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Shoeboxed vs Expensify: Which Expense Management Software is Best?

by Envoice
9 min read

If you’re a freelancer or a small business owner, you’re well aware that keeping track of your expenses and receipts is crucial for your pre-accounting tasks and being ready for tax time. While looking for a comprehensive expense tracking solution online, you may have encountered these apps: Expensify and Shoeboxed.

This guide will compare Expensify vs Shoeboxed in terms of their key features, pricing, ease of use, and other key factors. We’ll also go in-depth into the capabilities of their receipt-scanning apps and integrations to help you decide which service is best for your business.

Read this guide to learn more.

Expensify vs Shoeboxed: An Overview


screenshot for expensify.com website

Expensify is a powerful expense tracking software with effective financial management tools. Its expense management features include filing expenses, reimbursements, approval workflows, mileage tracking, and credit card reconciliation. It also has affordable pricing plans, making it an ideal tool for small business owners.


screenshot for shoeboxed.com homepage website

Shoeboxed is a popular receipt scanning and document management service. The platform offers tools for accurate receipt capture via the Shoeboxed mobile app, turning your paper receipts into data for expense reports and tax filing. It also has features for batch document processing (Magic Envelope) and integrates with popular accounting software.

Expensify vs Shoeboxed: Side-by-Side Comparison

Expensify Shoeboxed
Pricing Starts at $5/month (free account available) Starts at $29/month (30-day free trial available)
  • Expense management
  • Receipt scanning
  • Reporting and insights
  • Invoicing
  • Mileage tracking
  • Travel reimbursements
  • Spend management

Unique Features

  • Global reimbursements
  • Budgets
  • Virtual cards
  • Expense tracking
  • Document processing and management
  • Receipt management
  • IRS-accepted receipt capture
  • Mileage tracking
  • Expense reporting

Unique Features

  • Business card management
  • Magic Envelope
  • Gmail receipt sync
Integrations Over 40 apps Over 10 apps
Security SSL data encryption SSL data encryption
Cloud storage Yes Yes
Interface  SaaS/Cloud/Mobile Saas/Cloud/Mobile
Customer Support Email and live chat Email/Phone support
Reviews 4.5/5 [1] 4.4/5 [2]

Key Features

Expense Reports

Expensify allows you to create a detailed expense report from your scanned receipts. You can import your business expenses and credit card transactions automatically through credit card import. The platform offers a seamless approval and reimbursement process for your employees.

Shoeboxed lets you create a comprehensive expense report using receipt data. It streamlines the process by automatically compiling all categorized receipts, which you can export in PDF or CSV. However, a report cannot contain over 450 receipts.

Receipt Management

Expensify offers a quick way to scan receipts through SmartScan. The feature automatically reads receipt data, specifically the merchant, date, and amount. After creating an expense report, your receipts are saved automatically into your Expensify account.


shoeboxed.com screenshot showing scan receipts categorize

Shoeboxed lets you scan receipts and categorize them manually using the Shoeboxed mobile app. However, if you want them to be automatically categorized, you can send them to Shoeboxed via Magic Envelope or on your account dashboard. Receipts processed by Shoeboxed are IRS-certified, meaning they are audit-ready for tax filing and compliance.

Expensify – Additional Features

Global Reimbursements
Expensify allows you to track and manage cross-border reimbursements. You can send reimbursements on the platform and let your employees receive their money in their currency. The feature supports withdrawals from 24 countries with USD, CAD, GBP, and EUR accounts and deposits in over 190+ countries globally.

Expensify lets you and other admin users set monthly or annual budgets for your organization’s expenses, such as travel and meals, for a specific department, team, or set of employees. The feature will notify users when the budget crosses a particular limit (e.g. when it’s 50% or 75% spent).

Virtual Cards
One of Expensify’s spend and bill management features is its unlimited virtual cards for employees, which employees can use for online transactions. You can set spending limits for each card, like a fixed amount for one-time use or monthly limits for recurring subscriptions.

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Shoeboxed – Additional Features

Business Card Management
If you have several business cards from various vendors or partners, Shoeboxed can help you transform that contact information into your online contact list. You can send the cards via Magic Envelope and let the platform do the job for you. Also, you can export your contact list to various platforms, including Gmail, LinkedIn, and Microsoft Outlook.

Magic Envelope

screenshot showing Shoeboxed’s Magic Envelope document processing tool

Shoeboxed’s Magic Envelope is a document processing tool that allows you to send receipts, business cards, and other documents directly to the Shoeboxed team via snail mail. Once your documents are received and processed, you’ll receive digital copies and organized databases containing extracted data from those documents.

Gmail Receipt Sync
If you mainly use Gmail to receive receipts from online transactions, you can automatically import receipts from your inbox to Shoeboxed to easily track and manage your expenses. You can then manually input receipt data for your expense report or send them to Shoeboxed through email for document processing.

