Phillip Riese has served as a member and chair of our Board of Directors since August, 2013. He brings 30 years of executive and operating experience to his Board service, combined with an additional 20 years of working with some of the most innovative, disruptive, and rapidly growing public and private companies and their management teams around the world.
Phillip spent 18 years at American Express (NYSE: AXP) in a variety of positions, and over the last 8 years of his service was the president of the Consumer Card Group and chairman of American Express Centurion Bank. He had previously been a division executive at Chase Manhattan Bank, responsible for their Merchant Services business, and before that, a partner of M.C. Geffen and Associates, a consulting firm in South Africa.
Over the past 20 years, Phillip has served on a number of public and private company boards around the world, and today is a board member of Remitly (Nasdaq: RELY) as well as Array, Betterment, Cross River Bank, Mpower and Relay Network. He also advises a number of CEOs and venture funds globally and serves as a board member of Accion, a not-for-profit dedicated to global financial inclusion.
Phillip earned a bachelor’s degree in Commerce from Leeds University in England, an MBA from the University of Cape Town in South Africa and a Master of Science degree from MIT's Sloan School of Management.
Michael Massaro has served as our Chief Executive Officer and a member of our board of directors since December 2013. A passionate leader deeply committed to enhancing the value Flywire provides to its employees, clients, payers, partners, shareholders and more, Mike has led the growth of the business from a concept into a world-leading payments enablement and software company. He has overseen Flywire’s expansion into new regions while aligning Flywire’s global team with the company’s strategic direction, including the company's Initial Public Offering (IPO) in May of 2021 and multiple strategic and value-enhancing acquisitions. His background spans global payments, mobile software and hardware, and e-billing at high-growth technology companies, including Carrier IQ and edocs, Inc.
Mike has been named Entrepreneur of the Year by Ernst & Young, one of the 100 Most Intriguing Entrepreneurs by Goldman Sachs, and a CEO of the Year by Comparably, among other distinctions. Under his leadership, Flywire has been rated one of the World’s Top FinTech companies by CNBC, voted a Most Loved Workplace and been named a top place to work by the U.S. News & World Report, Fortune, INC and more. He earned his Bachelor of Science degree in Management Information Systems from Babson College.
Alex Finkelstein has served as a member of our board of directors since 2011. A co-founder and General Partner at Spark Capital, he has played a leadership role in the firm's growth and success. Alex has a strong track record of identifying and backing innovative businesses; in addition to leading the investment in Flywire, he led Spark's investments and was the first institutional investor in 5min Media (acquired by AOL), Soundhouse (acquired by Apollo), Talkspace (Nasdaq:TALK) and Wayfair (NYSE:W).
Prior to joining Spark Capital, Alex wrote and sold a number of television shows that he sold to major networks including FOX, E!, Discovery and ITV1 (U.K.). Previously, Alex was a member of the investment team at two Softbank venture capital firms, and worked at Cambridge Associates.
Alex holds numerous board and advisor roles, including Member of the Board of Directors at Higharc, GetYourGuide and TravelPerk. Alex holds a B.A. in Political Science from Middlebury College.
Matt Harris has served as a member of our board of directors since January 2015. For more than 30 years, Matt has been investing in visionary fintech founders and their businesses in the areas of payments, lending, capital markets, insurance and real estate. He is particularly interested in backing companies building next-generation embedded fintech tools that will challenge and compete with traditional banking, lending and B2B payments through increased transparency and security.
Matt started his investing career at Bain Capital private equity in 1995, having worked previously at Bain & Company. In 2000, Matt founded Village Ventures, which he ran for 12 years and where he focused on early stage fintech investing. In 2012, he rejoined Bain Capital Ventures (BCV). He has served as a member of the board of directors of AvidXchange Holdings, Inc., (NASDAQ: AVDX) a provider of accounts payable automation software and payment solutions for middle market businesses and their suppliers, since July 2015. He also served as a member of the board of directors of Billtrust, a provider of cloud-based software and integrated payment processing solutions, until December 2022. He currently serves on the board of directors for Finix, Justworks, Moov, Onbe, Orum and others.
Matt attended Williams College and serves as a Trustee of Williams College as well as a member of the College’s Investment Committee and co-head of the Non-Marketable Assets Committee, and is the former Chair of the Board of the Williamstown Theatre Festival. He is also a board member at Endeavor, an organization leading the global movement to catalyze long-term economic growth by selecting, mentoring and accelerating the best high-impact entrepreneurs around the world, as well as the boards of the Partnership Fund for New York City and the Innovation Advisory Council for the New York Federal Reserve.
