Flywire

New Delhi
Total Offices: 2
1,200 Total Employees
Year Founded: 2011

Flywire Career Growth & Development

Updated on August 12, 2026

Frequently Asked Questions

Career Progression Paths

Flywire provides employees with numerous opportunities to grow by combining continuous learning, internal mobility, leadership development and exposure to a fast-growing global fintech business. As the company expands its global payments platform across education, healthcare, travel and B2B, employees are encouraged to build new skills, take on broader responsibilities and pursue career paths across functions and international teams. Guided by its value of Evolved Learning, Flywire views professional development as an ongoing process rather than a one-time milestone, helping employees grow alongside the business. 

  • Learning is embedded into the culture: Flywire encourages employees to actively seek feedback, challenge assumptions and continuously expand their knowledge. New hires participate in structured onboarding, while employees have access to ongoing learning resources, professional development programs, mentorship and leadership support throughout their careers. Rather than limiting growth to formal training, employees are encouraged to learn through cross-functional collaboration, solving complex customer challenges and taking on new responsibilities. One employee shared that Flywire is a place where you are constantly learning, while another described it as an environment that "encourages curiosity, feedback and reflection."
  • Global mobility and cross-functional experience: With offices and teams spanning North America, Europe, Asia-Pacific and Latin America, Flywire gives employees opportunities to collaborate across regions and business units while gaining international experience. As the company continues to grow organically and through acquisitions, employees can expand their careers by moving into new roles across engineering, product, customer success, sales, operations, marketing, finance and corporate functions. This global exposure helps employees broaden both their technical expertise and business knowledge.
  • Leadership development through ownership: Flywire's culture encourages employees to take ownership early in their careers and contribute beyond their immediate responsibilities. Managers are expected to provide regular coaching and feedback while empowering employees to lead initiatives, collaborate across teams and develop new capabilities. Employees highlight that leaders are approachable and trust employees to make meaningful contributions, creating opportunities to build leadership skills regardless of title.
  • Growth supported by a rapidly expanding business: Career opportunities are reinforced by Flywire's continued business growth. In 2025, the company processed more than $32 billion in payment volume, generated approximately $550 million in revenue, served more than 4,600 clients (now over 5,300 clients) globally and continued expanding its software and payments platform through new product innovation and strategic acquisitions. As Flywire enters new markets and develops additional solutions, employees have increasing opportunities to work on large-scale initiatives and grow their careers alongside the business.
  • External signals:
    • Career opportunities: Employees rate Flywire highly for career opportunities, reflecting positive experiences with learning, advancement and professional development. (Glassdoor)
    • Leadership confidence: A majority of employees approve of CEO Mike Massaro, indicating confidence in the company's leadership and long-term direction. (Glassdoor)
    • People-first workplace: Great Place To Work found that 96% of employees say management trusts people to do a good job without watching over their shoulders, supporting a culture that empowers employees to take ownership and grow. (Great Place To Work)
    • Best workplace recognition: Flywire has been recognized as one of the Fortune Best Workplaces in Financial Services & Insurance, reflecting a strong overall employee experience that includes opportunities for development and career growth. (Fortune; Great Place To Work)

Bottom line: Flywire offers strong career growth opportunities by combining continuous learning, global collaboration, leadership development and meaningful ownership within a rapidly growing fintech company. Employees have opportunities to build new skills, expand into new roles and grow alongside a business that continues to innovate and scale globally, making it an attractive environment for long-term career development. 

Flywire's Candidate Tradeoffs

If you’re weighing whether Flywire is the right fit, these are the core tradeoffs to consider.

  • Cross-function mobility encouraged: Flywire places greater emphasis on cross-functional mobility and long-term leadership development.

Flywire Employee Perspectives

Tell us about your recent promotion or role change. 

I was recently promoted to team lead, global client experience at Flywire. In this role, I am fortunate to manage a passionate global team of specialists and associates. Our team is based in the United States, United Kingdom, Spain, Singapore and Japan. Together we provide support and training to a global client base. My team is responsible for serving clients across Flywire’s education, travel, healthcare and B2B verticals. This role was a homecoming as I started my Flywire career on the client experience team.

I joined Flywire as a client experience specialist in 2022 after spending a decade in higher education. Within a year, I was promoted to a senior client experience specialist and assisted with escalations and developing new SOPs. In Fall 2023 I was promoted to payment experience team lead for the Americas. In this role I was able to develop strong people management skills, oversee support for key products and collaborate with all aspects of our business.

 

What will this new role or skill let you do? 

