Are you on the hunt for a new expense management software provider?
It’s not an easy decision to make.
With so many highly-rated platforms out there, making the right choice can seem quite daunting. We also understand you don’t have the time or resources to roll the dice on an expense system.
You need to know you’re buying into the right product first time around.
While it’s always up to the provider to allay any concerns, you can take some control of that process yourself by attending sales calls and demos armed with a strong roster of questions to put to their sales rep.
In this blog, we’ll go over eight of our top questions to ask your potential new expense management service provider in order to get the best possible information out of them.
In today’s post, we’ll be going into the details on each of these questions and discussing why each is important to cover when running through a sales demo or pitch from an expense management provider.
However, if you’re too busy to capture all that information right now, here is a quick rundown of the eight questions you must ask when you speak to any provider:
When evaluating expense management software, one of the first things to consider is whether it genuinely simplifies life for employees. If the process feels slow or complicated, people won’t use it consistently.
Modern tools should make expense capture effortless.
Features like mobile receipt scanners let employees snap a photo of a receipt and have key details extracted automatically, removing the need for manual entry. With a mobile app, expenses can be submitted on the go, too.
A clean, intuitive interface also helps even non-technical staff submit expenses quickly, while other inclusions such as fraud detection and built-in mileage tracking reduce errors and cut down on follow-up questions.
Knowing the software you’re buying into has features like these is essential.
You can read our guide on crucial expense management features here.
A great expense management platform doesn’t just capture expenses, it streamlines how they move through the business.
When assessing software, it’s important to understand how well it automates and simplifies approvals, because slow or inconsistent workflows are one of the biggest causes of reimbursement delays.
Modern systems should allow you to customise approval routes to match your policies, whether that’s a single manager sign-off or multi-level approvals based on department, spend category, or amount.
The experience should be just as smooth for managers as it is for employees. Mobile approvals are now a must-have, letting managers review, approve, or flag expenses instantly.
Automation also plays a key role.
Look for features like instant notifications, reminders for pending approvals, and automatic routing of reports to the right people. These tools keep the process moving, reduce back-and-forth, and ensure compliance is maintained without slowing the business down.
Security should be one of the first things you evaluate when choosing expense management software. The platform will hold sensitive financial data, and you need to be confident that data is protected.
A secure system not only reduces risk but also builds trust across your organisation.
Look for platforms that ensure data is protected whether it’s being uploaded from a mobile device or stored in the cloud. Industry standards like PCI-compliant data handling and ISO compliance criteria are essential, especially if your process involves payment information.
Regular third-party security audits and penetration testing show that the provider takes data protection seriously.
Compliance features are equally important. Secure, cloud-based storage should include audit trails, time-stamped activity logs, and reliable retention policies to support internal audits and tax requirements.
With these controls in place, you get both peace of mind and a more robust, transparent expense process.
Mileage claims are one of the most commonly mishandled areas of expense reporting, so it’s crucial to choose software that makes tracking simple and accurate.
Look for a system with a built-in mileage tracker that lets employees log journeys directly from their phone. The best platforms can auto-calculate distance using GPS and apply your predefined mileage rates automatically, removing guesswork and manual calculation errors.
For finance teams, mileage data should be easy to export, review, and audit, ensuring every claim is transparent and compliant.
Your expense management tool cannot sit in isolation. It needs to work seamlessly with the systems you already rely on. Ask whether the software integrates with your ERP, payroll platform, and finance tools so data flows automatically across the business.
This reduces manual entry, eliminates duplication, and improves accuracy.
It’s also important to know whether integration is included or sold as a premium add-on. Clarify the setup time and level of technical involvement required.
Finally, understand what information syncs automatically, so you know exactly how the integration will streamline your processes.
Expense data becomes far more valuable when you can analyse it easily.
Look for software that offers clear, customisable reporting so you can track spend by department, project, category, or employee.
The significance of in-built functionality to create exportable reports can also never be overstated. For tax preparations, audits, and internal reviews, this feature is a must.
Likewise, real-time dashboards give decision-makers instant visibility into spending trends and financial analytics data, making them another important inclusion and well worth asking about.
Pricing models vary widely, so understanding the full cost upfront can make your decision-making process a lot more straightforward.
Some platforms charge per user per month, while others use feature-based or tiered pricing. Premium capabilities, such as ERP integrations or advanced reporting, may come at an extra cost, so it’s essential you know this before you move ahead with any conversation.
Ask about setup fees, onboarding charges, and ongoing support costs to avoid surprises later. It’s also worth checking how the pricing scales as your team grows. The right software should offer flexibility without forcing you into higher tiers prematurely.
Even the best software needs strong support behind it.
Ask what onboarding is available for employees and administrators to ensure everyone can use the system confidently from day one. Response times matter too.
Fast, helpful support can prevent delays when issues arise. This can be a bigger risk with larger platforms, so keep a sharp eye on reviews as well.
And to finish, training should be available for new features and updates, especially if you’re managing a large or distributed workforce. Dedicated customer success resources are a strong sign that the provider is invested in your long-term success, not just the initial sale.
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