With its latest $25 million financing, ShopKeep POS has come a long way from being the cobbled together point of sale software service for a single wine shop in Brooklyn’s leafy Ft. Greene neighborhood.

The company’s history began six years ago with Jason Richelson’s frustration over finding a good enough point of sales software to run his expanding empire of wine shops and high-end grocery stores.

From those humble beginnings the company has grown to become the software vendor managing point of sale transactions for over 10,000 stores with over $1.8 billion in receipts.

“We used the city’s resources to get started, and after building a prototype in my wine store we moved to a city-sponsored co-working space called The Hive to get on our feet,” Richelson said.

For the company’s first two-and-a-half years Shopkeep was backed by receipts from Richelson’s wine businesses and grocery stores, before raising a $2.2 million seed round from Tribeca Venture Partners, TTV Capital, and Contour Venture Partners. A $10 million Series A followed in 2012 led by Canaan Partners.

Now Thayer Street Partners has come on to lead the Series C, with participation from all of the company’s previous investors and additional support from individual investors Tom Glocer, the former chief executive of Thomson Reuters and a Thayer Street advisory board member, and Matt Coffin, the founder of LowerMyBills and a frequent Thayer Street collaborator.

The company has also expanded beyond its Brooklyn borders to fancy new digs in Manhattan’s SoHo neighborhood and even opened an office in Belfast to begin its international expansion. Richelson says a West Coast office is also in the cards, given the company’s most recent round of funding.

Beyond customer acquisition and geographic expansion, ShopKeep has also been busy with launching new products. In January it started selling its mobile point of sale software and released a new design interface for iPad point of sale software.

“What we’ve done with ShopKeep is we’ve moved all of your data into the cloud and in the cloud you have the ability to do a whole bunch of data analytics,” Richelson says. “An example of what we’re doing there is very simply our dashboard app. Now in the palm of your hand you can see how much you’ve rung up in sales, and how much is in your cash drawer. Storeowners understand in real time how their business is running.”

“In my store, if I wanted to understand my inventory turns I had to go down to my basement run a report and export it into excel.”

ShopKepp charges $49 per month for each register that uses its software and the company also sells all the point of sale equipment a small business would need to get off the ground including a stand, a swiper, a receipt printer. “We see it as a service,” says Richelson. “We just sell it to our customers and deliver it and help them set it up remotely.”

One of the biggest opportunities Richelson sees for ShopKeep and other point of sale software vendors going forward is the imminent demise of support for Windows XP. “There are millions and millions of transactions that run on Windows XP and are going to have to get replaced,” he says. “Small brick-and-mortar retailers are going to have to take some time to understand what’s going to happen with Windows XP,” since Microsoft ended its support for the operating system.

As ShopKeep continues to expand, Richelson has his eye firmly set on one prize. “I’m really happy to have been able to start this business in New York City,” he says. “There are no billion dollar software as a service businesses that have been born in NYC. That’s our goal.”

Alissa McCue

Alissa McCue

Alissa McCue has over 10 years of marketing and public relations experience working for top brands in retail and technology. As Senior Manager of Public Relations at ShopKeep, a leading iPad Point of Sale System, Alissa is focused on highlighting ShopKeep's major achievements and thought leadership in the POS and technology space for independent businesses.