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Meet Alyssa Henry, One of Jack Dorsey's Secret Weapons at Square

Henry, who previously ran a huge chunk of Amazon's AWS unit, now runs Square's largest division.

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.

Alyssa Henry has largely managed to stay out of the spotlight while building a long, impressive career in the tech industry. That’s starting to change.

Henry joined Square last spring from Amazon, where she ran a giant chunk of AWS, the cloud computing and storage business that has become a $5 billion juggernaut. In her new role, she has quickly established herself as one of the main reasons why some people close to Square believe Jack Dorsey could get away with being CEO of both Square and Twitter indefinitely.

And if Dorsey ever leaves his CEO role at Square — a possibility he’s rejected not once but twice — several insiders believe she should be on the short list of internal candidates to replace him.

Henry joined Square in April 2014 with little fanfare in Silicon Valley. Part of that could be because she came from Seattle, where she worked eight-plus years for Amazon and more than 10 at Microsoft. She most recently ran all of AWS’s file storage businesses, including its core S3 product.

Henry was first hired to oversee the engineering teams working on Square’s infrastructure and payments platform. Her role grew larger late last year when she took over responsibility for all design, product and engineering teams building software products for Square merchants.

At AWS, she loved the fact that small Internet companies could run their websites inexpensively with Amazon’s software products. She was attracted to a similar mission at Square.

“I see Square on a very similar mission but for non-tech entrepreneurs,” she said in an interview.

Henry now leads the largest division at Square, overseeing several hundred employees. As Square gears up for an IPO — which the company has yet to confirm — a lot is riding on the ability of Henry’s unit to build up a portfolio of products with strong profit margins that would help Square continue to diversify.

In the last year, Square has unveiled a host of new products that it tries to upsell to business owners who originally came to Square for its core checkout software and payment processing service. There’s a payroll product, email marketing tools and a new instant deposit feature that allows businesses to access funds from customer payments right away. Square is also providing cash advances to merchants that now total $1 million a day, and could look to become an actual lender in the future.

One of the key changes Henry has made to manage this growth was structural, she said: Reorganizing her teams into three divisions around payments, financial services and marketing services.

“What you want to make sure is you’ve got teams that have clear customer focus: Who are we building for and why,” Henry said. “Making sure that was really really clear. And then as teams grow, you want to make sure you get that decision making and ownership pushed down as far as you can go.”

To live up to its $6 billion valuation and hype, Square will likely need several of these new business ideas to take off. If they do, a lot more people will get to know Henry.

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