The foyer of'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."

Smart thinking

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.

Trading up

There was the sense of a startup and a neverending appetite for scaling up transactions per second and cutting out latency, Jack says. Jack joined Betfair's Advanced Technology Team and then the venture capital wing, Betfair New Ventures, holding £170m in assets. But all the time Betfair was looking at the ability to use its system - effectively a trading platform - for the financial markets rather than just concentrating on betting markets. Jack led the spin-off Tradefair operation with the ability to handle up to 100,000 transactions per second in memory on an open-source MySQL database, and he admits that converting the Betfair technology for a financial trading platform was "a real game-changing challenge".

Another key challenge was to find a permanent leader. "I recruited my own boss," he says, after having interviewed many well-known captains of industry. That act was the prelude to Jack's leaving Betfair and he says that he was not tempted to make the job his own sinecure. "If you focus on your own career you not only limit where you can take the business, everything gets limited. I felt I'd done my time and my financial investment was safe."

Jack says he was approached about taking CEO roles but feels there is plenty of time, predicting that "There will be a demand for multi-skilled leaders at companies that are fundamentally technology businesses. It's easier to retrofit business skills than technology skills."

So what attracted him to a rather different job at Thetrainline?

"It felt very similar to Betfair and it's at that same moment of transition," he says. "It's cracked a difficult problem with a significant percentage of online advanced ticket sales being made through Trainline systems, but it can do so much better. It's at an inflection point."

He says his knowledge of fast-moving businesses will stand him in good stead at Thetrainline. "I would be a terrible business-as-usual CIO - I need the challenge of making things significantly more predictable, repeatable and cost-effective to help our customers. I love inventing new solutions," he says.

He has a clear idea of the opportunities- at the outfit, which is the biggest independent retailer of UK train tickets and provides web sites and contact centre capabilities for 14 of the 18 UK train operators.

"It's about good customer service ... the basic proposition is value - paying £30 rather than £130 - and convenience; picking up tickets at machines, on your phone, print and home and smartcard," he says. "I loved what it stood for and I get to work with some fabulous people."

However, he acknowledges the challenges that lie ahead, including managing a mixed portfolio of retained talent, outsourced and offshored staff. Thetrainline has 50 staff in the UK as well as 200 in India and also uses Capgemini for hosting. Jack says the environment is highly regulated, with lots of back-to-back SLAs covering complex agreements. "It's quite a tanker to move to get all that in the right direction," he says.

His current plan is to create a director of development role and spread his bets so there is a standing capacity bolstered by outsourcing partners and a burst-mode capacity on tap for when it is needed.

The customer-facing site as it stands is "good, and we are enhancing it all the time as we develop the underlying platform", according to Jack. He adds that what is not seen by the visitor is the sheer effort in managing how all the disparate "quirks" from all the various UK rail operators work and all of the back-office effort in managing the sites and contact centres of the train operators.

Like many a CIO, Jack has a recurring dream of stopping the world to get off for a while before starting over but knows that planned downtime is as distant a memory as the days of steam or the train network before the infamous ‘Beeching Axe'. "If you could just stop the business, change would be easy," he laments. "However, we have a huge number of channels and a growing customer base and increasingly demanding partners who we want to delight."

Full steam ahead

But the line ahead has plenty of options for scenic diversions, he says, with "mobitex" tickets sent to mobile phones, smartcards, the ability for customers to print their own tickets and more business travel package deals all being mulled over to make letting the train take the strain a more attractive proposition than ever.

Jack wants Thetrainline to be an innovator. The company already boasts a nice set of capabilities such as an email alert system for when advance tickets become available, a carbon footprint saving calculator, a timetable gadget for iGoogle and a best fare finder. It's also refreshing to see a site that has a page dedicated to telling visitors about areas of product innovation.

As a daily commuter on the Reading-London line, Jack knows all about modern rail travel and that it's not always a case of Leon Redbone's "kick off your shoes, you're doing fine", but he is playing his part in unclogging the arteries of UK travel. It's in all of our interests to wish him a safe and useful journey.

David Jack: CV

1988-1992: Ashton-Tate, test manager

1992-1994: SPC, SQA manager

1994-1995: Superbase, director of engineering

1995-1997: Novell, consultant

1997-2001: Digitivity/APM, director of operations, director of engineering, director of development
(sold to Citrix)

2001-2004: Zygon, CTO

2004-2008: Betfair and Tradefair, director of engineering, director of advanced technology, director of new ventures, Tradefair managing director

2009:, CIO


Thetrainline is the UK's biggest independent online retailer of train tickets, selling across all train companies on all national routes. In total, it can access over 293 million fare and journey combinations and claims to have sold to 3.3 million travellers since 1999, handling over 14 million transactions and holding details of over 8.4 million registered users.

It also provides websites and contact centres to 14 of the 18 franchised train operators. Thetrainline also provides business travel services, serving what it says is a £1.3bn annual market.