The foyer of Thetrainline.com's offices is slightly surreal - at least for those unaccustomed to seeing sheep in an indoors working environment that is several storeys high in a modern block in Aldgate, London. They're not real sheep, of course, but a mock flock, strategically placed to support the company's latest marketing campaign, suggesting that travellers should think independently and buy their tickets in advance to save on prices. In case you're still in doubt as to the nature of the business, the space is covered in posters replete with laborious puns (‘knitwit', ‘silly ewe' and so on) and there is a kiosk for buying tickets.
I'm here to meet David Jack, the recently arrived CIO of the company that has developed a popular way of finding out route and price option information as well as purchasing tickets for the UK's rail network. Highly likeable, clearly cerebral and possessing plenty of boyish enthusiasm and energy, Jack is something of an unusual occupant of the role as much of his career has been spent on the supply side with a roster of companies that reads like a directory of the client/server computing age, from dBase developer Ashton-Tate, through pioneering Windows database firm Superbase, to SPC of Harvard Graphics slideshow fame, once-mighty LAN software giant Novell and king of server-based computing, Citrix.
Jack supplies me with exhaustive details of his CV, pointing out lessons learned on the way. The stories are variously fascinating, funny, insightful and occasionally painful. The last category is evidenced by the history of Jack's short-lived contracting company where he says he learned that having a legal document in your hands doesn't necessarily guarantee that you'll get paid, and the bitter takeaway here was: "Don't hire your own friends because it's embarrassing when things go wrong and you have to lay them all off."
A more fruitful time in his career came in the late 1990s which saw him working for a Java software company called Digitivity that sold out to Citrix in 1998, a time when thin-client computing was booming and Citrix's stock value multiplied. There, he says, he learned to "talk technology but more importantly represent the customer, learn product management, build a team and talk commercially. I was gathering skills as I went along."
It was at this point that he realised the importance of not underestimating himself. "Sometimes remembering you're smart is important. If you're good at delivery, that adds so much more to your portfolio."
As CTO at business consultancy Zygon, Jack learned another lesson in understanding how to deal with multi-channel retail giants like Halfords, changing prices on 10 million items at a stroke for a sales campaign to take the game to its rivals.
But perhaps his biggest learning experience came at Betfair, the online betting phenomenon where he led a team of developers that grew from 40 to 120 in number, but which "felt a bit like lots of children playing football and following the ball too closely". He studied things like the correlation of revenues compared to uptime and had a split role that enabled him to spend half his time thinking about engineering and half on commercial matters. He describes the business hypergrowth experience as "frantic but fun", with long days interviewing, spinning up multiple projects and running development teams while all the time being surrounded by highly creative and numerate people.
"Every project had a plasma screen attached to document updates on how much was being spent; there were three-month deadlines to determine whether the ROI case was being proven," he says.