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As vendors build out aggressive cloud strategies, two behemoths are going toe-to-toe for marketshare in the office productivity applications space.

Although Google  beat Microsoft to the punch in the cloud computing world with the launch of its successful Google Docs portfolio of cloud applications, Microsoft has been playing catch-up lately, announcing a stronger commitment to its cloud strategy in March.

Even as Google continues to tempt Microsoft Office and Exchange customers to Google Docs and Gmail for their business needs, Microsoft builds on its both its on-premise, hosted and cloud software offerings. According to David Hoff, vice president of technology at Google Apps partner Cloud Sherpas. Cloud Sherpas has successfully migrated thousands of customers from Exchange to Gmail environments. At the same time, Jamin Spitzer, director of platform strategy at Microsoft, said that many customers that previously switched to Google Apps have made the switch back to Microsoft offerings as its cloud applications have become available.

A choice for either vendor comes with its own advantages. On one hand, Microsoft offers a cloud platform that is already familiar to business users working with Microsoft Office, Exchange and Outlook. On the other, Google provides a strong cloud track record and an already very active and mature applications development platform. Both sides claim better costs and ROI for the customer.

“From a customer’s perspective, so many of our customers are looking at Google Apps because they’re still on Exchange 2003,” Hoff said. “They just don’t have the manpower and resources to continually care and feed the existing product with all the time and effort it takes to do the updates.”

Hoff said that many Cloud Sherpas customers have chosen Google over Microsoft because they’ve seen a lack of multi-tenant environment capabilities in hosted and cloud-based Exchange. Exchange Online customers have faced challenges of all being stuffed in the same Active Directory, whereas Gmail was built from the ground up to be highly scalable and multi-tenant, he said. He noted that they’re fundamentally different architectures.

Spitzer said the initial driver behind Google Apps three to five years ago was about consuming a pay-as-you-go email environment, which is something Microsoft didn’t have at that time. Now it does, he said. Just as Hoff said Cloud Sherpas has seen thousands of businesses migrate away from Exchange, Spitzer said that he’s found a lot of companies that originally migrated to Google now returning to the Microsoft fold.

“We’ve taken a very deliberate and thoughtful approach to what we’re doing,” Spitzer said.

One of the major difficulties in migrating away from Microsoft productivity and email software and infrastructure is in data migration. According to Hoff, data migration is dependent on decisions made by the customer, and businesses with very strict cultures around message management will likely find the transition difficult.