Finance leaders are investing billions in AI and automation, but expense management remains one of the last major corporate headaches

Yes, enterprises are increasingly migrating away from legacy expense management systems.

Rising maintenance costs, poor user experiences, and fragmented financial data are driving CFOs and finance teams to replace traditional platforms such as SAP Concur and Oracle iExpense with modern, AI-powered spend management solutions including Ramp, Brex, Emburse, and Airbase.

For many employees, few workplace tasks generate as much frustration as filing an expense report.

Despite years of investment in digital transformation, countless organisations still rely on processes that require staff to collect receipts, manually enter transaction details, submit claims for approval and wait for reimbursement.

Finance teams then spend hours reviewing expenses, checking policy compliance and reconciling transactions before payments can be processed.

It is a workflow that has remained largely unchanged for years, even as artificial intelligence reshapes other parts of the enterprise.

Now, a combination of AI innovation, growing business travel activity and increasing pressure on finance departments is raising a question that many organisations can no longer ignore: are enterprises finally ready to move beyond legacy expense systems?

Defining Legacy Technology

In enterprise IT, “legacy” is often used as a polite euphemism for technology that has fallen behind modern standards. While definitions vary, many organizations consider systems more than five years old to be legacy platforms.

Given the pace of technological advancement, five years can represent multiple generations of innovation, leaving businesses dependent on software and infrastructure designed for a very different operating environment.

The challenge is not simply age. Legacy systems frequently become barriers to efficiency, agility, and growth. Many continue to function as intended, which creates a false sense of security.

Yet the true cost of outdated technology is rarely found in software licensing or maintenance contracts. It appears in slower business processes, higher security exposure, limited integration capabilities, and reduced employee productivity.

A distinction should be made between legacy and expired technology. Legacy systems may still be supported and operational, while expired systems have moved beyond vendor support, security updates, and compatibility with modern applications and devices.

The Hidden Cost of “Good Enough”

One of the most common misconceptions surrounding legacy technology is that it saves money.

Because the original investment has long been depreciated, organisations often view these systems as low-cost assets. In reality, the largest expenses are frequently hidden.

Employees working with outdated software spend more time navigating cumbersome interfaces, managing manual processes, and compensating for limitations that modern platforms have already solved through automation and intelligent workflows.

Systems built around green-screen interfaces, command-line navigation, or rigid process structures may continue to operate, but they often slow decision-making, increase training requirements, and create unnecessary friction across the organisation.

Over time, these inefficiencies accumulate. Productivity declines, user frustration increases, and organisations find themselves investing significant resources simply to maintain the status quo rather than advancing strategic objectives.

What appears to be a cost-saving decision often becomes an expensive constraint on growth and competitiveness.

The pressure on finance teams is mounting

Finance departments have become increasingly strategic over the past decade.

Modern CFOs are expected to provide real-time insights into company performance, support business growth, manage risk and identify opportunities for greater efficiency. At the same time, they face growing demands around compliance, governance and cost control.

According to Deloitte’s latest CFO Signals Survey, digital transformation remains one of the highest priorities for finance leaders entering 2026.

The survey found that nearly 90% of CFOs believe artificial intelligence will play an important role in their organisations over the next two years, while automation remains a major area of investment.

The challenge is that many finance teams continue to spend significant time on administrative processes that offer limited strategic value.

Expense management sits high on that list.

Why CFOs are paying closer attention

Several factors are pushing expense management higher on executive agendas:

• Business travel spending continues to rise globally.
• Finance teams face increasing pressure to improve productivity.
• Compliance requirements are becoming more complex.
• Organisations are seeking greater visibility into employee spending.
• AI tools are making large-scale automation increasingly practical.
• Employees expect workplace software to be as simple as consumer apps.

What was once viewed as a routine back-office function is increasingly being examined as a potential source of operational inefficiency.

Travel spending is surging again

The renewed focus on expenses is closely tied to the recovery of corporate travel.

According to the Global Business Travel Association (GBTA), global business travel spending reached approximately US$1.57 trillion in 2025, with growth expected to continue throughout 2026.

A separate GBTA survey found that 84% of travel managers expect budgets to either increase or remain stable during 2026.

That growth creates a direct challenge for finance teams.

More flights, hotel bookings, client meetings and business-related purchases inevitably lead to higher volumes of expense claims. Organisations that were already struggling with inefficient processes are finding those challenges amplified as spending activity increases.

For large enterprises processing thousands of transactions each month, even small inefficiencies can create substantial administrative costs.

The problem with legacy systems

Many traditional expense management platforms were designed for a different business environment.

Their primary objective was recording and documenting spending after it occurred. While that approach met compliance requirements, it often created a fragmented and time-consuming experience for employees and finance teams alike.

