Tech Leaders to Know: Rob Cleghorn

At the heart of ClearPoint’s technology strategy is Rob Cleghorn, a leader who brings both creativity and pragmatism to the table. As CTO, Rob isn’t just focused on the “what” and “how” of technology, but on the “why” , ensuring that innovation drives meaningful outcomes for people and businesses.

We sat down with Rob to learn more about his journey, philosophy, and what’s next for tech in New Zealand.

If you weren’t in tech, what career path would you be in?

“A career where you get to design something, build it, and see the outcome. I love the creative design phase and the process of proving that the thinking works, or discovering you need to go back to the drawing board and iterate until you get the outcome you’re after.”

For Rob, it’s always been about creation. Whether in technology or another field, his passion lies in building something tangible and meaningful — a mindset that carries through to his role as a tech leader.

What makes a great software engineer stand out?

“There are many qualities, however I believe the most important is passion. A passion for the technology itself is important but just as important is a passion for the outcomes the technology creates. If you really care about what you’re creating, you’ll naturally care about the technology and the quality of the approach you use to build it.”

Rob believes passion fuels innovation. It’s not just about knowing code, it’s about caring deeply for the impact of what’s being built. That balance of technical curiosity and outcome-driven focus is what he sees as the hallmark of truly great engineers.

What’s your go-to productivity hack or tool?

“I’m loving the AI mobile apps on chat mode; OpenAI, Gemini, Claude, and Grok all have chat mode. Connect your phone to Bluetooth in the car and have some deep dive conversations on anything from the latest news to a problem on your mind. These conversations seem to get better with each LLM upgrade.”

For Rob, productivity is about leveraging AI to think differently. His hack: using AI as a sparring partner, not just a tool, but a co-pilot for ideas.

What are the biggest challenges facing tech companies in New Zealand today?

“I think the biggest challenges are interconnected: a lack of ambition, courage, and tech leadership, which results in us not thinking big enough. Yet, we’re in an amazing place where, similar to the cloud movement a decade ago, our size is becoming less of a constraint. If we can lead with strong technology foundations, embrace AI, think bigger, and reconnect with our ‘number 8 wire’ innovation roots, we can absolutely be the next big tech innovation hub.”

Rob sees both a challenge and an opportunity: the need for bold thinking. With the right leadership and willingness to scale beyond borders, New Zealand has the potential to punch well above its weight in global technology innovation.

Final Thought

Rob Cleghorn embodies what it means to be a tech leader with vision,

blending creativity, passion, and practicality with a bold belief in New Zealand’s potential. Whether he’s exploring the latest AI tools or championing a culture of curiosity and courage, Rob continues to shape how ClearPoint and the wider industry think about innovation.

And if you catch him at an event, don’t miss the chance to join the conversation, he’s one of those leaders you’ll always leave with a new idea from.

Rob Cleghorn, CTO at ClearPoint