Services
Riders book ahead online and drivers take cards and tips in the car, while corporate accounts get an invoice after each trip. Payaroo helps you set up the Square tools that make it work.
Square, made easier with Payaroo.
What your transportation business needs
A limo or black car job is often booked days ahead by someone who isn't riding: an assistant, an event planner, a wedding coordinator. The rider expects a clean car on time, and the company paying expects one tidy invoice.
In the car, you need payments that work at an airport curb or a hotel door, with a tip prompt the rider can see. Taxis, shuttles, couriers and movers get paid in their own ways, but the basics carry over: take cards on the road, invoice the regulars and know who has paid.
Ride requests come in by phone, text and email, and one missed message means a missed airport pickup.
How Square helps A free Square Appointments booking site takes ride requests any time, puts each one on a driver's calendar and sends automatic confirmations and reminders.
Riders want to tip on the card, and drivers miss out when there's no easy way to add it.
How Square helps Square Terminal and the Square POS app on the driver's phone show a tip prompt before or after payment, with presets you choose and a custom amount.
Companies book rides for executives and guests and want one card charged or one bill to approve.
How Square helps Save the company's card with its signed authorization and charge it after each ride, or send an invoice they pay online by card or bank transfer.
Cell service drops on a long run, right when the rider is ready to pay.
How Square helps Square Reader can keep taking cards offline and process them once the phone reconnects; Square recommends reconnecting within 24 hours. Tap to Pay can't work offline, and any offline payment later declined, expired or disputed is your responsibility.
Recommended setup
The Square tools that matter most for a transportation business — and why each one earns its place.
A free booking site where riders and assistants reserve airport runs, hourly charters and wedding cars, synced to your calendar.
Travels with the driver's phone, takes chip and tap and keeps taking payments when the signal drops.
Keep a corporate client's card on their profile, with signed authorization, and charge each ride without asking again.
Send a trip invoice after the drop-off or bill a company for the month's rides, payable by card or bank transfer.
A tip prompt on the rider's side of the payment, so card fares come with an easy way to thank the driver.
Driver schedules, timecards and custom permissions for dispatchers and drivers.
Square's transportation page points to dispatch and limo software here; those apps are built and supported by their makers.
Remind past clients about prom season, weddings and holiday parties by email, or by text if they opted in.
How Payaroo helps
Tell us how your business works. We'll help you understand the Square tools that fit.
Core capabilities
Riders pick a service, such as an airport transfer, an hourly charter or a wedding package, and a time on your booking site. Offer it at the customer's location and the booking can ask for the pickup address, which needs a paid plan.
Square Terminal, or the Square POS app on the phone that Square Reader pairs with, shows the tip screen before or after payment. Offer Square's smart suggestions or three presets of your own, plus a custom amount.
With a signed authorization (Square Contracts has a template for it), save a client's card and charge it after each ride from the POS, an invoice or the booking calendar. Cards tapped from a phone wallet can't be saved.
Give each driver a bookable calendar with their own hours and services, and choose who can see everyone's schedule. Square doesn't calculate drive time between bookings, so build the deadhead into each ride's length.
A hotel shuttle contract or a company's standing commuter run can bill on a recurring invoice, charged automatically to a saved card or a verified bank account.
When an assistant calls to book and pay, type the card number into the Square POS app. Typed-in payments need a connection, so take them from the office rather than a dead zone.
Hardware options
You don't need every device. Start with what matches where you take payments — and add more later.
A small Bluetooth card reader that pairs with your phone or tablet.
A small Bluetooth reader for the driver's phone: chip and tap anywhere the phone has service, and offline for up to 24 hours when it doesn't.
A compact, battery-powered card machine with a built-in receipt printer.
Shows riders the tip screen and prints a receipt in the back seat. It runs on Wi-Fi, so it suits cars with a Wi-Fi hotspot.
Accept contactless cards and phone wallets on your own phone with no extra hardware.
Take contactless cards and phone wallets on the driver's own phone with nothing else to carry. It doesn't work offline.
Software and tools
Online ride booking, driver calendars and automatic confirmations and reminders.
Trip invoices, monthly account billing and recurring invoices for contracted routes.
Driver schedules and timecards, with permission sets for dispatch and drivers.
Third-party dispatch and limo software that connects to Square, supported by the companies that make it.
Email and opt-in text campaigns for proms, weddings and corporate event season.
How it works
One realistic day at a transportation business, with the setup above doing the work.
Setup finder
Answer a few quick questions about your transportation business. We'll stop as soon as we can point you to a useful starting setup.
Tell Buckaroo how your business works and he'll help you figure out which Square tools make sense.
FAQs
Square Reader pairs with the driver's phone for chip and tap and uses the phone's connection. Tap to Pay takes contactless cards on the phone itself with no reader, as long as there's service. Square Terminal adds a tip screen and printed receipts but runs on Wi-Fi, so it fits cars with a hotspot.
Yes. A tip prompt shows on Square Terminal and in the Square POS app on the driver's phone or tablet, before or after payment. You can use Square's suggested tips or set three presets of your own. Riders can also enter a custom amount.
There are two ways to set it up. Keep the company's card on file, with their signed authorization, and charge it after each trip. Or send invoices they pay online by card, Apple Pay, Google Pay or ACH bank transfer. A fixed monthly contract, such as a hotel shuttle, can go on a recurring invoice.
Square's transportation page points to dispatch and limo software in the Square App Marketplace. Those integrations are built and supported by the software companies, so check what each one syncs with Square before you switch.
Square's transportation page is written for passenger services like limos, chauffeurs, taxis and buses, and it doesn't mention couriers or movers. The general tools still apply: invoices with deposits for a moving job, payment links by text, cards on file for business clients and Square Reader or Tap to Pay at the door.
Square sets its own pricing. Square Free has no monthly subscription (processing fees apply to each fare) and includes the online booking site, invoices and cards on file. Square Plus and Premium add driver scheduling with Square Shifts, Square Marketing campaigns and pickup addresses collected at online booking. Check Square's pricing page for current rates, and we'll help you decide which plan your fleet needs.
Tell us how rides get booked and paid today, and we'll suggest a setup. Square reviews your application and verifies your identity and business before approving the account. From there, Payaroo helps you set up ride services, driver calendars, your booking site and readers for the cars.
Related businesses
Repair estimates, signed approvals, parts counts and customer updates.
Estimates, signed approvals, deposits and payments at the customer's door.
Recurring cleans, online booking, cards on file and invoices for commercial jobs.
Tell us how rides are booked and paid, and we'll help you choose the booking, payment and invoicing setup that fits.
Square reviews and approves every account. Call Payaroo at 972-431-0439.
Square is a product of Block, Inc. Square, the Square logo and related marks are trademarks of Block, Inc. and/or its subsidiaries. Payaroo is an independent company. Payaroo is not Square or Block, and nothing on this page describes a partnership, reseller relationship, certification or endorsement.
Square product details on this page were checked against Square's website on September 25, 2026. Square sets its own features, plans, pricing, fees, eligibility and hardware availability, and these can change. Confirm current details on Square's website before you sign up. Square pricing · Square fees
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