Common issues include:

• Manual receipt collection and storage.
• Delayed expense submission.
• Lengthy approval workflows.
• Limited visibility into spending until claims are processed.
• Difficulty identifying duplicate or fraudulent expenses.
• Significant administrative workloads for finance departments.

The result is a process that often feels disconnected from how modern businesses operate.

Executives increasingly expect access to real-time financial information, yet many expense systems continue to function as retrospective reporting tools.

AI is changing the conversation

The latest generation of expense management technology is focused on reducing or eliminating manual work.

Rather than requiring employees to complete reports after spending occurs, modern systems aim to capture, categorise and verify expenses automatically.

Artificial intelligence is playing a central role in that shift.

Today’s platforms can:

• Extract information directly from receipts.
• Automatically categorise transactions.
• Match purchases against company policies.
• Identify missing documentation.
• Flag unusual spending behaviour.
• Detect potential duplicate claims.
• Monitor spending patterns across teams and departments.

Instead of finance staff manually reviewing every transaction, AI systems can analyse large volumes of spending data in real time.

This dramatically changes the economics of expense management.

For organisations handling tens of thousands of transactions annually, even modest reductions in manual processing can translate into significant productivity gains.

Major software vendors are betting on automation

The push toward automated expense management is becoming increasingly visible across the enterprise software market.

Travel and expense provider Navan has invested heavily in AI-driven automation capabilities, promoting a future where traditional expense reports become largely unnecessary.

Meanwhile, enterprise software giants including SAP, Oracle and Workday are embedding AI into broader finance and procurement workflows, aiming to automate routine administrative tasks across multiple business functions.

The message from vendors is becoming increasingly consistent.

The future of expense management is not about creating faster reports.

It is about removing the need for reports wherever possible.

Compliance remains a major driver

Efficiency is only one part of the equation.

Many organisations are also focused on strengthening financial controls.

Expense fraud and policy violations continue to cost businesses significant amounts each year. Duplicate claims, unsupported expenses and policy breaches can be difficult to identify when finance teams are reviewing only a sample of transactions.

Automated systems provide a different approach.

Rather than checking a small percentage of claims, AI-powered platforms can evaluate every transaction against company policies and historical spending patterns.

Key compliance benefits include:

• Continuous auditing of expenses.
• Real-time policy enforcement.
• Improved detection of anomalies.
• Better documentation management.
• Greater visibility into company-wide spending.
• Reduced reliance on manual reviews.

For heavily regulated industries, these capabilities are becoming increasingly attractive.

Why some organisations are still hesitant

Despite the benefits, replacing an established expense management system is rarely simple.

Expense platforms often sit at the centre of a broader finance ecosystem that includes:

• ERP software.
• Payroll systems.
• Corporate card providers.
• Travel booking platforms.
• Procurement systems.
• Tax and accounting software.

Replacing one component can trigger broader technology projects that require significant investment and organisational change.

Many enterprises also remain cautious about introducing new AI-driven processes into areas involving financial controls and compliance.

As a result, some organisations continue operating legacy systems despite recognising their limitations.

The numbers behind the shift

Several statistics illustrate why expense management is receiving renewed attention in 2026:

Enterprise finance and expense management by the numbers

• US$1.57 trillion — Global business travel spending in 2025 (GBTA).
• 84% — Travel managers expecting budgets to increase or remain stable in 2026 (GBTA).
• Nearly 90% — CFOs who believe AI will be important to their organisations within the next two years (Deloitte).
• 50% — CFOs identifying digital transformation as a leading priority heading into 2026 (Deloitte).

Taken together, these figures highlight a finance environment where increasing transaction volumes are colliding with growing expectations around efficiency and automation.

A turning point for enterprise finance?

Expense management rarely attracts the same attention as cybersecurity, cloud computing or generative AI, yet it remains one of the most widely used and frequently criticised business processes inside large organisations.

The difference in 2026 is that the technology needed to automate much of that process has finally matured.

Artificial intelligence is no longer being discussed solely as a future capability. It is increasingly being embedded into everyday finance operations, allowing organisations to automate tasks that previously required extensive human oversight.

That does not mean legacy expense systems will disappear overnight. Large enterprises move cautiously, particularly when financial processes are involved. Existing integrations, compliance requirements and organisational inertia remain significant barriers to change.

However, the direction of travel is becoming clearer.

As business spending grows, compliance obligations increase and finance teams seek greater efficiency, organisations are beginning to question whether manual expense reporting still makes sense.

For many enterprises, the issue is no longer whether expense management can be automated.

The question is how long they can afford to keep doing it the old way.