In this post, we explore both platforms, outlining their features, benefits, integrations, and unique approaches to handling expenses and bookkeeping. Whether you are a startup, small or mid-sized business, or simply an individual looking for smart financial management tools, understanding the differences between Expensify and Pilot can help you choose the right solution for your needs.

Introduction

Expense management and bookkeeping have evolved significantly with the help of technology. Modern tools not only simplify the process of expense reporting and receipt scanning but also streamline bookkeeping tasks that were once time-consuming and error-prone. Expensify and Pilot are two solutions that have carved out their niches in this landscape. While Expensify primarily focuses on expense reporting, receipt processing, and travel expense management, Pilot takes bookkeeping, CFO services, and tax preparation to the next level for startups and growing businesses.

This blog post examines the two platforms closely, discussing key features, use cases, integration possibilities, and pricing options. By the end, you will have a clear picture of how Expensify and Pilot fit into your organization’s financial ecosystem.

What Is Expensify?

Expensify is a cloud-based expense management and accounting solution that simplifies the way individuals and businesses track, report, and manage expenses. Here are some of its core features:

• SmartScan Technology:
  Expensify uses SmartScan to read receipts in real time. Users simply snap a picture of a receipt, and the app automatically extracts key information such as date, amount, and merchant details.
• Expense Reporting:
  With its intuitive interface, Expensify allows users to create and submit expense reports that integrate seamlessly with credit card data, bank statements, and even travel itineraries.
• Corporate Card Integration:
  Expensify works hand in hand with corporate credit cards. For example, receipts captured with your Expensify account can then be matched to credit card charges, making reconciliation a breeze.
• Delegated Access and Co-pilots:
  One of Expensify’s unique features is the ability to assign a “copilot” to your account. This means you can safely delegate tasks—such as expense submission, approvals, or account settings management—to another user without having to share your login details.
• Automated Expense Workflows:
  The software supports automated workflows that speed up the process of merging receipts, matching transactions, and even reconciling account data. Features like off-line expense reporting, real-time updates, and robust filtering options help ensure every expense is properly tracked.
• Mobile and Web Applications:
  Expensify offers robust apps for both mobile and desktop users, making it simple to capture receipts on the go and then review or approve them later from any device.

Because of these features and its flexibility, Expensify has grown popular among businesses of all sizes—from small startups that need efficient expense management to large enterprises that require advanced reporting and integration capabilities.

What Is Pilot?

Pilot is a modern bookkeeping and financial services platform that focuses on providing high-quality bookkeeping, CFO services, and tax preparation for startups and growing businesses. Here are some of Pilot’s key characteristics:

• Automated Bookkeeping:
  Pilot’s platform is designed to automate many of the manual bookkeeping tasks that business owners typically face. This means that data from your company’s financial records can be more accurately organized without the need for extensive manual input.
• Human-Assisted Bookkeeping Services:
  Unlike some purely automated systems, Pilot also pairs you with a dedicated finance expert. This expert ensures that your financial data is correctly categorized and that any discrepancies are identified and resolved quickly.
• CFO and Tax Preparation Services:
  In addition to bookkeeping, Pilot offers CFO-level insights and tax preparation services. Their experts help you understand your financial health and provide insights to support strategic decision-making.
• Integration with Existing Systems:
  Pilot works seamlessly with other financial tools, including integrating with platforms like Expensify and QuickBooks. This means that once your expenses are captured on Expensify, the data can be exported and further categorized into your Pilot bookkeeping system.
• Tailored for Startups and Growing Businesses:
  Pilot is particularly popular with startups that need more than just expense tracking. They offer a service that scales with your business, providing the financial clarity necessary to attract investors, manage cash flow, and ensure compliance.
• Pricing and Discount Offers:
  One attractive aspect of Pilot is the discount available to new users through partnerships. For example, there have been offers such as 20% off the first six months of Pilot Core when you sign up using your Expensify Card.

While Expensify helps you capture and manage your day-to-day expenses, Pilot takes that information and aggregates it into comprehensive financial reports, which includes bookkeeping, tax filing, and financial reporting services. This division of labor means that the two tools can be used in tandem, with Expensify handling the rapid capture of expenses and Pilot offering precision bookkeeping and high-level financial insights.

Key Features Comparison

When deciding between Expensify and Pilot or determining how best to integrate both into your business operations, it is helpful to compare their key features side by side.

