September 29, 2023

In a couple of weeks’ time, Jack Dorsey will be running Square’s business again. Dorsey founded the fintech company in 2009 before expanding its services and renaming it Block by the end of 2021. Square itself, the financial platform for small-to-medium businesses, became one of the businesses under the new company. Block also owns Cash App, installment payment provider Afterpay, website creator Weebly and a controlling stake in music streaming service Tidal. In February this year, Alyssa Henry was named the CEO of Square after years of serving as its EVP and head of its seller unit. Now, according to a regulatory filing seen by CNN, Henry is stepping down and leaving the company on October 2.

Dorsey will take on the additional role as “Square Head” in addition to helming Block, though it’s unclear if he will fill the seat permanently or will serve as a temporary leader until the next CEO takes over. “As CEO of Square, Alyssa Henry helped transform the business into a software-led technology company, guided the team during the uncertainty of global pandemic lockdowns, and expanded our breadth of services for small businesses around the world,” a Block spokesperson told CNN. “Square is what it is today in large part because of Alyssa‚Äôs leadership and we wish her the best in her future endeavors.”

Prior to joining Square, Henry led Amazon Web Services’ storage services division and oversaw software development, operations, as well as inbound and outbound product management for several teams. Her LinkedIn page still lists Square as her employer and doesn’t say where she’s headed next. Henry’s reason for departure also remains unknown, and Block didn’t say whether it was connected in any way to the outage Square experienced a few days ago. As Payments Dive notes, Square was out for almost a whole day, leaving merchants unable to process payments.

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