I get asked often what I recommend for invoicing clients. There are a lot of offerings. After all, you could do it the old fashioned way and use one of those invoice templates that Word and Pages offers (do people really use those?) But you’re probably using, or want to use, software that is built around the act of invoicing.

What do you need your invoicing software to do?

Are you a solo freelancer or a shop of 15? We all have different needs. Some of us, like designers who purchase stock photos and those who need to travel, need robust expense tracking. Or maybe you want integrated time tracking, and the ability to estimate new projects.

Before you choose a product, make a list of what you need your invoicing software to do. For example, my needs are pretty basic. I need a tool that has projects, and I need the ability to log time in these projects and generate invoices from unbilled time. Bonus points if it’s super easy to see who owes me what and when.

Desktop or Web Based?

Sometimes this is more a philosophical or aesthetic decision. I’m obviously biased towards web based software – Planscope can’t be downloaded. I personally don’t trust myself to keep my project information on my laptop. The chances of theft or hard drive failure, while thin, are still there. I trust that web application providers do daily backups and take care of warehousing my data. After all, that’s their job (and why I’m paying them.) And yes, we’re extremely paranoid and proactive about securing Planscope’s data.

I’m inclined towards web based software because they tend to run well in any desktop browser – meaning I can access it on my phone, iPad, laptop, or whatever connected computer is closeby. They’re also more likely to have some sort of collaborative abilities, a must if you’re not working solo.

List of some options for invoicing software:

• Harvest This is the product my team and I use. Features include time logging and running timers, reports on time logs (by client, project, staff, and so on), generated and manual invoices, recurring invoices (great for retainer agreements or hosting invoices), and expense tracking.
• Freckle Written by two friends of mine, Amy Hoy and Thomas Fuchs, Freckle is a beautiful and simple product meant to make the barrier of logging time as minimal as possible. It also boasts an emphasis on providing reflective analysis on your working habits: Are you spending too much time on unbillable time? Are you lagging on certain days? Features include dead simple time logging, quick reporting, a pulse view that visually shows your work output on a calendar, and invoicing.
• Freshbooks Freshbooks is a full featured product that satisfies a lot of the needs most small businesses have. Two features set them apart: They integrate with a lot of payment gateways, which is super useful if you accept credit card or echeck payments. They also can snail mail invoices, if you have strange, enterprise-y clients who requires such things. In terms of features, they’re pretty similar to Harvest: Time logs, invoices (recurring and generated), reporting, and expense tracking.
• FreeAgent A lot of our users across the pond use FreeAgent, which seems to be the most popular offering in the UK. Unique to most of the other time tracking and invoicing tools, they integrate with bank accounts and help you out come tax time. Other features include time logs, invoicing, drafting proposals, and expense management.
• Billings The only non-web based product on the list, Billings is a Mac and iOS application. Years ago, when the invoicing landscape was much more barren than it is today, I used Billings – and it’s obvious that it’s come a long way since then. Features include time tracking directly from your operating system, generated and recurring invoices, reporting, and a native iPhone client.
• LessAccounting Written by my super friends Allan Branch and Steve Bristol, LessAccounting has everything a small business needs for bookkeeping. I don’t believe they offer time tracking, but they do let you generate invoices (remember: bakeries, record shops, and other companies that don’t bill for time use it!) Besides invoicing, they integrate with hundreds of banks, let you create project proposals, track vehicle mileage, run reports and manage contacts.
• Harpoon Harpoon includes all the features you’d expect from a powerful, online invoicing system. But Harpoon sets itself apart with some very practical financial planning and goal-setting features. You can set a financial goal for your business and then map out your expected and collected revenue on a yearly calendar as you work towards meeting your goals. Harpoon also provides an assortment of financial metrics you don’t find in most other invoicing apps, including letting you know when it’s safe to take a vacation. You also get a robust time-tracking system, expense tracking, project scheduling, and accounting reports.

Other time tracking tools (that don’t have invoicing)

• Mite This is another European product, which has worked hard to design a very clean, very simple interface that stays out of the way. Features include time logs and running timers and reporting.
  
• Tick Tick is a simple time tracking tool that places an emphasis on fitting the time you log within a project budget. Features include easily adding time, quickly seeing what budget is remaining on a project, and reporting.