Shoeboxed vs Expensify | The Ultimate Battle (2023)

(Last updated on January 9th, 2023)

Shoeboxed or Expensify? Which expense management application is better in 2023?

Read this in-depth Shoeboxed vs. Expensify comparison to make a wise decision.

The name ‘Shoeboxed’ quite accurately reflects how many small business owners treated their expenses before easy-to-use expense management applications became available. Doing the accounts involved huge amounts of time-consuming data entry, including immense frustration if receipts or bank statements had got lost or were no longer legible; everyone dreaded the month-end torment.

Using a pre-accounting package to handle receipt and bill input saves time, which you can spend on activities that create value rather than on paperwork. It can also help save you tax, as you’re able to claim more deductions that you might have missed. And your accountant will also, most likely, be invoicing you fewer billable hours – another win!

However, the two applications we’re comparing here are not quite the same in the way they approach the task. Shoeboxed is much more small business focused, and it concentrates on the pre-accounting job. Expensify handles receipts, but it also delivers features to help businesses manage their expenses policies and approvals – and it scales up for enterprise use.

We’ve taken a good look at both products. Which is right for you? Read on to find out how they compare.

Shoeboxed vs. Expensify: Comparison At a Glance

1. Features
Winner: Expensify. Shoeboxed sticks to its pre-accounting forte, transforming your paper receipts into digital data. Expensify does this but it goes much further, giving you a whole expenses management system.

2. Pricing
Winner: Tie. Both applications have tiered pricing structures with a monthly subscription. Shoeboxed limits the number of items processed at each level while Expensify offers greater functionality in its higher-priced packages.

3. Ease of use
Winner: Tie. Both applications are easy to use – they are designed so a small business owner who’s not a geek is going to be able to get them working well.

4. Mobile Apps
Winner: Expensify. Both apps work well for receipt input and mileage, but Expensify offers other features such as expense approvals and time tracking.

5. Integrations
Winner: Expensify. Expensify’s links to travel provider platforms like Uber and Hoteltonight let you capture data automatically; it also links to major accounting applications. Shoeboxed doesn’t have as many integrations.

6. Customer Support
Winner: Expensify. Shoeboxed does offer phone support, but Expensify provides more resource, particularly during onboarding. Both companies could do better.

7. Setup
Winner: Shoeboxed. Neither application needs a lot of configuration – Expensify, being a bit more complex, needs a more intensive setup to sync to accounting software.

8. Reports
Winner: Expensify. Shoeboxed doesn’t really provide reporting; Expensify on the other hand has developed some good standard reports, and you can also customize reporting with a bit of extra effort.

Short Verdict

While Shoeboxed provides a useful service, we plump for Expensify as the best choice. Shoeboxed will get rid of your paper, but it won’t do a lot more. Expensify, on the other hand, will not just let staff scan in their receipts, but it will apply quite a lot of intelligence to your data, spotting duplicate receipts, and learning where different types of transaction need to be posted.

Expensify will also help you manage your expenses. It lets you specify policies, and it will automatically find and flag up violations. You’ll be able to create customized reports to spot trends in your expenses, and sync the application to your credit card accounts. All in all, we find Expensify delivers a lot more added value than Shoeboxed.

1. Features

These two applications both have similar functionality in terms of scanning in receipts, but otherwise, they have quite different sweet spots.

Shoeboxed basically is all about digitizing documents, though it does offer more than simple digitization. Submission of expenses is hassle-free, using a mobile app or Gmail plugin, or – for those who’ve not made it out of the paper-and-ink world – you can mail documents off in the ‘Magic Envelope‘ for Shoeboxed to do all the digitizing work. You can also use Shoeboxed to digitize business cards and export them to your contact management software.

Shoeboxed uses OCR (Optical Character Recognition) to extract the key data from receipts. You can then export the data to your accounting program instead of having to type it in. The scan of the original will remain ‘stapled’ to the transaction in your accounting system, so it’s a breeze to call it up if you need to check something, or for audit purposes. Shoeboxed’s scans are approved by the IRS, so you can throw the paper away – you’ll never need it.

You can also set up rules. You’ll be prompted when you first add a receipt from a particular vendor, and you can decide whether you want all future receipts from that vendor to be treated the same way. For instance, all receipts from Charlie’s Cappuccino Cafe can be posted to Meals / Entertainment just by ticking the box. You can also add new custom categories.

However, Shoeboxed doesn’t include time tracking. Nor does it allow you to set and manage expenses policies. This is where Expensify comes in – it has far greater functionality and goes beyond pre-accounting, to help you manage your expenses across your business.

