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Send estimates with options, get the contract signed before the first payment and bill each phase as it's done, on site or from the office. Payaroo helps you set up Square's tools for contractors.
Square, made easier with Payaroo.
What your contracting business needs
A remodel or a new roof isn't one payment. There's a bid the homeowner compares with two others, a contract, a deposit before materials are ordered, payments as each phase wraps and a final walk-through before the last check.
Specialty trades, from painters and tile setters to cabinet makers, run the same cycle on a smaller scale. What they need is one place where each job's estimate, paperwork and payments live together, whether you're on the site or at your desk.
Homeowners compare three bids, and a single number with no choices is easy to pass over.
How Square helps On a paid plan, send a multi-option estimate, say builder-grade, mid-range and custom. The client approves one online and it turns into an invoice automatically.
Lumber, shingles and tile get ordered weeks before the job is finished.
How Square helps Collect a deposit when the estimate is accepted, then schedule the balance by phase, from demo to rough-in to finish, in up to 12 milestone payments on a paid plan.
Printing, signing, scanning and filing contracts slows the start of every job.
How Square helps Attach a Square Contracts agreement to the estimate or invoice for the client to sign online. On a paid plan you can require the signature before they're able to pay.
Some clients pay at the final walk-through, while others are out of town and want to pay online.
How Square helps Take chip and tap on site with Square Reader, Handheld or Terminal, or send an invoice or payment link they can pay by card, bank transfer or Afterpay where eligible.
Recommended setup
The Square tools that matter most for a contracting business — and why each one earns its place.
Estimates, deposits and phase-by-phase billing in one place, with ACH so clients can pay large balances from the bank.
On a paid plan, lay out finish levels in one estimate so the homeowner chooses the scope and the price together.
Get the materials money before you order, then bill the rest by phase instead of carrying the cost.
Contract templates clients sign on their phone, with a signature required before the first payment on a paid plan.
Attach plans, change orders or progress photos so each invoice shows exactly what the payment covers.
Pairs with your phone for chip and tap at the walk-through, even on a site with no Wi-Fi.
Each client's address, notes, photos and paperwork on one profile, along with their payment history.
Text a link for a small add-on or a change order without building a full invoice.
How Payaroo helps
Tell us how your business works. We'll help you understand the Square tools that fit.
Core capabilities
On a paid plan, one estimate can hold up to nine packages, and the one the client approves converts into an invoice automatically. Estimates can also carry a deposit request or milestone schedule, a contract and attachments.
Ask for a deposit up front, then set milestones for demo, rough-in and finish, up to 12 payments on a paid plan. Square can send reminders before, on and after each due date, so you aren't the one chasing.
Attach your contract to the estimate or invoice. The client signs online and receives a signed PDF, and on a paid plan the invoice can't be paid until it's signed. Square doesn't give legal advice, so the contract language is yours to set.
Clients can pay invoices straight from their bank account instead of stretching a credit card or mailing a check. Recurring invoices, such as a monthly property maintenance contract, can autopay from a verified account.
Attach up to 10 images or PDFs to an estimate or invoice: the signed drawing, a change order, before-and-after shots. The client sees what each payment covers before they pay it.
If your business category qualifies, clients can pay an invoice in installments through Afterpay while you're paid up front. Amount limits apply, and Afterpay can't be used on payment schedules or recurring invoices.
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.
Small enough for a tool bag. It pairs with your phone by Bluetooth and uses the phone's data connection.
A pocket-sized point of sale with a built-in barcode scanner and camera.
An all-in-one pocket device with a camera and scanner, for showrooms and sites with Wi-Fi.
A compact, battery-powered card machine with a built-in receipt printer.
Prints a receipt at the final walk-through and takes swipes too; it connects over Wi-Fi.
Software and tools
Estimates, deposits, milestone schedules and recurring invoices, built from the truck or the office.
Contract templates clients sign online, attached to estimates and invoices.
Client profiles with job addresses, notes, files and payment history.
Let homeowners book a consultation or measure visit online, with automatic reminders.
Sales by service and by team member, with exports for your bookkeeper.
How it works
One realistic day at a contracting business, with the setup above doing the work.
Setup finder
Answer a few quick questions about your contracting 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
You can run most of it from a phone. Square Reader adds chip and tap using your phone's data, and Tap to Pay takes contactless cards with no reader at all. Square Handheld and Square Terminal are all-in-one devices that connect over Wi-Fi, which suits a showroom, an office or a site with a network. Terminal also prints receipts.
Yes. An invoice can request a fixed or percentage deposit and split what's left. On a paid Square plan you can set a milestone schedule of up to 12 payments plus the deposit, with automatic reminders around each due date. Afterpay isn't available on payment schedules.
Square Contracts lets you attach a contract to an estimate or invoice, and clients sign online and get a PDF copy. Requiring the signature before payment needs a paid plan. Square notes it doesn't give legal advice, so the contract terms are up to you and your advisers.
Yes. Square Invoices offers ACH bank transfer alongside cards, Apple Pay, Google Pay, Cash App Pay and Afterpay, so a client can pay a big balance from their bank account instead of a card.
Not to get started. Square Free has no monthly subscription (you pay processing fees on payments) and handles estimates, invoices, deposits and basic contracts. Square Plus or Premium adds multi-option estimates that convert automatically, milestone schedules of up to 12 payments and contracts that must be signed before payment. Square sets its own pricing, so check Square's pricing page for current rates. We can help you weigh whether those features matter on your jobs.
Tell us how you bid, bill and collect today. Your application goes to Square, which reviews it and verifies your identity and your company before approving an account. Then Payaroo helps you set up your estimate line items, contract templates and payment settings.
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Recurring cleans, online booking, cards on file and invoices for commercial jobs.
Tell us how you bid and bill, and we'll help you set up estimates, contracts and payments that match the way your jobs run.
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
Square reviews every account application, including identity and business verification, and decides whether to approve it. Payaroo can't guarantee approval, pricing, processing terms or the availability of any feature.
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