Shifting Role of a CEO: Conversation with Rachel West of Safari Portal

Leading Naturally: Conversations is a series exploring the real stories behind leadership. These are conversations with people building meaningful work while navigating complexity. We talk about the moments that changed them, the questions they’re still holding, and what it takes to lead with clarity, courage, and humanity over time.

Rachel’s journey is one many founders recognize. The business grows, but at some point, it asks for something new. Not just more effort, but a different way of leading. This conversation is about that shift.

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Rachel — thank you for the conversation. Your journey is inspiring, and I know there is so much more to come. Your creativity and drive are contagious.

Q. Safari Portal has become a successful travel technology company, but not necessarily through the “traditional startup” path. Can you share the story of how it came to be?

A. Safari Portal really came from lived frustration. I had been running a high-end tour operator for many years and understood how fragmented everything was—beautiful ideas and experiences being held together by spreadsheets, PDFs, and manual processes.

We didn’t set out to “build a startup” in the traditional sense. We started by solving very real, very specific problems for a small group of people, and then just kept going deeper. Everything grew organically from there—product, customers, revenue, team.

Because of that, we’ve always been extremely product- and customer-led. We didn’t raise capital early on (and still have never taken any outside investment), so every decision had to stand on its own. That forced a level of discipline and clarity that has shaped the company in a really meaningful way.

Q. When you think back to the early days, what did you have to learn, or unlearn, about leadership as the company grew?

A. Early on, I equated leadership with being involved in everything—every decision, every detail, every problem.

What I had to unlearn was the idea that being “close to everything” meant I was adding value. In reality, it was often the opposite.

I’ve had to learn that leadership is much more about creating clarity, setting direction, and trusting other people to execute—sometimes in ways that are different from how I would do it. Letting go of control was one of the hardest shifts, but also the most important.

Q. Was there a point where you realized the business needed a different version of you as a leader? What prompted that shift?

A. Yes, there was a point where the business was growing, but I was becoming the bottleneck.

Decisions were slowing down, the team was waiting on me too often, and I could feel that the way I had been operating wasn’t going to scale.

That was the moment I realized the business didn’t just need more people—it needed a different version of me. One that was less reactive, more structured, and more focused on the bigger picture rather than the day-to-day.

Q. When we first started working together, you were carrying a lot personally inside the business. What changed for you, both practically and mentally, as you began stepping into a more strategic CEO role?

A. Practically, I started to build real structure—clear ownership, clearer decision-making frameworks, and better systems around the team and the product.

Mentally, the biggest shift was moving from “holding everything” to trusting that things could move forward without me being involved in every step.

It created a lot more space—not just in my schedule, but in how I think. I’m able to spend more time on strategy, partnerships, and where we’re going, rather than constantly reacting to what’s in front of me.

Q. You’ve been intentional about not trying to lead this business alone. How has having outside strategic and coaching support shaped your growth as a founder and CEO?

A. It’s been incredibly important.

Being a founder can be very isolating, and it’s easy to get stuck in your own patterns or perspectives. Having outside support has given me both clarity and accountability.

It’s helped me make better decisions faster, and also step back and look at the business more objectively.

Q. What have you had to stop doing in order for Safari Portal to keep growing?

A. I’ve had to stop being the default decision-maker for everything.

I’ve also had to stop over-polishing or over-owning parts of the product or experience that others on the team are fully capable of leading.

And more broadly, I’ve had to stop equating effort with impact. Just because I can do something doesn’t mean I should.

Q. One thing I’ve always admired about Safari Portal is how much care you put into both the product and the client experience. Where does that instinct come from?

A. A lot of it comes from the travel industry itself.

This is a relationship-driven, detail-oriented business where the experience matters just as much as the outcome. That mindset has always been very natural to me.

We’ve always believed that the tools travel professionals use should reflect the level of care they provide to their own clients. That’s where the focus on design, usability, and experience comes from.

Q. Safari Portal has built a loyal client base, and many of your customers become true champions of the platform. How do you stay close to what they need while still continuing to evolve the product?

A. We stay very close to our customers—we talk to them constantly, and we pay a lot of attention to how they’re actually using the platform.

At the same time, we don’t build purely reactively. Our role is also to anticipate where the industry is going and help lead customers there.

It’s a balance between listening deeply and maintaining a clear product vision.

Q. You’ve built a team that is largely made up of women. Was that intentional, or did it happen organically? How has that shaped the company’s culture?

A. It happened organically.

We’ve focused on hiring people who are thoughtful, detail-oriented, and genuinely care about the product and the customer—and that has naturally led to a team with a strong female presence.

It’s created a culture that is collaborative, high-accountability, and very client-focused, which has been a real strength for us.

Q. What values most shape how you run Safari Portal today, and can you think of a decision where those values really guided the way forward?

A. A few values really stand out: quality over shortcuts, long-term thinking, and respect for both our customers and our team.

There have been moments where we’ve chosen not to pursue faster growth or easier revenue because it didn’t align with how we want to build the business.

Those decisions aren’t always the obvious ones in the moment, but they compound over time and shape the kind of company you become.

Q. As you look ahead, what feels most exciting to you right now—about the business, the team, or the kind of leader you’re still becoming?

A. What excites me most is how much more we’re able to do now that the foundation is in place.

The product is evolving quickly, especially with new integrations and AI capabilities, and the team is operating at a much higher level.

Personally, I’m excited about continuing to grow into a leader who can scale with the business—staying close to what makes Safari Portal special, while also building something much bigger.

Q. And finally, because I always love this question—if you were to describe your career in travel and entrepreneurship as something in nature, what would it be, and why?

A. Probably something like a river.

It hasn’t been linear or predictable, but it’s been steady, and it’s kept moving forward. There have been moments of resistance and moments of flow, but over time it’s carved its own path. That’s very much how this journey has felt.

Thank you, Rachel.

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There’s a moment many leaders reach, though they don’t always name it right away. The business is working. It’s growing. And yet, something feels off. The way you’ve been leading no longer quite fits what’s next.

Not because you’re doing it wrong, but because the role itself has changed.

Rachel names that moment clearly: the shift from being deeply in everything to creating clarity for others. From holding to trusting. From operator to CEO.

If something in this conversation felt familiar, it might be worth asking:

What version of you got the business here, and what version is it asking for now?

And if you’re in that in-between space, you’re not alone. I spend a lot of time with leaders navigating exactly this transition. I’m always open to a conversation.