"Train travel is a great product. If we encourage people to take journeys by rail that they would not have taken that is wonderful. I'm passionate about rail. I feel frustrated that people don't understand the value of the proposition. But the modal shift from air to rail is very real. If we can get people out of cars we have done our jobs. We are an extremely green enterprise," he enthuses.
CIO met Jack at the new HQ for Thetrainline.com that is suitably close to a rail line at Farringdon, London. The office has more in common with the Google European HQ across town than the perceived fustiness of rail enthusiasm. Bright colours, big screens of data, break out areas and artistic images remind one and all that a rail renaissance is speeding through Britain.
"One of the joys of being CIO of Thetrainline is that I get to surprise people about how successful we are. We are the top UK travel website after easyJet," he says of the airline that topped the 2012 CIO 100. Thetrainline.com is a top 20 UK visited website according to traffic watchers Hitwise he says.
"As a technologist that is great and it is nice to be part of a household name," Jack says. "The level of growth at the company is double digit year-on-year."
"As a nerd the fact that we run in three different vertical markets is hugely challenging. It is a hard thing providing a technology platform for train operating companies (TOC) and then again to the travel management companies," he says.
Thetrainline.com operates as an independent retailer; an e-commerce provider through its retail technology to the train operating companies and as a business-to-business supplier to travel management companies and direct to business clients through a direct to corporate offering.
"It is a who's who of the FTSE 250 that do business with us," Jack says. "All of it comes from the same servers. We could have occupied the white label space in one of three ways. We could have stamped our name on it; secondly we could have built a product for every train operating company that would have had a high degree of adaption for each customer but would have been unsustainable for us; thirdly we can and have built a proprietary portal product for the TOCs." The latter is the strategic decision that was booked in.
"We offer hundreds of parameters, but when a customer looks at First Great Western, Virgin or South West Trains they cannot tell they come from the same operator," he says. "For us it is a very sustainable model."
As the platform is enhanced by Jack's team, functionality can be shared across both the traineline.com site and the other sites and API customers that the business supports. The train operating companies, which are operating a government granted franchise benefit from partnering with Thetrainline.com as they don't have to invest capital in an e-commerce ticketing platform for their websites.
"It is a regulated industry that sometimes feels nearer to financial services than retail," Jack says of the complexity of operating across the three business verticals of Thetrainline.com. "We provide retailing, fulfillment, payment, and all the associated support systems that you would expect from a full service business."
A further advantage to the rail operators is that when the pressure is on and rail demand peaks, everyone operating the national rail infrastructure in the UK is under the same level of pressure. This was put to the test back in 2010 when Icelandic volcano Eyjafjallajökull erupted and demonstrated the weakness in the global airline trade.
"When the volcano went off, the load on our systems went up between 20 and 40 per cent and we survived and delivered a service, as did all of our customers," he says.
In the last year CIOs travelling cannot have escaped an increase in advertising by alternative rail ticketing online services. So is there increased pressure on Jack and the senior management team?
"The portion of the retail market hasn't changed, but the other players in the market have changed. An interesting side-affect is that every retailer of train travel helps us. Other players are helping get the message across that you can buy your tickets online and that is not a bad thing."
"We have one view of the customer, one service layer for all three vertical markets. We have invested heavily in our software and hardware platforms, but we are very crareful to get the most we possibly can for our money. In the last three years we have moved to an entirely new platform," he says of the journey Thetrainline.com has been on since the last .
"On top of supporting a growing business, in the first year we focused on upgraded the software platform and in the second year virtualised everything, all our development, test and productions environments and then in the third year we completed PCI accreditation as a Tier 1 retailer at the most stringent level. To achieve this over a full year we run a project to ensure all the customer care data is secure. That has been tough, but it has driven structural levels of security.
"We have implemented full token authentication so all the credit card data is placed to a token," he says. PCI compliance is the barrier to Thetrainline.com moving wholesale to cloud computing as Jack says there are legitimate security concerns, but he has no "religion" on public or private cloud if cloud adoption does join his strategy.
