Our Leadership Team
Meet the FlyMates who are making it happen.

Mike Massaro

CEO

As Chief Executive Officer of Flywire, Mike has grown the business from a concept into the global and growing company it is today. He has overseen Flywire’s expansion in North America, Europe, and the Asia-Pacific regions while aligning Flywire’s international team with the company’s strategic direction and increasing the visibility of Flywire globally. Mike began his career as part of the technical risk services practice at PWC, LLP.

His background spans global payments, mobile software and hardware, and e-billing at high growth technology companies, including Carrier IQ and edocs, Inc. He earned his Bachelor of Science degree in Management Information Systems from Babson College. Mike is also a 2019 recipient of the Ernst & Young Entrepreneur of the Year Award in Financial Services, which recognizes unstoppable entrepreneurs who redefine the way we live, work and play.

Mike Massaro

Rob Orgel

President and Chief Operating Officer

As President and Chief Operating Officer, Rob leads Flywire’s global payment network, business operations, finance, legal, compliance, and corporate strategy functions. Rob brings extensive experience with 20 years in the payments/receivables ecosystem to Flywire, including hands-on experience in legal, compliance, finance, go-to-market, business development and global operations.

Prior to Flywire, he spent close to 10 years at Apple where he was part of the leadership team that developed, launched and grew the Apple Pay business and global expansion as well as the launch of the Apple Card. Before that, Rob was Chief Operating Officer at Quattro Wireless at the time it was acquired by Apple. Before that, Rob played key leadership roles at m-Qube, a first-of-its kind carrier billing and payment platform that was acquired by Verisign, and edocs, a leading e-billing and payment solution acquired by Siebel (subsequently acquired by Oracle).

Rob holds a Bachelor of Arts and Master of Arts degrees in International Relations from Stanford University and a Juris Doctor degree from Harvard Law School.

Rob Orgel

Cosmin Pitigoi

CFO

Cosmin Pitigoi has served as our Chief Financial Officer since March 2024. Mr. Pitigoi has over 20 years of experience in finance leadership roles. Prior to Flywire, Mr. Pitigoi was SVP of finance at PayPal, leading a global cross-functional team across FP&A, operational finance and pricing, along with serving on the board of directors at Paidy and the audit committee chair of the PayPal Giving Fund.

Prior to PayPal, Mr. Pitigoi held leadership roles at eBay across investor relations, business unit FP&A and treasury. He began his career in operational and finance roles at E*Trade and Barclays. He holds a B.Comm. from Stellenbosch University in South Africa and an M.B.A. from Santa Clara University.

Cosmin Pitigoi

Peter Butterfield

General Counsel & Chief Compliance Officer

Since joining Flywire in early 2015, Peter Butterfield has served as General Counsel & Chief Compliance Officer. His responsibilities include the management of all legal, compliance, regulatory, risk, and security matters for the business. Peter previously spent 15 years in various senior management roles within Devonshire Investors, the private equity arm of Fidelity Investments, and its operating companies. Before joining Flywire, Peter lived and worked for over a decade in Tokyo and Singapore managing legal, risk, and compliance functions, and leading the ex-Japan APAC operations for KVH Co., Ltd. He has an undergraduate degree from Bowdoin College and holds a law degree from Columbia University.

Peter Butterfield

Gary Cunningham

Chief People Officer

As Chief People Officer, Gary Cunningham leads Flywire’s global people and culture functions, including talent acquisition, learning and development, people operations, employee experience and wellness.

Cunningham has over twenty years of leadership experience in employee development and human resources related functions, including most recently at Waymo (an Alphabet subsidiary), where he led people and recruiting operations. Prior to Waymo, Gary spent over eight years at Oerlikon, a global engineering and manufacturing organization. There he was Vice President & Global Head of HR for one of Oerlikon’s largest divisions, where he led diversity, equity, inclusion and culture initiatives, talent acquisition and management, performance management, international merger and acquisitions, and employee integration.

In addition to his professional roles, Gary has held Board of Directors and membership roles in organizations including Affinity Insurance, the AIDS Foundation of Chicago, Society of Human Resource Management, and the Human Rights Campaign. Gary holds a Bachelor’s Degree from Texas A&M University and a Master Degree from North Park University, and has completed his executive education at Harvard Business School.

