Coming To America - A CEO's Journey
- Dermot Duggan

- 2 days ago
- 7 min read

Twenty-eight years ago, my wife and I packed up our lives, took our family of 3 young children, and moved to America.
At the time, I was working for Sun Microsystems and had been offered the opportunity to relocate and lead part of Sun’s global marketing business. On paper, it looked like an exciting career move. In reality, it became something much bigger than that.
I still remember the feeling of arriving in the U.S. Everything felt larger, faster, more ambitious. The energy was different. The pace of decision-making was different. Even the way companies thought about growth was fundamentally different from what I had experienced in Europe.
What started as an adventure turned into the next 25 years of my career.
During that time, I held a number of senior leadership roles at Sun, travelled extensively, and had the opportunity to work with some of the world’s most prolific technology companies. Later, after leaving Sun, I co-founded a business focused on coaching and supporting CEOs across both the U.S. and Europe as they scaled their companies.
Over those years, I began to notice something important.
Almost every European founder who considers expanding into America initially sees it as a market expansion exercise. A new geography. A bigger customer base. A commercial opportunity. But the companies that succeed eventually realise it is something much deeper than that.
America changes the way you think about building a company. It changes your expectations around speed, talent, leadership, capital and execution. It forces a founder to evolve.
I’ve now had the privilege of watching many European and UK founders go through that same journey themselves. Some adapted exceptionally well. Others struggled far more than they expected. And in almost every case, the challenge was not simply entering a new market, it was learning how to operate inside an entirely different business environment.
That is the perspective this article comes from. Not theory, but lived experience. Both my own, and the journeys of many founders I’ve worked alongside over the years.
The starting point is always the same: why bother with America at all? The simple answer is: Scale.
The United States remains the largest and most important technology market in the world, it is larger than Europe combined. From a GDP perspective, the U.S. is approximately $27 to $28 trillion, compared to the EU at around $18 to $19 trillion and the UK at roughly $3 to $3.5 trillion, which means the U.S. economy is about 1.5 times the EU and roughly 8 times the UK. For most growth companies, that translates into a significantly larger total addressable market, which makes the U.S. extremely attractive even when cost and complexity are taken into account.
However, scale is only part of the story. A second major driver is speed. Everything moves faster in the U.S. Customers decide faster, deals close faster, capital moves faster, and teams scale faster. There is a level of urgency in the market that changes the entire operating rhythm of a company. Alongside this is the signalling effect: If you succeed in America, people pay attention. Investors pay attention, customers pay attention, even the competitors pay attention. In many ways, America is the key market that validates everything else - and that is a very powerful dynamic.
So it's easy to see why the US is so attractive to founders - but one of the biggest mistakes European CEOs make is assuming that America is simply a larger version of Europe, when nothing could be further from the truth. The behaviours are different, the expectations are different and most importantly, the go-to-market motion is different. In Europe, decisions are often slower, with more consensus building, more caution, and a stronger emphasis on certainty before commitment. In America, decisions are generally faster, with more willingness to act first and refine later. That single difference fundamentally changes how you sell.
European buyers are often focused on reducing risk, while American buyers are often focused on increasing upside. In Europe, you typically need to prove something will work before you win the deal. In America, you often need to show what becomes possible if it works. That creates a completely different commercial conversation and it changes how you position your company, how you structure your sales motion and how you build your team.
There is also something more subtle but equally important: In America, vision matters more than many European CEOs expect. Customers do not just want to understand what your product does today; they want to understand where you are taking them, what future you are creating, why it matters at scale. European and UK CEO’s often struggle with this concept, as it feels fake and not grounded in reality. However, if you cannot answer those questions clearly, you will struggle to break through.
Physical presence plays a far bigger role in America than many European CEOs anticipate. Relationships compound faster in the U.S. than in most other markets. Being visible, being present and being known accelerates momentum in a way that is difficult to replicate remotely. Nowhere is this more obvious than Silicon Valley, where it feels like a tightly connected ecosystem, everyone it seems knows everyone else. In the early stages, in my experience, you cannot simply remote-control your way into the U.S. market - in fact that can be the path to failure, and wasted investment.
