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I run a small but very successful startup, that has been around for 13 months now. We are a 10 person team, but are rely on an aging Exchange 2003 server for our email, calendar, and contact support.

Yikes.

The reason - our initial seed funding was by a private equity firm, that has a diverse portfolio, but unfortunately has been slow to upgrading their infrastructure due to the economy (they were heavy real estate investors, trying to make a jump into different industries).

As an affiliated/child company, we were happy to get our email set up for us without extra cost or effort, but with such an aging system, its really starting to become a problem. If you needed further confirmation, Exchange 2003 does not work well with Mac OS Mountain Lion... At All.

So now that we're growing at a faster rate, and this email/calendar problem is starting to become a problem for the business. Luckily, its my job to solve it.

What are the recommended 'best practices' to get enterprise-grade email/contact/calendar support for a 10-250 person company? At the current rate, we think we may need to support that many users in the coming 1-2 years, so I'd like to develop a program that is going to work for us until we can afford to drop $50,000- $100,000 on our own Exchange 2016 server.

Something I've learned in my life (that has kept me away from Google, in particular) is that it is of utmost importance to own and control my information. I do not want anyone searching or using my email content for 'Big Data' initiatives, and I absolutely want the ability to delete, export, and update what I want, when I want, where I want. Obviously obeying any/all laws - I do not want that to sidetrack the discussion, please.

So I figured I'd ask the other businesses on Stack Exchange - Does anyone have some advice on what to do? I've looked at Rackspace, Office 365, and a couple of others, but have not yet made a real commitment. Anyone have experience conquering a similar problem and have any advice for a young startup founder?

Thanks for any comments,

Charlie

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My understanding is that Google does not use email for big data initiatives and that you have all the control that you are asking for. Take a closer look at their T's&C's and privacy policy. Otherwise, very few private companies would use Google apps for mail, but many do. – Kekito Oct 11 '12 at 1:39
Try horde/imp. You can make it to perform what you want. Note that there is no Exchange replacement, it always comes with something you need to adjust / add to make it fully functional for yourself. Then there is hosted exchange, which is one of the best solutions available, and the best if directly from microsoft. – Andrew Smith Oct 11 '12 at 14:14

3 Answers

up vote 3 down vote

I am a year plus into my most recent start-up, having a background working in both start-ups and having worked as a senior manager in the biggest two companies in Seattle (airplanes and software). In those massive companies we had every bit of technical infrastructure we wanted (and some dog food we did not want). When I left to start my current company I was really concerned that I had become used to the luxury of having Exchange, SharePoint, IM, VOIP, etc. I had looked into Office365 (formerly BPOS) while at MSFT and was sincerely impressed with the dedication to security and the Software as a Service model they were rolling out. So now eighteen months or so later...

Office365 is by far the best service offering I have seen in my thirty years, especially at the $6/person/month. You can start with as little as ONE seat (total bill $6), and add and remove people any time you want with instant web portal provisioning.

Each person has FULL Exchange 2010, connected to Outlook on the desktop, WebAccess, iPhones, Windows Phones (also incredibly good), Android, etc. We have full online presence information, so when you are typing an email to someone it tells you if they are online, etc.

Each person also has full Lync on their computers and mobile phones. It includes full HD video chat, audio and instant messaging, and unlimited size file transfer. All encrypted. You also get full screen cast and online meetings with Lync online. We even tested the file transfer functionality. For pure amusement we dragged and dropped a 4 GB ISO file of Windows 8 onto Lync and the transfer worked perfectly despite the size. Our filed tech even installed Win8 from that ISO file to confirm it worked.

The most underrated feature is SharePoint online. Even with only one seat (license) you get a public website that you can "back end" with SharePoint parts. Dead simple and easy to maintain. You also have private internal SharePoint sites for your team, as well as any special projects. We make a separate SharePoint site for each client project, so each project team has separated file storage, calendar, task lists, wikis and more. You can even invite NON-Office365 guests using free Windows Live/Hotmail or Outlook.com accounts.

I could go on for another several paragraphs about extra functionality you can use, such as building mobile web applications against Windows Azure, and your Office365 accounts already use Azure Active Directory. That gives you a fully deployed mobile web cloud that works across the world. Again that Azure Active Directory integration is FREE with Office365.

My one complaint (and they are working on this) is being able to upload my own SSL certificate for my public website. Everything else is already full SSL using MSFT (x.509) certificates.

I have found using a private Lync cloud so useful with one click screen sharing, etc. that I have bought a few $6 accounts for my non-technical parents. Now they can see my presence (including when I'm "busy" in a meeting), and I can have a quick (secure) video chat with them. From that conversation view I can take over their computer screen to offer assistance. The functionality is fantastic.

