Pegasystems CEO Alan Trefler doesn't just use his company’s flagship conference, PegaWorld, to sell technology, but also to feed his competitive instincts.

With a classic American beer in hand, the former world chess champion seamlessly beat 29 opponents at the event earlier this month – only bothering to sit down on the few that required a little extra thinking – before finally tasting defeat at the hands of a Frenchman.

The following day, he emerged in a pair of scandalously short shorts to show off his ping-pong skills. The irony of the name of the hotel these events took place in – Gaylord National Resort – seemed lost on the American attendees, but not on the English journalist whose credit card was blocked upon his bank noticing an uncharacteristic purchase in The Gaylord during Capital Pride weekend in Washington DC.

Despite his impressive chess credentials and longevity at the helm of a leading technology firm, Trefler hasn't changed much since founding the company 31 years ago – he is still tremendously passionate about enterprise software, and his publicists still fight to get him to wear a suit that fits.

Ultimately, Pegasystems is Alan Trefler – insiders say he is involved at every part of the business from top to bottom, and several gigantic posters of his face, advertising his new book, stared down on delegates in a god-like manner throughout the conference. He personally signs off every press release and insists on meeting every member of staff, which now exceeds 2,500.

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But he’s not the only interesting character at Pegasystems. Senior VP Kerim Akgonul rode off the stage on a scooter following his keynote, while James Bond fanatic David Wells, MD for Europe, made a genuine effort to meet and take a selfie with every one of the event’s 3000-plus attendees, a PegaWorld record attendance.

Gimmicks aside, however, it is abundantly clear that these people know technology and understand their customers’ needs. The lack of any kind of product launch or update made a refreshing change to the PR-spiel that normally dominates conferences like this. Instead, the company was happy for reporters to freely form their own opinions through interviews with customers and senior execs. Why? Because they’re confident in their technology and the way they do business.

That technology now revolves around the digitisation of the enterprise. Traditionally a BPM and CRM company, Pegasystems now wants to be positioned as a trusted partner to businesses that want to transform through innovation. Its ‘Build for Change’ solution is a unified platform that enables users to build enterprise applications a lot faster than traditional programming technologies.

At the heart of this digital transformation is what the company calls SMACT, the amalgamation of five of the biggest trends in enterprise IT: social, mobile, analytics, cloud and the Internet of Things.

Pegasystems has invested heavily in this area over the last year, including over a million hours of engineering. It can be notoriously difficult for public companies to convince investors that such investment is necessary but, as Trefler told Information Age, ‘it helps when you own most of the shares’.

Indeed, it also helps when Pegasystems' revenue exceeded $500 million for the first time last year, a factor that saw shares in the organisation jump 122% to a record high – consequently making Trefler, who owns over 52% of the company, a billionaire.

And the investment in SMACT is paying off. The majority of Pegasystems’ customers, Trefler said, already have a ‘material amount’ of mobile and analytics in their enterprise, and he believes 80% to 90% will be ‘SMACT’ed to a major degree’ in 12 months' time.

But it’s not all about technology – the transformation to a digital enterprise also requires a significant culture shift on the people-process side.

'I think one of the hardest parts we find with some of our clients is for the people to internalise that they should not be part of the requirements process, but they should be part of the build process,’ Trefler said.

The best implementations, he said, are those that take a small amount of business people – not trained in IT, but with a ‘techy aptitude’ – and train them for a couple of weeks before embedding them in the project team.

‘It has an enormous cultural change on many constituencies. Firstly, it has a big impact on people because suddenly they’re empowered and enthused.

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‘Secondly, it has a big impact on IT because IT is definitely used to thinking of the business guys as people who need to be kept at arm’s length and are communicated only through requirements documents and business analysts.

‘So the cultural shift is pretty huge on both the business side and IT side, and it also empowers the organisation to do more radical things.’

This ability to fundamentally change the culture of business is central to Pegasystems’ vision of digitisation, and democratisation of how technology happens.

As a company that has survived 31 years in a space that has seen many competitors come and go, CIOs can do far worse than trust the vision of the man in an ill-fitting suit.