Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on.
Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge productivity booster, between meet and groups and drive and docs and calendar and sheets and such, not to mention chrome sync and sign-in with google, etc. And federated management of all of that together in the admin interface, along with integrated legal archival and discovery. Well worth the monthly cost (what is it, like $10?). If your employees aren't worth that much every month, you shouldn't be hiring them.
It's also much more usable cross platforms than the nightmare that is MS Office. Outlook is terrrrrrrrible.
In what way? I’ve used both Google Workspace and Office 365 during my career. I don’t dislike Google Workspace, but Office 365 is notably more mature, capable, and complete. (I mostly use Macs, but the web apps work the same on any browser/OS.)
Also, and I'll never get tired of saying it, if you have both a personal and a business-managed Microsoft account you better give up computers and be a hunter gatherer, it'll save you a world of pain.
Tools like GAM used to make things easier and expose just how much UI Google never bothered to write, but at least as of this year I can’t find a feature in Google Workspace that isn’t in MS365, plus you have -all- of Azure right there.
Email: Outlook UI and hotkeys are totally different from MacOS, Windows, and Web. Rules don't really work and are impossible to debug. Search is terrible. Threading is terrible (expands the subjects of each child message, but not their bodies... whyyyy).
Calendar: How the heck do you find an event you previously declined but changed your mind on? Why does Teams and Outlook both offer a calendar, with subtly different UIs and features, and the web interface is totally different yet again? It is incredibly slow (things take multiple seconds, like loading someone else's calendar, or clicking on an event it has to take time to load in the attendees...). The "suggested times" feature is hard to find and there's no visual guide (like a week view); also it again seems different between the apps.
Teams: Oh god. This... is what they came up with? It's sooooo slow on startup. It duplicates Outlook notifications. It is hard to find the meeting you're supposed to join when you first clicked on a join link, but then it asks you to login, etc. It's so much less feature-ful than Zoom, yet so much harder to use (and uglier) than Meet. Why do the chat rooms persist not only after a meeting but get resurrected later in the week, and why do they notify you for chats in a meeting that you're not even in. The share screen sidebar is atrociously hard to see to determine which window you're trying to share. Like... literally all the basics they got wrong, and this one software has the worst UX of anything I've seen.
Excel, Word, etc.: My god, the UI has gotten even worse, the forced OneDrive integration is terrible, etc...
I grew up using Microsoft stuff until Google started popularizing their online suite. In the years since, every employer except this most recent one has used Google and while it never struck me as particularly pretty, it was pretty easy to use for the most part. I was actually kinda curious to try the Microsoft stuff again, figured they had 20 years to catch up, it's gotta be better now, right? Nope. I've never hated a stack as much as this, even as a long-time Windows user... in fact it's going to be one of my questions for employers in the future, and a big red flag.
Sorry, I know I sound pretty agitated about this. Their software griefs me on a daily basis and is the single thing I hate the most about my job. It's just SO terrible. I guess YMMV, eh? I didn't realize there were actually people out there who preferred the Microsoft stuff... of the folks I've spoked to casually, all vastly preferred Google's implementations. But that's just anecdotal.
As an IC, I used to miss meetings due to the Google calendar browser notification being so tiny and unintrusive. Contrast with the totally in your face Outlook meeting notification that can't be missed.
On the other hand, I seem to get 3-4 reminders about the same meetings -- even ones I'm already joining -- between Outlook and Teams.
No one should send emails that should land in a human's inbox directly off a bare random IP.
At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.
> At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.
You really really should not need to be doing this yourself. I've had to fix a few of those and it's REALLY not worth anyone's time.
Getting email from Google is $6/mo, Microsoft $6/mo, Zoho $1/mo, Proton $4/mo, Fastmail $3/mo, etc.
Then it's just set it and forget. You don't have to track down quarantined messages, cross-examine a bunch of headers, check blacklists and whitelists, figure out how your SPF is propagating, blah blah blah... it's just not a wise thing to skimp on.
Do you really want your startup employees to be running into email problems while you're still trying to establish yourself as a business? At some huge corporate scale it might make sense to in-house this again (and even then it's questionable), but it's certainly not worth having a dedicated person (or generalist IT scapegoat) waste time setting this up and debugging it in a small or medium-sized business.
If you're on Chromebooks instead, Google's offering obviously makes sense there.
If you're on Macs or pure Linux not sure, but you may end up using web interfaces a fair amount anyway.
This is setting up SSO btw. MS management tools are a dumpster fire.
For background, the number's coming down these days but not long back I managed a lot of Exchange clusters. I'm not afraid to manage mail, I just know it isn't worth it.
The customer support group emails are forwarded from Zoho to Freshdesk (also free for one support email).
Automated emails (like login alerts) are sent from Cloudflare MailChannels / AWS SES; and replies, if any, to those automated emails are routed back in to a Zoho group mail.
At a prior startup, we only choose Microsoft because of their willingness to sign a BAA (HIPAA).
Elsewise, just do Google Workspace. Cost is reasonably for what it costs.
I know this is anathema to many people here. If you have a business made of 5 coders and your customers are other coders, you can do whatever you want.
Workmail has a better management interface for the admin whereas Google has a better user UI (at least for the webapp).
Here's why we use O365 for email:
1. Gmail tabs get lost in your sea of tabs, while Outlook being a desktop app means it's easy to alt / tab over at any time.
2. It's really easy to manage multiple mailboxes with O365 (via Outlook), while Google doesn't work super well for multiple profiles.
3. O365 has better support through their reseller partners (we use AppRiver) while dealing with things we don't know a lot about (SPF / DKIM / distribution lists / shared mailboxes / etc).
4. (I believe) O365 is much less likely to shutdown our account for unknown reasons than Google.
5. Lastly, I was exposed to O365 while working at a SaaS in the Microsoft ecosystem. For the first few weeks I hated it, and missed Gsuite, but overtime I came to love O365 and hate Gmail.
Don’t waste time self-hosting. You job is to make sure your company is successful, product-market fit, blah, blah, you know the drill: that is core. Everything else is context.
- Usage based pricing rather than per seat
- As cheap as $19 per year
- No deliverability issues
- Good instructions on how to set your DNS settings.