Gary Cunningham

David King

CTO

David King is Flywire’s Chief Technology Officer, leading all technical platforms and teams. A self-defined serial entrepreneur with a passion for the intersection of technology and business, David has founded several companies including infiNET Solutions, Inc, one of the first companies to deliver SaaS solutions to higher education. There he architected and managed an automated tuition billing and commerce system for major universities in the United States and helped the company process more than $16 billion annually. In 2006, after Nelnet, Inc. (NNI) acquired infiNET, David served as president of their higher education division as well as led the transformation to become an online medical education program and data security company. Prior to joining Flywire, David also co-founded OnPlan Holdings (acquired by Flywire) where he leveraged his background in payments, analytics and billing to develop innovative solutions for healthcare and education. He currently sits on the advisory board of insITe, a technology business management software company, and Wine Country Online, a destination management organization for promoting California’s Wine Country. David holds a Bachelor of Science in Mathematics and Physics from Westminster College, and a Master of Science in Physics from Miami University.

David King

Allison MacLeod

CMO

As Chief Marketing Officer, Allison leads Flywire’s global marketing strategy. Her focus is on amplifying the company’s brand, and scaling its performance in marketing, global communications and sales enablement efforts. She has over 15 years of marketing experience, including seven years at Rapid7. There, she focused on building and optimizing the company’s growth by building and scaling demand generation, technology and analytics, and building strong teams. Previously, she worked at Forrester in several digital and field-based roles that included establishing the research firm’s international corporate marketing function in Europe and driving its online localization strategy. Allison holds a Master of Arts in Integrated Marketing from Emerson College, and a Bachelor of Arts in Communications from the University of Massachusetts, Amherst.

Allison MacLeod

Barbara Cousins

CIO, CISO & Internal Audit

As Chief Information Officer (CIO) and Chief Information Security Officer (CISO) and head of Internal Audit, Barbara leads Flywire’s security, risk and privacy functions. Barbara brings 25 years of experience in risk, security and privacy as well as a general understanding of the legal and regulatory environments affecting information handling and controls across a broad array of industries i.e., financial services, healthcare, education, technology, energy, life sciences and agriculture.

Prior to this role, Barbara was the Information Security Officer for Devonshire Investors (Fidelity) where she managed 22 companies based in the U.S and internationally and was a trusted advisor to individual company’s board members, senior executives and their clients on IT risk and security issues. Barbara has hands-on experience in managing a number of crises from the civil unrest in Tunisia to the Japan earthquake/tsunami/radioactive materials release in March 2011.

Before Fidelity she was Director of IT Risk and Security for KPMG US and International. She had global responsibility for building and implementing security, privacy and risk programs covering various IT Initiatives.
Barbara Cousins

Sharon Butler

EVP Global Education

As Executive Vice President of Global Education at Flywire, Sharon brings over 20 years of experience in sales and customer success and currently leads the global sales and account management teams across ten offices globally for Flywire’s Education vertical. Sharon has been a pioneer in the education payment space and helped to evangelize on a global scale the importance of the student payment experience and choice for education based payments. As Flywire’s first employee she has not only built and scaled Flywire’s Education sales and client success teams across the globe, but also championed educational cross-border payments to lead Flywire to a presence representing more than 2,000 education clients across 240 countries and territories.

Sharons’ deep understanding of the education markets have enabled not only world-class cross-border payment options, but also the expansion of Flywire’s comprehensive receivables solution to better serve client payment needs.

Prior to joining Flywire, Sharon held roles as North East Regional Sales Director for Tuition Management Systems, and District Sales Director for SkyTel, a division of Verizon Business and leading wireless technology provider. Sharon has a degree in Communications with a minor in Business from Bridgewater State University.

Sharon Butler

John Talaga

EVP Healthcare

John brings more than 20 years of experience to his role as Executive Vice President of Healthcare. He has partnered with hundreds of healthcare providers to develop and innovate patient billing and payment solutions. Prior to joining Flywire, John was co-founder and CEO of OnPlan Holdings (acquired by Flywire), which launched healthcare’s first automated payment plan solution, as well as the next generation student tuition management solution for education. John also co-founded HealthCom Partners in 2001, which launched PatientCompass, a pioneer in patient-friendly billing and healthcare’s first online account management solution. After HealthCom sold to McKesson (MCK) in 2006 as the first acquisition to form RelayHealth, John led the patient billing and payment business at RelayHealth for five years before launching and leading the healthcare vertical for doxo, a multi-biller payment network. He is a member of and has presented extensively with Healthcare Financial Management Association (HFMA), Healthcare Information and Management Systems Society (HIMSS), and the American Association of Healthcare Administrative Management (AAHAM). John holds a bachelor’s degree from the University of Dayton.

