Jessica Twentyman meets… a CIO rewriting the rulebook

“What kind of CIO do I want to be at this company?” That’s the question that David Jack asked himself when he joined Hyperion Insurance Group as CIO in November 2013.

The answers he came up with are admirably detailed and unexpectedly provocative: his 10-point ‘CIO rulebook’ sets out his stand as an agent for change in a notoriously conservative industry when it comes to technology adoption. A good CIO, he says, adapts their “CIO-ness” to the environment in which they find themselves.

But David Jack doesn’t intend to be your average insurance-company CIO and Hyperion isn’t your average insurance company. At this mid-size but fast-growing company, the management team believe that its agility and entrepreneurial smarts stand out in a commercial insurance market dominated by three players: Marsh, Aon and Willis. Its disruptive approach, meanwhile, has won it the backing of equity investment firm General Atlantic Partners, and the loyalty of corporate customers, which in its last fiscal year boosted revenues by 51% to £166.6 million ($275.5m).

With that in mind, Jack’s CIO rulebook draws on his previous experiences, working for online train ticket sales company thetrainline.com, internet betting site BetFair, and software company Citrix. It takes as its inspiration his ambitions for a future where, if not a household name, Hyperion’s becomes at least a boardroom name. And, by his own admission, it aims to provoke debate, even contention, in order to drive this single point home: “I’m here to transform Hyperion, not just to serve it.”

1. Plan on doing procurement wrong

IT procurement is an imprecise art and all the planning in the world won’t change that, according to Jack. “So what I’m going to do is make far more intuitive decisions and say openly that this is what I’m doing. If I consistently get procurement wrong, I’ll get fired. If I get it mostly right, I’ll be a hero. Either way, I’m hoping that Hyperion’s investors and board of directors appreciate that I have the experience to operate in this way.”

2. Data is easy - and Big Data is big easy

“To my mind,” says Jack, “Big Data is a red herring. It’s the business processes that matter.” In other words, if Hyperion is not capturing the right data, then it won’t get the insights it needs. “I’m going to focus on our business processes and make sure we’re capturing meaningful data across different product lines, different markets and different jurisdictions, and get the talent in place needed to exploit it.”

3. No-one who matters cares if it’s cloudy or not

According to Jack, end users at Hyperion don’t care about how he runs his systems: “What they care about is user experience and reliability. A lot of the cloud providers have lost track of that - but I haven’t.”

4. There’s nothing quite as productive as contention

“You need to encounter some resistance in the organisation. Lots of contention, demands and vested interests are good. They keep things moving along,” says Jack.

5. Concentrate on securing what you have, in order to get the freedom to disrupt

“I’ll get the technological and operational foundations right, and then I’ll disrupt the business, taking big steps forwards,” says Jack - but he’ll rely on his team to carry on the work of optimising and extending existing IT assets. “Good IT people will do that naturally, especially if you set their objectives right.”

6. Systems failure is desirable

“Failures find flaws, they drive change and they show you haven’t over-engineered IT. It’s counter-intuitive, because none of us like failure, but trying things, seeing where they go wrong and having teams ready to adapt to what they learn and then move forwards is a much better approach,” says Jack. “It’s an agile development approach to operational IT. Plus, it helps you identify the creators in your IT organisation.”

7. Retailers are boringly brilliant

As Jack points out, there’s not a single multichannel retailer in the UK top ten that doesn’t know exactly how many people visited their website yesterday, who they were and what click-through rates were achieved. “Yet B2B companies still think they’re so much smarter than ‘the grocers’,” he says. “That’s nonsense: we’ve all got a lot to learn from retail.”

8. Don’t waste time on buy-in

“Figure out who gains from a change, and just accept that some [changes] are simply driven top-down and there is no point in seeking consensus - just do it,” Jack advises. Other projects, however, are all about the practitioners and, in these cases, practitioners should be front-and-centre in the decision-making process.

9. Concentrate on the great people

“I’ve fortunately inherited some great people and I’m going to put lots and lots of effort into developing them,” says Jack. “I’m going to spend time identifying the great talent in my business and throw myself into doing what I can to give them the challenge and scope to grow to be superstars.”

10. CIOs are best when they can’t spell

“I say this as a dyslexic,” laughs Jack. “By exploiting the CIO’s cloak of nerdy invisibility, and asking simple questions on company strategy, you can get an awful lot done. The tail can wag the dog.”

If his rulebook ruffles feathers or creates waves that make for choppy waters, David Jack is entirely unapologetic. It’s exactly what he wants. Not only that, he says, it’s what Hyperion’s investors and management want from the company’s first group-wide CIO, too. This is his chance, he says, “to set the operating bounds of the CIO, in a business with huge ambition”, and he’s grabbing it with both hands.