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Three Questions for Square Now That Jack Dorsey Is Officially Working Part Time

With Square's IPO on the way, here are three key questions investors are probably asking.

Johannes Simon / Getty Images via Thinkstock
Jason Del Rey has been a business journalist for 15 years and has covered Amazon, Walmart, and the e-commerce industry for the last decade. He was a senior correspondent at Vox.

Jack Dorsey is officially back as Twitter’s permanent CEO, which means his other company, Square, has to share him for good (for now). Plenty of people who have worked closely with Dorsey think he’s up for the challenge of doing both. But the timing couldn’t be much worse.

Square, his small-business payments and services company, has filed confidentially to go public and is expected to unveil its S-1 soon. That raises a few key questions about how Dorsey plans to run two public companies simultaneously and how it will impact Square. Here are three:

1. How will it affect Square’s IPO? We’ll see how good a salesman Dorsey is when he and other Square executives meet with potential investors during the company’s IPO roadshow. The team will surely face questions about Dorsey’s dual role and how Square will operate as a result. Expect there to be some messaging around the strength of Dorsey’s executive team and letting the company’s financial results speak for itself. But what happens if the company gets off to a rocky start in the months after it goes public? Which brings us to …

2. Who’s really running Square? Sarah Friar is Square’s CFO, Francoise Brougher is essentially the revenue boss and Alyssa Henry runs product and engineering for the vast majority of the business. They’re all well respected, but none has emerged as the clear-cut No. 2, a position that was designated to former COO Keith Rabois, who left the company in early 2013. The current setup might work with a full-time CEO, but it’s not clear how it will with one who’s working part time. If Square doesn’t answer this question, expect some investors to keep banging the drum about it.

3. Why doesn’t Dorsey leave his Square CEO role and remain chairman? Dorsey backed himself into a corner once he said he would remain Square’s CEO no matter what. But the truth is, he didn’t really have a choice because of the timing; if he had left in the lead-up to Square’s IPO, he would have torched it. But it’s far from an ideal decision, and one I’d be surprised to see remain this way indefinitely. If Square puts together a few positive quarters in a row as a public company, perhaps Dorsey steps out of the CEO role and elevates someone from within. If it runs into trouble in its first few quarters, things could get very ugly very quickly.

In response, Square’s head of communications, Aaron Zamost, wrote via email: “Jack has never wavered from his commitment to leading Square as CEO. As a leader who sets our strategy and aligns us all to a common purpose, Jack has built a deep bench of talented senior executives to help execute on that vision. And as he has shown for the past several months, he has the ability, passion and commitment to lead both companies effectively.”

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