While Berkowitz chose to join Microsoft and take over the MSN line, Luong has moved to Zazzle, known for its customized products like USPS postage stamps.

Luong held a central position in Ask.com’s management of search products and other operations within IAC Search and Media. He came to Ask when that company purchased Octopus Software.

Also, Luong once worked for Microsoft, and had a hand in the company’s “Software as a Service” initiatives. Those initiatives have begun to manifest as various Windows Live products.

“I’m excited about the opportunity to bring my expertise to bear for Zazzle’s benefit,” Luong said in a statement.

But why are the top people at Ask jumping ship, at a time when Ask is growing in search share, and has been the beneficiary of a more substantial promotional push by IAC?

Luong’s move looks like the usual change of creative venue, going from a corporate monolithic culture to the more freewheeling challenge of a younger company. Berkowitz’s switch to Microsoft, as the vice president responsible for MSN, proves more curious.

Windows Live has received the bulk of Microsoft’s most public developmental and promotional efforts. MSN appears poised for relegation within the Windows Live brand. Berkowitz leaving Ask to hook on with a division that could be absorbed within the Windows Live apparatus does not seem logical on its surface.

One possible future that could take place, and best take advantage of Berkowitz’s experience, would have him on a path to replace Kevin Johnson, co-President of Microsoft’s Platforms & Services Division and Berkowitz’s boss.

Johnson’s background in sales and marketing doesn’t look like the skillset a technology-driven company like Microsoft needs to steer it into open search engine and advertising warfare with Google and Yahoo. Perhaps Johnson will be moved higher within the company, or has plans to follow Jim Allchin out the door.

Berkowitz probably didn’t take the MSN job just to be a caretaker. It’s more likely he has nowhere to go but up at Microsoft. Maybe he’ll pick up a few things from Zazzle as gifts for Johnson when he does.

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David Utter is a staff writer for WebProNews covering technology and business.