There's a moment in the life of every promising TravelTech company when the pressure to hire becomes almost irresistible.
The product is gaining traction. Revenue is growing. Investors are asking about the scaling plan. New markets are appearing on the horizon. The founder is stretched between product, customers, fundraising, partnerships and hiring.
And the natural conclusion often sounds something like this: "We need someone senior to take us to the next level."
A Chief Commercial Officer. A VP of Business Development. A Head of Expansion. Someone with the experience, network and credibility to accelerate growth.
I understand the logic. And I've seen it destroy more momentum than almost any other decision a founder can make at this stage.
Not because the person was wrong (though sometimes, it turns out to be very wrong...). Not because the founder made a bad hiring decision — the intention to grow was never in question. But because two things weren't honestly assessed before the contract was signed: whether this person's way of working, deciding and leading was genuinely compatible with the culture of the organisation — and whether the product was mature enough to open the doors that senior profile was expected to open.
The pattern behind many failed senior hires
The scenario is remarkably consistent.
A company closes a Seed or Series A round. Investors want evidence that growth can scale beyond the founder. The board begins asking about commercial leadership. The founder starts searching for a senior hire.
They find someone good. Sometimes someone excellent. A profile with a track record in a larger company, with market relationships, with the kind of CV that makes the board feel confident.
Six to twelve months later, the story looks very different. The hire has left. Or perhaps they're still there, but nothing is moving. The organisation feels frustrated. The founder feels disappointed. The board starts questioning what happened.
The post-mortem almost always points to the same conclusion: the company hired the right person at the wrong stage.
The question nobody asks
Most founders believe they are hiring someone to scale execution. What they're often doing is hiring someone to solve strategic uncertainty.
Which market should we prioritise? Which customer segment is truly our sweet spot? What commercial model is actually repeatable? Which expansion opportunities deserve investment?
If those questions remain unresolved, you're not hiring a commercial leader. You're hiring a co-founder. And those are very different conversations.
Exceptional commercial leaders can accelerate a strategy. They can refine it, stress-test it, challenge assumptions. But they rarely create clarity where none exists. Senior talent amplifies what already exists. It does not replace the need for strategic direction.
Why TravelTech is different
This challenge exists across industries, but TravelTech creates additional complexity.
Unlike many software businesses, growth isn't simply a matter of adding more salespeople. Selling into hotel chains is different from selling to independent properties. Entering Saudi Arabia requires a completely different approach than expanding into Germany or the United Kingdom. Working with hotel owners, management companies, tourism boards, OTAs and distribution partners requires different relationship strategies, sales cycles and value propositions. And then there's the integration complexity — each region comes with its own ecosystem of PMS, CRS, channel managers and local platforms. Underestimate that, and you don't just slow down the sale. You can close the door to an entire market before the conversation even starts.
In many TravelTech businesses, expansion decisions are geographic before they are organisational. Founders aren't only deciding who to hire — they're deciding where to focus, which markets matter most, which partnerships will unlock growth and which opportunities should be ignored for now.
Hiring senior talent before those decisions become sufficiently clear multiplies the risk considerably.
What "ready" actually means
One of the biggest misconceptions in scaling businesses is the belief that readiness is linked to funding milestones. It isn't.
Being ready for senior talent has very little to do with whether you've raised a Seed round, Series A or Series B. It has everything to do with organisational clarity.
It means you know what you're selling and to whom, well enough that a senior commercial person can build on it rather than discover it. It means you have a repeatable sales motion, even if it's imperfect and even if only the founder is running it right now. It means you can articulate what success looks like for this role in twelve months — not in aspirational terms, but in concrete ones.
And it means — this one matters more than most founders acknowledge — that you're hiring to execute a strategy, not to create one from scratch. If the fundamental strategic questions about which market, which customer, which model are still open, you're not hiring a CCO. You're hiring a co-founder. And those are very different conversations.
That final point about absorbing seniority is often overlooked. A highly experienced executive who has spent years operating within structured organisations may struggle enormously in a founder-led business where priorities change weekly, processes are evolving and decisions remain centralised. That isn't a capability issue. It's an environment issue. And no amount of talent can completely overcome structural misalignment.
What great investors understand — and what the others get wrong
Investment pressure is one of the most consistent drivers of premature senior hiring. Not because investors are wrong to want commercial leadership. But because the timeline that makes sense for a fund doesn't always match the timeline that makes sense for the company.
A fund has a portfolio to manage, a thesis to validate, and LPs to report to. Seeing a senior commercial hire in place feels like progress. It looks like execution. It signals that the company is moving from founder-led everything to a scalable structure.
What it sometimes signals instead is that the company has spent six months of runway on a salary, an onboarding process that didn't work, and a departure that will make the next hire harder to recruit and harder to trust.
The best investors I've worked with don't push founders to hire faster. They push founders to gain clarity faster. They encourage founders to stay close to customers, to remain involved in sales longer than feels comfortable, to validate commercial assumptions before delegating responsibility to someone else. They understand that senior talent should amplify a proven model — not compensate for the absence of one.
