However, fewer than 10 people left the company's IT department because of the change and many workers were happy to update their skills and try new jobs.
The company also stopped referring to the IT department as the, well, IT department. Now, they're not IT workers. They are tech workers. That change is meant to erase the wall between tech and business, bringing all those employees on to one page with the common goal of focusing on the business and not simply keeping email and databases running.
The renaming, retraining and the new jobs that workers had to assume were all part of a big culture shift for the tech department.
Another obstacle was figuring out what to do with the company's legacy systems.
While the Weather Company has 80% of its services and apps running on the cloud, it's that last 20% that will be the toughest to deal with.
"There are still legacy systems you have that are hard to re-architect or are fundamentally built to not be compliant with what the cloud needs," Williams said. "I want to get off some of these legacy systems or upgrade these legacy systems, but they have architectures built 15 years ago for an [on-premises] data centers, and they're not built to move to the cloud."
He added that if the old app is not a core need with a solid ROI, it's difficult to get the company behind the expense and effort of either rebuilding the app or tweaking it enough to work on the cloud.
"The harder, more complex and ingrained parts of your business are still hard to move to the cloud," Williams said. "I think the enterprise space still has a hard time with this.
IDC's Mahowald agreed that the legacy systems are the hardest to deal with.
"I'd say all migrations face this," Mahowald said. "It's those custom applications you built over time or a lot of SAP or Oracle ERP… It's really unwieldy to re-platform it. And if they do that, the performance might not be the same [on the cloud] and their users won't be happy."
At this point in the migration, it may come down to old apps that only a few people are using. Is it worth it to re-engineer them to work on the cloud?
"Of the 200 apps running in the data center, maybe 70 of them might not have been used in the last two months," Mahowald said. "Then maybe you shut them down and see who complains. If you get a phone call to the help desk, then you have a conversation with the business unit using it. Is it worth the money it would take to move it to the cloud? If it is, then they are paying for it."
Sign up for CIO Asia eNewsletters.