Simplify and Succeed: Modernizing Your Tax Strategy

For many tax teams, the idea of adopting new software can feel like one more thing piled onto an already overwhelming workload. Between managing deadlines, juggling spreadsheets, and keeping up with constantly shifting regulations, who has time to evaluate, implement, and learn an entirely new system?

The answer, according to insightsoftware's Gerry Nunez, is that you can't afford not to. In the first episode of The Tax Operations Playbook a new podcast series produced in partnership with CFO.com Gerry breaks down the biggest barriers to tax software adoption and shares practical strategies for getting your organization to the other side. Here's what you need to know.

Why Now Is the Time to Rethink Tax Technology

Beyond internal inefficiencies, broader market forces are accelerating the need for modernization. Increasing regulatory complexity, real-time reporting expectations, and global tax reforms are placing new demands on tax teams. At the same time, many organizations are dealing with fragmented systems and data silos that make it difficult to respond quickly or accurately.

Legacy tax technology simply wasn’t built for this environment. As a result, teams spend too much time reconciling data, validating outputs, and managing risk manually instead of focusing on strategic insights. Modern tax solutions address these challenges by centralizing data, improving transparency, and enabling better collaboration across departments. They also provide the scalability needed to adapt as regulations and business structures evolve something that outdated systems struggle to support.

Forward-thinking tax leaders are setting a new standard for their technology. Instead of patching together workarounds, they’re looking at capabilities essential for the future of tax.

1. Real-time consolidation to give tax leaders immediate visibility into the numbers.

2. Automation to eliminate manual work and reduce the risk of error.

3. Transparency and control so every calculation and adjustment can be explained.

4. Scalability to grow with the business and adapt to new regulations.

5. End-to-end coverage that unifies provision, planning, reporting, and compliance.

The Assumption That's Costing Tax Teams

One of the most common misconceptions Gerry encounters is the belief that if a tool works for finance, it must work for tax. It's an easy assumption to make after all, tax data is a subset of financial data. But the way that data is structured, reported on, and used is fundamentally different.

"Tax actually not only uses data, but they create data that they then use," Gerry explains. General finance tools simply weren't built with that nuance in mind. The result? Tax teams get handed a system designed for someone else's job and told to make it work which breeds frustration, inefficiency, and ultimately a negative association with tax technology altogether.

Add to that the fact that tax teams rarely have their own technology budget, and you have a function that's chronically underinvested in and underserved by the tools available to them.

Simplify and Succeed: Modernizing Your Tax Strategy

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The Hidden Risks of Spreadsheet-Based Systems

Many organizations are still running critical tax operations out of Excel or internally built tools. It feels manageable until it isn't.

Gerry points to two significant risk areas. The first is what he calls the "IP problem": when your tax process lives inside a spreadsheet that only one person truly understands, you've essentially made that individual indispensable. When they leave, the institutional knowledge walks out with them. No documentation, no handover, no safety net.

The second is governance. Spreadsheets are open systems anyone can make a change, and there's rarely an audit trail. For a function as consequential as tax, that's a serious vulnerability. Tax audits routinely reach back five years or more, and when they do, you need to be able to demonstrate exactly what happened, who made what decision, and why. A spreadsheet can't give you that.

Getting Past the "We'll Figure It Out Later" Mentality

Change is hard, especially when teams are already stretched thin. Gerry acknowledges this reality head-on: if you're a tax manager barely keeping up with your current workload, the idea of leading a software implementation feels like a risk, not a relief.

But that framing is the problem. The reason you're overwhelmed may be the very inefficiency that a modern solution could fix. Purpose-built tax platforms like Longview Tax from insightsoftware are designed to meet tax teams where they are with Excel-like interfaces that don't require a steep learning curve, out-of-the-box templates, and the flexibility to work the way your team already thinks.

The goal isn't to force a transformation overnight. It's to start with a proper discovery learn what's available in the market, understand how a solution maps to your specific needs, and build a realistic business case from there.

What Successful Adoption Actually Looks Like

Organizations that modernize successfully tend to share a few things in common. They have a champion within the team who understands the value and can advocate internally. They loop in stakeholders early IT, internal audit, finance leadership so there are no surprises when it comes time to buy. And critically, they involve the tax team itself throughout the design, testing, and rollout process.

Gerry also recommends thinking in phases rather than big-bang implementations. Incremental rollouts are easier to manage, easier to measure, and much less likely to burn out the people you need to make the project successful. Set targets, track them, and let early wins build momentum.

One often-overlooked consideration: make sure the solution can grow with your business. The platform you implement today should still be fit for purpose as your organization expands into new jurisdictions, acquires new entities, or faces new regulatory requirements.

AI Is Coming Is Your Data Ready?

No conversation about tax modernization in 2025 is complete without addressing AI. The potential is real: AI can surface relevant case law, flag anomalies, support scenario analysis, and dramatically reduce the time spent on manual research. But Gerry is clear-eyed about what AI requires to deliver on that promise.

"Garbage in, garbage out." AI is only as good as the data you feed it. Before your organization can meaningfully benefit from AI-powered tax tools, you need a clean, centralized, and well-governed data foundation. Without it, you're not getting insights you're getting confident-sounding errors.

There's also a talent dimension worth considering. The next generation of accountants expects modern tools. If your organization is still running on spreadsheets, attracting and retaining top tax professionals is going to get harder.

The Business Case Is There

The results speak for themselves. One insightsoftware insurance customer cut their tax provisioning process by over two weeks after centralizing their tax data. A large manufacturing organization automated 70% of their tax position items, freeing up 25–50% of their team's time for higher-value strategic work — —across more than 100 jurisdictions.

These aren't outliers. They're what becomes possible when tax teams stop making do and start advocating for the tools they actually need.

Want to see how Longview Tax can modernize your tax operations? Request a demo today and discover what's possible when your tax team has the right tools for the job.