Mid-market tax planning realities: behind the numbers, the mental load

When companies operate across borders, tax planning becomes a continuous, high-stakes challenge. Tax compliance is one of the highest costs for any business. Miss a deadline or get a filing wrong and companies risk double taxation, penalties and reputational damage. 

That pressure mounts in the face of other external challenges: constant updates to cross-border tax rules, volatile trade conditions and tougher transparency demands. Global tax assessment and reporting frameworks, like Pillar Two, mean finance and tax teams must gather and report more data than ever. According to a 2025 EY survey, 81% of organisations said OECD minimum tax rules are the most significant legislation they are facing.  In an environment of constant regulatory change, it’s more important than ever for global organisations to build resilience into their tax operating models.

These changes, and the constant vigilance that goes with staying on top of them, create a significant mental and operational load for finance professionals. CFOs, financial controllers and tax leads all feel the squeeze. Uncertainty increases as evolving rules meet fragmented systems and limited resources. For mid-market companies, that challenge is particularly acute.

The daily friction of ambition in mid-market tax planning

"In the mid-market, tax professionals face the same pace of regulatory change as large multinationals, but with fewer resources and leaner teams. Every domestic or international tax rule change or filing requirement lands on their desk, increasing the mental load and reducing the margin for error"
 

Tom Lickess, Global Head of International Tax Advisory & Tax Solutions at Vistra.

In mid-market firms, tax planning is rarely a friction-free process. For our clients, many of whom are mid-sized multinational companies, the pressures of tax planning are a recurring theme.

Take this example of a technology company we work with that is consolidating their accounting & tax compliance under Vistra across Asia, Europe and Latin America.  This global organization was dealing with multiple local tax & accounting agents, with no single source of truth. The organizational finance team was managing multiple different tax processes, systems and regulations, managing via email and spreadsheet – often receiving late notice of tax regulatory requirements or payments. Local tax rules would change with little warning: sudden updates to withholding taxes or permanent establishment thresholds force last-minute recalibration. The finance team was walking a tight rope: they were trying to enable growth and manage growing risk, often with imperfect information.

Other teams describe the feeling of being in constant ‘firefighting’ mode. As one SaaS company leader put it “tax planning meetings can turn into crisis sessions after an expiry or treaty change that wasn’t flagged early enough. The cost is time, stress, and a late-night rework.”

In another case, a manufacturer’s tax team had to piece together data from six different providers to model a new intercompany financing structure that could have been resolved with simple cash pooling and intra-group transfer pricing. Gaps and inconsistencies delayed strategic decisions and significantly increased the manual workload.

Fragmented data is a constant theme. Different providers, multiple systems and conflicting data conventions. Lean teams are stretched, trading time between delivering commercial priorities and firefighting for compliance. As complexity rises, so does the pressure on mid-market professionals to get it right, every time.

Why external pressures amplify the pain of cross-border tax planning

"Increased tax reporting, regulations and transparency are reshaping the tax environment well beyond the largest multinationals, tightening expectations around transparency and governance. For mid‑market firms, the challenge is meeting those expectations with lean teams, legacy systems and limited time."
 

Tom Lickess Global Head of International Tax Advisory

Changes in local and global regulations continue to raise the bar for finance professionals already stretched thin. According to PWC’s 2025 Global Compliance Survey, 85% of companies reported that requirements have become even more complex in the past three years. 

Take the OECD’s Pillar Two global minimum tax rules. Even though the OECD’s 15% minimum tax only directly applies to multinational groups with at least €750 million in annual revenue, mid-market companies are still feeling the effects. Many jurisdictions are adopting stricter rules and higher transparency standards, so mid-market firms below the threshold are now facing more rigorous data and reporting expectations from tax authorities. They’re also under extra scrutiny from auditors, boards and investors who want to see clear, defensible tax positions – no CFO or FD wishes to have a lack of tax certainty impacting their forward-looking projections or annual reporting. Tolerance for opaque approaches is waning, so mid-market companies need to actively get ahead of the legislation, even when they lack the extra resources needed to do so.

What ‘good’ looks like, and why it proves elusive

In an ideal world, mid‑market tax planning integrates with business planning and forecasting. It anticipates change and simulates outcomes before decisions are taken. Intercompany policies, cost allocations, withholding and transfer pricing are modelled proactively. The function delivers insight rather than simply compliance outputs, enabling decisions to be made with confidence and without rework. Here are some of the steps that mid-market firms can consider to make the cross-border tax planning process smoother.

• Document all entities and activities: Regularly record all legal entities, offices, and staff locations. This provides clarity and reveals risks early.
• Regularly review policies and processes: Establish and periodically update protocols for cross-border activity, expansion and global mobility to preempt compliance issues.
• Create cross-functional committees: Assemble representatives from tax, HR, and legal to review activities and oversee compliance holistically.
• Track employee mobility: Use platforms to log expatriate assignments, business trips and remote work to manage compliance risk in every country.
• Conduct regular corporate and indirect tax reviews: Perform tax gap and efficiency reviews, benchmarking, and supply chain analyses to detect inefficiencies, fulfil obligations and reduce tax leakage.
• Stay up to date with local laws: Monitor legislative changes in all operational jurisdictions, especially for permanent establishment, transfer pricing and indirect tax.
• Leverage technology and centralised data: Use compliance platforms and dashboards to aggregate documentation, deadlines and reports, reducing manual stress and error.
• Engage in scenario planning: Conduct risk reviews before events such as mergers, acquisitions, reorganisations, or entity wind-downs to address implications early and avoid last-minute crises.​

These measures are good in theory, but without external assistance, many mid-market finance teams simply don’t have the resources to follow through on these strategies. Instead, they risk getting stuck reworking versions and struggling to stay aligned, with slow progress, duplicated effort and wasted money as the outcome.

Where providers miss the mark

Large corporate groups are built for big, complex projects and tend to work best with other large organisations. Mid-market companies often find themselves getting less access to senior experts and not taking advice. Their projects are often handled by different local providers, which makes it hard to see what’s happening or keep things consistent. Costs can pile up from extra charges and unclear pricing. In the end, mid-market clients may end up paying more but don’t get the level of support, clarity, or flexibility their business really needs – all the while, the tax risks are not adequately covered.

Why Vistra is different

Tax planning can be challenging, but it shouldn’t be stressful. Vistra keeps things simple and clear, giving you peace of mind at every step. Our method is the same no matter where you do business; we deliver consistency, so you don’t need to lie awake at night worrying about surprises. You’ll have a dedicated senior technical manager who understands your business and helps you plan ahead, so your tax decisions always support your goals.

We keep you up to date with real-time dashboards, instant alerts, and clear records.  Our team guides you through each phase, design, implementation, and ongoing support to keep things smooth and easy. Most importantly, you will be free to spend time on what matters with the reassurance that comes from knowing your tax planning is in good hands.

If your team is permanently in firefighting mode, it may be time to reimagine how you handle tax planning. Mid‑market growth deserves a system designed for mid‑market realities. Vistra can help you shift from a reactive stance to a proactive one, building resilience into your tax planning model no matter what the future holds.

For more information on effective tax-planning for mid-market organisations download our checklist or contact our tax and accounting solutions experts today.

Tom Lickess
As Global Head of Tax Advisory and Tax & Accounting Solutions at Vistra, Tom leads global teams helping multinational clients navigate complex international tax, structuring, and compliance challenges. He brings over 25 years of experience advising on cross-border tax matters across multiple industries.