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Square Aims to Move Upmarket with Handheld POS Device

By Wesley Grant
May 13, 2025
in Analysts Coverage, Merchant, Point-of-sale
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square handheld pos

Happy waiters bringing food at the table and serving group of friends in a restaurant.

Some of Square’s best-known products are accessories that turn phones into point-of-sale (POS) terminals. But its new device, Handheld, removes the phone from the equation.

Roughly the size of a smartphone, Handheld features a built-in barcode scanner and camera. In addition to supporting traditional card payments and tap-to-pay, it also offers inventory management functions via the Square POS app.

According to the Verge, the app will soon get an upgrade that enables Handheld to adapt to different types of businesses—such as quick-service restaurants, retailers, or bars—based on the merchant’s industry.

“This is a great move by Square and fits well with their trend upmarket to larger merchants,” said Don Apgar, Director of Merchant Payments at Javelin Strategy & Research. “The original Square dongle that worked via a phone’s audio jack enables business owners to use their own device to accept payments, and Square still does that via a tap-to-phone app. These are great solutions for the smaller farmer’s-market types of merchants.”

“This new device is geared more towards businesses with employees—whether wait staff or sales assistance—and ties in seamlessly with Square point-of-sale,” he said. “You don’t want to rely on employees to use their personal phones to scan orders and take payments, and employees aren’t crazy about jobs that require that. Data security for payments can be an issue also.”

A Technology War

The unique demands of small enterprises have sparked a technology war, with many companies competing to become the preferred point-of-sale provider. Square and Clover currently lead the pack in the POS market, and their solutions were neck and neck in Apgar’s recent 2025 Small-Business Point-of-Sale Scorecard.

While both Clover and Square offer systems adaptable to nearly all merchant applications—from fine dining to bicycle shops—Clover’s system edged ahead due to its greater depth of features.

Room to Go Deeper

With Handheld priced at $399, Square aims to provide a more affordable alternative to Clover’s Flex system, which offers handheld POS devices for $749. Still, Square operates in a dynamic field marked by constant innovation.

“There’s always room to go broader,” Apgar told PaymentsJournal. “There’s always room to go deeper. With the speed at which these developments are coming out, it’s nothing less than an arms race in small business POS.”

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Tags: CloverHandheldPoint of SalePOSSmall Business POSSquare

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