I hadn’t heard of Expensify before I saw a TechCrunch piece on the company this afternoon. I happened to have several expense reports outstanding for a consulting client. I hate doing expense reports – scanning all the pieces of paper, putting together a cover document and putting everything into a PDF. Except during the relatively rare interludes in my career where I’ve had an assistant I can thrown receipts at and then race out of the room (Hi Andrew!), I’ve always been really bad at these. I have no excuse: my first boss taught me many useful skills, and precise receipt keeping was one of them. I just hate doing the reports. For that matter, I was never all that good at getting the receipts to my assistants.

So after reading the TechCrunch article I logged into Expensify, and half an hour later all my consulting expense reports but one were done and sent off. All of my expense reports for Linked Medical, our new startup, were done too, and filed in the “pay when we have more money” bin. I don’t think any web based tool has ever become so essential to me so quickly. One of the first “ASP model” web applications I ever used was the Ariba purchasing system, after my early-2000s startup became part of a much larger company. It was truly terrible. Fortunately I had an assistant.

Expensify’s product is pretty far from that original Ariba system. Sure, the software isn’t perfect, and a few of the rough edges are downright weird considering the overall level of polish (uploading a “.htm” file receipt gives you an error message, while “.html” works just fine). But they did at least six things right, and those six things are relevant for lots of different applications:

1. Make it brain-dead easy to start. I typed in my email address and was done. They sent me an email which I later clicked through to set my password. There was zero friction, which is incredibly important. I could also have logged in with my Google credentials, which is a nice touch – but this was actually faster.
2. Make it easy to explore. The home screen is a series of big boxes identifying common interests for new users. I’d heard about the mobile tool first, and it was one click to learn more. The basic navigation is very simple, and maps to things like “Receipts”.
3. Use Mobile for the right things. This is really important. I do not want to create an expense report on my Android phone. I probably don’t want to create one on my iPad either. When I’m mobile, I want to do one thing: easily record expenses. So the mobile app does that very well – I can photograph a receipt with my phone, and/or enter expense details on a simple screen. There are two big buttons when I open the application, one for each option. It’s very responsive. And I don’t need to keep the small receipts anymore.
4. Integrate seamlessly, but don’t make me do it first. Another box on the home page is “Link Credit Cards.” It took two minutes to link in my American Express, and then I had a huge list of transactions to choose from.
5. Give me multiple avenues to learn the software. I can add expenses to a report from the report, or I can look at expenses and add them to a report. Same with receipts. I never found myself having to go back into the wrong area of the application. When I looked for a feature, it was there.
6. Don’t make me learn the whole thing. Expensify supports “policies” for corporate expenses. There are some other features there too around submissions and approvals. I don’t need those yet, so I didn’t have to use them, learn about them, or worry about them. As it happens I have looked at them, and they’ll be useful in the future – I just don’t need them now. Complexity kills, especially when you want casual users to adopt a system without external support. Expensify landed me as a customer because I was able to finish an expense report in 15% of the time it would have otherwise taken.

They also do a good job of thinking about ways that new technology lets you change the underlying workflow of an old process. In this case, it’s expense reports for receipts under $75. If you link a credit card, you can import expenses and the system generates an “eReceipt” for that charge. Expensify prints it in the report and adds a bar-code, and it can be verified with the site later. The company will stand behind the fact that the expense was imported from a credit card statement, up to and including during an audit from the IRS. If your corporation accepts the eReceipts, you can stop carrying around those little printouts from taxis. This is something that the old Ariba system – or any non-cloud expense account system – simply can’t provide, because it relies upon the trusted connection to the credit card company, and on Expensify’s willingness to stand behind the integrity of that data.

When turning workflows into products, it makes to ask what capabilities are available now that weren’t available on paper or weren’t possible electronically with the technology of a few years ago. The eReceipts are a great example of this. Development for the iPad should be triggering a lot more of this kind of lateral thinking, as we all adjust to touch-and-swipe interfaces instead of keyboards and form fields.

Naturally there are a few things Expensify can improve on. I’m glad I didn’t need to take a training course to use the tool, but a five-point introduction to the core concepts would have been nice. The most opaque thing about the system is the relationship between receipts and expenses. It’s not actually all that hard to figure out, and the system gives you helpful messages. But an introduction presentation would have made things clear from the get-go. Dropbox does a great job with that.

Any time you’re asking users to think about the attributes of a data model you’re asking for a certain amount of trouble. In this case, the idea of “reimbursable” and “unreimbursable” expenses also needed some clarification. Since I was in consultant mode when I was doing today’s reports there’s no concept of “unreimbursable” – but I’d unclicked the default when I was linking my credit card because I thought that leaving it as “reimbursable” would make more work for me as I filtered through expense lists. It turns out this is useful for corporate cards, which makes sense – but I’ve never carried a corporate card where I didn’t get the bill myself (oddly, this was true even when I worked for the Federal government).

The bottom line: a very useful service and a great source of ideas for making other web applications easier to use. Oh, Expensify guys -please add an “email receipt” feature like TripIt’s, if you haven’t already.