Square Handheld is a waiter's dream come true — and it's something I wish I had 20 years ago

Tom's Guide

14-05-2025

One of the hardest jobs I've had in my life was waiting tables. It taught me the art of putting on a poker face — and it also forced me to have better time management skills.
That's because of the amount of back and forth time I've wasted taking orders, entering them into the POS (point of sale) terminal, and then delivering the orders. That's why the Square Handheld is the gadget I've dreamt about all these years.
You've probably interacted with Square to some degree and don't realize it, as many businesses use its mobile payments solutions to process transactions for sales. It's very similar to Apple Pay, Google Pay, Samsung Pay, and other mobile payments.
The company's latest all-in-one mobile payments solution is the Square Handheld, which looks like a chonky smartphone, but can be used for an array of tasks. Not only does it handle payments via tap-to-pay with your phone, but it also serves as a tool to place orders, categorize inventory and seat guests.
It's exactly the kind of thing I would've died to have on me serving tables over 20 years ago. Back then, I was already thinking forward and ended up using a Windows Pocket PC PDA that allowed me to jot down orders with a stylus — but the Square Handheld is that and much more.
Square sells a range of processing terminals, but the Square Handheld is a mobile POS system that truly does everything that servers and waiters need to do their jobs effectively.
If you've ever worked in the food industry like I did, you know that time is the most important commodity at getting a good tip because no one wants to wait long for their orders.
First of all, it can be used to seat guests at specific tables through a system that essentially creates a floorplan — complete with table numbers and how many guests to seat.
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Rather than wasting time taking orders and going back to a POS terminal to put them through the kitchen, you can use the Square Handheld to do everything right there. This is a big deal because you can even send drinks to the bartender to create and have it ready by the time you're done taking orders, all at the table.
If you've ever worked in the food industry like I did, you know that time is the most important commodity at getting a good tip because no one wants to wait long for their orders.
And finally, the Square Handheld can take payment in a number of ways — from tap-to-pay with your phone, or traditional credit card swipes. I can't tell you enough how this impacts the customer experience because how long it takes to process a payment could be the deal breaker that could get you good or bad tip.
Instead of the extra time dropping off the check, taking the payment, and then processing it at a POS terminal, you can do everything right then and there with the Square Handheld.
As much as I would've loved to use the Square Handheld during my server days, it has a purpose beyond restaurants. In fact, I think it offers a comprehensive solution for small businesses such as retail clothing shops, pop-up stores and much more.
That's because the Square Handheld can be used to categorize products you might sell and inventory. With its integrated barcode scanner, you could easily add products to your inventory — so that you're not forced to manually do it on a terminal or computer.
This makes it much easier to keep track of inventory stock, which could also be synchronized with sales from an online store they might set up.
For salons or barber shops, this device can be used to create appointments with Square's own workflow system. This ensures that everything is synchronized, including customer data.
Bouncers at bars or clubs could also use the Square Handheld to scan licenses to verify they're the proper age to enter by scanning the bar code found on the back of their drivers' licenses.
You'll have to fork over $399 to pick up the Square Handheld, while an optional $39 cost that can get you a Belkin SheerForce Case to protect it. Thankfully, it has an IP54 rating on its own to protect it against dust and water splashes — but the case would help to cushion drops.
While you could get away with using Square's free plans to handle the essentials, just know that transactions still incur fees to process payments. For example, an in-person payment fee consists of 2.6% + 15¢ per transaction.
Additionally, if you need some of the more advanced functions to tailor to your business' needs, like the ability for restaurants to create floorplan layouts, you'll need to subscribe to one of Square's plans.
For this exact feature, you'll have to subscribe to the Square Plus plan that costs $69 per location/month — but it also comes with more reporting and analytics for businesses to look at.
Yes, it's an investment, but convenience comes at a cost. I can certainly appreciate it from a waiter's perspective, since it saves a lot of time and would allow for quicker transactions. If time travel were possible, I would absolutely bring this back and give it to my 20-year old self.