Canonical, the company behind the Ubuntu Linux distribution, is undergoing significant changes in management. Founder Mark Shuttleworth has stepped down from his role as the CEO so that he can increase his involvement in the software design and development process. Jane Silber, who has long served as the company's chief operating officer, will be taking over as CEO. To fill the COO vacancy left by Silber's ascension, Canonical has recruited Matt Asay, the former vice president of business development at open source content management software company Alfresco.

Asay seems like a good choice for Canonical in some key ways. He accumulated knowledge of the enterprise Linux ecosystem during his time at Novell and he brings a wealth of real-world expertise in monetizing open source software from his experiences at Alfresco. Despite these strong points in his favor, there are also some reasons why he is a surprising choice for Canonical. In particular, Asay has always been an extremely vocal skeptic of Linux's viability on the desktop. During the month that he has been working for Canonical, his views on the matter seem to have evolved considerably.

Asay's opinions about Linux and open source software are well known because he writes a blog at CNET. He has consistently been supportive of Ubuntu's vision and identified it in 2007 as Linux's best chance for desktop success. Despite his enthusiasm about Ubuntu's commitment to usability, he doubted its potential to make a real impact.

"I will admit to being a Linux desktop nonbeliever. It feels a bit like yesterday's battle fought with the wrong weapons: geekiness rather than ease of use. There's a chance—still a slim one, but a chance nonetheless—that Ubuntu will change that," he wrote in 2007.

In a more strongly-worded piece a year later, he declared that Linux on the desktop was a lost cause. He thought that Ubuntu might have a chance on netbooks, but argued that the real opportunities for open source are in the cloud.

"I am an ardent open-source advocate, but I admit to perplexity as to why the Linux community so desperately wants its year on local systems. Who cares?" he wrote in 2008. "It's time to move on. Next year won't be the year of the Linux desktop anymore than 2010 will be. Why? Because we don't need a Linux desktop. We need to accelerate efforts toward the cloud, which is open source's game to lose."

A short time after he joined Canonical, he had a revelation. In a complete reversal of his previous position, he boldly declared that the year of the Linux desktop isn't just imminent, but has already arrived. He came to this new conclusion about desktop Linux after spending a few days running Ubuntu. Yes, all it took to convince Asay of Ubuntu's viability was actual hands-on experience with the software. A dedicated Mac user since 2002, he apparently never bothered to seriously test a Linux desktop distro until after he joined Canonical.

"In my new role at Canonical, I've switched to using Ubuntu on my Lenovo ThinkPad X200s and have found Linux comfortably routine. Like my Mac, it just works—no drama with day-to-day Internet activities like e-mail, Web browsing, IM, Twitter. It lets me do all the things I used to do, and still largely with the same applications I used on my Mac," he wrote recently. "The desktop battle is largely over for Linux. There's really no reason not to use it, other than habit."

In an interview with the Linux Foundation that was published yesterday, he elaborated on some of his new opinions. Pointing to the strength of Linux in the mobile and embedded markets and Ubuntu's improvements to Linux usability, Asay said in the interview that Linux has an opportunity to surpass rival Apple.

"Apple leads in some areas, but I think if we were to tally up its total record against Linux, and not simply in the narrow categories it chooses to target, we'd see the balance weigh heavily in Linux' favor," he said.

The mixed messages and conveniently sudden transformation into a true believer could raise some serious questions about his credibility. I happen to think that his reversal of opinion is genuine (he wouldn't have joined Canonical if he thought it was doomed), but he seems to be overcompensating a bit in his newfound enthusiasm for desktop Linux. It could be problematic because he risks making his endorsement of the platform sound insincere.

It's going to take him a while to earn the trust of the Ubuntu community. Practically all of Canonical's previous and ongoing efforts to monetize the distro have been met with a certain degree of concern by some users and contributors. The volunteers who have helped to make Ubuntu a success are wary of being exploited and are slow to accept Canonical's monetization strategies.

As the COO, Asay will play an important role in making Ubuntu become commercially successful. If the community is distrustful of Asay's motivations and agenda, it could exacerbate the friction that arises when Canonical seeks new revenue streams to make Ubuntu sustainable. He needs to prove to the Ubuntu community that he truly cares about Linux on the desktop and is not just out to make a quick buck. His previously dismissive attitude about the relevance of desktop Linux is obviously not particularly conducive to that. It's not an insurmountable obstacle, however.

Although Asay's views about the Linux desktop have a clear continuity problem, it's important to acknowledge that his position about open source business opportunities has largely been consistent. He has always been a strong proponent of seeking success in the cloud. This is a strategy that Canonical is already starting to embrace: over the past year, we have seen the company place an increasingly strong emphasis on the cloud in its commercial offerings. The Ubuntu One service is emblematic of that shift.

He doesn't know much about the Linux desktop, but Asay is well-equipped to help guide Canonical's cloud strategy and turn it into a successful business that will sustain the company as it pursues its desktop ambitions.

Update: Matt Asay has posted a response in the discussion thread.