What you need from your e-mail system (Test-driving Google Apps Premier)

Before I became a marketing wonk I was a knowledgeable technologist, which is probably why I've never once enjoyed any e-mail system that I have used or implemented. Over the last 15 years, I have tried pretty much everything, from Pine to Zimbra, to MS Exchange to Lotus Notes and several different IMAP and POP options. Every time it's the same thing--the system works within reason but is never great. And there is always something that bites you in the rear.

I first started outsourcing e-mail to managed providers in 2003 when I worked for a CEO who demanded MS Exchange and we only had Linux boxes. It was never great and it was too expensive to boot. But the offerings have gotten much better and at this point I can't see a small- or medium-sized business running its own mail server. It's just not necessary.

Here are my fundamental hopes for e-mail:

• Reliable delivery of mail (dare to dream)
• Reliable delivery of mail on mobile devices (Blackberry and iPhone)
• Shared calendaring with administrator abilities (i.e. admin access)
• Backup and recovery
• Reliable SPAM prevention
• Sync across multiple computers and devices

There are only a few systems that I know of that do this effectively (MS Exchange, Zimbra, Gmail) and the first two don't do all of the above without third-party apps--specifically the mobile piece.

At my company we've changed mail systems no fewer than five times in less than two years. Lest you think we're just crazed about IT let me outline the story:

1. Webhost + E-mail (IMAP) at Dreamhost
--We were only about 15 people at this point and it was manageable

2. Webhost + E-mail (IMAP) at Rackspace
--We doubled in size and moved to the managed mail servers. Unfortunately there was no calendaring

3. E-mail move to Gmail (Mission aborted due to lack of IMAP)
--We learned the hard way that Gmail Premier wasn't ready for prime time one sad day when we realized that you couldn't POP or get your mail via IMAP

4. E-mail back to Rackspace

5. E-mail move to Zimbra at Contegix
--We moved to Zimbra about nine months ago and we've had some mixed results. Zimbra running on RHEL have both had 100 percent uptime. However, as of the last month we've run into multiple instances of messages getting lost as well as entire e-mail boxes getting wiped. This might be due to the new release but no one can figure it out (though the Zimbra team has provided heroic efforts)

6. Google Apps Premier (Round 2)
--Besides hitting all of my list above, the SF.com integration is the key piece for us.

As of this past Friday we started a beta with a few users maintaining both the Zimbra and Gmail. So far, the Gmail is good. In fact, its Gmail, just with our domain. The main trick is that it's integrated with SF.com and so we now have records of sent mail tracked which enables collaboration on accounts. More on this in a separate post.