Just for extra information there are Exchange Online ONLY accounts (no SharePoint or Lync, etc.) for $4/person, and accounts all the way up to $20/person that include FULL Office 2010 (soon to be Office 2013) for up to FIVE computers per user seat. So if you have a $20 account for "Jane" she can install Office Pro on her work desktop, work laptop, home desktop, husband's laptop, AND her new Windows 8 tablet (you know Jane wants a new Surface tablet), all under that same one seat license.

So while I can get all the MSFT software including Exhcange essentially for free, and I know how to setup and manage Exchange, SP, Lync, etc., the Office365 price and features made it a no-brainer for my start-up. I will never go back to the time and money to manage my own infrastructure for those services.

BTW, I think you get a free evaluation period with Office365. Good luck and I hope this helps.

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Thanks for the very detailed comments. I think I'm going to give Office 365 a trial for the company. It seems like an OK solution, for the near and medium terms. Do you know how I could test a deployment of addresses/users on Office 365, while also maintaining my existing email service for the rest of the company? Is it possible to point single email addresses to another service, or do they all need to point to the same server for DNS reasons? – CDD Oct 12 '12 at 20:36
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Here is my suggestion for under $10. Buy any domain name at one of the registrars. Have fun with the domain name, since it will be your test. You might consider the possibility that you would be documenting the system to people within your company, so think "age appropriate" fun. The rest is free. Office365 offers a full access free trial where you can use your test domain, or your Office365 address can be pointed to from an existing DNS service. They also create a free name for you in their domain. The process will take a basic level user about an hour, split over two sessions. That's it. – OnTheShelf Oct 13 '12 at 3:37
I think I'm sold on Office 365 - But what I'm worried about is continuity. How can I migrate from my Exchange 2003 to Office 365, without the DNS freaking out? I'm not worried about email databases, or any per-user edits, but it seems O365 wants me to add a TXT record, and then add users after that. I'm pretty worried that when I start editing the DNS records, my existing email addresses are going to stop functioning. Any advice here? Again, pretty hesitant to take first steps. – CDD Oct 15 '12 at 20:32
This is nothing to worry about. Microsoft is generating a long unique string, and then showing you how to add that as a bit of text retrievable through DNS. What this proves to MSFT is that you have enough control of that DNS to have added the text. MX (mail exchange) records determine where your email is received. If you change your domain to MSFT, you will point your MX records to them. If you just authorize the move of the domain to Microsoft (which I recommend - my transfer was flawless), then they will do all of the work for you. Enjoy. Keep us updated. – OnTheShelf Oct 16 '12 at 3:29
up vote 1 down vote

We have been extremely happy with Google's services. They do not mine data of paying customers, or clutter their webmail with ads and such. $50/user/year is extremely reasonable. We were early adopters and have had no downtime that we have noticed. We work with some companies that use Exchange and Office365 and they have all expressed issues with inefficient spam filtering. We have had absolutely none of that. No false positives, and I cannot recall a single bit of SPAM getting through to my inbox, nor have I heard of anyone mentioning that they have.

We really could not be happier. It does everything that we need, for a great price and it just works.

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I use gmail for my personal email, and actually my university mail (again, I'm still in college, despite the 'running the tech' stuff that brought me to this message board). I still have some reservations for being 'married to Google'. I'll have to take another look at it though. – CDD Oct 12 '12 at 15:35
I am a fan of Google too, but not for how they treat user data privacy. Your mileage may vary. If you are AT ALL concerned about data privacy, make sure your vendor meets and will contract to comply with HIPPA standards (Health Insurance Portability and Accountability Act). Office365 does. See trust.office365.com In addition to data privacy and portability, SPAM and malware has never been an issue through Office365 for any companies I know using it, and obviously there are no web ads for the Office365 services. – OnTheShelf Oct 13 '12 at 17:46
up vote 0 down vote

While you don't buy the Exchange 2016 you mention, perhaps you can find DavMail a very useful and cheap (no cost) solution.

From the website:

Ever wanted to get rid of Outlook ? DavMail is a POP/IMAP/SMTP/Caldav/Carddav/LDAP exchange gateway allowing users to use any mail/calendar client (e.g. Thunderbird with Lightning or Apple iCal) with an Exchange server, even from the internet or behind a firewall through Outlook Web Access. DavMail now includes an LDAP gateway to Exchange global address book and user personal contacts to allow recipient address completion in mail compose window and full calendar support with attendees free/busy display.

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I was merely being forward looking with the 2016 comment. I realize it is nothing available on the market at the moment. I apologize if that was confusing or misinterpreted. I'll take a look at DavMail, seems like an interesting option. I wonder how they keep it 'free'? – CDD Oct 12 '12 at 15:33
@CDD: The 2016 comment was not confusing, I could have used a :-) to signal that I've understood it. I just used it to emphasize that you can have a workable solution, keeping your infrastructure and adding davmail to the mix. It works very well for me in a workstation (personal) mode. It can also be used in a server (shared) mode. If it works for you, consider donating some amount to the project. – Luis Oct 12 '12 at 16:39

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