An Experience with Pay with Square

I went to San Francisco recently for some interviews. One of the companies I ended up speaking with was Square. I’m a big fan of the company.

I believe I know quite a bit about Square and its products. But I only tried its card reader first hand, not Pay with Square, which is probably one of the coolest way to pay. So to familiarize myself better with the product and the process (and to take advantage of the $10 credit) (and to slightly boost my candidacy without shame) I went to a bar in SF where they took Pay with Square as payment.

I opened the app, opened a tab — all very straightforward. Picked my drinks and signaled the bartender. I said “put it on Razeeb… ” as was instructed by Square. Unfortunately there was a band playing so it was very difficult to hear, I had to repeat it 2–3 times and I mentioned Square. The bartender apparently wasn’t familiar with Square so he called the manager. He came to me and I asked “you guys take Square right?” he said “of course!” So I asked him to “put it on Razeeb….” He knew immediately what to do, apologized for the inconvenience and I got a push message on my phone saying a payment with Square was just made.

Beautiful.

Now some questions.

1. Which takes less time? Showing your credit card and a signature or paying with Square?

In this situation paying with my card would have been quicker. Keep in mind, that bar wasn’t an ideal place to hear because there was a band playing. But most bars/clubs probably wouldn’t be an ideal place for Square.

So it seems there is a time and a place to use Square.

2. Is the phrase “put it on…” clear enough?

I would argue not yet. For some perspective the bar was blocks away from the Square HQ.

Clearly businesses need to train their employees about Square — but the phrase doesn’t mention Square specifically so it can be difficult to understand. Maybe “Square me on…” or something similar will be more clear. I think the current phrase is perfect but it will take some time to gain mass understanding.

3. What stops businesses from adding charges to customers freely?

I’m sure most business wouldn’t, plus customers have to open tabs voluntarily. But I can foresee a lot of disputes that Square has to handle — like credit card companies.

All these can be addressed quite easily though.

Unfortunately, my interview with Square didn’t end up working out. Next time hopefully. On the bright side, after I sent a tweet (90% genuine, 10% candidacy boosting) about Pay with Square it got favorited by… Keith Rabois! — COO of Square.

Later I found out he always favorites tweets about Square. Damn.

Originally published at razeeb.com on Jun 20th, 2012.