Marketing is another major difference. In Europe, marketing supports sales, whereas in America, marketing is the growth engine. Thought leadership, category creation, executive visibility, and narrative are not optional extras: They are central to how companies win.
If I had to simplify the entire difference based on my 25 years of experience, it comes down to this: European go-to-market strategies tend to optimise for certainty, while American go-to-market strategies tend to optimise for opportunity. In the U.S, people generally believe that things can be bigger than they are today and that belief shapes behaviour, investment decisions. People and therefore companies are more willing to commit, to try and to take calculated risks.
There were challenges as well: I had to acclimate our family to the US, build a network from zero, learn a new business culture in real time, and do it all without the support system I had at home. Looking back, moving to America fundamentally changed how I think about life and about business. It made me more ambitious, more direct, and more aware of how much growth is shaped by the environment just as much as capability.
For CEO’s that have made the huge decision to expand into the US, there comes an important business and personal decision: Should I move to the States or try to remote pilot it from wherever I am based?
Over time, I have seen this same decision play out in very different ways with CEOs I work with, and both paths can be successful.
One particular CEO reached the conclusion that if America was going to be the biggest opportunity, he needed to be there - so he moved, including relocating his family. His logic was simple: if the most important customers were in the U.S., he needed to be close to them, and if the most important partnerships and future capital were there, he needed to be embedded in that ecosystem. Once he moved, things accelerated significantly. Sales cycles shortened, relationships formed faster, hiring improved, and his understanding of the market deepened. However, it also came with challenges, particularly around family adjustment, logistics, and managing a more complex operating structure across geographies. When he reflects on it, he would make the same decision again, but he would prepare more carefully for the personal impact.
Another CEO made the opposite choice, and decided not to relocate. Instead, he built a strong U.S. leadership team and travelled frequently, staying anchored in Europe while remaining deeply engaged in the American market. That model also worked, and the company built meaningful traction in the U.S. without the founder moving. However, the trade-offs were different: Momentum took longer to build, relationships developed more slowly, and feedback from the market was less immediate. He also paid a considerable personal toll in both time and money from travel and managing across timezones - It required exceptional local US leadership and a highly disciplined operating model.
Both approaches worked, but they required very different trade-offs.
After seeing this decision play out repeatedly, a few things become clear:
First, America is not a plug-and-play expansion; it is a fundamentally different operating environment. Second, founder presence matters more than most European CEOs expect, especially early on. Third, relocation can accelerate growth, but it comes with real personal cost. Fourth, success almost always depends on the quality of local leadership. And finally: This is not just a business decision; for most founders, it becomes a family decision whether they expect it to or not.
In practice, there are four common models you should consider for expansion into America:
1. The first is the fly-in CEO, where you remain mainly based in Europe and travel frequently, which works for early exploration but limits momentum.
2. The second is the local general manager model, where you hire strong U.S. leadership and remain anchored in Europe, which can scale well if the hire is right.
3. The third is the split-time model, where you divide your time equally between Europe and the U.S., which increases presence but can become personally demanding.
4. The fourth is full relocation, where you move to the U.S. and operate directly from the market, which provides maximum immersion but also requires the highest level of personal commitment.
When CEOs are making this decision, I encourage them to think about a few things: First, how strategic the U.S really is to their business. Second, whether the timing is right or whether they are moving too early. Third, whether this requires them personally or whether someone else can lead it. Fourth, the impact on their family and personal life. And fifth, whether they are truly committed to a multi-year journey rather than a short-term experiment.
The question is not whether America is attractive, because it clearly is. The question is whether you are prepared for what it actually takes to win there. Expanding into America is rarely just about entering a market; it is about changing how your company operates and, in many cases, changing how you lead. For some CEOs, that will mean relocating. For others, it will not. But either way, it is one of the most important strategic decisions they will ever make.



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