That's a subtle distinction. But it often determines whether a hire succeeds or fails.
The SMYT Readiness Framework
Before launching a senior executive search, I encourage founders and investors to assess five critical areas honestly — not for the board, not for the pitch deck, but for themselves.
Commercial Clarity. Do you clearly understand how customers are acquired, converted and retained? Not the vision — the model. If the honest answer is "we're still figuring that out," the search should wait or the brief should change.
Founder Readiness. Has the founder developed sufficient understanding of the sales process to effectively transfer ownership? The best senior commercial hires inherit a process, even an imperfect one. They don't invent one from zero.
Organisational Readiness. Can the company genuinely support and leverage senior leadership? Budget, team, decision-making authority, access to the founder, clarity on what's in and out of scope. If you can't answer this, you're not ready to onboard someone senior.
Expansion Readiness. Are the strategic decisions around market priorities sufficiently clear to support execution? If you need someone to explore new markets and build commercial hypotheses from scratch, that's a different profile and a different conversation than hiring to execute on something already validated.
Cultural Compatibility. Will this individual's operating style strengthen or disrupt the existing organisation? This one deserves more than a checkbox.
Sometimes the answer isn't a full-time senior hire. Sometimes what a company needs first is someone who has been there before — an interim or fractional profile who can build the commercial foundations, stress-test the market assumptions and create the conditions that make a permanent senior hire not just possible, but successful. It's not a lesser solution. In many cases, it's the smarter one.
The thing that doesn't appear on the CV
I'll say this from experience, because I've lived it firsthand.
A genuine star joins a founding-stage team — track record, relationships, presence, everything on paper exactly right. And within months, something that took years to build starts to fracture. Not out of bad intention. Because the environment required a way of working that was genuinely incompatible with theirs. And because nobody asked the hard questions early enough.
The painful irony is that it usually ends with the star leaving. But the team they leave behind is different from the one that existed before they arrived. And rebuilding that — the trust, the dynamic, the culture — takes longer than anyone budgets for.
Cultural fit is often treated as the final stage of an executive search process. In my experience, it should be one of the first. Not in the superficial sense of whether people get along — but in a much deeper sense. How does this person make decisions? How do they handle ambiguity? How much structure do they need to operate well? How do they build trust in an environment where everything is still being built?
A person who thrives in structure can suffocate a team that runs on autonomy. A person who moves fast can destabilise a team that needs steadiness. A leader accustomed to abundant resources may struggle in an environment where creativity and adaptability are daily requirements. Neither profile is wrong. The mismatch is.
The larger the profile of the hire, the greater the potential impact when the fit isn't right. Because senior leaders don't only influence strategy. They influence culture, decision-making, trust, team dynamics. And once those foundations are disrupted, rebuilding them takes far longer than most companies anticipate.
The best protection against this isn't a longer interview process. It's a founder who is honest — with themselves first — about what their team can absorb, and what it can't. And a search process that treats cultural alignment not as the last filter, but as the first.
When it is the right moment
I don't want to leave the impression that the answer is always to wait. It isn't.
There are moments when a senior commercial or expansion hire is exactly the right decision — and when moving quickly on it creates genuine competitive advantage. When you have a validated model and the constraint is execution capacity. When you're entering a market where relationships are the primary barrier and you need someone who already has them. When the founder's time is genuinely the bottleneck and the cost of their attention being on sales rather than product is measurable and significant.
In TravelTech specifically, there are also market windows that don't stay open indefinitely. Saudi Arabia is the clearest current example: the opportunity is real, the timeline is defined by Vision 2030, and being eighteen months late to a relationship-driven market has consequences that are hard to reverse. In those contexts, the pressure to move is legitimate — but the answer isn't to hire faster. It's to be more precise about who you need and why.
The best senior hires I've placed at this stage all share something in common: the founders who hired them could answer every question in the framework above before we started the search. Not perfectly. But honestly. That honesty — about what's ready and what isn't — is what allowed the hire to land well and stay.
A final thought
The most expensive hiring mistake in a scaling TravelTech company is rarely just one thing.
Sometimes it's the wrong person. Sometimes it's the right person at the wrong moment. Sometimes it's an exceptional profile dropped into an organisation that wasn't ready to receive them. In practice, it's often a combination of all three — and the honest conversation about which one applies is precisely the one that happens least.
Senior talent doesn't resolve strategic ambiguity. It can build foundations, create structure and unlock growth — but only when the fundamental decisions about market, model and culture have been faced honestly first. Put the right person into a company that has done that work, and things accelerate. Put them into one that hasn't, and you won't just fail to grow — you'll damage what you already built.
The founders who get this right aren't the ones who hire fastest. They're the ones who are honest earliest — about what their company is ready for, what their culture can absorb, and what their product can actually deliver once that senior door opens.
Hiring is not the strategy. It's the consequence of having one.
