How antiquated accounting tools are failing you during tax season

Tax season. The most notorious source of stress in the accounting world.
It doesn’t matter if you’re in the public or private sector, in a large or small organization; you likely anticipate months of headaches when the new year rolls around. And the accounting software available today doesn’t offer much of a remedy.
As a former accountant and CFO, I know firsthand how frustrating manual processes can be. No matter how much you want to be efficient, you simply can’t be when you’re using antiquated, slow tools.
Luckily, these days, you have a choice: You can modernize your accounting processes with automation to improve the accuracy and speed of the critical reporting your tax team needs. Let’s talk about why the time to consider a transformation is now.
1. The industry is struggling with a shortage of skilled professionals
The accounting profession is at a crossroads, with 42% of firms unable to take on new clients due to staffing limitations. Teams are stretched thin, and during tax season, there’s no room for error.
Automated systems can lighten the load. They take over time-consuming, repetitive tasks and alleviate the pressure of relentless manual data entry, reconciliations and report generation that characterize the dreaded tax period. You can free up time to offer other services, like strategic financial planning and client advising, even during this historically busy season.
The team at Jabil, a global manufacturing services company, saves 95,000–120,000 hours per year by automating their month-end close process using Finance Automation by Redwood. These savings trickle down to the tax team, making the entire organization more efficient and innovative.
Imagine how much more revenue — and impact — you could generate during this time when your competitors are knee-deep in paperwork that your team no longer has to worry about.
2. Rework drives up costs — especially when it involves tax filing
In manual accounting workflows, one error — e.g., on a financial statement — can create a ripple effect that causes incorrect tax filing. Submitting tax returns already consumes massive resources, and having to rework them is beyond costly.
Your team will spend extra time identifying and correcting errors. You could incur fines or penalties for late or inaccurate tax filings. Worst case? Errors could trigger audits. In 2024, the IRS announced plans to triple its audit rate for large corporations, expecting to audit 22.6% by 2026.
Accurate, consistent data will protect you in the event of an audit, but as much as we’d love to believe people can provide that, they can’t. To err is human, after all. While we can forgive each other on a personal level for making mistakes, the reality in accounting is that small mistakes can snowball into expensive and stressful problems.
Rather than putting pressure on your employees to achieve a standard of perfection that only machines can reach, why not allow the machines to step in and help?
3. Manual processes limit scalability
During tax season, you might have to hire temporary staff or pay significant overtime to meet deadlines. These stopgaps don’t address the root issue: an inability to scale to fluctuating demand.
Lack of scalability can be compounded by the fact that accountants take 49.8% more sick days in March than in any other month of the year. You may hire seasonal employees only to have the long hours get the best of them.
Automated accounting systems can effortlessly process high volumes of transactions, even during peak periods. You no longer need to rely on seasonal workers who are vulnerable to mental and physical burnout. Built-in scalability saves money and gives your permanent staff the time and freedom to think about ways to improve your services and offer even more value to clients.
With automation, you’ll also get visibility into your financial operations at scale. The right finance automation tool will allow you to step back and see how you’re using resources. This impacts hiring and other major decisions year-round.
5 signs your tax processes are falling behind
- You’re relying on seasonal staff or paying excessive overtime.
- Your tax team complains about waiting for data from Accounting.
- You’ve missed filing deadlines or incurred penalties in the past three years.
- Tracking tax liability across jurisdictions feels like guesswork.
- Team members are overwhelmed, and you worry about turnover.
More risks you don’t need to take
While the above are core considerations, there’s a good chance you also struggle with a few other frustrations around tax time:
- Delayed financial reporting: When your tax team has had to wait for Accounting to close the books or correct errors, they’re more likely to rush and end up making mistakes.
- Siloed teams: If tax and accounting departments use disconnected systems, there’s a huge risk of duplicating efforts or not communicating about critical components of tax preparation.
- Unknown tax liability: Especially if you operate across multiple jurisdictions, tracking liability is a monumental task that’s complicated by not having a centralized system.
Your automation platform should speed up reporting, integrate accounting and tax processes and drive seamless data flow so you don’t have to worry about compounding problems during an already tense time.
Automate now to ease next year’s tax burden
Tax planning shouldn’t feel like a last-minute sprint, but it will if you continue relying on antiquated software solutions. Starting the process of automating today will gift everyone on your team a major sense of relief come tax time next year.
Thinking like a leader means seeing this as an opportunity rather than just another challenge. Automation can be a strategy for long-term success. Slogging through inefficiencies for another year and dreading those months leading up to a tax deadline is not a strategy at all — it’s barely surviving.
The earlier you start automating your accounting, the sooner your tax team will notice the benefits. And I suspect you’ll see them in every corner of your financial operation, too.
Set up efficient accounting processes to ready your business for everything tax season brings and save your team from burnout. Leave the spreadsheets and accounting tools behind — choose record-to-report automation.
About The Author

Caitlin Steel
Caitlin Steel is a passionate product leader with a mission to revolutionize the accounting profession. As VP of Product Management for Finance Automation at Redwood Software, she leverages her deep understanding of both the challenges and potential of finance to develop innovative automation solutions.
Caitlin's accounting journey began in the ‘80s, grappling with the first version of Excel. This experience ignited a lifelong quest to make accounting not just functional but inspiring. She brings a unique perspective, informed by her prior roles as a CFO and senior leader in product management at BlackLine, XaCTLY, OpenGov and other successful software companies. This experience has instilled in her a commitment to delivering high-impact products that empower teams.
When Caitlin steps away from the world of finance, she chases adventures. She's a champion for rescue dogs and enjoys lending a hand on her sister's ranch. This zest for new experiences fuels her creativity and brings fresh perspectives to her work.