The chat assistant

One sentence is the new
calendar interface.

Caliyo's chat panel sits on every screen. Schedule a meeting, find a slot, check today, or surface conflicts — type or tap a quick action. No menus. No multi-step modal. Just a conversation that ends with the calendar updated.

See example flows
Caliyo AI
Available
Working late, Greg? I'm here to help.
Your calendar assistant, at your service.
Quick actions
Four flows · same input

Every quick action is a real conversation underneath.

The buttons are shortcuts for the four things you do most. Anything beyond that, type it. Caliyo handles the same flow either way.

Flow 01

Schedule a meeting

Type the intent, confirm a slot, send the invite. The whole flow lives in chat — no separate form.

Caliyo AI
Available
Schedule a 30-min check-in with Maya next week.
Maya is free Tuesday 2 PM, Wednesday 10 AM, or Thursday 3 PM ET. Tuesday 2 PM lands in your protected afternoon — want to send it anyway?
Use Wednesday 10 AM.
Done. Here’s what I’m about to send.
Check-in · Maya Okonkwoproposed
Wed, May 14 · 10:00 – 10:30 AM ETMaya O. (external)
Check-in · Maya Okonkwoconfirmed
Wed, May 14 · 10:00 – 10:30 AM ETMaya O. (external)
Ask Caliyo anything…
Flow 02

Find available time

Constraint goes in, ranked options come out. Each slot is annotated with the rule it matches or breaks.

Caliyo AI
Available
Find me 90 minutes for deep work, mornings only, this week.
Three windows match. The top one keeps your “no Mondays before 10” rule.
Free windows · this week
Tue · 9:00 – 10:30 AM
Matches all rules
Thu · 8:30 – 10:00 AM
Adjacent to standup
Fri · 9:30 – 11:00 AM
Breaks 50-min default
Block the first one as Focus.
Held Tuesday 9:00 – 10:30 AM as Deep Work. I’ll auto-decline anything that tries to land there.
Ask Caliyo anything…
Flow 03

Show today’s schedule

Caliyo summarizes the day in two sentences and lists the agenda — context first, then detail.

Caliyo AI
Available
What does today look like?
Four meetings, two protected blocks, no conflicts. Your next thing is in 42 minutes.
Today · Wednesday, May 7
9:00Deep work · Pricing memo
10:30Design review
12:00Lunch
14:001:1 with manager
15:30Deep work · Customer notes
Brief me on the 2 PM.
Pulling your last three threads with your manager. The agenda is in your inbox — Q2 OKRs, hiring update, and a check-in on the pricing memo.
Ask Caliyo anything…
Flow 04

Check for conflicts

Conflicts come with a recommended fix, not just a flag. Approve in one tap, or counter.

Caliyo AI
Available
Any conflicts this week?
Two. Both are fixable without bothering anyone.
Tuesday · 2 PM overlap
Vendor sync2:00 – 3:30 PM
1:1 with Maya3:00 – 3:30 PM
Fix: Trim Vendor sync to 60 min. Both meetings keep their start times. Maya is preserved.
And on Thursday, your Q3 plan block runs into a Friday client readout. I’ll move the readout to Friday 11 AM — same client, same length, no email needed.
Apply both.
Done. Two hours of deep work recovered this week.
Ask Caliyo anything…
How the assistant behaves

Six rules Caliyo follows in every thread.

Type or tap
Quick actions for the four most common asks. Plain English for everything else.
Aware of your rules
Caliyo respects your protected blocks, your “no Mondays before 10,” and your hard stops — by default.
Confirms before sending
Every external action surfaces a card you approve first. Internal holds happen instantly.
Asks once, applies forever
Tell Caliyo “always trim vendor calls to 30” once. It defends the rule from then on.
Brings a fix, not just a flag
Conflicts arrive with a proposed resolution. Approve in one tap, or counter.
Reversible
Any change Caliyo makes can be undone with “undo that” — including invites that already went out.

Stop clicking. Start asking.

Caliyo's chat assistant is included on every paid plan. Early access available through waitlist · no credit card.