Payments via iPhone: Stay with Square or soar with Sail?

A little over a year ago after credit card processing giant Verifone(s PAY) attacked Square with an open letter and created an app to exploit so-called vulnerabilities in Square’s system, Verifone’s Sail is competing directly with Square. In addition to mimicking its business model, the company has even copied the wording from Square’s merchant agreement.
But as a small business owner who processes credit cards, ultimately I care about how well the device and service performs and enhances my business. I’m delighted the field is opening up a bit and hope to see a feature race between the two companies. After comparing the services from a variety of angles, I’ll probably be sticking with Square for most transactions with my iPhone and iPad.
Here’s what I found when I compared Square and Sail head-to-head.

Device ergonomics

In the few weeks I’ve used both devices, I’ve found the Square reader to be simply more portable. It fit into the coin pocket of my jeans on my service clipboard. The Sail reader’s stabilizing “sail” limited its portability. In my pocket the plastic jabbed into my thigh and it was simply too big to fit in the coin pocket in my service clipboard. Additionally, the Sail reader worked with fewer external cases due to that stabilizing plastic, while the Square reader fits more iPhones(s AAPL).
That stabilizing plastic was a helpful feature when actually swiping the card. Anyone who’s used Square’s reader knows it takes some finesse to hold the reader and get a proper scan without the dreaded “retry.” Movement of the reader during a swipe requires another swipe which slows you down as a merchant and annoys your customer. Sail swiped right each and every time because the reader didn’t move.


Sail advertises a lower cost per transaction of 2.7 percent compared with Square’s 2.75 percent. Sail on the surface is a better value, but Sail’s Go Plan charges 3.7 percent for American Express while Square’s flat pricing stays the same. If you accept American Express often, then Square is clearly a better value.
If you type the card number rather than swipe (because the customer doesn’t have the card, or it doesn’t read), then Square’s rate is 3.5 percent plus a 15 cent transaction fee. Sail’s rate is higher here at 3.7 percent for all cards, including American Express, but no transaction fee.
Sail offers a ProPlan for $9.95, which reduces the rate to 1.95 percent for swiped transactions and 2.95 percent for keyed-in transactions as well as 2.95 percent for all American Express, both keyed and swiped. Unless you average over $13,500 $1,350 in swiped sales a month, the Go Plan is a better value.
Because I see quite a few American Express cards Sail’s surcharge makes it unattractive for me.

The iOS App

The Sail payment app is currently iPhone-only, though it works on the iPad. The Sail app was confusing to me; in particular, to add an item to an order I had to click on the amount of the order rather than the list on the left side of the app screen. The “Sail” icon in the upper right was to change payment methods. None of these were intuitive for me.

I also didn’t like the annoying warning that the device needs to be connected each time I open the app.

By comparison, the Square app on the iPad is full screen and includes the ability to sell individual menu or inventory items, but the iPhone Square app only allows you to describe an item and not select multiple items for sale.
Sail allows you to add inventory items and even use a bar code scanner via your iPhone 4, a feature lacking in all versions of the Square app.
Square’s iPhone and iPad app interface puts everything you need on that front screen and for me was easier to use


As of this writing, Sail’s main competitive advantage is its network of support. Square offers support primarily through email and occasionally via Twitter. The times I have contacted Square, I’ve had to wait a few days for a response, but fortunately these were non-urgent issues.
Sail has an actual phone number and U.S.-based reps I can call for support anytime. During my review I called them twice. Both times my call was responded to quickly though support had trouble answering the most basic of questions, such as “Am I charged for a refund?” That question required multiple periods on hold and a call-back to tell me, no, I’m not charged when I refund a customer. My previous merchant account did charge me for refunds. As far as Twitter support goes, my tweet to the @sailpay account was answered within 90 minutes.
Since I am rather tech-savvy and have been taking credit cards for eight years through my small business, I don’t have many questions. New business owners, or at least those new to credit cards, might appreciate live phone support.

Reporting and receipts

On credit card statements, Square merchants have an “SQ” in front of their name while Sail merchants get the full business name on the statement. That’s a big feature for me as a business owner as it keeps my branding consistent and could reduce chargebacks if a customer doesn’t recognize what the SQ means.
Square tends to protect customer information more than Sail does in the reporting, which is ironic given Verifone’s initial concerns about security. Square’s online statement only includes the last four digits of the cardholder’s account while Sail told me the full name of the cardholder. This was very handy to help me reconcile my invoices with payments.
Both Square and Sail include GPS coordinates on the transaction and receipt and will not allow you to process a card unless this is on. Square has the bonus feature of sending the receipt via SMS.

Establishing an account

Set up experiences were nearly identical. I went online with Sail and created an account and requested a reader. New Square customers can do that or purchase one directly from Apple and get the cost of the reader rebated to their merchant account.
Neither service required a credit check, but did ask some verification questions. Business owners like myself who don’t want a credit check done (and potential ding to their valuable credit rating) will appreciate this feature. When I attempted to sign up for Intuit’s GoPayment service, they required a credit check and I wasn’t willing to unfreeze my protected credit to test out their service.
Both Sail and Square require bank account information for direct deposit payments. They’ll make a small series of deposits as sa test so they know they’ve got the right account which they’ll withdraw once you verify the deposit.
Square’s reader is generic and can be used for any account while Sail’s reader is serialized and directly associated with my account and can be deactivated if lost or stolen.

Bonus features

Both Sail and Square have some added features that may be of particular value to business owners, depending on the situation.
Square has the “Pay with Square” app that allows a customer to conveniently open up a tab and pay without having to swipe their card, though this isn’t true NFC. I’ve only used it a few times, but it is both fun and handy to walk in and pay by saying “put it on my tab.”
Verifone is focused more on features for the business owner and will allow the owner to upgrade to a full-fledged card reader (and NFC capabilities) with the VX520 card reader that has been announced but not released.


Square’s polished app along with the lower charges for American Express and the ease of carrying around its reader makes it my preferred way to accept credit cards. Square’s hip image is also a factor as they feel to me like they’re closely aligned with Apple’s branding. Sail seems, well, more “PC” in its approach. Businesses starting out and those who have cost as their bottom line concern might prefer Sail.
Other business owners that don’t accept American Express or have large monthly transaction value will find Sail’s ProPlan a nice middle ground before getting a full merchant account that often requires a contract and pesky PCI compliance fees. I’ll use the Sailpay at my office since portability isn’t an issue and I’ll keep using both for a while just so I can keep an eye on any changes in features or quality.
You might wonder why I didn’t include PayPal’s Here. Simple: for me it isn’t “here.” I applied the day Ryan’s article came out and I have yet to hear from them. They are more focused on large merchants, it appears, rather than small businesses. If and when I get a Here reader, I’ll be sure to report my findings.