Building iTOO with vision, culture and specialist obsession
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Every now and then, our industry needs a reminder that new energy still matters. Not the noisy kind. The kind built on deep expertise, long-term intent, and an entrepreneurial appetite to go where the risks are getting more complex, not less.
That’s why I was genuinely disappointed when I read the news about Etana, and equally energised when iTOO re-emerged with fresh momentum. In a market that can feel dominated by legacy structures and predictable moves, iTOO’s story is a useful case study in what happens when a leadership team decides, quite intentionally, to “have another go”.
In a wide-ranging discussion with Justin Nailer, CEO of iTOO, we unpacked the catalysts behind the business, how it has grown tenfold in ten years, and why the company’s leadership playbook is built around a deliberate tension: be expert achievers, while still acting like mavericks of progress.
Where iTOO came from: a core team and a market signal - Justin traces iTOO’s roots back to a core group of people, starting with founding shareholders Paolo and Rob, both of whom held leadership roles at Hollard and were central to Etana’s original journey. When Etana was sold back to Hollard, the team stayed on for a period, but the itch remained. They enjoyed the experience of building something distinctive and wanted another opportunity to do it again.
The real catalyst, though, was strategic. As they looked around the market, they saw a gap forming in what Justin calls the intangible risk space, particularly liability, casualty, and the growing suite of risks connected to them. It wasn’t only about competitive landscape. It was about trend recognition. Globally, liability and intangible risks were accelerating in importance, and the team believed Africa would feel that pull too.
That became the starting thesis: focus on specialist and niche risks, build a business that is known for expertise, and back it with a leadership team that trusts one another and has a proven underwriting track record.
Many of iTOO’s leaders have been together for 15 to 20 years. Justin describes this as a meaningful advantage: a team with shared history, shared scars, and the kind of trust you can’t manufacture quickly.
Why Justin put his hand up - Justin is open about the fact that he wasn’t there on day one. He joined about two years after iTOO was launched, stepping in when it became clear that what the founders were building had scale and serious potential. He saw an opportunity worth committing to and, in his words, began to form his own dream and vision for what iTOO could become.
For Justin, leadership starts with a premise: if you don’t have an exciting dream and vision, it’s hard to get people to follow.
But vision alone isn’t enough. Culture, he says, is fundamental, especially in insurance, and even more so in specialist lines. This is a people business twice over: you rely on deep technical experts to understand complex risks, and you rely on broker relationships to distribute, advise, and build trust with clients.
Add to that iTOO’s ownership structure, an independent, majority family-owned business – and you have a further advantage Justin value: the ability to align incentives to merit and performance, make faster decisions, stay entrepreneurial, and still hold a long-term view without being dragged by quarterly pressures.
His formula, in summary: set the dream, build the culture, align incentives, and stay entrepreneurial with a long runway.
The 10-year milestone: What changes when you’ve already won once - iTOO recently hit a milestone that most start-ups only dream about: tenfold growth in ten years, both on top line and bottom line. Justin speaks about it with pride, but also with an eye on the next chapter.
The question now is more demanding than “how do we grow?” It’s: how do we do it all over again?
“Set the dream, build the culture, align incentives, and stay entrepreneurial with a long runway—this is how iTOO turns specialist expertise into scalable impact.”
