[CyanLite2]

Cloud migration specialist here. Biggest thing I see is the culture. Large shops will be 80% infrastructure and 20% developers. Infrastructure folks almost always will be fired after a successful cloud migration. Middle Managers want to keep a large staff and budget to justify themselves. CIOs often come up through the infrastructure career path and don’t trust firewalls if they aren’t made by Cisco or SANs that they can’t touch. (“So you’re telling me that their homemade switches are better than Cisco?”) I even had a CIO of a Fortune 1000 ask me what brand of fiber optic cables are in use in AWS. Overall it’s mostly shops putting their head in the sand hoping they can go another 2-3 Years in their cushy “Director of Infrastructure” jobs.

Most of my success comes not from selling to IT but the CFO or Board. Once they realize they can eliminate a dozen or so SAN Storage or networking engineers then the cloud doesn’t seem so expensive after all.

[toomuchtodo]

Conversely, I’ve seen executives fired out the door when the public cloud costs were much higher than on prem costs, and the savings didn’t materialize (either the execs had drank the cloud koolaid, or the business changed direction).

Edit: There is no silver bullet. Model your needs, make sure your model is accurate. You might still be wrong if your model doesn’t match reality due to unanticipated deviations.