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August 23, 2021

Revenues at Square have grown more than tenfold since Alyssa Henry joined the payments company in 2014. Along the way, she’s received stock worth more than half a billion dollars.

If you’re buying something at a store, there’s a good chance you’ll be paying through Square. The company’s little white readers—some models no larger than a credit card—have become ubiquitous fixtures at restaurants, retail stores and even farm stands.

Millions of businesses, or “sellers” as the company calls them, use Square to process their transactions, generating $1.5 billion of the San Francisco-based company’s $2.7 billion in total gross profits last year. The Seller business is at the crux of why Square has ballooned from a $2.9 billion market capitalization at its 2015 IPO to a $110 billion in market capitalization today.

Masterminding the growth is Alyssa Henry, 51, a longtime Amazon executive who joined Square in 2014, the year before the business went public. Henry—who debuts this year on Forbes list of America’s Richest Self-Made Women, with an estimated net worth of $555 million—started her career as a programmer for an insurance company before being hired by Microsoft, where she climbed the ladder over the course of a decade. After seven years at Amazon—the last four spent as a vice president for its cloud provider Amazon Web Services—she joined Square in May 2014 to lead its infrastructure team. She became head of Square’s Seller team six months later, inheriting a business that was still struggling to build out software around its white reader. Over the years, she’s gotten Square stock as compensation and now owns a 0.3% stake in the company.
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