In 2011 Twitter co-founder Jack Dorsey returned as head of product at the company. The catch: He kept his position as chief executive of Square, the payments company he also co-founded. He was often seen briskly walking back and forth between the San Francisco offices of both companies, located just a few blocks from each other in the SoMA neighborhood.
Four years later, Dorsey finds himself in a similar situation—only this time, he’s Twitter’s interim CEO. (On Thursday, an embattled Dick Costolo announced that he would step down after almost five years in the role.) Which prompts a new question: Will the distraction of taking Twitter’s top job weigh on Dorsey’s performance as Square’s chief executive?
On a call detailing Twitter’s changing of the guard, Dorsey said that the deep leadership teams of both companies would enable him to take on a dual role.
But there are key differences between 2011 and today. Back then, one could argue that Dorsey almost had a Square CEO in then-COO Keith Rabois. Known as a seasoned Silicon Valley operator, he’s helped build companies such as PayPal, Slide, and LinkedIn. And though he was second to Dorsey, he was deeply involved in all parts of Square’s nascent business and generally well-liked by most employees. (He once likened his role at Square to “an emergency room doctor” that triaged and fixed issues.)
Rabois left Square in 2013. Sarah Friar, then the company’s CFO, ended up taking on much of his operational baggage temporarily. (Friar was previously an analyst at Goldman Sachs and SVP of finance at Salesforce.) Several months later in 2013, Square hired Françoise Brougher from Google to fill other former Rabois responsibilities; she leads business, sales, and operations.
One question, given the Twitter news: Just how many additional hats Brougher and Friar might wear with Dorsey splitting his time with another company.
Another: How the shift will impact the rest of Square’s bench, which also includes Gokul Rajaram (an early Google and Facebook engineer who manages Square’s consumer products e.g. the restaurant-delivery service Caviar), Alyssa Henry (a former Amazon engineer who oversees the company’s business and merchant-focused software such as Square Register), Kevin Burke (Visa’s former chief marketing officer, now tasked with customer acquisition), Jesse Dorogusker (formerly of Apple, now leads hardware), and former Googlers Brian Grassadonia (runs Square Cash), Dana Wagner (general counsel), Aditya Roy (chief people officer), and Aaron Zamost (communications chief).
Square clearly has a far deeper bench than it did in 2011, and all of its senior executives seem capable to lead their own operations. What is unanswered is whether this team can coordinate well enough to allow for Dorsey’s absence or whether one can step into a broader leadership role, similar to Rabois in 2011, to fill his shoes.
It’s a critical step. Square is at a turning point in its six-year history, one proving that strong product and business leadership isn’t just nice to have but necessary for its future success. After suffering what some called an identity crisis, the company refocused to provide services to small- and medium-sized businesses, a move that has created additional revenue streams. (Previously, it made money solely by taking a percentage from every transaction processed by a merchant, a business known to be rather low-margin.)
It now offers cash advances (via Square Capital), peer-to-peer payments, booking services, disputed purchase protection, analytics and marketing tools, and instant deposits for merchants through its Register app. Last week, Square debuted new hardware that will accept mobile payments from iOS and Android devices. The company’s data efforts and risk analysis have also been a product focus.
Meanwhile the company has shuttered several consumer-oriented products in recent years, among them Square Wallet and Square Order.
There have been unconfirmed rumors of acquisition interest in the company, but Square last fall raised $150 million in new funding at a rumored $6 billion valuation. An IPO has long been discussed as a possible outcome for the company; sources close to the company say that, contrary to past reports, Square is actually making money and could be IPO-ready later this year.
All eyes on Dorsey, then. It’s unclear how long Dorsey will continue as Twitter’s leader as its board searches for a permanent replacement—or even if Dorsey is in contention for the top spot. (He’s not part of the CEO search committee.)
Jack Dorsey as the next double-CEO, à la Tesla and SpaceX’s Elon Musk? Stay tuned.
