The way retailers handle purchases is changing rapidly because of electronic payments, New York-based ShopKeep is betting it can help push this evolution even further. The so-called point of sale is no longer limited to traditional cash registers built around PC-based hardware and software. Companies such as startup Own Point of Sale in San Francisco and point-of-sale giant NCR offer software to process sales transactions on tablet devices.

The idea seems to be getting more traction in the industry as retailers replace their old registers with iPads to process sales. ShopKeep wants to position its technology to make retailers lives easier at lower costs. Many retailers today use point-of-sale platforms based on the old-school Windows XP operating system that’s specially configured to have touch screen monitors, says Jason Richelson, CEO and co-founder of three-and-a-half-year-old ShopKeep, Such units can cost about $3,000 each by his estimates. He believes drastic changes lie ahead in terms of the technology that retailers want. “A huge upheaval is going to happen over the next three years in the point-of-sale space,” he says.

Given the costs of traditional systems, Richelson sees a place for his company to offer retailers a less expensive option on comparatively lower priced tablets. The ShopKeep platform is used by small and midsize retailers, he says, as well as larger companies.

Investors including Tribeca Venture Partners, TTV Capital, and Contour Venture Partners are backing ShopKeep’s plans to disrupt the POS scene.. In January, ShopKeep announced it raised $2.2 million in a Series A round.

Richelson says his company is generating its own revenue and expects to be break even on cash flow within the next year. “We’re getting close to paying our bills” he says.

ShopKeep offers two main types of software. The management platform runs in the cloud and is accessible through the Apple iPad, Google Android-based tablets, and other Web-enabled devices. Retailers can use this software to oversee inventory and other store-related data via the Web.

The technology gets a bit more specialized when it comes to handling sales transactions. Small businesses—many have just one or two stores—that sign up with ShopKeep must use an iPad app if they want to conduct transactions with the platform. The iPad can be mounted on a counter much like a traditional register. ShopKeep sells iPads packaged with additional equipment such credit card readers to charge consumers. Richelson says ShopKeep largely supports the iPad because of the device’s widespread adoption among small businesses.

A Java version of ShopKeep’s sales software exists for Android tablets but he says that platform is only available for larger, enterprise customers.

Richelson is not alone seeing tablets as a potential future for point of sale systems. Square in San Francisco for example makes a credit card reader that functions with Apple iOS and Android devices. Square also offers an iPad app for processing sales.

Embracing new types of electronic payments is part of ShopKeep’s long-term strategy. At select coffee shops, ShopKeep’s software is set up to accept payments from customers who want to use their PayPal accounts. The platform may expand to include electronic payments from such services as Dwolla and LevelUp, Richelson says.

ShopKeep’s roots extend to a wine store he opened in 2004 called The Greene Grape in the Fort Greene section of Brooklyn. Some of the challenges he faced as a retailer inspired the creation of ShopKeep. “I was having trouble with [computer] servers in several of my stores where they kept crashing,” Richelson says. Fixing those databases himself became a hassle. He also wanted a way to monitor his stores’ sales from his home office. “I could not easily see what was going on each store,” he says. “That’s not the way things work in today’s world.”

Back in 2008, he looked for cloud-based point-of-sale systems to resolve his dilemma, but he did not find anything that fit his needs. That inspired the development of ShopKeep. Early funding for ShopKeep came from the stores. Richelson has since handed over the reins for The Greene Grape stores to a partner.

ShopKeep has a staff of 30 and plans to add up to 15 more hires, thanks in part to its latest funding. The company also moved into a 4,300-square-foot office on Broad Street at the end of June compared with the 2,100 square feet of space it previously occupied within the same building. Richelson says he plans to stay in the space at least one year while hiring more staff. He expects his company to continue growing as retailers adopt new technology. “Tablets will be replacing those [point of sale systems] over the next three to five years,” he says.

Independent retailers everywhere are looking for ways to improve the shopping experience, extend loyalty programs and better engage with their customers. Now customers can check in with PayPal and check out at the register at nearly 2,000 merchants with the iPad POS solution from ShopKeep POS. With the launch of the PayPal partnership, nearly 2,000 merchants nationwide who use ShopKeep POS as their POS system can now accept PayPal cardless payments at the flat rate of 2.7 percent. ShopKeep’s cloud-based solution enables small businesses to add PayPal as a payment option into their existing point of sale systems without upgrading hardware.

