Square’s flagship store is Sightglass coffee - a hipsteresque coffee shop in San Francisco. Jack Dorsey - a partial owner of Sightglass and the CEO of Square - rolls all product features out at Sightglass coffee for user experience testing.

One of Square’s products is Square Wallet - an app to pay for things with your iPhone. Square Wallet is not a new idea. Many companies, including Google and Paypal, have tried to push out similar products.

But, The Square experience at Sightglass coffee is amazing. The experience impressed me so much that I want the experience to be everywhere. It is an order-of-magnitude better than the current system.

After downloading the app you enter your credit card information and then a list of stores that accept Square wallet are displayed. You then click pay. This isn’t the amazing experience.

When paying at Sightglass, there is an option for Hands-Free Checkout. Turning Hands-Free Checkout on makes the Square experience exceptional.

Once enabled, you walk into the store, place your order, and then tell them your name. The barista charges you without you ever having to touch your wallet or your phone.

I enjoyed the experience so much that after paying at Sightglass I wanted to do the same thing at Starbucks. Square and Starbucks struck a deal to allow Starbucks customers to pay with Square Wallet and I was excited everyone could have the same experience I had. However, the Starbucks experience was not as enjoyable.

At Starbucks, Hands-Free Checkout isn’t available. To pay, you need to pull out your phone, open up the wallet app, select Starbucks from the list, and then show the employee your phone - which displays a QR code - which they scan. The Starbucks experience lacks the magic I enjoyed at Sightglass. I still have to reach into my pocket to pay. This experience doesn’t displace the traditional payment system.

Removing all the Point-of-Sale systems Starbucks uses would be expensive, but necessary, if everyone wanted to have the same enjoyable experience at Sightglass.

Security Concerns

Hands-Free Checkout uses geolocation to identify your Phone is close enough to authorize a payment at Sightglass coffee. Security and privacy concerns are similar to RFID and NFC. But there are two unique concerns to Square.

If I’ve locked my phone I can still make Hands-free payments. Additionally, notifications are displayed when my phone is within proximity of a store I’ve authorized for payments. It’s possible a thief could steal my phone and use it like a credit card at authorized locations. This is a smaller security concern than the current system. If someone steals my wallet, they can use my credit card anywhere, not just at authorized locations.

Secondly, If this becomes a universal experience for making payments, what prevents malicious entities from making unauthorized charges to people walking by? Again, a smaller concern, but much different than the current system in place.

There are smarter people than myself who love breaking these systems and fortunately Square is employing some great security people so I’m not concerned.

Bring It To Everyone

Once I used the Hands-Free Checkout to order a coffee at Sightglass I immediately understand how square could displace the payment industry. To pay, you simply need to be present.

I hope people don’t stop using Square Wallet because of the unimpressive experience they have at Starbucks. Hands-Free Checkout is what makes Square Wallet amazing. More people need to have the same experience I’ve had. The experience was so good, I don’t want it to go away. I want to use Hands-Free Checkout at the stores and restaurants I frequently go to.

The next time you’re in San Francisco, go to Sightglass coffee and use the Hands-Free Checkout option. I’d love to know your thoughts.

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