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The Future of Retail: Our Interview with Shopkeep’s Jonathan Bensamoun


This week we’re sitting down with Jonathan Bensamoun, head of product and resident retail guru at Shopkeep. Shopkeep is “point of sale software” (POS), ie the software that drives the registers and inventory when you buy at retail stores. Unlike most POS systems, Shopkeep is cloud based, runs on iPads, and (gasp) is actually fun to use. Cool stuff.

Read on for our full interview.


VM: Before we get started, what’s your pitch? What is Shopkeep, who is it for, and why is it awesome?

JB: ShopKeep POS is a cloud-based iPad POS system for retailers designed to be the simplest way to make smarter business decisions.

To that end, we are expanding on the traditional notion of a point of sale system. Merchants would like to have tons of tools and services available to make their business more efficient and increase demand such as couponing, delivery, advertising, mobile payment.We believe that the platform we are building is the centerpiece of this business architecture. Using all these services becomes so much easier and smarter if they are associated with transaction and inventory data – that’s why we like to think of ShopKeep POS as a technology integration platform.

Also, storing data and having it available only in your store is a risk and a daily burden for merchants. Data should be stored securely, accessible from anywhere and merchants should not have to worry about it.

We do all this on a tablet with a slick UX/UI. Every tap is anticipated, measured and optimized. Next time you order a burger try to count the number of time the cashier taps the screen – we are changing this.

VM: On the one hand, point-of-sale systems are just tools, like any other piece of software. On the other hand, they’re client facing, meaning they’re central to a store’s brand and experience. How do you view Shopkeep playing into that? If I’m a small business owner, what are the implications for my customers when I adopt a system like this?

JB: The POS is right in front of the customers. ShopKeep is good looking and fun to see in action. Customers are curious, ask questions, and merchants love using it. Our merchants develop an emotional relationship with their ShopKeep register.

VM: SaaS has been around for over a decade now, yet POS solutions have been slow to adapt, especially compared with the CRM or project management space. Why is that? What took so long?

JB: SAAS for local businesses is a no brainer – it just fits the business case. Store owners are often not in the store; Cashiers operate the store, store owners want to see their sales, control their pricing and inventory, manage their employees and have the analysis available to help them make smarter decisions for their business.

I believe the main reason for slow adoption is the need to educate the industry. Distribution has been historically very decentralized. You have strong ISO / reseller channels that take a long time to get educated and that have financial incentives to sell extra hardware to the store owners.

Next time you order a burger try to count the number of time the cashier taps the screen – we are changing this.

On the other side of the equation, store owners are used to seeing someone walk into their store and sell them something. Funny story – a few months ago we had a merchant show up and knock on our door to “buy ShopKeep” – literally he was expecting us to have bundles in boxes in the backroom to give to him right there. We sat him in our conference room and walked him through the ordering process on our website. That was a very interesting experience. He was miles away from understanding that he could just go online and order a system and set it up himself – in minutes. Merchants are used to having guys come and run cables in their stores, “configure” the server, etc. We are busting that myth.

VM: A corollary to the last question is that the POS market is ripe for Shopkeep-like innovation. Is this a case of whoever scales first takes the prize? If so, what’s Shopkeep’s strategy? What are the roadblocks?

JB: We don’t believe in the get-big-fast model – especially in our business. It’s a very fragmented market, there won’t be one big winner. There will be a few good companies of decent size who will survive in the end.

We focus on building the best experience for our merchants, helping them create new efficiencies in their business and building our distribution channels with existing players.

VM: How important are integrations in the POS space? Is that something customers are asking for? Why or why not?

JB: It is very important. It is the reinvention of the platform that merchants should have available to run their business.

VM: You’re VP of Product at Shopkeep. What’s your vision for the product? Where is it going from here? What trends do you see?

HB: I am very excited about where we are going to be in the next few months. To me our product is still an embryo of what we are really trying to create. We are building features that will change the merchant experience.

We are aiming for something that will entirely wow them. We are at this point where merchants ask us to build something, then we meet with them and show them what we are working on and we can see the light in their eyes. It’s a great feeling. This reflects the efforts we have done on every front over the past year. Our technical team is of incredible quality and I deeply respect every individual on the team for their dedication and work ethic. We are very selective in who we hire and this strategy is paying off.

VM: As consultants we’re perpetually interested in the changing relationship(s) between vendors, partners and clients. In your view, how does cloud computing affect that triangle, particularly in POS? How is today’s situation different than, say, the situation 10 years ago?

JB: Cloud computing has changed the game in many industries and software development was critically impacted. In addition to decreasing the cost of building a scalable architecture, it allows you to focus on executing your strategy. 10 years ago we would probably have 5 engineers in charge of maintaining our systems and measuring our uptime. Today we are just always up – that’s a given.


VM Associates is a New York City based cloud computing consulting firm. We help companies transition into newer, better, smarter software. Contact us to talk about your business, the cloud, and how we might help.

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Chris Bliss works at VM Associates, an end-user consultancy for businesses looking to move to the cloud from pre-existing legacy systems.