Last week, a Ferrari-driving geek became chief executive of a 244-year-old Scottish newspaper company.

It’s safe to say that Johnston Press has never before witnessed the likes of Ashley Highfield.

The former BBC and Microsoft executive is a rank outsider, a immigrant from the digital realm. He has never sold classified advertising by the column centimetre. Neither is he recognised as an accomplished cost-cutter (like his predecessor). Nor is he a debt-addled deal-maker (like his predecessor’s predecessor).

In fact, Ashley Highfield is about as far away from business-as-usual as it’s possible for Johnston Press to get.

Perhaps this explains why Highfield let it be known on Twitter that he had actually read all 280 of the company’s local newspapers before taking over as chief executive.

If you don’t share the boardroom’s DNA, it makes sense to appeal to the masses. In this respect, Highfield’s tweet strikes a positive note in a company whose boorish commercial myopia has become legendary.

But Highfield’s arrival at Johnston Press also underlines a broader shift that’s becoming increasingly obvious.

We’re now starting to witness a long overdue exit for chief executives of the Baby Boom generation. Many of these bosses couldn’t, or wouldn’t, deal with digital transition — largely because they’d spent their formative years basking in the afterglow of analogue media’s defining triumphs in the 1980s and 1990s.

We’re also witnessing the rise of a new generation of managers who got their big breaks in the online world from the late 1990s onward. What’s different about these bosses is their hard-won understanding of digital platforms, online sales and the power of data. They might not be digital natives. But as digital immigrants go, they’ve adapted extraordinarily well to changed circumstances.

Highfield got his start as a programmer, and then became a management consultant before spending eight increasingly controversial years at the BBC. After the anti-climax of leading Project Kangaroo into the buffers of a competition inquiry, he took on Microsoft’s sizeable UK publishing business, overseeing both search, display and mobile. During the noughties, Microsoft threw everything at the challenge of hauling its online display properties toward break-even. Highfield will have learned plenty during his three years there.

In some (if not all) ways, his arrival at Johnston Press mirrors what has happened at EMAP, where 54-year-old David Gilbertson has been replaced as chief executive by 41-year-old Duncan Painter.

During Gilbertson’s reign, EMAP added value to its content, but lacked the resources to make transformative acquisitions. Painter’s track record suggests that he may discover a more radical in-house recipe.

In media industry terms, Painter’s CV is unconventional, to say the least. After starting his career at the heavyweight end of the IT industry with Hitachi Data Systems, Painter ended up as chief executive of the data analysis company Clarity Blue. In 2006, it was acquired by Experian. Four years later, Experian sold a controlling share in the business — and eventually, the rest of its shares — to BSkyB.

The company may have been renamed Sky IQ, but Painter was still there, organising what the company’s web site calls a “a team of brilliant minds” equipped with “maturity, experience and technical excellence”. The pride isn’t entirely misplaced: Sky is rightly renowned for its data-driven marketing prowess, and Painter played a pivotal role behind-the-scenes role in its development.

The situation in which Reed Business Information found itself in 2010 wasn’t quite so dire as that which dogged EMAP and Johnston Press, but it was threatening.

Part of the solution was to replace RBI’s outgoing chief executive Keith Jones (who started his career as a graduate trainee at IPC in 1977) with someone who had proved himself in the digital arena. This turned out to be Mark Kelsey, formerly COO at RBI in the UK, who had been the managing director of totaljobs.co.uk at its launch, and who — according to RBI itself — led the company’s “transformation to an online publisher” while working for Jones.

The more you look, the more evidence emerges of a rising generation of new stars. At Guardian Media Group, for example, there’s 43-year-old chief Andrew Miller, closely associated with the successful digital transformation of Trader Media, and now in the driving seat at a national newspaper group.

Elsewhere, when the private equity firm Exponent acquired some of the nation’s biggest newsstand titles from BBC Magazines this summer and injected them into Immediate Media, the emergence of Tom Bureau as the company’s chief executive looked like another step forward.

Bureau is every bit the consumer publisher. But his roots are 100 percent digital. Bureau sold his first online ad business to Felix Dennis in the mid-1990s. Subsequently he was part of the team that raised £25 million to “experience the full dot.com rollercoaster” with the launch of Silicon.com, a technology site. Then, as the UK managing director of CNET Networks, Bureau learned plenty about the harsh struggle to generate online profits.

Where the geeks aren’t totally in control, they’re in a position to exert significant influence. It’s not unusual to see pairings of old and new. At Immediate, for example, Bureau runs the show, but he also reports to a strictly Establishment chairman, in the shape of Stephen Alexander, the former chairman of EMI.

At TSL Ltd, the private equity-owned publisher of the Times Educational Supplement, there’s another, similar-looking arrangement. Louise Rodgers, formerly a publisher at UBM, is CEO, but Bill Donoghue, formerly the CEO of a quoted UK tech vendor, is COO.

At the very least, appointments like these signal a willingness to look beyond the usual suspects. And there are reasons for investors to feel confident. Importing tech-literate talent from outside has worked well for UBM. The company’s chief executive David Levin (headhunted at the age of 42 in 2005 from the mobile OS company Symbian) has arguably managed transformation better than many of his peers. Today, he looks like a pioneer.

The changing nature of media boardrooms

Let’s not get too carried away. Some of the new breed will remake their companies, transforming middle management in their own image. Some won’t. A few will fall foul of the same old imperatives, prioritising dying revenue streams at the request of shareholders. Not all of today’s media businesses will make it to the digital future.

What really matters is that Big Media is changing — from the top down. Hundreds, if not thousands, of frustrated digital types working inside Big Media will breathe a cautious sigh of relief. Finally, the Baby Boomers are moving on, taking with them those memories of analogue triumph that all too often curdled into complacency.