The software upgrade in year one was to standardise the backend architecture of Thetrainline.com onto a shared SOA and at the time leaving his Oracle systems largely untouched. When CIO UK met with Jack he had just completed a deal with Oracle to implement its Exadata system as part of a key information systems programme for this year.
"The virtualisation program was important to make the cost of provisioning our service as cheap as possible, Exadata provides a great platform to support our growth at reasonable cost," he says.
"We have strong relationships with IBM, they really treat us like a long term customer, they are really helpful and they don't feel like a big firm to us to deal with.
With so much transformation on the tracks within his department, it is no surprise that Jack is using Agile project methodology.
"We have running programs like CRM that are outside of the technology team, but with technology team help," he says of the good alignment that exists within the organisation.
"We moved from being largely outsourced to a more even split between outsource and insource during these three years. I wanted to get a grip on our delivery and operation levers," he says of the increased levels of development and IT operations that are now operated in-house.
"We have a wonderful relationship with our key suppliers, so it wasn't a case of being unhappy. I feel strongly accountable so I had to have direct control. Where we are outsourced we now manage resources directly so that have every lever available to us. This means we have moved from paying a pointless risk premium based on SLA to having a collaborative, adult relationship with our third party providers.
"One of the biggest challenges we had was trying to convince our suppliers that I was not insane for wanting to take all the risk," he jokes.
Capgemini remains a major provider to Thetrainline.com, the firm being the original builder of the first Thetrainline.com website to depart onto the internet.
Jack has a development site in India as well as UK operation and in both ensures that support and development teams sit together. Jack's other major outsource supplier Thoughtworks shares a floor with Capgemini in India to prevent conflicts and Jack ensures they see themselves as Thetrainline.com India.
"Uniquely for an Indian based development team they are very challenging to the way we think. They challenge the way I think in the way I expect my employees to do.
"Technology is in the heart of supporting this business and we have a large technology team. We have over 200 people split roughly 50/50 between the UK and India. We invest in an ambitious programme of product and system innovation and the executive team meet weekly to discuss, review and approve the direction we take."
Jack sits on the board of directors and reports directly to the CEO.
"I have delighted in the support from the board members. They have taken the time to learn why technology is important to this business and they have been supportive of my doing big challenging things," he says.
"I rarely have to explain technology to this business, the challenge is that they are incredibly demanding and you can't suck through your teeth and say it's 'demanding', that doesn't cut it."
Jack splits the IT operation into three distinct teams; IS, Development and Governance. IS operates the systems, datacentre, development, business analysis, quality assurance and testing. Governance is responsible for portfolio management and looking at what the organisation will do and how with technology. The governance team also deals with the TOC clients.
"Mobile for us is really exciting. Every CIO says it's important, we demonstrate that it's important as so many people use it all the time," he says of the two million mobile users Jack already has and he expects Windows 8 to increase the uptake.
"I sit on the train to work and I see printed confirmation slips, the App and you can see that people see the value in what we do. On our mobile offering travel is just three clicks and that is transformational if people do that rather than jump in their car. We are beginning to transform the customer experience," he says.
Transformation of travel experience looks set to be a continuing theme for Jack, Thetrainline and TOCs over the coming years. For the TOCs there is the need to extract value from legacy ticketing infrastructure, while consumers and the government desire a nationwide equivalent to the London Oyster smartcard used by Transport for London operates. Mobile phone based solutions may well be the answer everyone seeks.
"It's fair to say they see it as an opportunity, but there are challenges as they have concerns about parallel technology, but they are deploying mobile at a rate they can consume. I expect certain routes will see its deployment more rapidly than others. We can only encourage and support the journey.
"The technology nirvana is near field communications (NFC) as consumers will be able to walk through a gate as the ticket has been delivered onto their mobile device.
"Rail travel is still growing, £20 billion is being invested in increasing capacity," he says. While capacity at Thetrainline.com continues as the organisations departs into new relationships with Google and Skyscanners, making its service the leading online platform.