The Flywire client experience team supports clients using Flywire’s SaaS products, ensuring a positive user experience through training and support.

In this new role, I will lead our transformation from customer support to customer experience, introducing self-service and AI features to enhance support options, scale efficiently and maintain high service standards.

Key priorities include improving client contact reasons for better data quality, refining contact procedures to engage the right stakeholders and enhancing messaging to improve communication while reducing manual effort.

Additionally, I am privileged to manage and develop a talented team of client experience FlyMates, helping them set goals for both company success and personal career growth. With their deep product knowledge, we will continue to deliver high-quality, effective service to our clients.

 

How would you describe the culture of internal mobility and upskilling?  

At Flywire, growth and internal promotion are infused within our culture. I joined Flywire with a limited background in customer support. Regardless, Flywire helped me develop critical skills to advance my career. I was fortunate to be promoted within a year of starting with the company. Within two years, I was promoted to a management position, entrusted to manage a talented team and make key decisions. I received extensive support from our Managers Taking Flight program for new managers.

I feel incredibly fortunate to have made such progress in such a relatively short period of time. From day one, our leadership made it clear that FlyMate development and internal promotion were key parts of our culture. Our OneFlywire internal advancement program is open to all FlyMates who have been with the company for at least a year. The program is very effective at matching existing talent with new opportunities for growth. Several of my team members have also benefited from the program. They advanced to new opportunities throughout the company. The program also serves as a beneficial recruitment incentive that allows us to attract top talent.

Joe McIsaac
Joe McIsaac, Team Lead, Global Client Experience

Flywire encourages employees to take ownership of their careers by exploring new opportunities and building on their existing strengths. Employees say the company supports internal mobility, making it possible to transition into new roles while continuing to develop professionally under the guidance of experienced leaders.

“I fought for the career path that I knew was right for me. After spending 2 years in a Relationship Management role at Flywire, I knew I was ready to take on a new challenge. Career progression is very important to me. So when I saw an opportunity to move into a role which utilised my existing skill set, whilst giving me the opportunity to grow and develop, nothing was getting in my way! I am extremely proud that I was successful in my application for the Payables Manager role and am learning every day from an incredible female leader.”

Alysha Ayres
Alysha Ayres, Payables Manager

Flywire encourages employees to pursue new career paths by providing opportunities to expand their skills and take on new challenges. Employees say the company invests in their success by offering the guidance, flexibility and support needed to transition into roles that align with their long-term career goals.

“Before Flywire, I was in an operational/reporting role at an investment management company and wanted to pivot into a position that was more closely tied to business strategy and revenue. After a lot of hard work gaining some relevant experience and networking, Flywire took a shot on me and hired me onto the Global Payments team to handle credit card partnerships and strategic revenue growth projects. They then provided the guidance and flexibility that allowed me to succeed in a position that required a very different skill set than I was used to.”

Aimee Schumaker
Aimee Schumaker , Director, B2B Channel Partnerships

Flywire Employee Reviews

Working on the Travel team at Flywire is great - It has given me the opportunity to take on projects and responsibilities to elevate my own career growth. In addition to that, I get to work and collaborate with amazing people from all over the world

Annie
Annie, Director, Partnerships
Annie, Director, Partnerships

I have been able to grow my career due to the encouragement and support provided by the company on any given day. From all of the internal and external trainings that are offered to us, to the mentoring and coaching I receive from my fellow FlyMates, I never feel that I am "stuck" in my personal or professional career growth.

Maicol
Maicol, Senior Manager, Client Success Operations, Travel
Maicol, Senior Manager, Client Success Operations, Travel

I love working at Flywire because every day I’m inspired by the incredible people here. Their authenticity, passion, and creativity make this such a special place. It’s amazing to be part of a team that genuinely cares, supports each other, and is committed to making a difference. I’m grateful to grow and learn alongside such talented individuals!

Ilona
Ilona, Lead Experience Manager
Ilona, Lead Experience Manager

Flywire's Benefits

Allows employees to pursue continuing education during work hours

Encourages knowledge sharing and cross-functional collaboration

Hosts Lunch and Learns

We host FlyBytes monthly to share exciting news and updates across departments so teams stay updated and informed of exciting work happening around the globe!

Job training & conferences

Managers hold regular development check-ins

Provides opportunities to take on expanding responsibilities

Provides paid industry certifications

Provides structured onboarding for new employees

Encourages lateral mobility to expand skills and impact

Posts new positions internally and encourages employees to apply

Promote from within

Provides customized development tracks