#42: How to Hire iGaming's Next Superstars

I find myself in an interesting position with fast-scaling companies and a soon-to-be-announced business that’s going to be a monster. Success breeds success, but it also breeds complexity. The biggest complexity? Hiring. And lots of it.

The immediate challenge is obvious - we need great people. But the deeper challenge is that both myself and my leadership teams are increasingly time-poor. The reality of rapid scaling means we often don’t get very long to assess whether someone could be the next superstar... or the anchor that drags down our momentum.

It's a challenge that's particularly acute in iGaming. We operate in an industry where a single hire can make or break your trajectory. Technical expertise? Check. Gambling knowledge? Check. Personality fit? Check. And if they don’t have gambling knowledge, are they adaptable? Check. There are a lot of boxes to tick.

Yet after 17 years in this industry and hundreds (perhaps thousands?) of hires across multiple companies, I continue to strategise how to hire better people faster. Today, I'm going to share some thoughts on how to identify high-quality candidates faster.

Not because I'm a hiring guru (I've made plenty of mistakes), but because I believe getting this right is one of the most important skills we can develop as leaders in this industry. After all, what's the point in having the perfect strategy if you don't have the right people to execute it?

The Three Power Questions That Never Fail

Let's talk about traditional interviews for a moment. You know the type - where candidates recite their carefully rehearsed career history. At the same time, you nod along, pretending that knowing where they worked five years ago is somehow going to predict their future performance.

The cost of getting it wrong? It's not just the obvious financial hit - though burning through a six-figure salary package while watching your momentum stall isn't fun. The real cost is time. Time spent managing a poor performer. Time spent rebuilding team morale. Time spent fixing mistakes. Speed is everything, so lost time is a luxury we can't afford.

So here are the three type of questions I’ve begun incorporating into interviews:

#1: The Industry Depth Test:

Here’s what’s called the "infinite depth" question - a strategic probe that would take days to fully answer if the candidate truly knows their craft. For a marketing role, it may be asking them to explain how they would approach player acquisition in a newly regulated market.

An expert naturally cascades through market analysis, channel strategy, and compliance requirements. They'll discuss the balance of brand versus performance marketing, local content nuances, and cohort-based optimization.

The depth of their knowledge reveals itself in the details. Keep asking "why" until you hit the boundaries of their expertise. The point isn't to find someone who knows everything but to understand exactly where their knowledge ends.

#2: The Superpower Deep Dive:

Ask candidates to identify their superpower within their area of expertise. For a social media head, they may answer “Instagram growth”. So ask questions about everything you know about the topic, and see what you learn. They’re the expert, and you should come away from that interaction, having learned a lot.

So for example, I know that Instagram as a channel is becoming increasingly driven by “interest-based” discovery, so could ask questions about that. And they might talk about creating content around specific cohorts that your brand is looking to target, content frequency, analysing results from your tests, and how to iterate and keep growing.

If they’re an expert, I’ll learn a lot from this interaction. But if they can’t teach me anything, then they’re probably not a good fit. These questions also help me to place them and see where they might fit within the goals of the business.

#3: The Real-World Scenario:

Present a specific challenge your business faces. This is especially important when we’re growing start-ups; even for a senior role, I want thinkers and people who can strategise. Not someone who has moved up the corporate ladder because they became good at people management.

So this could begin by suggesting that you brainstorm ways to fix the current issue. Maybe players are registering for the product but not depositing. I’m looking for answers beyond the common sense, generalised answers. Or how they’re asking questions to understand the problem better.

Reading Between the Lines

Beyond the specific answers, the most revealing signals often come from how candidates think and communicate. Watch how they handle the edges of their knowledge - the best candidates openly acknowledge gaps and explain how they'd close them, rather than trying to cover with vague responses. They naturally tie their experience to business impact, showing they understand that execution trumps theory.

Pay attention to their curiosity depth. Surface-level questions about your business suggest surface-level thinking. The strongest candidates demonstrate intellectual rigour by probing into your tech choices, business model assumptions, and strategic direction. They're not just answering your questions - they're trying to build a complete picture of the challenge ahead.

But most importantly, to hire correctly, especially if it’s a position outside of your area of expertise, you need to interview enough candidates to make good comparisons. For marketing, I probably know if someone is a good candidate straight away. But for another position, I need to compare the responses I received.

The 30-Minute Paradox

Here's what I've learned after countless interviews across multiple ventures: The best hiring decisions often happen fast. When you have a clear framework and know what to look for, 30 minutes is usually enough. The candidates who make you think "maybe" are usually "no's" in disguise.

But the landscape of talent is changing. As our industry continues to evolve at breakneck speed, we need people who can evolve with it. The future belongs to those who can spot these adaptable talents early - those who might not have the perfect resume but have the perfect mindset. I think that in today’s world, the ability to learn might just be the most valuable skill of all.