Feature Requests

When scheduling from a Handoff Router in ChiliCal with multiple assignees, it would be helpful to manage the assignees directly from the scheduler before booking. Ideally, the booker would be able to: Keep an assignee as required Change an assignee to optional Remove an assignee from the meeting entirely This would help support joint-call scheduling scenarios where the router suggests multiple assignees, but the booker may need flexibility depending on availability or business context. For example, if a meeting is intended to include both an OM and AM, but the AM is unavailable or not needed for that specific call, the booker could remove the AM or make them optional without needing a separate meeting type/router path. This would reduce double-booking issues, prevent unnecessary calendar invites, and give teams more flexibility while still using the Handoff Router/ChiliCal scheduling experience.

Ramp bookers have discoverd a loophole in our blind round robin - they set up blind round robin to stop cheating reps but reps have discovered they can reassign to anyone, in any distribution, through the reassign function in app. It would be important that we can prevent this from happening on blind round robins given that they companies setting that up want that functionality for a reason. They consider this an urgent issue to be addressed

Currently it is only possible to reassign one meeting at a time as an admin. It would be useful to reassign multiple meetings at once. For example, when one rep is leaving the company their existing meetings need to be reassigned to other reps. Having the ability to reassign all of their meetings at once would be very helpful for offboarding.

When double round robin is used in Chili Piper, the second participant pool is selected as a flat group with no conditional logic applied. Teams running paired AE/SE selling motions need the second slot to resolve dynamically based on deal attributes evaluated after the first slot (AE) is already matched. For example: route to the appropriate AE queue first, then evaluate device count and third-party product flags to determine which SE pool to draw from, or whether to include an SE at all. The requested behavior is a second assignment node that evaluates its own set of conditions independently after the first assignment resolves, selecting the appropriate pool (or no one) based on those conditions. Without this, admins have to duplicate routing rules for every AE segment times every SE scenario, which scales badly and creates maintenance overhead. This is specifically a gap from the AE's perspective as well: even when SE inclusion is objectively appropriate by deal size, the AE may decide not to bring one on the first call. So the feature also needs to support making the second-slot assignment optional or overridable by the assigned AE.

When HubSpot has duplicate lead records, HubSpot randomly selects one to update while Chili Piper correctly identifies and updates the intended lead. This creates a mismatch: Chili Piper assigns the meeting to one lead, HubSpot assigns ownership to a different lead, and that lead gets distributed to a different rep. The result is a meeting owned by one rep and the lead owned by another. Chili Piper should be able to update multiple lead records simultaneously, or at minimum, surface and reconcile assignment when duplicates exist in the CRM, so that ownership assignment stays consistent across both systems. When this breaks, a rep receives a lead they have no meeting context for, while the rep who actually owns the meeting doesn't receive the lead. For high-cost, time-sensitive leads this is a material operational failure.

Admins who need to adjust a specific rep's weighting across multiple distributions have to open each distribution individually and make the change manually. For teams with 20+ distributions sharing the same agents, this is a significant time investment for what should be a simple operation. Admins should be able to update a rep's weight across all distributions they belong to from a single place, rather than navigating into each distribution one at a time. The workaround today is using the API to script weight changes, but that requires knowing the user ID, knowing every distribution the rep is in, and running the API manually, which is not viable for most admins.

Routing rules that assign work to specific reps must be updated manually whenever someone joins or leaves a team. There's no way to point a rule at a team object and have it stay current automatically. Customers are requesting the ability to define routing rules at the team level, so that when team membership changes, the routing logic updates without manual reconfiguration. This maintenance burden grows directly with team size and turnover. Sales teams with frequent rep changes, regional expansions, or ongoing onboarding face repeated admin overhead just to keep routing accurate. Team-scoped rules would eliminate an entire class of recurring manual work.

Meeting participants are statically configured on Meeting Types or added manually at booking time. There's no way to dynamically include additional participants, such as a solutions engineer or regional manager, based on field values evaluated during routing. Allow routing rules to include an action that adds one or more participants to a meeting dynamically, based on field values present at the time the rule fires, such as territory, account tier, or product interest. High-value deals often require specific team members in the room based on deal characteristics. Manually managing participant addition at booking time is error-prone and doesn't scale. Dynamic participant logic at the routing layer ensures the right people are included automatically without requiring reps to remember who to add.

When a rep's calendar becomes disconnected from Chili Piper, any meetings assigned to them are effectively orphaned. Admins have no way to reassign those meetings to another rep, leaving them in a broken state with no path to resolution short of manual calendar reconnection. Allow admins to reassign meetings to a different user even when the original assignee's calendar is disconnected, so those meetings can be recovered and handled without requiring the original rep to reconnect first. Calendar disconnections happen during offboarding, credential resets, and OAuth token expiry. The inability to reassign in this state means affected meetings either go unattended or require rep intervention that isn't always possible, which is a poor outcome for both the rep and the prospect.

When blind round robin is configured in a Handoff router, the booker can only see availability for the single next-up assignee. There is no way to enable "show availability for all" alongside blind round robin. This creates a problem for SDR teams operating in fast-paced environments where the next-up rep may not have near-term availability. The only options today are to use blind round robin and accept a potentially slow booking, or show availability for all and allow cherry-picking, which undermines fair distribution. Admins should be able to configure Handoff to use blind round robin for assignment credit while still showing availability across all eligible assignees in the matched pool, so bookers can select the earliest available slot without knowing which rep it belongs to. Fair distribution and booking speed are both valid operational goals but currently force a trade-off. Showing combined availability without revealing whose slot is whose would satisfy both, preventing cherry-picking while still allowing bookers to find the soonest meeting time across the full pool.