You can sync Expensify with your credit card accounts, and it will also calculate mileage automatically through its mobile app (though annoying it doesn’t save addresses that you visit). It also picks up transactions in travel apps you’ve integrated, like Uber, Trainline and Lyft, as well as hotel booking apps. You can even use it to arrange travel itineraries.

It goes a lot further than Shoeboxed in letting you set up rules. You can also set up and administer your expenses policies, and run multi-level approvals through the application. It will automatically track any violations. Expensify also lets you reimburse employees on a next-day basis by direct deposit, and automates the process so as soon as you’ve approved the expense, the payment is set in motion.

Expensify uses machine learning to keep improving its accuracy and efficiency. For instance, it will learn from the way you file receipts from particular vendors where they ought to go. It can then match receipts automatically to the correct categories in your accounting software, and all you have to do is approve it – you don’t have to type in tags or tick the boxes.

Automation is a real strength for Expensify. One of the features we like its its ability to spot duplicate receipts and automatically flag them up. It also syncs daily with your credit card data, picking up transactions and matching them to receipts. And it supports multiple currencies, which is good if you export.

Shoeboxed does its job really well and can save you a lot of manual data entry. But Expensify goes much further, giving you a true expense management system as well as dealing with your receipts.

Winner: Expensify

2. Pricing

Expensify starts with a free service giving up to 25 SmartScans a month, which for a small business might well be enough to get started. Further packages are tiered to appeal to different types of business, from solopreneur up to larger corporate.

Expensify offers its own corporate credit card to all US businesses. Users of the card will get a 50% discount on the top two ‘Collect’ and ‘Control’ package subscriptions. Note that pricing is per month per user – so if you have multiple users the price will rack up.

Plan	Pricing per user per month	Functionality
Free	Free	Up to 25 SmartScans/month., other functionality as for Track or Submit
Track	$4.99	Mileage tracking, auto-categorize: freelance or solo entrepreneur
Submit	$4.99	Same as Track but for multi-employee businesses: submits receipts to manager / accountant
Collect	$5 with Expensify card $10 unbundled	Adds auto-sync to accounting software, reconciliations
Control	$9 with Expensify card $18 unbundled	Adds corporate card management, approval workflows, HR/ERP integration

To benefit from the bundled fee, 50% of more of spend must be on the Expensify card.

Shoeboxed has a three-tiered pricing system. Each level entitles the user to a certain number of items processed, with separate allowances for physical and digital documents. All levels allow unlimited users.

Plan	Pricing $/month paid annually	Pricing $/month paid monthly	Functionality/limitations
Startup	$18 first year: then $23	$22 for first 6 months, then $29	One mail-in a month, 600 digital documents a year doesn’t include QuickBooks integration
Professional	$36 first year: then $47	$45 then $59	Unlimited mail-ins, 1800 digital and 1800 physical documents a year includes QuickBooks integration
Business	$54 first year: then $71	$67 then $89	36,000 digital and 3,600 physical documents a year includes QuickBooks integration

Expensify, because you have to pay for each additional user, is likely to add up to more for most businesses with more than a handful of employees. If you’re only interested in the pre-accounting package, you may get a cheaper package with Shoeboxed.

However, we consider Expensify excellent value for money given the extended functionality that it offers. For solopreneurs and freelancers, the free version could work well. We’d also recommend using the Expensify card and then taking the Collect package – with the card, it only costs a cent more than the limited Track and Submit packages, but delivers quite a lot more in the way of useful features.

Winner: Tie

3. Ease of Use

Shoeboxed actually offers the easiest interface of any that we’ve seen – just drop all your paper receipts in an envelope and send them off! Receipts can also be scanned in using Shoeboxed’s OCR to generate the data. The data is then saved and can be exported to your accounts package.

The website also makes it incredibly easy to manage the data, just dragging and dropping items as required.

Expensify, despite it more complex functionality, remains highly intuitive. Its workflow is easy to use; it’s simple to set up policies and approvals, and to see which expenses need to be approved before publishing to the accounting system.

Staff will find the SmartScan mobile app easy to use – it’s now the main way for staff in many companies to submit expenses and upload receipts. The app’s ease of use and speedy processing times can help improve compliance and timeliness of filing expenses.

Expensify only has one major issue, which is that the links to banks and credit cards are not always robust. If they get out of sync, the application won’t work, and users report issues getting them reset.

Winner: Tie

4. Mobile apps

Shoeboxed’s mobile app is available on both iPhone and Android, and is simple to use. However, some users are annoyed by the auto-rotate, which forces them to take the picture more than once in order to get the orientation right. The UI is now a little outdated, too, and the app gets mixed reviews.

