Kayak has had a rough road in preparing for its eventual IPO. The company initially filed back in November of 2010, however, at the time the Google/ITA deal stood in the way. It was reported that ITA powered a whopping 42% of Kayak’s overall search queries – not great when your company’s bread and butter is provided by a third party, never mind, a third party that is now owned by Google.

Today, Kayak took another blow as its former CFO has joined another travel startup. According to a piece on TechCrunch, Israeli startup, Superfly, has poached Kayak’s first CFO, Willard (Bill) Smith, – the CFO that Kayak had hired to bring them public last year. According to Smith’s LinkedIn profile, it looks like he left Kayak officially in March, although it was not widely reported.

According to travel tech site tnooz, the move clearly looks like a shot at Kayak’s search capabilities.

Smith, who declines to talk about his Kayak departure, says a new generation of travel search companies will be using Big Data to provide suppliers segmented profile data on customers so they can truly deliver targeted, personalized offers to “the serious and elite traveler” while the established search companies are being left behind.

Even with this setback, CNBC is reporting that Kayak’s IPO roadshow could still begin as early as next week.

We will update you on the Kayak IPO as we continue to learn more.