One of the most tedious tasks that we’ve all hoped we could do without is tracking receipts. It doesn’t matter if you’re a young corporate hotshot, a one-man startup, a small business owner, or a high-powered on-the-go executive: at one point or another, you’ll have to gather those receipts for office expenses, keep track of those credit card and online payments, and spend time – hours, sometimes – on entering data into your financial records. Bo-ring. It can keep you off working on what really matters, too. But do any of us have a choice? We want to be spared tax-related hassle. We need to stay on budget.

Enter the app called Shoeboxed, which basically combines free online software with a paid scanning service to literally digitize and organize your receipts. Shoeboxed is the secretary we all wished we had, the receipt tracker who would never mind the time-consuming task of collecting receipts and doing the math for us busy bees.

So how does it work? First, you mail in your receipts (no matter how crumpled) using postage paid envelopes provided by Shoeboxed. Or you scan them. Or you take a picture of the receipts using your mobile phone or the Shoeboxed iPhone app. Buying from an online merchant? Don’t worry: Shoeboxed also allows you to simply E-mail your online receipts directly to your Shoeboxed account.

Even if you don’t sign up for a premium plan, Shoeboxed allows you to upload and organize an unlimited number of scanned receipts using Shoeboxed’s web-based collection point. This alone – secure, private access to your financial information (Shoeboxed has been certified by TRUSTe) – should make it worth your while to try out the added features of a paid account, which ranges from $9.95 monthly to $49.95 depending on the maximum number of receipts that can be scanned.

With a paid premium account, your virtual receipt-tracking secretary works even harder. Shoeboxed digitizes and enters the data for you in a useful format – and this is done with an accuracy that’s very reliable. So the photos of receipts that you took with your mobile phone, the papers and things that you’d mailed in, the online receipts you’d E-mailed – all these are converted and organized into a neat, easy-to-understand data file, which you can then edit yourself, or manage, or even export. To enhance the accuracy of digitizing your receipts, Shoeboxed extracts the data with Optical Character Recognition (OCR) then human-verifies it before it makes its way to your secure account.

The Shoeboxed system sets itself apart by adding a bunch of neat features apart from the ability to have a sweeping glance of all your digitized receipts. It takes expense reporting to a whole new level of efficiency and convenience. You can categorize data into 15 purchase classifications (meals/ entertainment, computers and Internet, etc.), pull in things like vendor names and payment types for cross-referencing, and even export all or selected data to PDF, Excel, CSV, Quicken, Constant Contact, Quickbooks, Freshbooks, and Evernote. With a Business account, you’ll even have your own quarterly backup CD provided by Shoeboxed.

And it’s not just receipts. The app can do the same thing with business cards, which is to say, Shoeboxed can digitize and save contact information from your business cards so that you don’t have to keep losing and looking for them. You can let Shoebox do the job even when you’re out of the office and on-the-go. Just take a picture of the cards with your smartphone.

Shoeboxed is, if not a necessity, worth every office employee or businessman’s try. There’s nothing quite as awesome as logging in and seeing all the receipt tracking and expense reporting work done for you. Not only are you spared the math and the typing; you’re also making time for yourself to do what really matters. Oh – and, of course, you’ll never lose a receipt or business card again.