on evolving technologies and increasingly complex payment solutions. The company's focus on innovation, global collaboration and continuous learning creates opportunities for employees across engineering, product, customer success, operations and corporate functions to broaden their experience as the business grows.
- Leadership reinforces culture and employee development: Flywire's leadership emphasizes maintaining a strong culture as the company scales globally. Through clearly defined values, regular communication and an expectation that leaders remain accessible and invested in their teams, employees are encouraged to take ownership, contribute ideas and continue developing professionally.
- External signals:
- Employee recommendation: A majority of surveyed employees would recommend Flywire to a friend as a place to work. (Glassdoor)
- CEO approval: A majority of employees approve of CEO Mike Massaro, reflecting positive confidence in the company's leadership. (Glassdoor)
- Exceptional employee experience: 95% of employees say Flywire is a great place to work, while 96% say management trusts employees to do a good job without excessive oversight. (Great Place To Work)
- Inclusive workplace recognition: Great Place To Work employee surveys also found that 97% of employees say people care about each other and management acts ethically, reinforcing Flywire's reputation as a supportive workplace. (Great Place To Work)
Bottom line: Many employees recommend Flywire because it combines meaningful work in global payments with a collaborative, values-driven culture that encourages ownership, continuous learning and professional growth. Supported by strong employee feedback and national workplace recognition, Flywire has built a reputation as a company where employees can develop rewarding careers while helping modernize payments around the world.
Flywire's Candidate Tradeoffs
If you’re weighing whether Flywire is the right fit, these are the core tradeoffs to consider.
- Flywire emphasizes accessible, engaged managers who provide regular support and alignment, though that often includes more frequent check-ins and active collaboration.
Flywire Employee Perspectives
Employees describe Flywire as a place where ambitious professionals can build meaningful careers without losing sight of what matters most outside of work. They say the company's growth has created opportunities to achieve significant career milestones while supporting employees through different stages of life.
“My proudest moment as a woman? Picture this: May 26, 2021, the day Flywire went public. Back in 2010, I left a great job to start this venture, juggling it all with two young boys. With my husband's rock-solid support, we faced the challenges head-on.
Standing on the NASDAQ stage, celebrating success, and realizing it was also my youngest son's 17th birthday. Tears welled up — a mix of joy and remembering the tough journey. Surrounded by my family, I felt an incredible sense of pride. It wasn't just about business success; it was about proving that with determination, you can balance a thriving career and a happy family. That moment was about us – the journey we conquered together.”
Flywire Employee Reviews
Flywire's Benefits
Encourages autonomy and ownership from employees
Managers give public shoutouts and celebrate employee milestones
Managers offer consistent feedback loops
Provides resources to build team camaraderie
Encourages lateral mobility to expand skills and impact
Posts new positions internally and encourages employees to apply
Promote from within
Provides customized development tracks
Defined values and mission statements
Implements team-based strategic planning
Leadership is transparent and communicative
Mistakes are treated as learning opportunities
Open office floor plan to encourage communication and collaboration
Prioritizes mission-driven work in decision-making processes
Uses an OKR operational model to clearly define goals and priorities
Utilizes an open door policy that encourages accessibility
Established expectations for communication between time zones
Offers a remote work program
Provides work from home flexibility
Utilizes a flexible work schedule
Flywire provides employees with a flexible work schedule that includes Flexible start and end times.
