The Scariest Job in the World: Head of Tax for a Multinational Group

This article was previously published on the Regan van Rooy website.

Forget about deep-sea welding or lion taming, or in South Africa, being a farmer or a policeman. There’s a new contender for the title of “World’s Scariest Job,” and it’s probably not what you’re thinking. In fact, it’s even more terrifying because it involves spreadsheets, an ever-growing web of international regulations, and bosses who think “tax planning” is something you do with a calculator and a strong cup of coffee once a year. Welcome to the nerve-wracking, red-tape-laden, ever-changing nightmare world of being the Head of Tax for a multinational group.

You’ve probably heard people say that tax law gets more complex every year. Well, they aren’t exaggerating. Being the Head of Tax means you’re like a contestant on a never-ending game show called “Who Wants to Avoid a Tax Scandal?” The rules change every time a new episode airs, and every season (or fiscal year) brings fresh and scary plot twists.

One minute, you’re navigating the labyrinth of international tax treaties, transfer pricing regulations, and VAT conundrums. The next, you’re trying to decipher the latest EU directives, OECD guidelines, and digital services tax rules that seem to be written in ancient hieroglyphs. Just when you think you’ve got it all figured out, some country decides to change its tax laws overnight, like a giant game of regulatory whack-a-mole, or your group decides to set up in a new territory with a whole new set of tax rules. And don’t even get started on BEPS (Base Erosion and Profit Shifting). If that doesn’t sound scary, try explaining it to your CFO while keeping a straight face.

Speaking of the CFO, let’s talk about your boss. Here’s the thing: the CFO doesn’t really understand tax and doesn’t really care about it until there’s a tax problem and then they care a lot. They treat it like an annoying popup window that keeps interrupting their day. “Can’t you just make this go away?” they ask while checking their email for the latest market trends. You try to explain the risk of a multi-million-dollar tax penalty from your subsidiary in Brazil, but their eyes glaze over, and they nod absentmindedly, thinking about next quarter’s earnings call.? And as far as your CFO is concerned, if you can’t summarise the problem in a two-line email, it’s not important. That is, until a tax authority from another continent comes knocking, and then they suddenly morph into the embodiment of urgency and concern.

Then comes the day you dread the most: the revenue audit. It’s like being summoned to court, except you’re both the defendant and the lawyer, and the judge is a tax inspector with a magnifying glass and an appetite for obscure documentation. You find yourself digging through records from five years ago, trying to remember why you structured that one deal through a holding company in the Netherlands. It’s like searching for a needle in a haystack, only to realise the needle is made of fine print and the haystack is the entire company’s global operations.

And when either the revenue authorities or your external auditors find something (because they always do), you’re the one caught holding the smoking gun. “Why didn’t you know about this?” demands the CFO, who, just days earlier, suggested you “handle it quietly” without causing a fuss. Suddenly, you’re the most sought-after person in the company, but not in a good way. Everyone wants answers, from the finance team panicking about their revised budget to the CEO wondering if they’ll still get their bonus after the tax penalty is paid.

The Endless Stress: Why Coffee is Your Closest Ally (and Possibly Your Only Friend)

Being the Head of Tax isn’t just a job; it’s a lifestyle (although some might say a life-sentence). A lifestyle that involves consuming caffeine like it’s water, coping with constant stress, and surviving on a few hours of sleep. Your mantra is, “I’ll rest after tax filing season / year-end,” but when you’re dealing with a global company, tax season never really ends and one year-end follows fast upon the last. You’re stuck in a perpetual loop of quarterly filings, cross-border compliance, revenue audits and year-end audits. Your stress level is so high that you could probably power a small country with your anxiety alone.

The Verdict: The Only Thing Scarier Than Tax Authorities Are Your Daily Duties

So, why is being the Head of Tax for a multinational group the scariest job in the world? Because every day, you walk a tightrope stretched across a chasm of international compliance nightmares, with hundreds of tax jurisdictions below, each waving their own unique set of rules and penalties. Your safety net? A CFO who doesn’t really get what you do and auditors who are ready to pounce the moment you blink.

Lion tamers can keep their lions; at least they know what they’re up against. Deep-sea welders can keep their oxygen tanks; at least they know how much air they have left. The Head of Tax, meanwhile, faces invisible dangers and lives in a sea of paperwork where the oxygen of time is always running out. So, the next time you meet a Head of Tax, give them a nod of respect (and maybe a strong coffee). They’re living the scariest job in the world, and they could use a little appreciation – and a lot of caffeine.

If you’re nodding in agreement with this, come and join our webinar where I will chat with a few special guests about what it really means to have the scariest job in the world.