Easy invoicing and card payments.
Square makes taking a card payment dead simple, and its invoicing is free to start. If your whole need is 'send invoice, get paid,' it does that well.
But Square isn't contractor software. It doesn't run estimates into contracts into jobs, it doesn't track job profit, and it doesn't keep your books or mileage. Job Assistant does all of that — and still lets your customers pay by card online — for $25/month.
When Square Invoices is the better pick
Businesses that mainly need to send a quick invoice and take card payments, especially if they already use Square for point-of-sale.
| Feature | Job Assistant | Square Invoices |
|---|---|---|
| Starting price | $25/mo | Free + fees |
| Built for | Contractors | General payments |
| Invoicing | ✓ | ✓ |
| Estimates (line-item) | ✓ | Basic |
| Digital contracts / e-sign | ✓ | ✗ |
| Online card payments | ✓ | ✓ |
| Scheduling & self-booking | ✓ | ✗ |
| Per-job profit tracking | ✓ | ✗ |
| Bookkeeping + mileage | ✓ | ✗ |
| Customer portal | ✓ | ✗ |
Square Invoices pricing as of 2026. Subject to change. Comparison reflects our understanding of publicly available information.
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Start your free trialCan I use Square for contractor invoices?
Yes, Square can send invoices and take card payments. But it doesn't offer contractor essentials like line-item estimates, e-signed contracts, scheduling, per-job profit, or bookkeeping — which is where Job Assistant goes further.
Does Job Assistant take card payments like Square?
Yes. Customers pay invoices online by card through Stripe, and the invoice marks itself paid — so you keep the easy-payment experience while gaining the full contractor workflow.