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 six 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. At the end of the series, I’ll post a summary capturing the most common learnings and pitfalls founders should be aware of when entering the US market.

Story 2 is of a company that has the following situation:

• Team in NZ: ~120
• Team in US: ~10
• Time in market: ~4 years
• Revenue: $27m NZD ARR (total company)

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

Lessons From Our Second (and Third) Shot at the US

Expanding into the US isn’t a one-and-done kind of thing. For us, it’s been more like a series of experiments - some successful, others expensive. We’ve had a few cracks at it now, and while we’re still learning, we’ve come a long way from our early attempts.

We’re now seeing real traction: 20% of our new revenue is coming from the US, and we expect that number to grow. But it’s been a grind to get here.

Strategy:

We first tried selling into the US remotely - around 3 or 4 years ago. We sent someone from New Zealand to lead the charge, but it was COVID, we couldn’t travel, and everything was stacked against us. Costs ballooned. The exec team couldn’t be there. We pulled back.

Then we tried again - this time with more intent. We opened an office and sent someone over who really understood our business. The person we chose to send over this time was pivotal to our success. He knows the product, can sell, builds relationships, and gives us feedback we can actually act on. That was the turning point. The fact he is an all rounder and can interpret customer needs into product insights has been critical.

We didn’t go in with unrealistic expectations. We knew we had to grind it out. There wasn’t a magic moment. It was ugly. We just won deals - one by one - and slowly it got easier.

Our approach this time: win ugly, win any way you can. If this means flying to a customer to close a deal and put in the extra edge or do tactical things like buying donuts - we do it. If it means staying up for a night to ship and demo a new feature, we win like that. We build what’s missing fast, even if it's messy.

Market-wise, the US is different. The bar for product-market fit is higher. Everything has to work better. You can get away with less in other markets - here, not so much. The terminology is the same, but the expectations aren’t.

Our biggest product difference was integrations. That’s our edge. We went to market with our integrated version of the product. It’s more complex, but it solves deeper pain. And the market is big enough that we don’t need to go wide - we’re going deep.

We’re closing larger deals here than we were used to. More $30–50k than $5–10k. That changes how you approach everything - from marketing to customer success.

We’ve learned not to rush scale. You can throw resources at it once you know it works, but before that? Don’t force it. Don’t try to skip the grind. We were lucky we didn’t have investor pressure to go fast—we had time to figure it out properly.

People and Culture:

Hiring was one of the hardest parts. Early on, if you don’t have a trusted person grinding it out in-market, everything is harder. You lose a lot in translation. Americans are great at storytelling, and without someone on the ground who speaks your culture, it’s hard to get the full picture of how things are really going.

At the start, hiring people who fit your DNA is near impossible. You can’t just teach your culture - it’s more subtle than that.

The cultural differences may appear small, but they are actually profound. In many ways it’d be easier if they literally spoke a different language, like French. You’d be more aware and sensitive of the potential disconnect.

We eventually got to a place where we could work with a recruiter we knew and trusted. Once there’s a bit of critical mass, people can see a career path with you - it gets easier.

Early-stage hiring is weird. You want entrepreneurial people, but you also ask: why would someone that entrepreneurial join a startup instead of starting their own thing? The person you need at the very beginning is different to the one you need when you're scaling.

Best advice we’ve heard - and lived - is to assume you're going to get it wrong the first time. People can look and sound right but still not work out. Burn rate sneaks up fast.

Hire as a last resort. First, try to scale with what you’ve got. Only hire once you're really clear on what needs to be done and who’s the right person to do it.

Key Takeaways:

• Start with someone you trust deeply. Sending Sharif at the right time made all the difference.
• Product-market fit is harder in the US. What works elsewhere might not fly here.
• Don’t scale too early. Nail it first. Then go hard.
• Build ugly. Win ugly. Don’t wait for perfection—just solve the problems as they come.
• Integrations were key. If we’d known earlier how impactful our NetSuite integration would be, we would’ve prioritised it sooner.
• Hire slowly and intentionally. Don’t outsource your culture too soon. Teach it first.

Connect with Barnaby, here.