Square’s Man On The Street Desperately Wants To Know The People Behind Your Business

Andy Santamaria’s job is “understanding the story” of each of the living, breathing merchants Square works with.

Square’s Man On The Street Desperately Wants To Know The People Behind Your Business

People have all sorts of unusual obsessions or infatuations; for Square’s Andy Santamaria, it always happened to be small business. Santamaria worked for a while at a coffee shop in Minneapolis, which whetted his appetite to learn how small businesses worked. He’d pass by a pizza place, or a clothing shop, and he’d have to know how the place operated. “I’m very curious. I’m interested in almost everything,” he tells Fast Company. So Santamaria started a blog in which he interviewed small business owners. His first subject: a photography studio that took pictures of merchandise for Target.


“I just thought it was the coolest thing ever,” he says. He started interviewing cupcake bakers, interior designers, you name it. “It was so much fun. I just decided to reach out to just about anybody.” Within a year, he was interviewing the likes of Tony Hsieh, the CEO of Zappos, and soon ad agencies were hiring Santamaria to help them tell the stories of their clients.

It’s this passion for small businesses and their minutiae that Santamaria brings to his current job at Square, where he holds the position of “Small Business Research Lead.” Santamaria is Square’s man on the street, pounding the pavement, fostering relationships with small businesses, and serving as a conduit for information between the payment company and its clients. Santamaria always seems to be out around the Bay Area, or on the road–he reckons he spends less than half his time at the office.

It’s his job, in essence, to understand whatever Square’s clients may be going through. “When somebody’s having a problem balancing a cash drawer, I sit down and learn how to balance a cash drawer,” he says. Eventually, he translates the frustrations of small business owners vividly back to Square’s own engineers.

He’s something like Square’s in-house reporter; its traveling bard, even. “I think that understanding the story of the business–the story of the people–is really important for our engineers,” he explains. “They don’t want to just hear, ‘Oh, I found 20 bugs.’ But if I can tell them a story that makes sense to them, that’s a more effective way to get at the problem.”

For instance: without Santamaria’s lobbying, it might have taken Square longer to implement what for many small businesses is a key feature–the ability to give discounts. (It’s a feature that finally rolled out last year.) “To an engineer, this doesn’t make any sense–why include a feature to let businesses make not as much money?” says Santamaria. And yet it’s something Santamaria kept hearing, again and again, that small businesses wanted, as a way to reward new and loyal customers alike. “It’s more of an emotional feature,” he explains. The latest software from Square lets merchants give discounts custom titles (“Friends of Bob,” “You Look Great Today,” or what have you) that appear on the receipt.

Santamaria’s enthusiasm for the gem of a small business is so well known at the Square office, that’s it’s come to acquire a nickname: “Andy’s weekend.” Santamaria routinely comes in after a weekend gushing about a new place he’s discovered; “I’m very particular about the places I go to, very purposeful about it,” he says. Now, “if they’re gonna go out to do something,” explains Santamaria, “they say, ‘Is this like an Andy’s weekend kind of place, or just a normal place?’”


His knowledge of Square’s customer base is particularly encyclopedic, says Lindsay Wiese, Communications Lead at the company. A journalist might call with a weirdly specific request–“Do you know a merchant who switched to an iPad as point-of-sale device just for aesthetic reasons?”–and Santamaria will often immediately be able to come up with something. Recently, Wiese was trying to dig up esoteric Square clients; she needed to go no further than Santamaria, who was ready with a car-and-dog-washing business, which is exactly what it sounds like.

Mitt Romney famously said that corporations are people; for Santamaria, that dictum is more vivid and credible than for most. Every small business, Santamaria thinks, is the story of the people who founded it, who run it. Get him talking, and soon he’s telling you about the husband-and-wife team–he a cop, she an ex-corporate lawyer–who decided to open a bakery out in Sunset Park in San Francisco to have more time to spend with their kids (it’s called Devil’s Teeth, and has “amazing beignets”). “There’s a certain type of courage a lot of small businesspeople have,” says Santamaria.

He intends to be one of them, someday. “I have various ideas I want to work on,” he says: he’s fascinated in shirt-making, for instance, but would just as soon have a little tapas and wine bar.

“I’d be the owner who’s always there, trying to make sure people are happy,” he says. “I think I’d be good at that.”

About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal.