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A confluence of events that are coming to head in the last year and coming year is creating significant opportunities in the retail point of sale space. The retail technology stack has become pretty stale in the last 10 years. What you see at many retailers is decade old technology. The existing legacy players have carved out their domain and have fought hard to fight off any change.

All this is changing due to a number of events that are coming to head now.

* EMV liability shift in October 2015 is forcing merchants to upgrade their payment terminals. When merchants are upgrading, they all want to future proof their investment. So, they are all looking at the latest and greatest technology. The new Verifone and Ingenico terminals are filled with every type of technology that they can think of. This includes wifi, BLE, high res lcd screens, etc. In addition, both Verifone and Ingenico have opened up APIs for third parties to write apps for these terminals outside of the secure PCI sandbox. Then you have newcomers like Poynt that is trying to disrupt this entire space.

* Windows XP deprecation: many of the existing pos, like micros and Aloha, run on top of Windows XP. With the Windows XP deprecation, retailers are required to upgrade their pos to maintain PCI compliance. Instead of spending thousands on upgrading to the latest Micros and Aloha POS, they are now looking at tablet based and cloud based pos systems. This allows companies like Revel, Square, and Clover to move into the space of existing legacy players.

The largest challenge for these newcomers (that many underestimate) is the depth of software in the aloha/Micros pos. These pos not only handle order management and payment, but they also run the entire store operation (ie inventory, payroll, scheduling, etc). For a newcomer to come in, it's very high cost to replace all of these functionalities. At Money2020, one of the speakers stated "Changing a Pos is equivalent to changing the way they run the business"

* POS as a platform. Micros and Aloha treated their platform as an ecosystem that they wanted to protect. They make it very difficult for third parties to innovate on it. For example, to get access to the Micros SDK, it requires a $25k license plus $1k per deployment. This is a great barrier to entry for startups. The new players have all created open ecosystems to enable third parties to write apps on them. Verifone, Ingenico, Poynt, and Clover have all gone as far as to create an app store to enable third parties to sell and distribute their app.

Where we are at now in the pos space is where we were then in the mobile space when the iPhone first came out. There are lots of opportunities to innovate in this space. Lots of developers and startups are waiting at the gate for the entire retail technology stack to refresh to get into this space.

Definitely very exciting times.

Totally agree. Many of the lessons learned in reliable systems on the internet are only beginning to be applied in the POS space.

Compared to the pricing that retailers are used to paying (easily $5000-$25000 per terminal) an iPad is a deal even if it must be replaced more often.

As you say, the depth to replace an entire Micros or Aloha setup would take years of development. (I have extended and developed POSs myself.) That is why I think the POS(s) with open data standards will win out, by integrating with existing inventory and financial tools.

There is a ton of room and will be competition, so focus will be key. The POS vendor no longer needs to develop the hardware or database, just the software. But -- high-volume POS UX is unlike any normal web or app UX. A intuitive POS that drives sales and proves it with easily exportable/readable data? I don't think there's a clear leader yet.

Agreed. A lot of the new players are trying to build pos like a consumer product with sexy uis and animations.

In qsr space, a 10 sec decrease in time equates to roughly 1% in revenue. (1)

Legacy Uis look terrible but they are built for speed. One thing that would help this space is applying learnings about A/B testing, metrics, and UX research in the POS space. If you can demonstrate to merchants using data that you can decrease time and increase revenue, that is a huge opportunity.

(1) http://hospitalitytechnology.edgl.com/news/Are-You-Fast-Enou...

I've been in a store when one of the Revel iPad terminals couldn't get online. highly annoying. Don't traditional POS rely on the telephone lines? Usually more reliable than my ISP, that's for sure.
I've been in an Apple store where their customized iPod Touches (or iPhones?) POS terminals couldn't get online. Irony of ironies.
In the past, yes POS card processing relied on a telephone connection to the processor, but this is less and less common. Regardless POS intranet was always isolated from the internet, for PCI compliance and security.

Only these new entrants have become reliant on an internet connection -- but most seem to be marketing the novelty of mobile technology, rather than creating an offline-first db-synced app built on proven internet technologies.

Shameless plug here – I build an iPad point of sale that does exactly that. It's called Ambur (amburapp.com). We started with a local SQLite DB, then built syncing depending only on the router functioning (i.e. no internet dependency, one iPad acts as a server) using Bonjour discovery, and I just added NAT traversal so people can still remotely access the point of sale. It's the best of all worlds! Now to find some venture capital...

BTW, why in the world don't any of the other point of sales do this? None of the stuff that's required is rocket science, you need a Core Data maven, a networking maven, and a decent UI programmer in the same room and you'll get a ton done. Removing reliance on a server seems like a no-brainer both for clients with unreliable internet connections with business-critical needs, and for avoiding complexity of having a "split brain" across iOS/the cloud for the service. It seems like server devs are valued over iOS devs for no clear reason.