Expense Management and Receipt Capture

• Expensify:
  • Powerful SmartScan and receipt upload functionality.
  • Automated merging of receipts with credit card transactions.
  • Fast mobile capture, making it ideal for traveling employees or field teams.
  • Multi-level approval systems to ensure expense reports adhere to company policies.
• Pilot:
  • While Pilot does not focus directly on expense capture, it relies on exporting expense data from platforms like Expensify.
  • Uses automated categorization to process the historical expense data received.
  • Focuses on accurate bookkeeping rather than real-time capture.

Bookkeeping and Financial Reporting

• Expensify:
  • Provides basic accounting functionalities including invoice tracking, expense categorization, and reporting.
  • Integrates with several accounting platforms, enabling a streamlined handoff of data.
  • Can generate reports that help track travel expenses, reimbursements, and overall cash flow.
• Pilot:
  • Specializes in professional bookkeeping, complete with human oversight.
  • Offers CFO services, giving tailored insights into your spending, budgeting, and tax positions.
  • Provides real-time Profit & Loss summaries, balance sheets, and cash flow statements.
  • Ideal for startups who need thorough financial analysis and reporting to make strategic decisions.

Delegation and Collaboration

Collaboration is crucial for businesses of all sizes. Both Expensify and Pilot support some form of delegation, but they do so in different ways:

• Expensify’s Copilot Functionality:
  • Allows the account owner to delegate access without sharing login information.
  • You can assign multiple copilots to your account, giving them either full access (including approval rights) or limited access (submit only).
  • This is particularly useful for larger teams where expense submission and approval can be streamlined by delegation.
• Pilot’s Human-Assisted Bookkeeping:
  • Emphasizes the human aspect by connecting you with a dedicated bookkeeping expert.
  • This expert functions as an extension of your finance team, often collaborating with other systems like Expensify.
  • Helps ensure that data migrated from your expense reports is accurate and compliant.

Integration Ecosystem

Seamless integration with other financial tools is vital in ensuring that your processes are efficient:

• Expensify:
  • Integrates with a wide range of financial software, including QuickBooks, NetSuite, and various payment processing tools.
  • The platform’s API allows for data sharing across systems which simplifies the merging of receipt data and credit card transactions.
  • Offers features like auto-matching of uploaded receipts with bank downloads, ensuring accuracy and minimal manual intervention.
• Pilot:
  • Works well with systems like Expensify to receive structured data for bookkeeping.
  • Its ability to integrate with accounting software ensures that the financial data collected via Expensify is accurately reflected on your books.
  • By integrating with platforms that manage expenses and invoicing, Pilot creates a smooth transition from expense capture to comprehensive financial reporting.

How They Complement Each Other

Rather than viewing Expensify and Pilot as competitors, many businesses can benefit by using both in tandem. Here’s how the two platforms can work together:

• Capturing Expenses with Expensify:
  Employees can quickly capture receipts on their mobile devices using Expensify’s SmartScan. This data can include details for travel, meals, and miscellaneous office expenses. The platform automatically creates expense reports that are easy to review and approve.
• Transferring Data to Pilot for Bookkeeping:
  Once expenses have been collected and approved, the consolidated data from Expensify can be exported to Pilot. Pilot then takes over with its automated and human-assisted bookkeeping process to categorize expenses properly, generate financial reports, and prepare data for tax purposes. This handoff is crucial to ensure that the numbers on your financial statements are accurate.
• Leveraging Pilot’s CFO Insights:
  With the financial data properly captured by Expensify and then organized by Pilot, you gain access to high-level insights from Pilot’s CFO services. This means detailed financial statements, cash flow analysis, and strategic advice on reducing costs or optimizing spending can all be provided.
• Discount Offers and Cost Savings:
  It is worth noting that Expensify’s financial ecosystem sometimes comes with offers that encourage using multiple products. For instance, using the Expensify Card for transactions can lead to discounts on Pilot services. An example would be a 20% discount off the first six months of Pilot Core, making the combined offer even more cost-effective for startups.

User Experience and Reviews

User experience plays a big part in staying efficient and secure with your financial data. Reviews from platforms like Trustpilot show a mixed bag of opinions for both Expensify and Pilot—but there are consistent themes.

Expensify Reviews

Many users praise Expensify for its ease of use:

• Users have commented that the receipt scanning and mobile expense submissions are fast and integrative, saving considerable time.
• The delegation feature (assigning a copilot) has been described as efficient, especially when multiple approval processes are needed.
• Some reviews mention that while setting up the account can have its quirks at times, the overall experience remains largely positive due to its intuitive interface.