Because of the cardless nature of the payments, it enables lines to move faster and because it is wireless, it has the ability to drive further traffic and sales to merchants and consumers. The PayPal customer simply checks in at participating merchants with his or her PayPal iPhone app and, at checkout, the customer’s name and photo appears on the ShopKeep POS iPad register. The cashier identifies the customer, finalizes the transaction, and the customer is automatically checked out of the store and receives a receipt by email. This point of sale solution enables brick and mortar retailers to efficiently ring up sales, manage inventory, build customer loyalty programs and remotely access real time sales.

I opened my first store in 2003. It was a wine store in Fort Greene in Brooklyn, called The Greene Grape and I realized pretty quickly that I had no idea what I’d gotten myself into.

I learned that when you run your own place, you are responsible for absolutely every aspect of it. You are running the books, managing inventory, training employees, looking into marketing promotions, forecasting for the coming months, trying to predict cash flow, cleaning the windows, scrubbing the floors and generally worrying that you’re forgetting something important.

In short, I found out that small business is hard. The hours are long, the worries constant and the market can seem incredibly fickle. It’s no secret that the failure rate for new small businesses in America is alarmingly high; across the country some 25 percent of new restaurants close their doors within the first year and 60 percent are gone within three years. These chances of success don’t exactly invite long nights of care-free and dreamless sleep. And yet, it is exactly the ability to break away from the worry and the day-to-day grind that enables a small business person to make good decisions and increase their chances of success.

One of the most overused quotes in business is, ‘Genius is 1 percent Inspiration, 99 percent Perspiration’. Young entrepreneurs are told that the right idea is only a small part of the equation and that, in reality, success comes from putting your nose to the grindstone and working long hours. Over the years, I’ve been exposed to a lot of small businesses, both as a merchant and as the founder of ShopKeep POS, and in my experience, hard work alone just isn’t enough. Of all those retailers that have been forced to close their doors, only a tiny percentage did so because of a lack of effort. The real danger to small business isn’t putting in enough hours behind the counter, it’s putting in too many.

The key to sustainable success lies in the 1 percent inspiration. And by inspiration, I don’t mean the sitting in a bubble-bath, screaming a Eureka moment favored by inventors and scientists; I mean the ability of an entrepreneur to make enough time every day to immerse themselves in the details of their business and make smart, insightful decisions. Not every moment is going to turn out to be game changing, but enough intelligent and thoughtful decisions in a row tend to equal a successful enterprise.

Lucky for us, there are a number of affordable, cloud-based programs available that can really help make day-to-day processes more efficient, give you more time, more information and generally get you closer to making smarter business decisions. I’m a strong believer in cloud-based applications and we use them everyday here at ShopKeep POS. I’ve listed a few of my favorites below.

WhenToWork makes it easy to schedule shifts, see when employees are working and fill empty slots with those who have availability. It keeps all employees in touch, so it makes the whole process much smoother. No more forgetting who’s supposed to open tomorrow.

For small business owners, that nightmare of you falling from a high cliff is often replaced by a tower of paper tumbling onto you, waking you up right as you are about to be buried. Use Bill.com for payables management and get some sleep. You and your accountant will have everything you need to manage day-to-day finances and cash flow.

I would also highly recommend FreshBooks which offers the ability to create and manage invoices, estimates, expenses and projects all in one place. It’s a really useful and easy to use tool for keeping the financial side of your business in good order. They also provide really great customer support which is something that is really close to my heart.

One thing small business owners sometimes miss out on are those amazing phone systems favored by larger corporations where everyone has the same prefix, and it’s easy to access the phone number of any employee. Ring Central offers an inexpensive cloud-based phone system that does what those legacy systems do, but even better. It also works with mobile phones.

For brick and mortar retailers looking to find a powerful point of sale system that doesn’t break the bank, it is now possible to get set up with a full-service POS system that includes an iPad register and stores data in the cloud. ShopKeep POS is designed to empower small businesses by giving them tools like advanced data analysis and new technologies like mobile payments that they historically have never been able to access.

There are an incredible number of resources available to the small business community to help them reduce stress, find more time and generally be smarter about how they channel their business efforts. Additionally, a lot of these services are able to integrate with one another — which can save you even more time.

Even with all the right support, It’s still a long, hard road to business success. That’s why ShopKeep POS has joined Open Sky in sponsoring The Small Business Breakthrough, a national movement to celebrate, recognize and promote small businesses and entrepreneurs in the United States. If you’re reading this and you want to support your favorite local business, you can nominate them for a Breakthrough Award on bigstagebigresults.com and then share the nomination via social media using the hashtag #sbbreakthru.