Eight years ago, Rainui and I started a company. We were two people with complementary skills and a conviction that we could build better technology for New Zealand organisations. We had no playbook for enterprise. No connections in the market. No venture capital. Just the work. If I could go back and tell that version of myself a few things, here's what I'd say.
Your First Ten Clients Define Your Next Fifty
The work you do in your first two years sets your trajectory. Not because of revenue. Because of reputation.
In NZ enterprise, every client talks to other potential clients. The market is small enough that your work speaks for itself, for better or worse. Those first ten projects establish what you're known for. If you deliver well, the next ten come from referrals. If you don't, you spend years rebuilding trust.
Choose your early clients carefully. Don't take every project that pays. Take the projects that let you do your best work. The ones where the problem is genuine, the client is engaged, and the outcome matters. Those are the projects that produce the referrals that sustain the business.
We were fortunate. Our early clients were mostly public sector and community organisations. The budgets were modest but the problems were real. People depended on the systems we built. That accountability shaped our standards more than any business strategy could have.
Delivery Is the Only Strategy
I've watched tech companies invest in marketing, sales infrastructure, and brand campaigns while their delivery was mediocre. It doesn't work. Not in NZ. Not in enterprise.
Your delivery record is your strategy. Full stop.
When you deliver consistently, clients become advocates. When you don't, no amount of marketing will overcome the reputation. In a market where everyone is one connection from your clients, the truth about your work travels faster than any campaign.
This means investing in delivery quality even when it's expensive. Hiring people who care about outcomes. Saying no to projects you can't deliver well. Choosing sustainable pace over growth. It's slower. It's also the only approach I've seen work over a decade.
We've never had a salesperson. But I wouldn't change it.
Isaac Rolfe
Managing Director
Hire Slowly, Fire Quickly (But Kindly)
This advice is everywhere. It's everywhere because it's true and because nobody follows it.
In the first few years, the pressure to hire is immense. There's more work than you can handle. Adding someone seems like the obvious answer. But adding the wrong person to a small team doesn't just fail to solve the problem. It creates new ones. Culture dilution. Quality inconsistency. Client-facing mistakes that take months to repair.
We've written about how we hire. The summary is: we're slow, we're picky, and we care more about how someone thinks than what they know. That approach has cost us growth. It's also the reason our delivery record is what it is.
When a hire isn't working, act quickly. Not cruelly. With clarity and support. But quickly. A mismatch that lingers damages everyone: the individual, the team, and the clients.
Cash Flow Will Try to Kill You
Enterprise projects have long sales cycles and lumpy revenue. You might close a large contract and then hear nothing for three months. You might deliver a project and wait sixty days for payment. Government clients sometimes take ninety.
I underestimated how much of running a business is managing cash flow. Not revenue. Cash flow. The timing of money in and money out. There were months in the early years where we were profitable on paper and couldn't make payroll on time.
The fix isn't complicated but it requires discipline. Maintain a cash reserve that covers three months of operating costs. Invoice promptly. Follow up on payments without shame. Negotiate payment terms before the project starts, not after. Structure contracts with milestone payments rather than lump sums on completion.
Nobody teaches this in computer science.
Learn the Business, Not Just the Technology
I have three degrees. Economics, Finance, Computer Science, and Honours in Economics. For years I thought the technology degree was the valuable one. I was wrong. The economics and finance background is what lets me understand client businesses, scope projects accurately, and price work profitably.
Enterprise technology isn't a technology business. It's a business that uses technology. The problems you solve are business problems. The stakeholders you work with think in business terms. The value you deliver is measured in business outcomes.
If I were starting again, I'd spend as much time understanding business fundamentals as I did learning to code. Strategy. Finance. Operations. Organisational behaviour. These aren't supporting skills. They're core skills for enterprise work.
Protect Your Energy
I wrote about stretch culture earlier this year. What I didn't write is how I learned those lessons. The hard way.
In the first five years, I worked constantly. Not because I was forced to. Because the work was interesting and the stakes were high and there was always more to do. I treated my energy as infinite and my time as the only constraint.
It caught up with me. Not dramatically. Gradually. Decisions got worse. Patience shortened. The creative thinking that differentiated our work became harder to access. I was present but not performing.
Building a sustainable enterprise tech company requires building a sustainable life. That sounds soft. It's the most practical advice I can give. The company's long-term quality is capped by the founder's long-term energy. Burn out and the company suffers long before you admit there's a problem.
Relationships Compound
The CTO you help with a tricky problem today becomes the CTO at a larger organisation in three years. The project sponsor who trusted you with their first digital initiative recommends you to their board colleagues. The developer you mentored starts their own company and sends work your way.
Every genuine relationship compounds over time. Not as a networking strategy. As a natural consequence of doing good work and treating people well.
Eight years in, our strongest client relationships are with people we met in the first two years. They've moved organisations, taken on bigger roles, and carried us with them. That kind of loyalty isn't purchased. It's earned through consistent, honest delivery over years.
It's Worth It
I won't pretend it's been easy. Cash flow crises. Difficult clients. Hires that didn't work out. Months where I questioned whether this was the right path.
But eight years in, we have a team I'm proud of. Clients who trust us with their most important projects. A delivery record that holds up. And work that genuinely matters to New Zealand organisations.
If you're thinking about starting an enterprise tech company in NZ, the market is ready for you. It's small but growing. The organisations need help. The problems are real. The work is meaningful.
Bring your best. Deliver consistently. Build relationships. Protect your energy. And give it time. Enterprise trust isn't built in a quarter. It's built over years. But once it's built, it compounds in ways that make the early struggle worthwhile.