A recent study found high-performing organisations are three times more likely to have leaders who personally own and model adoption of new capabilities. Not delegating transformation. Driving it.
Three times. Not marginally more likely. Three times.
That finding is about AI. But the principle isn’t.
Every significant technology shift separates the same two populations. Leaders who understood what was changing and got their hands dirty — and leaders who approved a budget, hired a consultancy, and waited for a board update. Cloud. SaaS. Digital. Data. The trend changes. The pattern doesn’t.
I wrote this week about the 5% producing real returns from AI whilst 95% saw nothing. The 3x organisations and the 5% are the same people. One measures leadership behaviour. The other measures outcome. That’s not coincidence. It’s causation — during cloud, during digital, during every shift that separated leaders from spectators.
The discipline is the same every time. Someone in the room who understands architecture well enough to make design decisions, not just investment decisions. Who knows the difference between decorating a workflow and redesigning a system. Who treats transformation as practice, not procurement.
Most organisations run the same playbook regardless of the trend. Buy the platform. Hire the team. Announce the partnership. Leadership’s contribution is approval and budget — the two things requiring the least understanding of what’s actually being built.
I’ve lived this across multiple cycles.
I took an enterprise underwriting platform from unrated to Everest Group Leader in twelve months. Not by buying better technology. By changing the product thinking. Design-in, not bolt-on. That set in motion an acquisition chain that culminated in a $2.5 billion transaction.
Then I applied the same discipline to AI directly. Two enterprise-grade systems conceived, architected, and built from first principles. Both in production. 151 patent claims across 15 inventions. Not delegated. Built — because the practice demands it.
That’s what the 3x looks like from the inside. That’s what the 5% actually did. Not a title on an org chart. Scar tissue from building things that work — regardless of which trend made it urgent.
$285 billion was wiped off enterprise software valuations because capital looked behind the “AI-powered” press releases and found bolt-on where architecture should have been. Replace “AI-powered” with “cloud-ready” and you’re describing 2015. “Digitally transformed” and you’re describing 2019. The press release changes. The leadership gap doesn’t.
Every software company is asking whether they have the right product leadership for this shift. They should ask harder: do they have leadership that will still be right for the next one?
Three times. Five percent. $285 billion. The answer isn’t another strategy deck. It’s leaders who build.
#ProductLeadership #CPO #EnterpriseTransformation #AI #InsurTech #Leadership
First Comment
The cloud migration separated the same populations. The companies that thrived weren’t the ones who moved fastest — they were the ones whose leaders understood what cloud actually changed about their operating model. Everyone else lifted and shifted, then spent a decade managing hybrid complexity nobody planned for.
Digital transformation. Same pattern. The companies that hired a Chief Digital Officer and gave them a budget produced slideware. The companies whose existing leaders understood digitisation as a design problem — not a technology problem — built competitive advantages that still compound today.
AI is the latest iteration. It won’t be the last.
The 5% producing real returns aren’t using different tools. They have different leadership — people who treat every shift as an architectural question, not a procurement one.
151 patent claims didn’t come from delegating. Two working systems didn’t come from approving budgets. They came from the same discipline that took a platform from unrated to Everest Group Leader. The practice transfers because it was never about the trend. It was about the thinking.
That’s the thread connecting every cycle. Not the technology. The leadership discipline that makes it land.