"No company has truly nailed how to make learning adaptive, continuous, and impactful at scale. MobieTrain has the potential to be that platform”.
In our Friday Five, we ask five main questions to our special guest. The red thread? There isn’t one. We range from a look behind the business scenes to insights into our guests’ personalities. From MobieTrain employees to beloved customers or topic experts, anything goes. Sometimes sweet as pie, sometimes razor-sharp, always to learn from each other.
Today’s Guest: Simon Caulfield
From New Zealand to the Netherlands, our Chief Commercial Officer, Simon, has experienced business through many cultural lenses and (consultancy) roles. In this Friday Five, we talked about navigating culture shocks, spotting red flags in teams, and why MobieTrain was an opportunity he had to say yes to.
From New Zealand to the Netherlands: what’s been your biggest culture shock in business?
“Coming from New Zealand, where everything is fairly straightforward, I was surprised by how complex business in Europe can be. I wouldn’t call it a complete shock, but it was a wake-up call. In New Zealand, everything’s a bit more relaxed, more direct, and people just want to get things done. It’s ranked as one of the easiest countries in the world to do business in for a reason. But in Europe? It’s a maze of cultural nuance and hierarchy.”
“Each country has its own unwritten rules. The UK, for instance, is very polite on the surface, but that doesn’t always translate into action behind the scenes. The Dutch are the opposite – incredibly direct, but you always know where you stand. And in places like Italy or the Middle East, it’s all about trust before you even talk business. You can’t just walk in and pitch; they want to know who you are, who you know, and whether they can rely on you long-term.”
“Those differences in regions, cultures and approaches are fascinating, but also something you have to learn if you want to succeed. I enjoy the challenge, but it took time to adjust to the level of nuance here.”
Can you learn how to work across cultures, or is it just something you pick up over time?
“You definitely can learn a lot, but not from a textbook. Experience is the best teacher. I was lucky to create a paper on International Business at university, and that gave me a bit of a head start.”
“I learned about cultural norms, market sensitivity, even how in some countries you should only address the most senior person in the room. The paper taught me how to teach myself and helped me become hyper-aware of all those kinds of things.”
“You definitely can learn a lot, but not from a textbook.
Experience is the best teacher".
“But of course, the real learning came later. What shaped me was being in those situations myself, reading the room and figuring out on the fly what’s appropriate. You learn to observe, to listen, and to adjust.”
“Emotional intelligence plays a massive role. Understanding tone, time it becomes almost subconscious. But it’s a constant learning curve and sometimes still a guessing game; no two situations are ever the same.”
Let’s jump into something different. What’s the best piece of business advice you’ve ever received?
“There are three that really stuck with me. First: don’t burn bridges. It sounds basic, but when emotions are high or the situation is difficult, especially in a personal or professional fallout, it’s easy to react. I’ve had moments where I wanted to say something sharp or cut someone off, but I took a beat. I’m glad I did. Those relationships ended up working out down the line, and I’ve carried that mindset with me ever since. Relationships matter, and the professional world is smaller than we think. A moment of ego can cost you a future opportunity.”
Second: don’t get defensive. When you hear something that stings, feedback, criticism, even an objection, your natural instinct might be to explain yourself and to push back. But if you can take a pause, sit with it, reflect, ask questions, and try to understand the why behind it, you often find gold in there. Some of the best growth I’ve experienced came from very uncomfortable but honest conversations.
And finally, be proactive. Some people constantly wait for the perfect moment or permission to act. Then you’re already behind. The most successful people I know don’t overthink it; they just start. The best results I’ve ever had come from making the call, drafting the plan, and sending the first email. Those small daily actions compound over time. It’s like compounding interest, sometimes maybe even boring at first, but consistency becomes very powerful over time.”
You’ve worked in some fast-scaling companies. What’s a huge red flag that you spot quickly when joining a new team?
“The biggest red flag? A closed mindset. When teams or leaders shut down new ideas because ‘that’s not how we do it’, you’ve got a huge problem. And it often comes from ego. People protect their status quo because it feels safe, even if it's not working.”
“I’ve walked into companies where junior people had brilliant insights, but no one took them seriously because they were not seniors. That’s a massive, missed opportunity and a mindset that kills innovation and momentum.”
“The best companies are ones where people, no matter their title,
can speak up, challenge ideas, and bring fresh perspectives.”
“I always reference the Radical Candour matrix: you want high performers who are also great cultural fits. Those are your rock stars. But high performers with bad attitudes? They’re toxic. They might hit their numbers, but they erode trust and motivation around them. And if you don’t address that early, it spreads.”
“The real test is: if this person’s mindset were multiplied across the company, would things improve or fall apart? You need to hire and promote with that in mind. The best companies I’ve seen are ones where people, no matter their title, can speak up, challenge ideas, and bring fresh perspectives.”
You’ve helped scale billion-euro companies. Why MobieTrain? What made you commit?
“It was the perfect mix of timing, opportunity, and people.”
“I’ve seen a lot of products and teams, some great, some just hype. But with MobieTrain, I saw something special. Not just in the product, but in the potential. Not just for mobile training, but for true employee enablement. Adaptive learning. Coaching. Real-time performance support.”
“There’s a real gap in the market for what we do. Companies constantly talk about training and performance, but no one’s nailed how to make learning truly adaptive, continuous, and impactful at scale. MobieTrain can be the platform that raises someone from average to high performer and makes that scalable.”
“But beyond the product, it was the people. I met our CEO, Guy and CTO Johan early on, and I was struck by how open and hungry they were to do things differently. No ego, no fluff, just a willingness to roll up their sleeves and get it done. That’s what drew me in, because that kind of leadership is rare. They’re ambitious, but grounded.”
“We’re not a nice-to-have. We’re a platform that impacts
sales, operations, retention: real business outcome.”
“And from a strategic standpoint? We’ve barely scratched the surface. We’re not a nice-to-have. We’re a platform that impacts sales, operations, and retention: real business outcomes. We’ve been too modest in our go-to-market approach. That’s changing. There’s a massive opportunity around the world, outside retail and hospitality...”
“We’re building the product and the team to go after that. Combine that with a strategy that’s bold enough to match the ambition, and I’m in. I know I can bring value, and I also see that I’ll learn a lot along the way. It isn’t just a job; it’s a chance to build something meaningful. That’s the sweet spot.”