John Talaga

Colin Smyth

VP & GM, Travel

As VP & GM, Colin Smyth leads the global Travel vertical, with a focus on solving complex international and domestic payments for our clients across luxury accomodations, tour operators and destination management companies. In his role Colin works with travel clients to simplify their payment processes and make their guests’ payment experience more enjoyable.

Colin brings over 15 years of sales and client success experience and currently oversees a global team located throughout Flywire’s offices worldwide.

Colin was one of the original members of the travel vertical and has led the team through its tremendous growth over the past few years. Prior to Flywire, Colin spent several years in the sales and digital media space. He began his career in capital markets and financial services with roles at both Lehman Brothers and Barclays. Colin holds a Bachelor’s Degree from Boston College.

Colin Smyth

Ryan Frere

EVP & GM, B2B

As EVP & GM, Ryan Frere leads our emerging global B2B vertical strategy, working with clients to streamline their payment processes and solve challenges in international receivables. Prior to this role, Ryan built and scaled Flywire’s global payments organization, leading a team of global thought leaders and experts, as well as building a proprietary global payments network.

Additionally, Ryan led Flywire’s payment expansion partnering closely with some of the top global banking institutions and payment partners in the world and drove our market expansion across Asia Pacific, Europe, Africa and Latin America. Ryan holds a Bachelors in Finance and Management Information Systems. Previous to Flywire, he ran international product management at Blackbaud.

Ryan Frere

Uday Seth

SVP, Business Operations & Corporate Development

As SVP of Business Operations & Corporate Development, Uday Seth leads Flywire's M&A, capital raising, analytics and business operations functions. Uday and his team have led some of Flywire's largest and successful initiatives, including Flywire's initial public offering, its acquisitions of Studylink, CohortGo, WPM, Simplee, and OnPlan, in addition to capital raises from Temasek, Goldman Sachs, Tiger Management and others. Additionally, Uday leads Flywire's overall strategy & strategic planning initiatives across the organization.

Prior to Flywire, Uday was involved in various capacities with other high-growth fintech companies such as PayPal and Klarna. He has also held roles at Bank of America Merrill Lynch and JLL Partners, a private equity firm based in New York. Uday holds a Bachelors Degree from Dartmouth College, and an MBA from University of Pennsylvania, Wharton School.

Uday Seth

Mohit Kansal

SVP, Global Payments and Payer Services

As SVP of Global Payments and Payer Services, Mohit is responsible for Flywire's world-class global payments network, pricing, growth, and FX risk management functions. Mohit has more than 15 years of global experience in financial services, tech startups, and payments technology, both as an operator and entrepreneur.

Since joining Flywire in 2016, Mohit has built a global team of payments leaders, who are responsible for driving revenue growth and market expansion through a mix of product innovation, partnerships, monetization strategy and risk management. In addition to his core team, Mohit also leads Flywire’s strategy and global cross-functional team responsible for payer growth initiatives.

Prior to Flywire, Mohit had a variety of experiences including working in financial services at Merrill Lynch in London and UBS AG in Hong Kong, starting up companies in hardware technology and financial technology sectors in Boston, and a stint with the Government of India on the unique ID initiative targeting 1.2 billion+ people. Mohit has an MBA from MIT Sloan School of Management and a B. Tech. in Computer Science and Engineering from Indian Institute of Technology Bombay.

Mohit Kansal

Eric Spear

Senior Vice President of Engineering

As SVP of Engineering, Eric Spear oversees all aspects of product development and engineering operations at Flywire. Eric has more than 20 years of experience in engineering leadership roles and has helped scale a global engineering team of more than 200 across four offices globally – which handles development, program management, site reliability, QA, product and UI and UX.

Prior to his current role, Eric held several key leadership positions, including Vice President of Engineering and Director of Product Management. Eric is an expert in scalable cloud technology and containerization. He easily navigates between technology strategy and business strategy, providing the sought-after skill of translating between the two to ensure alignment for the team and success for the customer. His ability to inspire and mentor engineering talent has been instrumental in attracting and developing top talent at Flywire.

Eric holds a Bachelor's degree in Computer Science from Clark University. Outside of his professional endeavors, Eric is actively involved in various philanthropic initiatives, particularly those focused on promoting STEM education and advancing diversity and inclusion in the technology sector. He is a passionate advocate for empowering the next generation of technologists and giving back to the community.

Eric Spear