The leadership team at Flywire is the driving force behind the company's strategic direction and key decision-making processes. They are committed to aligning every move with the company's mission, ensuring that each step taken propels Flywire towards its goals.
Bringing together expertise from various fields, this team fosters a culture of innovation and growth. Their collaborative approach not only drives operational excellence but also inspires the entire organization to reach new heights.
1) David King
David King, the Chief Technology Officer at Flywire, is responsible for overseeing the company's technological direction and ensuring the alignment of tech strategies with business goals. His role involves leading the engineering team and driving innovation to maintain Flywire's competitive edge.
Since joining Flywire, David has spearheaded several key initiatives, including the enhancement of the company's payment platform and the integration of advanced data analytics. His leadership has been instrumental in scaling Flywire's technology infrastructure to support global operations.
David's extensive background includes founding AmagiSoft and serving as CTO at OnPlan Holdings. With a strong foundation in physics and mathematics from Westminster College and Miami University, he brings a wealth of knowledge and experience to Flywire. For more details on David King's professional journey, visit Flywire CTO.
2) Michael Massaro
Michael Massaro serves as the Chief Executive Officer and Director at Flywire, where he is responsible for steering the company's overall strategic direction and ensuring its growth and success. His expertise lies in business development and corporate strategy, which he leverages to drive Flywire's mission forward.
Before becoming CEO, Michael held the position of VP of Business Development at Flywire, where he played a crucial role in expanding the company's market presence. His professional journey includes significant roles at Carrier IQ, Siebel Systems, and edocs, Inc., where he honed his skills in strategic accounts, product management, and solutions consulting.
Michael's leadership has been instrumental in leading key projects that enhance Flywire's payment solutions and global operations. His background in Information Systems & Finance from Babson College, combined with his extensive industry experience, enables him to make impactful decisions that propel Flywire towards its goals.
3) Rob Orgel
Rob Orgel, the President and Chief Operating Officer at Flywire, is responsible for overseeing the company's global operations and ensuring seamless execution of its strategic initiatives. His leadership is pivotal in driving operational efficiency and fostering a culture of continuous improvement.
Rob's extensive career includes significant roles at Apple, Quattro Wireless, and Aylus Networks, where he honed his expertise in business development and operational management. His background in international relations and finance from Stanford University, coupled with his legal education from Harvard Law School, equips him with a unique skill set that he leverages to propel Flywire forward.
At Flywire, Rob manages various teams and spearheads key initiatives aimed at enhancing the company's payment solutions and expanding its market presence. His strategic vision and operational acumen are instrumental in maintaining Flywire's competitive edge in the global market.
4) Gary Cunningham
Gary Cunningham, the Chief People Officer at Flywire, is responsible for leading the company's human resources strategy and ensuring the alignment of HR initiatives with business objectives. His role encompasses talent management, employee engagement, and organizational development, making him a pivotal figure in fostering a positive workplace culture.
Gary's extensive professional background includes significant roles at Waymo, Traditional Medicinals, Inc., and Oerlikon, where he honed his expertise in HR and talent management. Notably, he has overseen various teams and projects aimed at enhancing employee experience and operational efficiency, leveraging his education from Harvard Business School and North Park University to drive impactful HR strategies.
5) Barbara Cousins
Barbara Cousins serves as the Chief Information Officer and Chief Information Security Officer at Flywire, where she oversees the company's IT infrastructure and security strategies. Her dual role ensures that Flywire's technological framework is robust and secure, aligning with the company's overall business objectives.
With a career spanning over two decades, Barbara has held significant positions at Devonshire Investors/Fidelity and KPMG, where she honed her expertise in IT risk management and information security. Her leadership at Flywire includes spearheading critical initiatives that enhance the company's cybersecurity posture and operational efficiency.
6) Michael Ellis
Michael Ellis, the Chief Financial Officer at Flywire, is responsible for overseeing the company's financial strategy and ensuring fiscal health. His expertise lies in financial planning, analysis, and corporate finance, making him a key player in driving Flywire's financial success.
With a career spanning over three decades, Michael has held significant roles at companies like One Inc, BillGO, and CashStar. His extensive background includes positions such as CFO Advisor and Controller, where he honed his skills in financial management and strategic planning. At Flywire, he leads various financial teams and spearheads initiatives aimed at optimizing financial operations and supporting the company's growth.
7) Allison MacLeod
Allison MacLeod serves as the Chief Marketing Officer at Flywire, where she is responsible for leading the company's global marketing strategies and initiatives. Her expertise lies in demand generation, customer acquisition, and integrated marketing communication.
Allison's career journey includes significant roles at Rapid7 and Forrester Research, where she honed her skills in digital marketing and demand creation. At Flywire, she has spearheaded key marketing projects that have significantly enhanced the company's market presence and brand recognition.
8) Peter Butterfield
Peter Butterfield serves as the General Counsel & Chief Compliance Officer at Flywire, where he oversees the company's legal and compliance strategies. His expertise lies in commercial and regulatory law, ensuring that Flywire operates within legal frameworks while achieving its business objectives.
Peter's extensive career includes significant roles at KVH Co., Ltd., Devonshire Investors, and Mintz, Levin, Cohn, Ferris, Glovsky and Popeo, P.C. He holds a JD from Columbia Law School and an A.B. in History/Government from Bowdoin College, bringing a wealth of knowledge and experience to Flywire's leadership team.
9) Ryan Frere
Ryan Frere, the Executive Vice President and General Manager, B2B at Flywire, is responsible for overseeing the company's B2B operations and driving strategic initiatives to enhance business growth. His key skills include global payments, product management, and business development, which he leverages to lead various teams and projects.
With a career spanning roles at Blackbaud and The Cooper School, Ryan brings a wealth of experience in product management and international markets. At Flywire, he has held multiple leadership positions, including EVP Payments and VP Global Payments, where he has significantly contributed to the company's global payment solutions and operational efficiency.
10) Sharon Butler
Sharon Butler, the Executive Vice President of Global Education at Flywire, is responsible for overseeing the company's global education initiatives and driving strategic growth in this sector. Her role involves leading various teams to enhance Flywire's education payment solutions and expanding the company's market presence in the education industry.
With a career spanning over two decades, Sharon has held significant roles at Flywire, including VP Global Sales and Global Sales Director. Her extensive background in sales and management, coupled with her expertise in communications from Bridgewater State University, has been instrumental in driving Flywire's success in the global education market.
Flywire Org Chart
At the top of Flywire's organizational chart is Michael Massaro, the Chief Executive Officer, who steers the company's overall strategic direction. Reporting directly to him are key executives including David King (CTO), Rob Orgel (President & COO), and Michael Ellis (CFO), each responsible for their respective domains of technology, operations, and finance.
Supporting this core leadership team are other pivotal roles: Gary Cunningham (CPO) oversees human resources, Barbara Cousins (CIO & CISO) manages IT and security, and Allison MacLeod (CMO) leads global marketing efforts. Additionally, Peter Butterfield (General Counsel & CCO) ensures legal compliance, while Ryan Frere (EVP & GM, B2B) and Sharon Butler (EVP, Global Education) drive growth in their specialized sectors, all working collaboratively to align with Flywire’s mission and values.