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Comment by dangero | Hacker News Reader

I'll go first on my own question: Microsoft Outlook. While products like Google Apps for your domain have somewhat penetrated, Microsoft Outlook still has a strong corporate foothold while having super clunky software. It's expensive, and it requires infrastructure to use in most cases. Also, a lot of clients still want a native solution which things like Google Apps for domain don't provide.

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Not to be too wet of a noodle (and I'd certainly like Outlook to go away), but replacing Outlook at places where it is currently entrenched will require an absolutely Herculean effort. Not so much because Outlook the mail client or mail server is so great, but because of everything it ties into: calendaring, sharepoint, lync, custom LOB apps programmed to the Outlook APIs, etc.

When trying to talk people away from Outlook that entire secondary ecosystem has always been a much bigger roadblock than the lack of a native client or even the idea of storing corporate data in "the cloud" in my experience.

"When trying to talk people away from Outlook that entire secondary ecosystem has always been a much bigger roadblock than the lack of a native client or even the idea of storing corporate data in "the cloud" in my experience."

Wow, that is surprising to me. I wonder if there's an opportunity to provide a replacement for people who are just getting to the point of needing something like Outlook, but aren't entrenched yet.

To be perfectly clear, when I mention trying to talk people away from Outlook and them being resistant, I'm talking about IT people and management, not the common workers, who mostly all hate Outlook.

Agreed. Those who would love a replacement really have very little say in the matter. That's what anyone selling enterprise-y software has to deal with. You're usually selling to the people who won't be using it. This changes the conversation quite a bit regarding the benefits you emphasize about your offering. For instance, you may have to show a higher-up that they can save time/money by using your software rather than telling them they're employees will enjoy using it more because that high-up won't rightfully care.

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