When you’re hiring senior leadership into a scaling FinTech or payments business, experience matters - of course it does. You want someone who has operated in your market, understands the challenges ahead and has evidence they can deliver. But I increasingly think there’s another question that's just as important: What do they actually want to do next? A CV tells you where someone has been so far. It doesn’t necessarily tell you where they want to go. And that distinction can make or break a senior hire.
Experience vs ambition
Imagine two candidates.
Candidate A has already held the exact title. They’ve worked for the right companies, managed bigger teams and can point to an impressive list of achievements.
Candidate B hasn’t quite reached that level yet. But they’ve been operating just underneath it, taking on increasing responsibility, solving difficult problems and are hungry for the opportunity to step up.
Who do you hire? There isn’t one correct answer. Sometimes you need the battle-tested executive who has done it three times before. Sometimes the better hire is the ambitious number two who has something to prove. More often, I think the sweet spot is a blend of both: enough experience to reduce the risk, combined with enough ambition to be genuinely excited about what comes next. That is particularly important in a scale-up.
Scale-ups need more than a good CV
Senior leadership in a scaling FinTech isn't always glamorous. Things change quickly. Processes aren't perfect. Teams need building. Strategies change. People wear multiple hats. The person who was brilliant inside a 5,000-person organisation with huge budgets and established infrastructure isn't automatically going to thrive inside a 50-person business trying to become a 200-person one.
Equally, somebody who loves building may become frustrated once the business reaches the next stage. That's why cultural fit shouldn't mean: "Do I like this person?"
It should mean understanding whether the environment in which they perform at their best matches the environment you're actually hiring them into. What motivates them? Why this business? Why now? Do they genuinely want to build? Are they comfortable without all the answers? What happens when priorities change? Do they want the job you're offering - or simply the title, salary and next line on their CV? Those questions matter.
The best candidates aren't always the best interviewees
Senior candidates are generally pretty good at interviews. They know what they're supposed to say. Everyone is commercial. Everyone is strategic. Everyone is entrepreneurial. Everyone loves fast-paced environments. Unfortunately, they can't all be exceptional. The job of a good search partner isn't simply to find people with the right keywords & and send their CVs across.
It's to qualify them. Properly.
Ask the awkward questions. Challenge achievements. Understand what they personally delivered or made happen, rather than what their company or wider leadership team achieved.
Dig into failures as well as successes. Understand why they left previous roles & test their motivation. Work out what they want the next three to five years of their career to look like and, importantly, be prepared to say no to candidates who look good on paper but don't stand up to scrutiny.
Quality over quantity
I don't think clients should receive ten vaguely relevant CVs and be expected to work out which ones are good. That's what they're paying a search partner to do. My job is to do that work before the shortlist reaches the client. I'd rather present four Tier 1 candidates who I believe genuinely tick the boxes than complete a shortlist with people who might work. Because a senior mis-hire in a scale-up is expensive in far more than recruitment fees.
You lose salary - management time - momentum. And six months later, you can find yourself back at the beginning of the search, except now the business has lost six months of growth.
Hire for where you're going
Past performance matters enormously. But when I'm assessing senior candidates, I'm equally interested in what they want to achieve next.
Do their experience, ambition and motivation align with where the business is going?
That's where the strongest senior appointments tend to sit. Not experience or ambition. Experience and ambition, combined with the right environment, timing and cultural fit.
I've spent more than 20 years recruiting in the payments sector, and much of my role today is helping founders and leadership teams make these decisions as they scale - and honestly, finding a long list of potential candidates isn't the difficult bit.
Finding the right shortlist, though - and having the confidence to reject the candidates who don't fit on it - is where good search earns its value.
If you're scaling a payments or FinTech business and can't afford to compromise on a senior hire, that's exactly where I can help. Hire right first time.
