AI assistants for small business owners: schedule, email and replies
Which AI assistants can handle my schedule, email and replies if I run a small business?
Updated · 6 assistants ranked
Eight assistants describe themselves around email, calendar or errands; six of them took at least two of our Email replies, Connected apps and Routines tests and are ranked. This is a features-only view: we test replying on the right thread, using three tools from one message and a weekday briefing, not small-business work such as invoicing or customer support.
Top picks
- 19.0
Email 9Connected apps 10Routines 8Time to finish 6m 30s
- 28.3PokeBest free option
Email 9Connected apps 8Routines 8
- 38.0
Email 7Connected apps 7Routines 10
- 47.5
Email 7Connected apps 8Routines —
- 55.7
Email 8Connected apps 4Routines 5
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 | Average | |
|---|---|---|---|---|---|
| 1 | Town | 9 | 10 | 8 | 9.0 |
| 2 | Poke | 9 | 8 | 8 | 8.3 |
| 3 | Pally | 7 | 7 | 10 | 8.0 |
| 4 | szn | 7 | 8 | — | 7.5 |
| 5 | Familiar | 8 | 4 | 5 | 5.7 |
| 6 | Ka | — | 4 | 5 | 4.5 |
How this report works
Included are assistants whose catalog description mentions email, calendar or errands: Del, Familiar, Ka, Orchid, Pally, Poke, Szn and Town (checked 2026-10-26). They are ranked by the average of Email replies, Connected apps and Routines, with at least two taken; Del and Orchid have fewer and are not ranked. Scores come from the published score sheet and are dated 2026-10-27. 2 of the 6 ranked assistants (Familiar and Ka) 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. Szn and Ka have two tests each, so their averages are thin.
How to choose
- Look at Email replies first. The test checks the reply lands on the right thread, offers times that are really free and sounds like you, which is the part customers see.
- Decide whether it may send by itself. Many of these draft first and wait for your approval; confirm that setting before you connect a work inbox.
- Check the plan and the channel. Pally and Szn are free (Szn during its early preview); Town lists $15 a month with 30 free chat messages, Poke $19 and Ka $14.99. Familiar is on a waitlist.
Which AI assistants can run email and calendar for a small business?
Six assistants whose descriptions mention email, calendar or errands are ranked here, averaging from 9.0 for Town to 4.5 for Ka across the tests they took. The ranking table shows each score. None of the tests covers invoicing or customer support.
Can an AI assistant reply to my customers for me?
Several can reply to email; the Email replies test checks the right thread, times that are really free and your own voice. Whether an assistant sends without asking is a setting to check yourself before connecting a work inbox.
Which of these have a free plan?
Pally and Szn are free (Szn while in early preview). Town, Poke and Ka have a free tier and list $15, $19 and $14.99 a month; Town's free tier is 30 chat messages a month and Ka's is 10 messages a day. 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 sourceYeah i have an email for testing only and aach agent can be connected to different apps
Open sourceEvery five is just not good enough when other services like @interaction send me alerts nearly instantly.
Open sourceFrequently asked questions
Which assistant is best for this?
Town leads with an average of 9.0, ahead of Poke and Pally.
Is there a good free option?
Town is the highest-ranked assistant with a free plan, averaging 9.0.
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.