AI executive assistants: email, calendar and your day, compared
Which AI assistants work like an executive assistant for email, meetings and my day?
Updated · 3 assistants ranked
Three assistants call themselves an executive or work assistant, or say they triage email and prepare your day, and took at least three of our six tests on email replies, connected apps, routines, proactive help, permissions and memory. The scores are features only: we do not test meeting notes or delegation to a human team.
Top picks
- 18.4
Tested on 5 of 6Best: Connected apps10, Email9Time to finish 6m 30s
- 26.3
Tested on 6 of 6Best: Email8, Permissions8
- 34.3
Tested on 3 of 6Best: Email5, Connected apps5
Top pick: highest average here. Best free option: highest among assistants you can use for free. Fastest that's still good: quickest median time to finish among those averaging 7 or more.
Full ranking
| # | Assistant | Connected apps | Routines | Proactive | Permissions | Memory | Average | |
|---|---|---|---|---|---|---|---|---|
| 1 | Town | 9 | 10 | 8 | — | 8 | 7 | 8.4 |
| 2 | Familiar | 8 | 4 | 5 | 7 | 8 | 6 | 6.3 |
| 3 | Joshu | 5 | 5 | — | — | — | 3 | 4.3 |
How this report works
Included are assistants whose catalog description says executive assistant (Joshu), work assistant that learns your email, calendar and chat (Town), or triages email and preps days (Familiar), checked 2026-10-26. They are ranked by the average of Email replies, Connected apps, Routines, Proactive Help, Permissions and Memory, with at least three taken. Scores come from the published score sheet and are dated 2026-10-27. 2 of the 3 ranked assistants (Familiar and Joshu) carry pre-filled scores, which are placeholder estimates the site has not yet replaced with its own test runs, so treat their places as provisional. Joshu has three tests, so its average is thin.
How to choose
- Look at Permissions and Memory before you connect a work inbox. They score what the assistant says it can access, whether it follows your rules and whether you can see and delete what it remembers.
- Check the plan. Town lists $15 a month with 30 free chat messages; Joshu is open source and lists $95 a month; Familiar is on a waitlist.
- Pick the channel. Town is on WhatsApp, Telegram and an app; Joshu on SMS, WhatsApp, Telegram and an app; Familiar is app only.
Is there an AI executive assistant?
Three assistants describe themselves that way or as a work assistant or email triager: Town (8.4 average over five tests), Familiar (6.3 over six) and Joshu (4.3 over three). Familiar and Joshu carry pre-filled scores.
Does an AI executive assistant replace a human one?
These tests cover replying to email, using several tools at once and a weekday briefing. They do not cover travel for a team, meeting notes or judgement calls, so we make no claim that any of them replaces a person.
How much do they cost?
Town lists $15 a month with a free tier of 30 chat messages a month; Joshu lists $95 a month; Familiar has a waitlist and no listed price. Prices as checked on 2026-10-26.
What users say
So I asked my @TownAI agent to do it. It collated all the insights + made the deck
Open sourceoh no my instinct @muse and @TownAI are having a turf war whenever a new email appears
Open sourceFrequently asked questions
Which assistant is best for this?
Town leads with an average of 8.4, ahead of Familiar and Joshu.
Is there a good free option?
Town is the highest-ranked assistant with a free plan, averaging 8.4.
How did you test these assistants?
Every assistant got the same published tests, word for word, scored from three checkpoints and the number of corrections it needed. Each test is on the Dimensions page.