Gretchen Howard has served as a member of our Board of Directors since September 2023. An experienced operator and skilled leader, Gretchen is the former Chief Operating Officer of Robinhood (Nasdaq: HOOD), where among other functions, she oversaw brokerage, cash compliance and operations, HR and recruiting, customer trust and safety, as well as customer support and business strategy. Gretchen helped scale and lead the company through its IPO in 2021. Gretchen joined Robinhood after serving as a Partner with CapitalG, Alphabet Inc.’s growth equity fund. Prior to her role at CapitalG, Ms. Howard held various senior management positions at Google and Fidelity Investments.
Gretchen is on the Board of Directors of both Thumbtack, a technology company helping people confidently care for and improve their homes, and AllTrails, a mobile app connecting people to the outdoors. Passionate about giving back to her community, she is also a member of the Board of Trustees at Williams College and a former board member of the YMCA of San Francisco. She holds a B.A. from Williams College and an M.B.A. from Harvard Business School.
Carleigh Jaques has served as a member of the Board of Directors since 2024. Carleigh brings extensive experience in financial technology, payments, risk and capital markets to Flywire’s Board of Directors. She previously led multiple strategic and operational teams over the span of a 15-year career at Visa, Inc. (NYSE: V), where she was most recently the SVP, Global Head of Risk & Identity Solutions. In this role, she accelerated the growth of Visa’s global fraud detection business, which supports financial institutions and merchants with capabilities to make real-time decisions and authenticate account holders across Visa, the world’s largest payment network, and other payment types. Prior to that, Ms. Jaques was SVP and Global Head of Acceptance Solutions at Visa, where she led the transformation of the company’s merchant and acquirer capabilities including Tap to Phone, urban mobility and merchant digital solutions. In her prior role as SVP and GM of Visa’s Cybersource business, Ms. Jaques led one of the world’s largest digital gateways, including its international expansion, sales model transformation and entry into new markets, such as face to face acceptance. Earlier in her tenure at Visa, Ms. Jaques founded the Corporate Development and Venture function and led a number of strategic investments through joint ventures and acquisitions, including Visa's $23 billion acquisition of Visa Europe. Prior to joining Visa, Ms. Jaques was a technology investment banker.
Ms. Jaques is an Advisory Board Member at the Wharton AI & Analytics Initiative and has previously been named among the Most Influential Women in Payments by PaymentsSource. She holds a B.A. from the University of Michigan and an MBA from The Wharton School at the University of Pennsylvania.
Edwin Santos has served as a member of our Board of Directors since April 2021. Ed’s over 40 years of professional experience includes a distinguished career in banking, with experience in risk management, corporate governance, management advisory services, acquisitions, and reengineering efforts. He served for many years in various positions of significant responsibility with FleetBoston Financial Group, and prior to his retirement in 2009, Ed was Group Executive Vice President and General Auditor for Citizens Financial Group (NYSE: CFG).
Mr. Santos currently serves as a member of the Boards of Directors of the Providence Mutual Fire Insurance Company, Washington Trust Bancorp Inc. ( Nasdaq: WASH) and Fidelity Institutional Asset Management, a Fidelity Investments company. An active member of his community, he is also Past President of the Board of Trustees of Rocky Hill School, a former member of the Bryant University Board of Trustees and the former Treasurer of Crossroads of Rhode Island. He holds a Bachelor’s degree in Business Administration and Accounting from Bryant University.
Diane Offereins has served as a member of our Board of Directors since 2023. Diane is an eminent executive and trailblazer in the financial services industry, with unique experience scaling payments networks globally. She was previously the Executive Vice President and President, Payment Services at Discover Financial Services (NYSE: DSF), where she was responsible for the growth of the Discover Global Network, consisting of three payment networks – Discover Network, Diners Club International and PULSE. Under her leadership, in 2021, Discover’s payments business handled more than $500 billion in transaction volume and generated more than $533 million in pretax income. Throughout her tenure at Discover, she also held several leadership positions within the company, including Executive Vice President, Payment Services and Executive Vice President and Chief Information Officer. Prior to Discover, Diane held leadership positions at Bank of America (NYSE: BAC) and SouthEast Bank.
Diane is on the Board of Directors of Brighthouse Financial, Inc. (Nasdaq: BHF) where she chairs the Compensation and Human Capital Committee and serves on the Finance and Risk and Nominating and Corporate Governance Committees. She is also on the Board of Directors of LendBuzz, an AI-based auto finance platform that helps consumers obtain fair access to credit when purchasing a car. She was recently named one of the Most Powerful Women in Finance by American Banker. She earned her B.B.A. in Accounting from Loyola University of New Orleans.