Why Most Contractors Pick the Wrong Invoicing Tool | Service Tools Guide

Updated June 27, 2026

Most contractors pick invoicing software the wrong way. They search for "best invoicing app," read a listicle, and pick whatever sounds good. Then six months later they realize they bought the wrong thing. Here is how to avoid that.

Question 1: Do You Need Accounting or Just Invoicing?

This is the fork in the road. If all you need is to send estimates, convert them to invoices, and accept payment, you do not need QuickBooks. Invoice Simple does exactly this for $5.99/month. It is a tool, not a platform, and that is the point.

But if you need expense tracking, profit and loss reporting, or anything your accountant will look at, you need at least FreshBooks ($17/month) or QuickBooks ($30/month). The price difference is not about features. It is about whether you need accounting or just invoicing.

Question 2: Do You Bill by the Hour or by the Job?

If you bill hourly, you need time tracking built into your invoicing. FreshBooks handles this well. Invoice Simple does not have time tracking at all. If you track hours and then manually enter them into a separate invoicing tool, you are wasting time every single billing cycle.

If you bill by the job, time tracking matters less and you can use simpler tools.

Question 3: Does Your Invoicing Need to Talk to Your Other Software?

If you run a field service business and already use Jobber or Housecall Pro for scheduling, use their built-in invoicing. Adding a separate invoicing tool on top of software that already does invoicing is just creating extra work.

The only reason to use a separate invoicing tool is if your operations software does not do invoicing well or if you need accounting features your operations software lacks.

The Simple Framework

Solo contractor, flat rate jobs, just want to get paid: Invoice Simple ($5.99/month).

Small team, hourly billing, want light accounting: FreshBooks ($17/month).

Employees, payroll, inventory, accountant demands it: QuickBooks ($30/month).

Already use field service software with built-in billing: Use what you have.

Compare Invoicing Software FreshBooks vs QuickBooks vs Invoice Simple