CEO by Chance, Leader by Choice - My Journey to Learning How to Lead

From the Heart: Lessons, Laughs, and Leadership
— CEO by Chance, Leader by Choice - My Journey to Learning How to Lead

When I launched Roamlii (or Pathfinder365, which was our MVP name), it wasn’t because I had a lifelong dream of becoming a CEO. It was because I saw a problem—one that had been bothering me for years—and I was ready to build something better. Plus, I lost my job at a local resort when the pandemic hit, so I had some free time.

The leadership part? That came pretty naturally. I’ve always been someone who takes ownership, connects the dots, and moves things forward. But building a company and leading one are two very different muscles. And as Roamlii grew, I knew I needed to strengthen both...at the pace of a startup.

I didn’t fall into this—I stepped up to it

Leadership isn’t something you wait to be ready for

I didn’t stumble into entrepreneurship by accident. I’ve always had a mind for business, a curiosity for how things work, and a weird love for learning new tools and technologies. I’m the person who reads the manual—not because I have to, but because I strive for excellence in everything I build, even a shelf for my basement closet, and don't want to miss a critical step.

So when I noticed how disjointed and outdated the tourism tech landscape was, especially for small businesses, I didn’t wait around for someone else to fix it, because to be honest, no one was going to...and that's a story for another blog. First came the concept, which I hand drew on a giant piece of paper. Then the systems, I connected with a team of developers launching their own startup, to build out our initial framework (thanks eHelply!). And onward we went—building, learning, iterating, connecting, evolving, into the system that would become Roamlii.

What I didn’t expect (at least not right away) was how much leading a team would become the most fulfilling part of the work, and one of the most challenging too.

From solo builder to team leader

Creating space for others to thrive

In the early days, I wore all the hats. And honestly? I’m good at that. I can pivot from product strategy to writing sales copy to beta-testing new features before they launch, and then dig into some QB tasks. But I knew if I wanted Roamlii to scale, I had to make the shift from doing to leading.

That meant bringing in people who could own their lanes, and trusting them to run with it. It meant creating clarity, not just vision. And it meant being the person who sets the tone, not just the pace.

Leading well isn’t about doing everything yourself, it’s about creating the conditions where other people can do exceptional work. While I still wear many hats, the transition to "who not how" is definitely happening, and I'm shifting more and more of my energy in that direction.

I lead like I build—thoughtfully, and with momentum

Clear, kind, and not afraid to make the call

I’ve learned that leadership is a balance of decisiveness and empathy. People want direction, but they also want to feel heard. They want someone who can carry the weight, but who doesn’t pretend to have all the answers. They want to be led by someone who shows up with conviction—and also with humanity.

That’s the energy I try to bring to my team. Clear communication. Space for ideas. Accountability without micromanagement. Growth mindsets and striving for excellence in everything we do. And the understanding that we’re building something meaningful, together. Building a startup is less about taking now, and more about giving now to win as a team later.

I take this seriously, because the way a company grows is directly tied to how its leadership shows up.

Culture isn’t an afterthought—it’s the foundation

Leadership sets the tone, whether you mean to or not

You can’t “wing” culture. It doesn’t just show up one day. It’s built through every decision, every policy, every conversation.

I’ve been intentional about the culture we’re creating at Roamlii. One that values innovation without burnout. Progress over perfection. A healthy dose of curiosity. Respect for people’s time and talents. And space to be real humans, not just job titles.

That doesn’t mean we get it right every time. But we’re clear about what we value, and that clarity gives us direction when things get messy...because they do, and they always will.

Leading in real time

Strategy and adaptation go hand in hand

The market shifts. Technology evolves. Customer needs change. That’s just part of the game. But if there’s one thing I know, it’s how to move with it, without losing focus.

One of my strengths as a leader is being able to zoom in and out, switching between high-level strategy and in-the-weeds execution as needed. I know how to think critically, build systems, and pivot fast when something’s not working.

But I also know when to pause. When to listen. When to take the extra beat before making the next big decision. It’s not about moving fast for the sake of speed. It’s about moving smart, and knowing when to trust your gut. Like the Navy SEALS say, "slow is smooth, smooth is fast".

What leadership looks like now

For me, leadership isn’t about being the loudest voice in the room. It’s about being consistent. It’s about setting the vision, clearing the path, and being the kind of person people want to build with.

I lead by choice. Every day. And I take that responsibility seriously, because the business, the people, and the work deserve nothing less.

Is it perfect? Of course not. But I’m proud of how I lead. I’m proud of the team we’ve built. And I’m excited about where we’re going.

Leading something real

Roamlii isn’t just a tech company. It’s a platform designed to support real people building real businesses in the tourism space. That requires strong systems, yes, but also strong leadership. Leadership that’s adaptive, collaborative, and grounded in purpose.

That’s the kind of leader I aim to be. Not just for my company, but for the ecosystem we’re trying to support.

Let’s build better, together

Whether you’re building your own business, figuring out your next leadership chapter, or looking for tools that support tourism with more intention—Roamlii’s here for it.

👉 #GetRoaming and let’s lead with clarity, grow with purpose, and build the kind of industry we’re proud to be part of.

Yours in tourism, innovation and startups,

Founder & CEO
Roamlii