Expanding to the US is a major step for any Kiwi startup. Many of our portfolio companies have taken the leap - some have succeeded, and all have learned valuable (and sometimes expensive) lessons.

To help the next generation of founders navigate this journey, I set out to interview several of our portfolio companies about their experiences expanding into the US. While there are common themes, each story offers its own unique insights.

Over the coming weeks, I’ll be publishing anonymised stories from these companies, sharing real-world lessons on strategy, hiring, market validation, and execution.

Story 3 is of a company that has the following situation:

• Team in NZ: 10
• Team in US: 7
• Time in market: ~4 years
• Revenue: ~$8m USD (total company)

Here are the key lessons and thoughts written in the first person for easy reading.

What We Learned Entering the US (on a Tight Budget and a Bold Bet)

We always knew our market—and eventually, our exit—was going to be in the US. What we didn’t know was how hard, expensive, and humbling that journey would be. We got a lot wrong, but we also got some key things very right. Now, with north of $600k USD in monthly revenue and a solid team on the ground, we’ve found our rhythm.

Market Entry Strategy:

We started with a strong conviction: founder-led sales was the way to go. And we still believe that. The early traction we had—our first few hundred thousand in US revenue—came from showing up and selling ourselves. I did two weeks in Europe, two weeks in the US, two weeks in NZ, rinse and repeat.

We leaned into the young founder angle to get meetings. It worked.

That said, we were undercapitalised when we entered. We raised $3M USD, which felt like a lot at the time. It wasn’t. People costs in the US were far higher than expected. If I could rewind the clock, I’d spend more time raising and come in better armed.

That undercapitalisation may have actually helped us in hindsight—it forced focus, made us scrappy, and kept us close to the customer. But it also meant painful trade-offs, especially with hiring.

Focus & Segmentation:

We’ve now narrowed in on low-end professional sports leagues—a segment where we can win, serve well, and scale.

It wasn’t always like that. We tried twice to go after the US college market. We failed both times. The market is hyper-fragmented, hard to target, and almost impossible to do brand marketing into. Eventually, we pulled back and made a decision: ignore that segment.

That was a big unlock. The US is massive. You don’t need to boil the ocean—you need to find your corner of it. If we were starting over, we’d go even more niche from day one. Choose your customer, your product variant, your pitch—and be ruthless about what not to do.

Team Building:

Our team has taken time to get right. We’ve learned a lot—especially from our mistakes.

We hired a VP of Sales with a great résumé—but no industry background. On paper, it made sense. In practice, it didn’t work. We ignored our gut. We also felt pressure from the board to “level up” post-raise. That led us away from what had worked for us: scrappy, hungry BDMs.

Lesson: trust your instincts when hiring, especially for senior roles. When we didn’t, we paid for it (and had to exit quickly).

Once we leaned back into what worked—hiring people who fit our stage, not just the CV—we saw traction again.

We now use a mix of hiring channels:

• For IC roles: LinkedIn and cold job posts. We look for people who are functional, not overly ambitious, and a great fit for the task at hand.
  
  
• For managers and execs: We’ve only hired expats—from the UK, NZ, AU, and South Africa. We stick to networks and people who get our culture from day one.

One thing we’ve become crystal clear on is this: match the nature of the person to the nature of the sale. Ours is a long, relationship-driven sales cycle. Our customers buy on how they sell to their customers. It’s slow. We needed people with patience to match that rhythm.

Key Takeaways:

• Founder-led sales works—especially early on. Use the energy and authenticity you bring.
• Undercapitalisation can force focus, but budget more than you think—US hiring is expensive.
• Choose your niche early, and ignore the rest. The US is big enough that focus wins.
• Trust your hiring gut. Especially with senior hires. The stakes are too high to be polite.
• Match your salespeople to your sales process. Not just in skillset, but in temperament.
• Distributed teams are hard. We’d centralise faster next time.
• Don’t stress about brand early on. We weren’t great at it. But we delivered. Sales + product got us through.

We’ve built a team that works, a product that sells, and a business that’s growing. It’s still hard—but it’s working. And that didn’t come from a silver bullet. It came from mistakes, persistence, and eventually, alignment.

Connect with Barnaby, here.