Conversely, some users note that once bank connections fail or discrepancies arise, the system’s error messages can be frustrating. Despite that, the majority of users appreciate the comprehensive receipt management, which makes the expense process nearly automated.

Pilot Reviews

While Pilot does not have the same volume of consumer reviews as Expensify, businesses that have engaged Pilot’s services often mention:

• A significant improvement in clarity and accuracy of financial reporting.
• The benefit of working with a dedicated CPM (Chief Financial Officer) team to help with strategic decision-making.
• Enhanced peace of mind knowing that bookkeeping and tax preparation are being handled by experts who understand the challenges unique to startups.

The successful partnership between the two systems means that even if there are minor hiccups in the expense capture process, the consolidated financial insight provided by Pilot often offsets these challenges.

Pricing Comparison

Pricing is always a critical factor in choosing business software. Here is a general breakdown:

Expensify Pricing

Expensify offers several pricing plans designed to suit various business sizes:

• Free Plan:
  Ideal for individuals or very small teams who need only basic functionality. It includes features like receipt scanning, expense tracking, and basic report generation.
• Business Plans:
  Plans such as Collect & Control are available, starting from as low as $10 to $18 per user per month on a monthly subscription basis and lower amounts with annual billing. Pricing scales if you want multi-level approval, custom coding integrations, and advanced reporting.
• Individuals & Self-Employed Plans:
  Also offers plans that allow up to 25 SmartScans per month in the free tier, with additional scans costing a small fee (around $4.99 per user per month) once usage exceeds that threshold.

Pilot Pricing

Pilot’s pricing model is geared toward comprehensive bookkeeping and tailored services:

• Pilot typically charges a monthly fee that is determined by the complexity and volume of transactions processed.
• Their pricing includes not only the automation of bookkeeping tasks but also access to human experts who manage your financial records.
• By partnering with tools like Expensify, Pilot often creates bundled offers or discounts (such as 20% off for the first six months) for startup clients looking to adopt a combined approach in expense management and bookkeeping.

Comparing the pricing, while Expensify offers a freemium model ideal for daily expense management, Pilot positions itself as a higher-end service provider that invests in comprehensive financial accuracy and strategic insights. Your choice will depend on whether you need a lightweight expense tracker or an in-depth financial partner.

Use Cases for Businesses

Understanding when to use Expensify versus Pilot—or both—can help optimize your management of finances:

When to Choose Expensify

• High Volume of Receipts:
  If you have traveling employees or teams that generate numerous receipts and expense reports, Expensify’s quick capture and automated matching will save significant time.
• Delegation and Team-Based Expense Tracking:
  The ability to assign copilots and easily merge expenses with credit card transactions means Expensify is ideal for organizations where multiple people need to submit and approve expenses.
• Mobile-First Environments:
  Its mobile application is highly rated and perfect for professionals constantly on the move, ensuring expenses are captured in real time.

When to Opt for Pilot

• Startups Needing Precision Bookkeeping:
  Pilot is built specifically for startups who value accurate bookkeeping and CFO-level insights over simply tracking receipts. It’s a trusted partner for companies preparing for growth, raising capital, or undergoing audits.
• Complex Financial Data:
  Businesses with more complex financial needs—including multi-entity management, detailed tax preparation, and robust financial reporting—will find Pilot’s approach more suited to their needs.
• Desire for Human Oversight:
  If you prefer having a dedicated finance expert oversee your accounts and help guide strategic decisions, then Pilot offers that vital human element that complements automation with expert insight.

Integration and Workflow

One of the strengths of both Expensify and Pilot is their ability to integrate seamlessly with other financial tools and workflows:

1. Exporting Data Between Systems:
   Expensify’s export features allow you to transfer data effortlessly from your expense reports into your bookkeeping software—often into Pilot’s system—to ensure consistency across financial records.
2. Data Reconciliation:
   Expensify automatically reconciles receipts with posted charges on company credit cards. Pilot then takes over, reconciling aggregated data with broader financial statements to deliver an accurate picture of the company’s financial health.
3. Simplifying Audit Processes:
   With both systems capturing and verifying data at different stages, you benefit from greater consistency and transparency. This is especially valuable during audits or internal reviews, where having precise, verified data saves time and enhances trust with stakeholders.
4. Enhanced Reporting:
   Expensify offers standard expense reports, while Pilot supplements these with detailed financial statements such as income statements, balance sheets, and cash flow reports. Together, they provide a comprehensive overview that can inform business strategy.

