Flywire
Flywire Leadership & Management
Frequently Asked Questions
Flywire's managers are expected to lead with transparency, trust and continuous coaching, creating an environment where employees feel empowered to take ownership while receiving the support they need to grow. Rather than relying on hierarchical decision-making, the company encourages managers to collaborate closely with their teams, provide regular feedback and remove obstacles so employees can focus on solving complex global payment challenges.
- Managers prioritize coaching and professional development: Flywire encourages managers to serve as coaches who help employees build new skills, expand their responsibilities and pursue long-term career goals. Through regular one-on-one conversations, performance discussions and ongoing feedback, managers work with employees to identify development opportunities while providing the autonomy to take on meaningful projects. Employees also have access to mentorship, leadership development resources, internal mobility opportunities and continuous learning programs that reinforce manager support throughout their careers. One employee shared that Flywire's leaders empower you to own your work while always being available when you need guidance, while another described managers as approachable and genuinely invested in employee success.
- Leadership emphasizes trust, ownership and collaboration: Flywire's managers are encouraged to trust employees to make decisions and contribute ideas regardless of title or location. Teams regularly collaborate across engineering, product, customer success, sales and operations, giving employees exposure to leaders throughout the organization while encouraging cross-functional problem solving. Rather than closely managing day-to-day work, managers focus on aligning priorities, providing context and creating opportunities for employees to have a meaningful impact on customers and the business. This approach supports both innovation and employee engagement as the company continues to grow globally.
- Transparent leadership from the executive team: CEO Mike Massaro,, has emphasized maintaining the company's entrepreneurial culture as it scales globally. Leadership regularly communicates company strategy, business performance and organizational priorities while reinforcing Flywire's mission of delivering the most important and complex payments. This emphasis on transparency helps employees understand how their work contributes to company goals and creates stronger alignment across global teams.
- Recognition reinforces supportive leadership: Flywire encourages managers to recognize employee contributions both formally and informally. Leaders celebrate achievements through company meetings, team recognition, Slack channels and annual awards honoring collaboration, innovation and customer impact. This recognition helps reinforce Flywire's values while ensuring employees feel appreciated for their contributions beyond annual performance reviews.
- External signals:
- CEO approval: A majority of employees approve of CEO Mike Massaro, reflecting positive confidence in the company's leadership and strategic direction. (Glassdoor)
- Highly rated executive leadership: Comparably ranks CEO Mike Massaro in the Top 5% of similarly sized companies, based on employee feedback about leadership effectiveness and workplace experience. (Comparably)
- Leadership confidence: Flywire has an Employee Net Promoter Score (eNPS) of 73, placing it among Comparably's top-performing companies and indicating strong employee advocacy for both the company and its leadership. (Comparably)
- Ethical and trustworthy management: 97% of employees say management is honest and ethical in its business practices, according to Great Place To Work's employee survey. (Great Place To Work)
Bottom line: Flywire's managers lead by combining transparency, trust and continuous coaching with opportunities for employees to take ownership of meaningful work. Supported by accessible leadership, a strong learning culture and employee recognition, managers help employees grow professionally while contributing to innovative payment solutions that serve organizations 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
"I've worked in the Travel vertical at Flywire for over 5 years and have loved every minute of it. The team is collaborative and supportive both personally and professionally and it is a pleasure to tackle new challenges with them every day. It's incredibly rewarding to look back on the things we've accomplished together and I know there is so much more to come!"
Flywire's leadership emphasizes transparency, accountability and continuous improvement by encouraging open dialogue about both successes and challenges. Employees say leaders are approachable, candid and willing to share their thinking, creating an environment where honest conversations help drive better decisions and stronger collaboration.
“Mike openly shared his main concerns and the issues he found most intriguing, as well as areas he believed needed improvement. The CEO was not promoting the company's strengths but rather discussing its concerns and identifying shortcomings to drive improvement. He was providing an honest account of a typical workday. During the roundtable meetings he showed willingness to share knowledge and thoughts in an open and approachable manner. His responses were grounded in logic, knowledge, and good intentions.”
Flywire's leaders prioritize accessibility and open communication, creating opportunities for employees to ask questions, share perspectives and better understand the business. Employees say leaders take the time to listen thoughtfully and provide transparent, well-informed answers across a wide range of topics, helping build trust throughout the organization.
“We had a coffee with Mike in one of our breaks and he dedicated time to reply to all questions we threw at him. No matter if questions were simple or complex, Mike took time to listen carefully, understood our point of view and provided his own view on the matter — from investor relations, to technology, to office expenses, he always offered a very intuitive point on every subject we discussed.”
Flywire's Benefits
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
