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.


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.


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


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.


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?

11 thoughts on “What Billing Software to use?

  1. We went with Billings for our first year because you can make the invoice look exactly like you wanted it. That was impressive to us but I also lost two full days of work getting it to look right. This was before Market Circle released their cloud-sync system thing so another downfall was the fact that only one person had access to the data at any time. We were quick to realize that we wanted a web app to handle it. We hate monthly fees and love owning data so we used activeCollab from the get-go, but that was back when they had a Small Biz license that basically replicated BaseCamp. There was a Corporate version that included all things Invoicing so we upgraded to that and have loved it ever since. activeCollab has changed their pricing model recently, but it’s worked great for us and not having a monthly fee associated with anything project management or accounting has been great.

    1. Wow I never spent more than 5 minutes trying to customize Billings invoices since the interface was so terrible. I just picked one and went with it.

      I’ve seen activeCollab a few times but never really dug in to it. I’ll take a look at it for my needs.

      1. Yeah it was wicked arduous to get the invoice looking how we wanted, but when we did it looked really sharp. We asked some clients who we became close with if they took notice and the lackluster replies lead us to quickly realize that we were the only ones impressed with the outcome. Since then we use the standard (only) “design” that activeCollab offers. Many times invoices go straight to an accounting department anyways, so it has little to do with impressing the client after all.

  2. I currently use Billings – I too had an issue making it look good (not a very friendly interface for the templates), but managed to get a set of templates for invoices and statements that worked for me. Since I need to invoice in two different currencies, Billings is able to invoice in either currency (and not every invoicing app/web app has Guatemalan Quetzales as one of their options). So, since now they will be a subscription based service, I am open to other webapps…

    1. I would love it if Billings Pro would work, but if it doesn’t have a way for clients to pay online without my interaction it’s going to be a non-starter. I’d deal with it if I only had Paypal, but I’d love to have Stripe and Paypal.

      Guess I’ll find out when I really start to dig in to Billings Pro again.

  3. I ended up creating my own invoicing plugin for ChiliProject (project management system). The big time saver for me was the integration with my PM system. I would say “make the invoice for ProjectA for September” and the plugin would automatically know the client, A/P contact, hourly rate, total hours, and the tasks worked.

    In the end it took me about a weekend to build the features I needed. I didn’t want it to send invoices or reminders to my clients and when they paid me online I’d just enter the payment manually.

    It worked for me because I tend to work with regular clients over a long period of time so at the most I’d send out four invoices per month.

    (Another side benefit is that I was able to open source the plugin, which helped my marketing a bit)

  4. When I was freelancing full-time, I used Harvest – http://www.getharvest.com/ for billing. But if I had to choose again, I’d probably go with http://lessaccounting.com. They aren’t the cheapest, but I think they offer a lot more than simple time tracking and invoicing. (I love their approach to comparing competitors too. Definitely worth checking out.)

    If you’re looking to disconnect from a monthly bill, http://pancakeapp.com is worth a look. It’s a self-hosted solution, PHP-based solution.

    1. I’m always trying to disconnect from monthly billing on stuff and Pancake looks pretty decent. Hopefully I’ll have time to try that as well.

      I got to talk to Steven Bristol of Less Accounting on The Freelancer’s show and yes it does reporting but it’s not a time tracking app so you’d need something else to track that stuff for projects.

  5. +1 for Billings. I have built a payment form on my own site using Gravity Forms & Stripe, and then just record payments in Billings Pro. Creating custom invoices is a pain, but at least you have that option.

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