How to Get Started: A Step-by-Step Overview

To help you decide which solution—or combination of both—fits best, here’s a simplified step-by-step guide for integrating these platforms into your financial operations:

1. Set Up Your Expensify Account:
   • Create your account and integrate your company credit cards.
   • Configure your SmartScan settings to automatically process receipts.
   • Assign copilots (delegated users) who can handle expense submissions and approvals, ensuring that the workflow is efficient and secure.
2. Start Capturing Expenses:
   • Train employees to promptly snap photos of receipts using the Expensify mobile app.
   • Monitor the expense reports for errors, duplicates, or unmatched credit card charges.
   • Utilize Expensify’s automated tools to merge expenses and flag concerns.
3. Export Expense Data to Pilot:
   • Once your expense data has been cleaned and reconciled using Expensify, export it to your accounting software.
   • If you choose Pilot, coordinate with their team for the smooth integration of your expense data into their bookkeeping system.
4. Review Financial Statements with Pilot:
   • Work with your dedicated finance expert from Pilot to review monthly and quarterly financial statements.
   • Use Pilot’s insights to make strategic decisions about cost management, cash flow optimization, and budgeting.
5. Leverage Ongoing Integrations and Discounts:
   • Consider using additional features like the Expensify Card, which not only simplifies transactions but can also unlock discounts on Pilot services.
   • Engage in regular reviews to ensure that both systems are working together seamlessly.

The Future of Expense Management and Bookkeeping

As businesses continue to innovate and adapt to ever-changing financial landscapes, combining expense management and bookkeeping functions into an integrated approach becomes more critical. Expensify and Pilot exemplify the kind of specialized solutions that, when used together, allow companies to manage day-to-day expenses while maintaining robust financial reporting and strategic planning.

Looking ahead, both companies are likely to expand their service offerings. Expensify is continuously refining its expense report automation, mobile features, and integration possibilities. Meanwhile, Pilot’s focus on streamlined bookkeeping and CFO advisory services positions it as a key partner for startups and innovative companies seeking to unlock deeper financial insights.

In the future, expect further enhancements such as artificial intelligence-driven insights for cost reduction, improved data reconciliation, and even smarter delegation features within Expensify to support collaborative accounting. The market is moving toward a holistic financial management ecosystem where every transaction—from a coffee shop receipt to quarterly tax filings—is managed seamlessly, ensuring compliance, accuracy, and efficiency.

The decision between Expensify and Pilot does not have to be an either/or scenario. Instead, many businesses find that the true strength lies in using them together. Expensify offers exceptional features for capturing, processing, and managing expenses in real time, complete with a user-friendly mobile app, powerful integrations, and unusual features like copilot delegation. Across the spectrum, Pilot provides the expert bookkeeping, CFO advisement, and tax preparation services designed primarily for startups and growing businesses, ensuring that all financial data is accurate, compliant, and leveraged for strategic decision-making.

Ultimately, whether you choose Expensify or Pilot—or the hybrid solution combining the best of both worlds—your business stands to benefit from fewer manual errors, more accurate financial reporting, and better financial clarity overall. By aligning your expense management practices with robust bookkeeping and strategic financial insights, you position your organization for steady growth and long-term success.

If you’re still weighing your options, consider starting with a pilot program using Expensify’s free or low-cost plan to get a feel for the automation capabilities and user experience. Then, evaluate your needs for detailed financial oversight and consider integrating Pilot’s bespoke bookkeeping service into your workflow. With a clear understanding of your business needs and the capabilities offered by these platforms, you can make an informed decision that drives efficiency, transparency, and financial health across your organization.

By leveraging modern technology and expert advice, businesses can now handle the intricacies of expense reporting and bookkeeping with minimal friction. The future of financial management is here—and it is as much about smart process integration as it is about capturing every receipt.

Whether you are a startup seeking comprehensive financial insights or a mid-sized business looking to simplify expense management, understanding the differences between Expensify and Pilot is the first step toward optimizing your financial operations. With the right combination of automated tools and expert guidance, your company can achieve a streamlined, efficient, and strategic financial management process.

We hope this detailed comparison has provided you with valuable insights into expensify vs pilot. Let us know in the comments which features you value most in your expense management and accounting software. Happy managing!