A former Apple design chief explains how Jack Dorsey convinced him to quit and join Square

Jesse Dorogusker

Jesse Dorogusker is hardware lead at Square, the mobile payments company led by Twitter CEO Jack Dorsey.
In 2011, Dorsey persuaded Dorogusker to leave his role as a director of engineering at Apple, and instead join Square – which was just two years old at the time.
Dorogusker spoke to BI about why the left Apple for Square, the 'visionary' Dorsey, and why Square's latest product, the Terminal, could transform how small businesses operate.
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In 2011, Jesse Dorogusker was a director of engineering at Apple, tasked with designing accessories for its glossiest, glassiest gadget yet: the iPad. It was a boom time for the company, with 32 million iPads sold in the product's first full fiscal year on sale, not to mention some 72 million iPhones.

Talk of 'peak iPhone' was years into the future, and Apple had started the year hitting a $300 billion market cap. Apple was the company for any Silicon Valley engineer to work for.

But Dorogusker – who today serves as hardware lead at mobile payments fintech Square – had other ideas. Or, to put things more accurately, those ideas found him.

Dorogusker worked at Apple during its renaissance but was won over by Dorsey

"I joined Apple in 2003, and it was early iPod days," he recalls in an interview with Business Insider. "The iPod team was about 35 people. It was very separate from the computer company. We were the music startup inside the company."

It would have been an exciting time. The iPod was a revolutionary device, capable of fitting millions of songs onto a beautifully designed, tiny gadget. Apple would cement its renaissance with the launch of the iPhone, four years after Dorogusker joined the company.

original ipod 2001

"I really worked through the iPod era, into the iPhone era, into the iPad era," he says. "That was over eight years, [during] giant growth in the company; giant growth in the product line. I think we had sold two million iPods when I started, and probably finished up at over a billion. I just learned a tonne of tremendous experience, and I have tremendous respect for them. But then I met Jack Dorsey."

Dorsey is the chief executive and founder at Square. It's not his only day job — he's also the CEO of Twitter.

When Dorsey hired Dorogusker in 2011, Square would have been two years old. He would also have just started as Twitter's executive chairman, after Dick Costolo has replaced Evan Williams as CEO in 2010.

Jack Dorsey

"I didn't know Dorsey before I met one of his executives, [after] just a casual intro from a friend," Dorogusker says. "After talking to him for about 15 minutes, which I thought was just a meet and greet, it started to feel like an interview. I thought 'What's what's going on here?' Then the executive said 'I have an idea: you're going to meet Jack this week.'

"So I met Jack later that week. And Jack told this tremendously compelling story about financial inclusion; economic empowerment; building tools for small business owners – and how hardware could contribute to that.

"He had a very small hardware team at the time, and he had one piece of hardware: a little magnetic strip card reader that plugged into the audio jack over the phone. He aspired to do more, and better, and that story was tremendous."

Dorogusker was promptly hired to lead Square's hardware team – a role he still occupies today.

The result is Square's line-up of payment products, which allow small businesses to accept card and contactless payments, as well as carry out a host of back-end tasks. You can see Dorogusker's influences on those hardware products — all clean lines, and sleek white gloss.

Asked about the departure of Apple's influential design chief Jony Ive, Dorogusker simply says: "Jony and his team were tremendous. I've never seen anything better. It was totally inspirational: a lifetime of lessons in watching the way he works and the way his team works. It shows in decades and decades of the best products the planet's ever seen."

The Terminal is an all-in-one payments and point of sale system aimed at helping small businesses run more efficiently

Dorogusker says the move from a casual conversation with Dorsey to take over Square's hardware division was "surreal." But he describes his current boss Dorsey as a pragmatic man.

"Jack is a visionary, and very direct," he says. "Our first meeting was great. He said 'Here's what we're trying to accomplish. Here's the here's the kind of thinking I want to bring to company. We need people who can leave in that direction.' We had a good chat.

"The the idea of waking up in the morning and building tools for small businesses was compelling then; it's compelling; it'll be compiling deep into the future. [Small businesses] are a really fun audience to build for."

The Terminal – an all-in-one payments device that looks like a traditional card payment machine, but sleeker – is Square's latest attempt to do just that.

Square Terminal

Dorogusker calls the Terminal Square's "first all-in-one payments and point of sale system, from the ground up." It can carry out a whole range of payment-related business operations, from managing items and taking all forms of payment, to printing receipts. It lets business owners send invoices, review their transaction history, and review month-over-month and yearly sales.

It's still familiar enough, though, that anyone used to "clunky old keypad machines" will still find it easy to use, Dorogusker says.

He adds that feedback from business owners has been positive, particularly regarding the Terminal's size and efficiency. As he puts it, small businesses typically have to deal with "a 20- or 30-page statement at the end of the month" that enumerates every fee and every charge."

"In contrast, we charge one flat rate; we have no long term contracts," he continues. "You can buy the Terminal outright, and not be leasing it from us and paying 10 times more over the lifetime of the product. That's really to lower the barrier to entry for small businesses, but it's been surprisingly attractive to larger businesses who just want clarity.

"The way we run our business at Square is real-time monitoring of everything that's going on. Small businesses typically haven't had those tools. In fact, coffee shops usually know how many cappuccinos they sold by counting dirty cups. For the first time, a small business can do it all in software."

The release of the Terminal comes at a time of impressive growth for Square. The firm's total net revenue for the second quarter of 2019 was $1.17 billion, up by 44% year-on-year. The firm's net losses increased slightly to $6.7 million, from $5.9 million the prior year.

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