Jack Dorsey Looks to Simplify Commerce With Square

As chief executive officer of the forward-leaning payment firm, his goal, while still in the future, is to make the technology invisible.

Jack Dorsey

NEW YORK — Jack Dorsey sees retail at a digital tipping point.

This story first appeared in the January 16, 2014 issue of WWD.  Subscribe Today.

And, as chief executive officer of the forward-leaning payment firm Square, he wants to be at the nexus, rearranging the relationship between store and shopper while simplifying commerce.

It’s an audacious goal, but it’s the kind of change Dorsey’s pulled off before as chairman and cofounder of Twitter, which has reinvented everything from small talk to revolutions.

The five-year-old Square lets anyone with a smartphone accept credit card payments and offers a suite of features that can help retailers communicate with customers, identify them personally as they walk into the store and eliminate the often arduous checkout process.

Dorsey said the digital landscape will change rapidly over the next two years as consumers and merchants both push for enhanced technology.

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“There are two sides of the counter expecting a lot more,” Dorsey told WWD during an interview at Square merchant Utility Canvas in the West Village here. “It’s taking more and more of the time away from the transaction. There’s an experience that will become faster, easier and cheaper, and merchants will be able to communicate with their customers more.”

Dorsey’s goal, while still in the future, is to make the technology invisible.

“Technology is not something you obsess over,” Dorsey said. “It’s something that works just in time. The way I use Twitter is I get push notifications. You have to be in the world, [and] that’s why this technology is so important. [Square] allows you to be more in the world and focus on [the consumer] entirely. You don’t think about electricity — but we depend so much on it. That’s a true utility. You don’t even think about it unless someone points it out or it fails — which we will not do.”

Dorsey makes a point of unplugging regularly, despite his lofty position in the tech world. The ceo said he walks five miles to work every morning in San Francisco, maintaining a steady routine, always stopping at the same coffee kiosk.

But at work he’s going full speed.

Industry estimates project that Square will run $30 billion in transactions this year, and an initial public offering is said to be in the works for the near future and could value the firm at about $5 billion.

This would be the peak for most companies — but for Dorsey it might just be the beginning.

To date, Square has raised $341 million in capital from the likes of Starbucks, Sequoia Capital and Richard Branson.

And luxury titan François-Henri Pinault is believed to have gotten in on the action and taken a stake in Square through his Groupe Artemis investment vehicle. Dorsey and Artemis declined to comment, but if Pinault is such a believer in Square, it’s easy to imagine Gucci and the other brands at Kering, where Pinault is chairman and ceo, taking a close look at the technology.

Dorsey laughed off the talk of an IPO.

“It’s not something we think about in the company,” Dorsey said. “We’re not building a product for an IPO. An IPO is often seen as the goal, but it’s really just an event; it’s a fund-raising event. We’ve had fund-raising events, so it’s no different than that. All we can do is have a discipline so we can make a choice if the time comes.”

Square already works with millions of merchants — from independent coffee shops to Burberry — who all pay a transaction fee of 2.75 percent per swipe. Dorsey said the payment platform sees over one billion visits to participating merchants per year, spanning the U.S., Canada and Japan.

So far, Square has focused much of its energies on the independent retailer. “We had features that resonated with smaller folks,” Dorsey explained. “We had to start somewhere.”

But then Starbucks and Uniqlo approached Square — and Dorsey said Square can scale up and work for both artisans and the largest retailer.

It starts with the receipt.

“The goal of a receipt is to bring people back,” Dorsey said during a keynote address at the National Retail Federation’s Big Show Wednesday. “We talk a lot about offline, online and mobile commerce, and this is the one thing that connects them. This is commerce, and no matter where you are as a customer, this is how you engage with the store and the merchant more.”

He added: “We’ve been putting a lot of emphasis into seeing this receipt and this product as a way to communicate back with this customer and build a communication channel between merchant and buyer.”

This focus led to the introduction of Square Wallet in 2012, which helps bring the consumer and seller closer together, allowing for a highly personalized experience. Users log their financial data into the Square Wallet app and the information is saved so Square merchants, for instance, can know not only when a Square user walks in the door, but what their favorite order is.

And Dorsey’s Square is also exploring other frontiers in retail, with features catering to both the merchant and the shopper.

The payment platform, for instance, can do away with what Dorsey described as the “mechanical aspects” of commerce. Instead of waiting in line and paying at a cash register, the consumer simply leaves with their purchase and is sent a push notification (or receipt) on their mobile device, asking if they wish to engage further.

Last year, the company launched Square Market, an e-commerce destination for independent retailers; Square Cash, an instantaneous way to e-mail money to another user; Square Register, which streamlines the checkout for quick-serve restaurants, and Square Stand, hardware that transforms an iPad into a point-of-sale system for the brick-and-mortar world.

Square’s business model also sits directly in the center one of the burning issues of the day in retail: cyber security.

Asked about the woes at Target Corp., where digital thieves stole data on more than 100 million customers, Dorsey maintained that privacy and security aren’t an endpoint. He said an organization can never build the most secure system — all they can do is be 10 steps ahead of their peers and provide people with “simple and intuitive tools” to control their own privacy.

“We can’t see it as an ultimate destination because it’s constantly evolving,” Dorsey said.