I was a CFO — and accounting’s tech problem is worse than you think

I remember the exact moment I knew our accounting technology was failing us. It was late, and I was hunched over spreadsheets like a detective in a particularly boring, number-filled murder mystery. 

The victim? Accuracy. The weapon? Our outdated systems. 

They’d struck again, leaving behind a trail of missing data, mismatched numbers and enough manual rework to make a team of accountants weep. As CFO, I’m supposed to be the financial wizard, not buried alive under a mountain of spreadsheets. I swear, I could hear the “Jeopardy!” theme song playing in my head.

Now, I’ve escaped that spreadsheet purgatory, thank goodness. But I hear the same horror stories from our customers every single day. It’s like a support group for survivors of bad accounting software. And it’s clear: Accounting technology is still holding the entire profession hostage. Forget reporting deadlines, regulatory pressures or even the ever-growing data monster. Our industry’s real nemesis? Limited, clunky, soul-crushing software. It’s the digital equivalent of using an abacus while everyone else has a supercomputer.

I wrestled with outdated accounting programs for years, and it’s appalling to me that this is still something accountants are facing in the era of automation and AI. Clunky systems eat away at efficiency and keep you siloed and stuck in mountains of manual work.

There’s a massive opportunity to break free from legacy software and embrace modern solutions that are built to scale with today’s complex businesses. 

How did we get here, and why are some accounting teams still resisting change?

Tools made for a simpler time

If you walk into any typical Accounting department, you’ll find a patchwork of solutions that looks something like this:

• An on-premises ERP with accounts payable/receivable or reporting modules
• Multiple invoice scanning and data capture tools
• One or more billing systems
• A travel and expense management platform
• A set of spreadsheets to fill gaps in each function
• Add-on applications for tasks like asset management or reconciliation

That list doesn’t even scratch the surface in terms of payroll, vendor management, collaboration tools and other key activities.

Along with the sheer volume of platforms, their inability to connect is just not working for the modern enterprise. Many businesses now operate across multiple jurisdictions with different compliance standards. They rely on real-time data to make decisions on spending, hiring and new ventures. Stakeholders demand faster, more precise reporting to guide strategic moves. The core software accounting teams are using was never meant to keep up with these demands. Most legacy accounting systems are disconnected, creating bottlenecks and confusion and requiring manual data preparation, rework and manual reconciliation.

Each delayed financial statement has a ripple effect on the Finance team’s ability to deliver strategic insights and forecasts.

Every manual data entry or copy-paste action is a potential source of errors.

Disconnected systems isolate information and force you to spend far too much time chasing down key data.

The good news: This doesn’t have to be the reality. Automation solutions can address many of these issues head-on, but cultural and technological resistance often stands in the way.

Areas of resistance: Why an upgrade seems difficult

The word “risk” has a special place in an accounting context. Accountants are keenly aware that a single oversight in a ledger can result in hefty penalties, compliance breaches or reputational damage. Risk aversion, while ultimately a smart instinct, creates a culture where introducing new tools or processes is seen as a disruption that could invite more errors, not fewer.

Leadership teams that prioritize budget may also be skeptical. An automation initiative seems like a costly project with an unclear ROI. And there’s often no one fighting them to move forward — most accountants believe spreadsheets are “good enough.”

The comfort of legacy methods and the perceived reliability of spreadsheets can overshadow the cumulative (often hidden) costs of manual work: slow turnaround times, error corrections, overtime pay and burnout, to name a few.

Even if everyone agrees in principle that modernization is necessary, there are still technical challenges. Legacy systems often lack the APIs necessary to integrate with new platforms. Limited extensibility can keep you from ever achieving real-time data sharing.

Then, there’s the misconception that modernization requires customization. While custom solutions can be powerful, they’re not your only option. Leading automation platforms and cloud-based accounting solutions can be implemented without the same level of cost and complexity.

Myths vs. reality: Upgrading your accounting software

I get it: Even if they’re just beliefs that need to change, these are big hurdles to jump when you’re already overloaded with day-to-day tasks. But overcoming them must be a priority, because a technological upgrade is now imperative for companies seeking sustainable growth and resilience.

An industry wake-up call: Automation as the future

The fact is, if you’re attempting a finance transformation without automation, you’re doing it wrong. 

Unfortunately, many CFOs are skipping steps in their modernization strategy. A 2024 Gartner report found that CFOs are prioritizing AI adoption over financial technology selection, strategy and deployment in 2025. The problem? AI isn’t a shortcut — it’s an enhancement. Without automation as a foundation, AI’s impact will be minimal and siloed at best.

This disconnect is creating a fragmented approach to modernization. While some leaders chase AI capabilities, 49% of accounting firms still have no plans to use generative AI at all. Meanwhile, automation adoption remains inconsistent, even though 55% of finance executives aimed for a touchless financial close by 2025.

What I find in engaging with finance leaders who come to Redwood Software for guidance and solutions is that many of them have the best intentions but are struggling to execute on these goals. Setting your sights on automation with a capable and fully adopted platform is the right answer.

What modern finance automation enables

Modern finance automation integrates critical accounting functions like closing the books, processing invoices, reconciling bank statements and generating real-time financial reports into one seamless system.

The core benefits are clear:

• Consistency and accuracy as a result of standardizing repetitive tasks and removing the risk of human errors
• Speed achieved by faster data flows, approvals, reconciliations and more
• Scalability derived from processing large volumes of transactions without additional staff or hours
• Strategic insights that come about when accountants are free from manual drudgery

Energy Transfer’s experience using Finance Automation by Redwood is a great example: By applying the power of automation, the Fortune 500 energy company reduced the amount of time spent on bank reconciliations by 88% and streamlined capital project settlements and SAP user access provisioning.

Don’t miss out on the automation and AI movement

Even if you see the need for a tech upgrade, it’s possible you’re feeling overwhelmed by all of this. The first step doesn’t need to be a complete overhaul of your accounting and finance infrastructure. In fact, that wouldn’t be a wise endeavor.

Start small, perhaps with the tasks that contribute to a high-impact process such as record-to-report. Proving ROI on a focused project can help you gain buy-in and dispel the myth that new software is too disruptive or expensive. 
Ineffective, outdated accounting software is a liability. It’s time to automate, adapt and thrive, or get left in the dust. Redwood is here to help: Read more about how to achieve fully automated accounting.