Ease of Use

Expensify offers a user-friendly interface that lets you easily view your expenses and pending approvals. Its invoicing feature, New Expensify, is easy to use and allows you to send invoices to everyone, even if they don’t have an Expensify account. You can also manage to ‘batch up’ receipts so you won’t be constantly alarmed by incoming receipts.

Shoeboxed has an intuitive and clean user interface containing expense management features. You can easily view your uploaded receipts and business cards and check if your documents were processed manually or automatically. You can also add tags on receipts to keep them organized.

Receipt Scanning App

Expensify’s Expense Tracker app lets you scan receipts using SmartScan, which uses optical character recognition (OCR) for accurate text extraction. You track the status of your expense reports on the app and view insights about your spending. Your receipt captures are automatically saved on your account’s cloud storage.


screenshot for Shoeboxed Receipt Scanner app

The Shoeboxed Receipt Scanner app allows you to scan receipts and track mileage. It uses OCR technology to extract text data from receipts and store them in the cloud. However, some users had issues with the app’s auto-categorization feature for receipts, which may require you to do it manually.


Expensify has integrations with over 40 apps, which include accounting and finance software, HR platforms, practice management services, and travel apps. This includes QuickBooks, Oracle NetSuite, Xero, Sage, Microsoft Dynamics, Thomson Reuters, etc.

Shoeboxed has limited integration support for accounting software, pre-accounting tools, and tax management apps. It includes QuickBooks, Xero, Wave Accounting, and ScanSnap.

Note: Besides QuickBooks and Xero, Shoeboxed has very limited integrations with accounting and finance tools. If you want a scalable tool for expense management that connects to more apps, try Envoice. It integrates with key software like QuickBooks, Sage Accounting, Microsoft Dynamics, Xero, and more. Sign up now for a free trial.


Expensify has two main pricing plans: Collect ($5 per user monthly) and Control ($9 per user monthly). Both tiers include unlimited SmartScan credits and mileage tracking. They also provide access to tools like Bill Pay, expense approvals, credit card import, and ACH reimbursement. Expensify also offers a free version with 25 SmartScans monthly.

Shoeboxed offers three main pricing plans: Startup ($29 per month), Professional ($59 per month), and Business ($89 per month). All tiers have perks like unlimited users, cloud storage, receipt scanning, and mileage recording. The platform has a 30-day free trial on all plans and offers a 20% discount when you opt for annual billing.

Note: With its lowest plan (Startup) starting at $29 monthly, Shoeboxed’s pricing plans may seem expensive for most small business owners. For a cheaper alternative to your pre-accounting processes, consider an add-on like Envoice. It has tools that help you track invoices, approve expenses, make payments to suppliers, and more. Register for a free trial today.

Who is it For?


screenshot for expensify.com expense management page

Expensify is excellent for small businesses and freelancers needing effective software for expense management and accounts payable tasks. It has features for receipt management, custom approval workflows, ACH reimbursements, bill management, and customizable reports. The platform also integrates with various apps for accounting and finance, tax compliance, and other popular platforms.

Shoeboxed is an ideal expense management software for companies and self-employed businesses seeking a tax compliance tool. The platform helps you with batch document processing through Magic Envelope to create online databases from your receipts, business cards, and other files. It’s also practical for companies needing an expense reporting tool for QuickBooks.

Claim to Fame

Expensify is an excellent expense management and pre-accounting solution. It has robust features for receipt management, approval workflows, cross-border reimbursement processing, and expense auditing. The platform also provides tools to manage employee spending, like Budgets and virtual corporate cards.

Shoeboxed is a powerful expense tracking and document-scanning service. It offers Magic Envelope for batch document processing and is recognized by the IRS and CRS, making it an excellent pre-accounting tool for tax compliance and document management. The platform also integrates with key accounting tools like QuickBooks and Xero.


If you’re a self-employed individual or a small business owner searching for a feature-packed expense management software, Expensify is the right tool for you. It offers receipt scanning, expense tracking, custom approval workflows, and reimbursement processing features. It also has affordable pricing plans and integrates with major accounting and finance software.

On the other hand, if you’re looking for an expense tracking and file management tool, Shoeboxed is an excellent choice. You can send your receipts, business cards, and other business documents to the Shoeboxed team for bulk document scanning. It also offers receipt auto-sync with Gmail, mileage tracking, and integrations with QuickBooks and Xero.

However, if you want a scalable expense tracking solution for your growing business, try Envoice. It automates various expense tracking tasks, like receipt scanning, categorization, and multi-level approvals. The platform also has more affordable pricing plans and integrates with popular accounting and finance tools, like QuickBooks, Sage, Xero, Wise, and Microsoft Dynamics.

Curious about how Envoice can help automate your bookkeeping tasks? Check its key features now and make your pre-accounting process more efficient than ever!


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