Jack Dorsey On Square, Product Design And Company-Building (But Not Twitter)


Robert Hof, Contributor

November 5, 2013

Even if he declined to talk about what we all wanted to hear about–Twitter, which is expected to go public Thursday–Jack Dorsey had a lot to say about his philosophy of attacking a problem and forming a company to solve it.

Dorsey was interviewed at GigaOm’s Roadmap user experience design conference by GigaOm founder Om Malik, ostensibly to talk about “redesigning the user experience of everything.” Here (sometimes slightly paraphrased thanks to my slow typing) is what he had to say:

Q: How’s Square doing?

Dorsey: We’ve had two major launches in the past six months. With Market, a business can go from local to international with the flip of a switch. Three weeks ago, we released Square Cash. You have everything in your pocket that you need to transfer money.

Q: How does Square think about experience? What is the Square way of thinking that other people should think about as well.

Dorsey: We have a principle in the company, which is “show, don’t tell.” Square resonated when we released it more than four years ago. We want to make that internally we feel great about, that feels stunning, that we want to use every day. When you’re building for yourself, it’s easy to be passionate. We’re building for ourselves still.

Q: I love the little things about Square. How do you arrive at the decision to making the receipt such a focal point of the process, for example?

Dorsey: Credit cards don’t have the greatest feeling about them. So how do you abstract that away. So we focused on the receipt. It has a map and a picture of the product that was just sold, like a cappuccino. It’s an often forgotten-about communications channel. Our mission at Square is to make commerce as easy as communications.

Q: Is there room for improvement in the utility kind of commerce like Amazon?

Dorsey: Absolutely. Point of sale systems are a big point of friction for merchants. If you make it easier and faster, people have more time to spend on other things.

Q: What do you make of Square copycats?

Dorsey: It’s easy for a lot of companies to look at the competition and react purely to them. But then you’re doing someone else’s roadmap. So we have to have the confidence and conviction in our own roadmap. We’re going to see a lot of people doing similar things to us. We like our approach, which has a lot to do with the feeling of the transaction, a feeling of the trade. Our mindset is, let’s build one cohesive stack so there are no seams.

Q: What is the narrative of the end-to-end experience you’re talking about?

Dorsey: We want to meet our customers where they are. We made a full register (for merchants), to tell them what is the most popular item when it rains, for example. Week over week if you move your biscotti jar, your sales go down. We’ve had merchants who have looked at this simple data and have realized they can make 20% more if they stay open an hour later.

Q: How have your architected our company? Do hardware people talk to software people?

Dorsey: We wanted very very simple processes and practices. We give every one of our employees complete access to anything in the company. Any meeting of substance, someone is required to take notes, and they go out to the entire company: responsible transparency. People aren’t worrying about why they aren’t in that meeting. Everything we do is to drive people back to the work.

Q: Why did you decide this openness is way to go?

Dorsey: Selfishly, it’s just the simplest thing to do. It’s hard to keep secrets. We have very very few conference rooms. Anyone can walk around the office and you can hear things that never ever would happen serendipitously in a formal meeting.

Q: How do you use data to improve your user experience?

Dorsey: Our customer service and risk operations are in the front line every day, so if you don’t include them in the feedback loop, you’re losing a lot of valuable information. We hold events around the country to bring a bunch of local merchants to talk about the challenges and successes of building a business in that city.

Q: How do you frame this idea at Square?

Dorsey: The tool that’s helped me do the best is to frame the problem and work backwards from that. We break it into the smallest problems, simple problems that we feel we can solve in sequence. We have the self-direction to know when we’re heading in the wrong direction. It’s doing the work of painting what you want to do in the world and then breaking it down into small problems you can solve and having the patience to see it through.

Q: Patience is good, but businesses are under pressure from venture capitalists to do things quickly.

Dorsey: I had the same problem with Square: Why do you think you can move money around? You’ve never dealt with financial services. It was very much and uphill battle given my background. We just addressed it head on in our pitches, and not everyone funded us. I did a slide on all the things that could go wrong.

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