Square

What Square is

Square is the fastest way for a new contractor to take a card: download the app, get a free reader, accept payment the same day. Invoicing, recurring billing, and a basic customer directory are included at no monthly cost, which makes it a sensible starting point before you have software opinions.

What it does well

• No monthly fee and free card reader
• Same-day setup
• Invoicing and recurring payments included
• Clear, predictable pricing

Integrates with

QuickBooks · Jobber · Zapier

Integration lists change often and "integrates" can mean anything from a real two-way sync to a one-way push through Zapier. Ask the vendor which fields move, in which direction, and how often.

Before you commit

• Compare total effective rate, not headline rate: interchange, assessment, platform markup, and chargeback handling.
• Surcharging rules vary by state and card network. Get the compliance answer in writing.
• For financing, know who pays the dealer fee and how it affects your margin on a promotional plan.
• Check approval rates across credit tiers — a lender that only approves prime leaves money on the table.
• Make sure deposits and progress payments are supported, not just pay-in-full invoices.

How to judge it in a trial

Run one real job through it end to end — not the demo data. Quote it, schedule it, do it, invoice it, take the payment. Then ask the only question that matters on day 400: did the people who have to use this every day find it faster than what they do now? Friction you notice in week one compounds forever, and tool-hopping costs more than any feature gap.