What Billing Software to use?

What billing software I use (or what I recommend) is a question I get all the time.

Currently I use Ronin and it’s pretty good. I’ve got a full review in the works that will highlight my loves and hates with Ronin in the next few weeks.

Update October 2, 2013: Ronin was purchased by Godaddy and I refuse to do business with Godaddy so that means I will be getting a new system this year.

Update October 9, 2014: Someone just reminded me that I've never got back to update this. I did move of Ronin and I now use FreeAgent. I have a review in the works, but no ETA.

One thing I don’t believe in doing is switching billing software on a whim. Sure there are pain points in Ronin but the ‘cost’ of changing is high. I have to set up an account with the new service. Import any existing clients and reissue invoices.

Or I have to run 2 systems till any outstanding invoices are paid in the old one.

Then you count all the lost historical data like who pays on time and who doesn’t and what my effective hourly rate is over the year.

Unless you back track and add old projects (takes way to much time IMO) that historical data is gone.

Christmas Batching

I take a hard look at my billing software in detail around the holidays. Most of the time I have all my invoices paid by Jan 1st so making a change to a new system is as clean as it can be.

That doesn’t mean I don’t give another option a ‘spin’ in the middle of the year. I just know that I won’t be making the change during that ‘spin’ it’s a test drive. I purchase around Christmas.

Features

I have a standard set of features that I need in billing software to even make it in to my review list.

Automated Invoice/Late Payment reminders - Such a time sink to keep track of the email reminders and send them to clients all the time. I don't want to waste my time doing it and it can/should be automated by software for you.

Automated Taxes - If you need to charge taxes to clients, then it should be automated for you. Set up the rules in the app admin and then let the software work it out for you.

Online Payment Integration - You will get paid faster if you take payments online. Taking them online reduces the friction for your clients. If I can't hook up with Paypal and Stripe you're not worth looking at.

Flat Rate Billing/Hourly Tracking - I don't bill hourly but I do track my time and figure out my effective hourly rate. I want at system that allows me to set a price for a service and then track the time I spent on that. Then I don't want the client to be able to see the time. It sounds pretty basic but that has been a failing of most solutions, even Ronin is only okay at this.

Easy Time Tracking - I miss Billings and it's easy time tracking. You could just activate it from your keyboard and get going. This one is lower on my list, but it's something I do take a look at.

This year's candidates

These are the ones I want to take a look at this year. They may not have all the features above but on the surface they at least look like they are worth my time to investigate.

Billings Pro

Love that it’s a pretty cheap monthly subscription. Expenses can be the death of a small company. Getting away from as many of them as possible is a great idea.

FreeAgent

Really interested in the reporting aspects here. Looks much more full featured than Ronin reporting.

Solo

I tried the beta of this years ago and while it was pretty it didn’t stick. I don’t remember exactly why so I should take a look at it again.

Ballpark

Really just came across this recently based on a recommendation from Jesse Petersen but if he says it’s decent I’m up for trying it. The homepage is amazing and if they put 1/2 that amount of work in to the product it’s got to be awesome.

If you try Ballpark make sure to use Jesse’s code for 10% off, he’ll get 10% as well. code JESSEPETERSEN

Data ownership

One of the big stickers with the web based services above (not Billings Pro) is that you don’t ‘own’ the data it’s locked up on their servers. Even if they have an ‘export’ feature does the new system have an ‘import’ for it?

In light of that I’m also interested in hosting my own billing system in WordPress. So far I’ve found one option called WP Invoice.

My biggest ‘fear’ with WP Invoice is that it’s in the WordPress admin. I just don’t think that the WordPress admin is the best interface for software like this.

Can WordPress power an app like this? YES.

Are there any that I should be adding to my list? Why should I be adding them?