He’s worked in finance on Wall Street, as a software analyst at PricewaterhouseCoopers, and as founder of a dotcom funded in 1999 with $10 million. But Jason Richelson attributes his success today at the helm of a 10,000-customer, 100-employee software company to his experience running a wine shop in Brooklyn.

Richelson is co-founder and CEO of ShopKeep, a provider of cloud-based iPad point-of-sale and small business management software. He developed the product in 2008 in the back room of his store, the Greene Grape, to resolve his frustration with a Microsoft Windows point-of-sale system that he says contracted viruses and crashed often.

When most retail shop managers go in search of a POS system, they consider two choices, he explains: Buy a cash register for $300 and a credit card terminal for $200, or invest in a Microsoft or QuickBooks system for upwards of $5,000. ShopKeep users instead invest $1,200 for an iPad, stand, swiper, and software, and pay $50 a month to subscribe to ShopKeep’s data analytics and on-call customer service.

Richelson says his system reduces the hazards of accepting cash and credit cards on old-school registers that lack any customer tracking mechanism. And it eliminates the virus and crash issues that come with other operating systems. But more importantly, he says, ShopKeep adds value by accumulating a retailer’s data on the cloud and returning useful analysis via the ShopKeep dashboard on a smartphone or web browser.

He sees his business as being at the leading edge of a sea change in how the retail and restaurant industries transact. To be sure, ShopKeep is much more than an iPad cash register: “We’re about helping our customers run a better business—our software helps them manage inventory and employees, track customers, do e-mail marketing, and integrate with their accounting software,” he says. “And the power of cloud-based analytics gives them data to make smarter decisions.”

For instance, he says, “Say your wine store just got in a great Cabernet Sauvignon. ShopKeep can pull up the names and email address of every customer who has purchased a similar product and send them a heads up that the new wine is in stock.” Or, the tool can let a manager know how heavy sales are by the hour—crucial information for efficient staffing in restaurants and cafes.

The more data a business gathers, the more useful the analytics become, Richelson points out. And as new technology comes along, he says ShopKeep will change with the times. “When EMV chip and PIN comes to the U.S., we’ll enable it,” he says. “If a better way to do analytics comes along, we’ll employ that.”

Winning technology aside, Richelson says his company’s core values are what keep ShopKeep customers loyal. “Retail is a service business, and the best advice for any retailer is to make sure every customer has a great experience in your store. We treat our employees and customers the same way. We think of ourselves as a service business.”

In fact, Richelson says his management philosophy—some of which he shares in an online resource called Small Business 101—evolved from his retail experience. “Building a business is all about people, and about understanding how to make people happy and motivated,” he says. “The most important thing is to make sure our team is happy and loves to come to work every day. A lot of companies don’t think that way, and it took me a long time to learn that.” He gleaned many ideas, he says, from studying Warren Buffett and great companies such as In-N-Out Burger, Whole Foods, and Zingerman’s.

How does he keep employees motivated? “We have a big, open office environment, and I sit out on the floor with everyone else. It’s about them being able to talk to me and really understand our vision. It’s up to me to let employees know what a hard thing it is to open a retail business,” Richelson says. “When team members understand that ShopKeep exists to help small businesses and that customer care is super-important, they know it’s a worthy goal and then they’re really happy to come in.”

With revenues and customers tripling year-over-year since 2010, and a $25 million round of venture funding for a ShopKeep expansion raised just last week, the approach seems to be working.