Two inboxes, two calendars, two sets of habits
A Gmail address for the company you started and a Microsoft 365 address for the one that acquired you. Or work on Outlook and life on Gmail. Either way you're running two inboxes, two calendars, two sets of shortcuts and two mental models, and the switching isn't what costs you. The mistakes are.
The wrong calendar gets the client call. The reply goes out from the address that makes you look like a freelancer to your own board. The follow-up lands in the task list you only open on Thursdays.
One app fixes the switching. What you really want is one app that keeps the identities straight.
One workspace, separate identities
Putting two accounts in one window doesn't merge them, and it shouldn't. You still need to know which address is sending, which calendar is getting the meeting and which list owns the task.
In Otto the selected account decides all three at once. Pick the work account and the mail, the calendar and the tasks are the work ones. Tasks follow the provider too: Google Tasks for a Google account, Microsoft To Do for a Microsoft one. It's a single rule, so you don't have to remember a set of per-feature exceptions while you're moving fast.
Before any AI action, that account is on the card you approve, and so is the recipient list. Checking takes a second, and it's the one habit worth building if you live across two providers.
Two accounts is also where a slow app hurts twice. Gmail and Outlook both push new mail into Otto instead of waiting to be polled, so either inbox can show a message as it arrives. Folder switches come from Otto’s up-to-date inbox list, not from a fresh request to whichever provider you just jumped to.
Check the providers before you fall for the AI
How clever an assistant is says nothing about whether it'll connect your accounts. Settle the connection question first, then compare the help.
Shortwave supports Gmail and Google Workspace. Spark supports Gmail and Outlook, plus Exchange, Microsoft 365, iCloud, Yahoo and IMAP. Otto supports Gmail and Outlook. That's three different answers to the same question, and the wrong one puts you back in two apps however good the drafting is.
We last looked at prices in September 2026. Shortwave listed Business at $30, Premier at $45 and Max at $120 per seat a month. Spark listed a Free tier, Plus at $10 a month or $99 a year, and Pro at $20 a month or $199 a year. They're different products with different billing shapes, so compare what's included before you compare the numbers.
Their own pages are Shortwave pricing and Spark pricing. We've also written up the Shortwave comparison and the Spark comparison. Otto is ours, so read our side of those with that in mind.
Move one workflow first
Don't migrate on a Monday morning. Take one thread that needs an answer, a meeting and a follow-up, and run it end to end in the new app.
Then go and look. Is the sent message in the right Sent folder? Is the event on the calendar you meant? Is the task in the list you actually check on your phone? If all three landed right, add the second account and repeat the test there, because similar folder names and overlapping contacts make two accounts feel interchangeable long before they are.
Watch the time zones too. Work and personal calendars often disagree about them, and a proposal that reads fine in one is an hour off in the other.
Then decide what to move
Once a whole workflow lands where you expect, move your daily triage. Leave anything that's truly provider-specific where it already works. You can make this switch in pieces.
Otto Free includes one connected account with core mail, calendar and tasks, plus an AI allowance. Paid tiers add accounts and capacity. The multiple accounts guide explains how account context works, and pricing has the current tiers.
First published on the Otto Mail blog.
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