ShopKeep raises $25M as it aims to replace aging Windows XP point of sale systems

Expect to see more iPad-powered cash registers in the near future.

ShopKeep POS, a New York City-based startup that uses iPads and a cloud analytics platform to replace traditional cash registers, has announced a new $25 million round of funding led by Thayer Street Partners.

With ShopKeep’s third round of funding, founder and CEO Jason Richelson told me the company plans to continue its mission of helping small businesses by “using the power of the cloud to deliver actionable analytics.” The company’s platform can also help you manage inventory and keep track of employee hours.

Richelson brought up another intriguing opportunity for ShopKeep: replacing all of those older point of sale systems powered by Windows XP. Now that Microsoft has officially ended support for XP, stores are technically out of compliance if they use an XP-powered register for transactions.

“Because of [the] expiration of XP, there’s a really big catalyst to retailers all over to change their POS system, they need to upgrade,” Richelson said. “We really want to be there for them.”

ShopKeep costs $49 per register a month, plus the cost of an iPad and other point of sale equipment (which it also sells in bundles starting at $399).

Founded in 2008 at Richelson’s wine store in Brooklyn’s Forte Green neighborhood, ShopKeep was initially inspired by his own frustrations with existing point of sale solutions. Given his background as a small business owner, Richelson told me, ShopKeep emphasizes customer support, whereas other point of sale solutions from Intuit and Square may be more technology-focused.

ShopKeep now has more than 10,000 customers across the U.S. and Canada, and it has processed more than $1.8 billion in payments annually (based on its existing run rate). The company has tripled its revenue and customer growth every year for the past three years, Richelson told me. It spent much of last year building up its sales and marketing team.

ShopKeep has now raised $37.2 million in total. Existing investors, including Canaan Partners and Tribeca Venture Partners, also participated in this latest round.

Richelson’s ultimate goal? He wants ShopKeep to be the next billion-dollar SaSS company in New York City. But with things heating up around every aspect of digital payments, there’s a good chance ShopKeep could be snatched up by a company like PayPal (which it already partners with) or Google before that happens.

“The point of sale software space is a multibillion dollar industry,” Richelson said, denying any interest in a potential acquisition. “There’s a precedent to be a very big company here for ShopKeep. That’s our focus, with the goal of supporting independent brick and mortar retail.”