Conversion & Scheduling

Chili Piper users are requesting the ability for reminder emails to automatically detect and display the recipient's local time zone, similar to the functionality available during the booking flow. This feature would enhance clarity and reduce confusion for email recipients.

Right now the only way to remove reminders when scheduling a meeting is by using the calendar on the Home page of the personal app. Being able to remove the reminders within the scheduler before sending out the invite would be very helpful in situations where we know the customer will not need/want reminders.

When a reminder template is edited, the updated content only applies to meetings booked after the change. Meetings already on the calendar continue to use the reminder content that was locked in at the time of booking, so recipients can receive outdated messaging, old branding, or incorrect instructions even after an admin has updated the template. When a reminder is edited, automatically apply the updated content to all future reminder sends that have not yet been triggered, not just to new bookings going forward. A reminder template is updated because it needs to be updated for everyone. The current behavior creates a two-tier system where some recipients get the current version and others get a stale one, which undermines the purpose of making the edit in the first place and creates inconsistent communication at scale.

When a meeting is marked as a no-show in Chili Piper, there is no automated way to follow up with the guest. Reps have to manually reach out to reschedule, which is inconsistent and time-consuming at volume. Chili Piper should automatically send a reschedule email to the guest when a meeting is marked as a no-show, with a booking link so they can self-schedule without rep intervention. This should be configurable at the Meeting Type level. No-shows represent warm pipeline that hasn't converted yet. Every minute of delay in follow-up reduces the chance of recovery. Automating the reschedule outreach removes the manual step that most reps skip or delay, and keeps the momentum going without adding to their workload.

When a meeting is rescheduled or cancelled, the notification sent to attendees uses the same body copy as the original confirmation email. There is no way to configure distinct templates for reschedule or cancellation events, so guests receive language like "Thank you for scheduling your tour" when their meeting has actually been cancelled or moved, which creates confusion. Admins should be able to configure separate email templates for reschedule and cancellation notifications, with their own subject lines and body copy, independent of the original confirmation template. Sending generic or mismatched messaging on a reschedule or cancellation actively undermines the guest experience. A guest who receives "Thank you for scheduling" when their meeting was just cancelled is confused at best and distrustful at worst. Custom templates for each event type are a baseline expectation for any professional scheduling tool

The meeting time dynamic field currently stamps based on the assignee's time zone rather than the time zone selected by the guest at booking. When a prospect is in a different time zone than the assignee, the stamped time is incorrect from the guest's perspective, causing confusion and no-shows. Dynamic meeting time fields in confirmation emails and notifications should reflect the time zone chosen by the guest when the meeting was scheduled. Guests rely on these stamped times to know when to show up. When the time is displayed in the wrong time zone, it directly causes missed meetings, which is a poor experience for both the prospect and the rep.

There is no way to see whether a meeting reminder email was delivered, opened, clicked, or went to spam. When a prospect claims they never received a reminder, admins have no way to verify whether it was a delivery failure or a recipient issue. There is also no way to audit what message was sent or when. Chili Piper should provide per-reminder analytics showing delivery status, open events, and link clicks, along with a log of the message content and send time for each reminder that fired. Without email engagement data, teams cannot distinguish delivery failures from prospect claims, cannot optimize reminder content based on actual open and click rates, and have no audit trail when issues arise. For a workflow that directly impacts meeting show rates, the absence of basic email analytics is a significant blind spot.

Reminder settings currently allow sending to everyone or only to prospects who haven't confirmed, but there is no way to send distinct reminder content to each group. Teams that want to send a warm, anticipatory message to guests who accepted and a nudge to guests who haven't responded are unable to do so, forcing them to either send generic reminders to everyone or skip one segment entirely. Admins should be able to configure separate reminder sequences based on calendar invite acceptance status, so accepted and unaccepted guests receive messaging tailored to their situation. Invite acceptance status is one of the strongest signals available before a meeting. A guest who accepted needs a different message than one who hasn't responded. Treating them the same wastes an opportunity to reinforce commitment from confirmed attendees and recover unconfirmed ones before the meeting is lost.

The Twilio integration only supports one connected phone number per instance. Organizations operating across multiple regions are forced to choose a single number type, meaning they cannot send SMS reminders to both UK and international recipients simultaneously. UK anti-spam regulations block messages sent from US-based long codes, which means UK teams either cannot use SMS reminders at all or have to send them manually every day. Chili Piper should allow multiple Twilio numbers to be configured per instance, with the ability to assign number types by region or rule. For example, an alphanumeric sender ID for UK recipients and an international long code for all other markets. Without this, global teams are blocked from using automated SMS reminders at scale, creating manual overhead and inconsistent meeting reminder coverage across regions.

Email reminders can only be triggered based on a time offset before the meeting. There's no way to send a custom, templated email at the moment of booking, which blocks workflows like SDR-to-AE handoff introductions, booking confirmations with dynamic rep details, or immediate follow-up sequences that need to fire at booking time. Allow admins to configure a custom email that fires when a meeting is booked, with support for dynamic fields such as assignee name, prospect details, and rescheduling links. The email should support cc and bcc options to include additional stakeholders like the SDR who booked. Booking-triggered emails unlock a high-value workflow gap. When an SDR books on behalf of an AE, the prospect currently receives a generic calendar invite with no introduction to the AE and no context about what to expect. A booking-triggered email closes that gap without requiring a separate sequence tool.