The igaming reality: the higher you rise, the thinner the air gets

The promotion email arrived on a Friday. Chief commercial officer. The role you’d been working toward for 15 years.

Monday morning, you walk into the office differently. Same building. Same desk. But everything has changed. Your former peers now report to you. Your new peers are the CEO and CFO. People you always looked up to. The problems landing on your desk aren’t tactical anymore. They’re strategic. They have no clear answer. All of them are high stakes. And you have no one to tell you if you’re getting it right or wrong.

Welcome to the loneliest level in igaming.

When the game changes

Up until now, your career had a pattern. You saw a problem. You solved it. You got promoted. Repeat. But at C-suite level, the pattern breaks. The problems don’t have clear solutions anymore. Market expansion into Brazil? Could work. Could be a disaster. Your board wants a recommendation. Your team wants direction. The market won’t wait.

But here’s what nobody tells you: the job fundamentally changes when you can no longer learn by watching someone else do it first.

Every vice-president has seen a director operate. Every director has seen a C-level exec make strategic decisions. But when you become that C-level exec? There’s no one above you doing the job you can learn from. You’re supposed to just… know.

Except you don’t. And you can’t admit that to anyone.

A newly promoted chief product officer described it perfectly: “I spent 12 years learning how to run product teams. Nobody taught me how to deal with board politics or manage a CEO’s expectations”

The skills that got you promoted – hard work, operational excellence, technical expertise – they aren’t the skills you need now. But you’re already in the role. So you figure it out alone.

Three unspoken challenges every executive faces (but nobody admits)

1. Challenge one: The accountability vacuum

For your entire career, someone held you accountable. Your manager. Your targets. Your KPIs. Now? You set the KPIs. You define success. You report to a board that meets quarterly and sense checks the numbers look okay.

One CEO put it bluntly: “I can delay a decision for six months and nobody will call me out on it. My team assumes I’m being strategic. My board assumes I’m handling it. Nobody’s actually checking.”

Without external accountability, even high-performers drift. That strategic market pivot you’ve been 80% certain about? Still sitting in ‘analysis’ after four months. Not because you’re incompetent, but because there’s no way to be certain it’s the right move.

Your team can’t push you. They’re waiting for you to decide. Your board can’t push you. They don’t have the context. Your peers? They’re drowning in their own problems.

So strategic decisions that should take weeks take months. And nobody notices. Until the competitor who moved faster, innovates quicker and takes the market share you were analysing.

2. Challenge two: The expertise trap

You were promoted because you’re the expert. You know more about commercial strategy, product development or operations than anyone else in the building.

That expertise is now your biggest liability. Because when you’re the expert, nobody questions your thinking. Your team assumes you’ve already considered every angle. Your board trusts your judgement. Your CEO defers to your area of expertise.

But what if you’re wrong? What if you’re optimising for the wrong metric? What if there’s an approach you haven’t considered because you’ve been in igaming for 15 years and you’ve never seen it done differently?

One chief marketing officer had been running the same attribution model for three years. It worked. Revenue was growing. But a peer from a different operator asked one simple question about attribution. He hadn’t even considered it. Not because he was incompetent, but because nobody in his organisation knew enough to challenge him.

The more expert you become, the fewer people can tell you when you’re wrong.

3. The isolation tax

Here’s the thing nobody warns you about: leadership is structurally lonely. Not emotionally lonely (though it often is). Structurally lonely.

You can’t talk to your team about strategic uncertainty. They need you to be confident.

You can’t talk to your CEO about every doubt. They hired you to handle your area of expertise. You can’t talk about the messy reality at home. They don’t understand the context. And you definitely can’t talk to your competitors at conferences. Even when they’re the only people who’d actually understand.

One chief revenue officer described it perfectly: “I’ve got 47 people in my department. I talk to dozens of people every day. But I make every major decision completely alone.”

The isolation isn’t about lacking people. It’s about lacking people who can actually help you think through C-level problems without a hidden agenda. Your team wants to impress you. Your peers are competing with you. Your CEO is evaluating you. Nobody’s incentivised to just help you think clearly.

Why igaming makes this brutally worse

Most industries are lonely at the top. igaming is exponentially more isolating.

The pace is relentless – markets move quickly. Regulatory changes happen overnight. You’re making million-pound decisions on timelines that don’t allow for any delays.

The expertise is rare – how many people genuinely understand multi-jurisdictional licensing, player value optimisation and affiliate economics? Your CFO doesn’t. Your board doesn’t. Even other C-suite execs in adjacent industries don’t.

The career ladder is vertical – people get promoted faster in igaming than almost anywhere else. Which means you’re often making decisions you’ve never made before, with nobody around who has.

One COO at a major operator manages teams across six jurisdictions. Different regulations. Different player behaviour. Different commercial realities. When she’s making a call on market expansion, who does she ask? Her CEO hasn’t operated in that market. Her board doesn’t understand the operational complexity. Her peers at other operators? They’re literally her competitors. So, she makes the decision alone. Hopes it’s right. And deals with the consequences either way.

The hidden cost isn’t the occasional wrong decision. It’s the cumulative effect of making every decision alone and hoping for the best.

You move slower – because you’re confirming your own thinking instead of getting outside perspective and pushback from peers.

You take less risk – because high-stakes decisions could be career-ending when nobody’s there to say, “that’s reversible” or “I tried that, here’s what happened.”

You miss opportunities – because you’re so busy dealing with the day to day of a strategy you decided six months ago, you don’t have bandwidth to reconsider if it’s still the right strategy. Gaming moves quicker than that.

The uncomfortable truth

Leadership isolation isn’t a personal failing. It’s not imposter syndrome. It’s not a weakness you need to overcome. It’s a structural reality of how businesses are organised.

The higher you go, the fewer people who operate at your level. The fewer people who understand your problems. The fewer people who are incentivised to challenge your thinking. That’s not going to change.

But here’s what can change: whether you treat isolation as an inevitable cost of leadership, or as a solvable problem. Most executives accept it. They tell themselves this is just what leadership feels like. They get comfortable making decisions alone. They stop seeking outside perspective because it feels vulnerable to admit they don’t have all the answers.

The best executives treat it differently. They recognise that making decisions in isolation isn’t strategic. It’s a business risk. They actively build peer networks where they can test their thinking without political consequences. They create accountability structures that nobody in their organisation can provide. They understand that being the smartest person in the room doesn’t mean being the only person in the room.

The choice

You can keep making decisions alone. Hoping your expertise and experience are enough. Hoping you’re considering all the angles. Hoping the next strategic decision is the right one. Or you can acknowledge what every C-level exec knows but rarely admits: you need peers who’ve already made the decisions you’re about to make, who have no agenda except helping you think clearly, and who’ll hold you accountable when you’re stalling.

The question isn’t whether you’re isolated. At your level, you will be. The question is whether you’re going to do something about it.

Leo Judkins is the founder of The iGaming Leader Mastermind, a vetted peer advisory group where senior igaming executives act as each other’s personal board of directors. Leo will be hosting a series of sessions at the Power 50 Summit in Marbella, April 13-16.