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How Mike Massaro & Team Achieve Success With Industry Verticals

Yesware CEO, Joel Stevenson, talks all things sales with fellow entrepreneurs, CEOs, and sales experts. In this episode of The Hard Sell, Joel and guest Mike Massaro, CEO of Flywire, discuss how insights from your sales team are key to the success of your company.

About the Guest: As CEO of Flywire (Nasdaq: FLYW), Mike Massaro has grown the business from a concept into a 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.

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.

Meet Your Host

Joel Stevenson

Joel Stevenson is the CEO of Yesware - a leader in sales productivity software. Prior to Yesware Joel was the GM and founder of Wayfair's B2B division which he grew to several hundred million in revenue. He began his Wayfair career by leading the company's home improvement products division, followed by his role as Managing Director of Wayfair UK, where he drove growth of the company's international presence. Joel then served as Vice President of FP&A while Wayfair was making the transition to a public company.

Before joining Wayfair, Joel held a variety of sales and marketing roles at Ariba, Innovus, and Verizon and was a consultant at ZS Associates. Joel earned an M.B.A. from the Yale School of Management, a B.S. in Business Administration from the University of Illinois and studied Chinese at Harvard-Beijing Academy. He lives in Massachusetts with his wife and four children.

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