Being a small business owner, I know how vital it is to have a simple, effective way to bill your clients.  One that’s easy to use, integrates with your systems, looks good, and helps you get paid.  If you don’t get paid, you don’t have a business!  Whether you’re a designer, a planner, a photographer, a blogger, a butcher, a baker, or a candlestick maker, you need a decent software invoicing platform.

First of all, why would you ever want to deal with a paper invoice?  I don’t know that we’ve ever printed a paper invoice.  So ditch that old Microsoft Word template and join us here in the 21st century.  I need an integrated, easy, good looking system (for me and the customer) with which I can quickly distribute invoices electronically.

The systems are out there.  Two of my favorites are Square and Wave.  Square is the creator of the tiny “Square” card reader that you can plug into your phone, and they do probably some of the simplest transactions out there.  I love their simplicity and easy-to-navigate, but that does cost you a little bit in customization.

Wave is a full-featured small business accounting solution with a strong invoicing tool.  It’s a great solution if you want everything integrated into one for an extremely low price (read: free). It’s easy to match deposits with invoices once you have your bank accounts connected.

FreshBooks and QuickBooks (the most popular accounting solutions) also have outstanding, flexible invoicing tools that go along with their fabulous suite of accounting software.  Those solutions will cost you a little bit more, but their online software and interface is premium.  And for all the hate I gave paper invoices earlier, FreshBooks even has an option to print and mail an invoice for you, without having to go anywhere!

All that being said, here are some things to consider when using invoicing:

Don’t start with Invoice 0001.  This should be obvious, but I’ve seen it done before.  Don’t send your first invoice (or first invoice on the new system) and broadcast to your client that they are your first client!  Start with a random number, and go up from there!  I think I started with invoice 1112 or some other random number.  Use anything – 756, 1123, 4401, 510 – just not “Invoice 01” or 001, or 0001!

Use recurring invoicing where possible.  Do you serve a particular client on a regular basis, monthly or quarterly.  Don’t you dare spend your time sending them an invoice every month!  Use a system that allows for recurring invoicing that will send out invoices at the interval and time you specify.  Then, all you need to do is collect checks!  You can stop the recurring invoice if there’s a change or cancellation of the service you offer.

– People pay faster when it’s easy to pay.  Your quickest-paid invoices are going to have a portal, button, or link to pay online.  Square excels at this (they are a credit card processor), as does Wave (who employ the services of Stripe for payment processing), though QuickBooks and FreshBooks offer it as well.  QuickBooks and FreshBooks have their own payment processing that’s easy to utilize as well; QuickBooks Payments is actually some of the cheapest at 2.4% + 30¢.

– Consider a solution that integrates with your accounting – FreshBooks, QuickBooks, and Wave are all accounting/bookkeeping platforms that offer invoicing, so they’re going to integrate perfectly.  This is nice because you don’t have to pull up two systems to review your receivables.  If you can keep it all in one, that’s ideal.  Square is a payment processor and store platform, so it’s not ideal for this.

Use a customizable template.  Ideally, I want my client to see my logo, on a simple, clean interface.  I’d like to start with a template, and then customize it as much as I want, removing and adding things that I know would be helpful to my clients.  The simplicity of Square’s interface and system cuts its customizability a little bit, but it’s just so dang simple!  You’ll find the most customizable invoices with FreshBooks and QuickBooks.  While Wave is certainly more customizable than Square, it is still more template-y than the other two.

You didn’t realize there was so much to consider about invoicing, did you?  Well hopefully these thoughts will help you navigate to the system that will work best for you!

Question: What system do you use?  Have you ever had any invoicing mishaps because of a difficult-to-use system?