Shoeboxed has recently enabled mileage tracking on the smartphone, which is a step forward to becoming a more useful expenses management program.

Expensify also has a very simple to use mobile app for scanning receipts, but the app also lets you do more. You can approve reports from your smartphone, or investigate violations of your expense policies. Automatic GPS tracking also let you track mileage.

Expensify’s app gets better reviews from users, with the mileage application particularly appreciated by on-the-go business owners.

Winner: Expensify

5. Integrations

Expensify has 73 separate integrations, including major accounting systems such as QuickBooks Online, Xero, Netsuite, and Sage Intacct. It also integrates with Gusto payroll, and with time tracking apps like TSheets.

We think one of Expensify’s strong features is receipt integration. It links to a whole batch of different service providers such as Uber and Lyft, Travel Perk and Tripcatcher, and others. When staff book hotels, travel or parking through these applications, Expensify will automatically import the expense. It will also check whether the expense is in line with your policies, and flag up any violation.

Shoeboxed has fewer integrations. As well as supporting QuickBooks Online and Xero, it also supports Wave, one of the leading free accounts packages. We’d also point out that a number of QuickBooks users have found the syncing didn’t work well for them. Shoeboxed doesn’t have the integrations with travel service platforms that Expensify boasts; however, it does link to Evernote and Constant Contact, which some small businesses will find very useful.

Winner: Expensify

6. Customer Support

Shoeboxed offers phone and online support, while Expensify doesn’t offer phone support; so if you want to speak to a real person, that’s a mark in favor of Shoeboxed. However, some customers have found that Shoeboxed’s response is slow, and while there are plenty of video tutorials and useful articles on the site, some are dated.

Expensify offers online support for paid plans, and features a knowledge base and useful videos on its website. However, while support is good in the onboarding phase, it can falter later on. Month ends can be particularly fraught, seeing long wait times for the online chat service.

Support also seems unable to help with credit card syncing problems. This is one of Expensify’s few weak points.

Winner: Expensify

7. Setup

As both of these applications run in the cloud, there’s no installation to do, and setup is easy. Expensify may need a bit more effort upfront, as you’ll need to configure your policies and spend little time setting up rules to get the best out of the system. Expensify does provide support with onboarding, and this can be particularly valuable if you haven’t used this type of system before.

You’ll need to map categories and descriptions to the ledger account codes, too, to get transactions posting to the right place in your accounts. It’s not rocket science, but this could be time to use your accountant or bookkeeper to ensure things are set up right at the beginning.

Shoeboxed, on the other hand, can be run pretty much as-is. You’re going to need to do all of five minutes setting it up for the simplest implementation. Syncing to QuickBooks will take a bit more setup time, as with Expensify.

Winner: Shoeboxed

8. Reports

Expensify produces basic expenses reports and lets you save, print, or export them. It also enables commenting on reports, which can be useful as your business grows to accommodate more than one level of management.

You can also customize reports. It can be complicated to set them up the way you want them – this is one area that Expensify hasn’t managed to make very user-friendly. However, once you’ve set it up, you’ll get great insights into your expenses trends.

Shoeboxed produces standard reports, but you’re not going to get a lot of value add unless you customize. The reporting function feels to us a bit behind what Expensify offers. You’re probably better off exporting the data to your accounting package and customizing reports in there.

All data in Shoeboxed can be exported, including the scans of receipts, so you’ll always have your audit trail. And if the IRS comes calling, you’ll be able to show them the scans easily.

Basically, Expensify has a lot more to offer with reporting, and we’d expect that to continue, since larger businesses which need in-depth reporting make up a good proportion of Expensify’s client base.

Winner: Expensify

Final Thoughts

This review has really been a bit one-sided. Shoeboxed just doesn’t have the functionality to stack up against the fuller-featured Expensify. It’s mainly limited to scanning and data input, and though it has developed some other features, it doesn’t have the in-depth capabilities that Expensify provides.

Expensify offers so much more. It’s got almost all the same data input possibilities – though it doesn’t have a ‘magic envelope’ for companies with huge amounts of paper to process.

But on top of that it adds expenses management functionality which can help you keep control of what’s being spent. It also integrates with travel service provider platforms which saves you having to copy over data – your Uber or Lyft receipts will arrive automatically in your inbox.

Shoeboxed could help businesses which are drowning in paper – but with Expensify you’re not just cutting out paperwork, but also building an expense management system that will help you manage your costs. For us, that makes Expensify the clear winner here.

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