Marketing
16
min read

Calendly vs Chili Piper: A Comparison for Inbound Scheduling and Routing

If you’re in the process of evaluating Calendly or Chili Piper and want to find out how they stack up against each other, you’re at the right place. We’ve put together all you need to know about both solutions, including their pros and cons.

Charanyan
June 21, 2023
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If you're here, you're either expecting imminent growth in your sales team or a surge in inbounds from your marketing effort or both. 

Automating the inbound scheduling process in this situation is a common and effective massive efficiency at this stage, combined of course with other operational efficiencies. You might also just be going through due diligence to ensure that your inbound tech stack is defensible and provides enough RoI at your renewal conversations. 

In any case, you're already bought in on the value of turning your inbound conversions into booked meetings right away rather than have your sales teams play email ping pong to try and book meetings. 

Both Calendly and Chili Piper are great choices to add to your consideration set in this situation, with similar value propositions and notable differences in how they provide value and the way their solutions are designed.

This comparison focuses solely on the inbound scheduling and routing aspect of the two products. Scheduling in the Outbound motion is relevant only for Chili Piper, and not relevant or available in Calendly and isn’t covered in this analysis.

This will be typically relevant for marketers, sales leaders, Ops professionals (Revops, Sales ops, Marketing Ops, GTM ops). If you're looking for information about the individual calendar link capabilities of Calendly, typically used by individuals/agencies, this might not be the right read for you.

Basic Capabilities

Let’s start with the basics that an inbound scheduling product should cover. Both Calendly and Chili Piper are capable of:

  • Automating meeting scheduling based on web form submissions
  • Generating and adding a conference link to the calendar invites automatically
  • Distributing meeting amongst the sales team
  • Using hidden field values to qualify form fills and disqualify others
  • Send information back to the CRM for booked meetings

In effect, both products are capable of streamlining the process of meeting scheduling from your form and getting meetings booked on your sales team's calendar. Where they vary is what matters most.

Key Comparison Criteria

Comparing CRM Integration in Calendly vs Chili Piper

We’re starting here since this is typically a basic qualifier for any product you’re adding to your stack. If the product doesn’t integrate and requires that you replace your CRM to even get started, you’re either looking at a product that’s pretty early or your CRM is pretty niche. In either case, it’s a dead end. So let’s look at what Calendly and Chili Piper work with. 

Calendly's CRM integration

Calendly's routing module integrates with Salesforce and Hubspot to the extent of:

  • Using the email address or domain to look up existing ownership of an account, contact or lead to assign the visitor to the same owner's calendar.
  • Adding a meeting activity against the contact in the CRM along with the meeting details.
  • Updating the meeting outcome based on the outcomes marked in Calendly

You can of course use Calendly without a CRM integration if you're adventurous and are ready to deal with a ton of Zaps and some Javascript just to get basic attribution and data flow in place for all the meetings being booked.

 

Chili Piper's CRM integration

Chili Piper's CRM integration is a basic requirement to get started with their routing module and integrates with Hubspot and Salesforce. The integration covers:

  • Routing of leads based on a combination of form data and information from the CRM.
  • Email address or domain based lookup of existing ownership at an account contact, or lead level to route form fills to existing owners. 
  • Automation of meeting activities being logged in the CRM.
  • Cancellations and reschedules being logged against meeting activities

Note: If your sales team integrates their calendar with their CRM, to automatically log all meetings on their calendar against the contact/lead record, both Chili Piper and Calendly end up creating duplicate records of the same activity in your CRM.

As of this writing, there is no solution but to disable the CRM integration which means none of the calendar events booked outside of these solutions flow back to the CRM which is a huge hindrance for sales folks.

Web Form Integration in Calendly vs Chili Piper

Calendly’s form integrations

Calendly's integrations with Web Forms, as of today, is limited to: Hubspot forms, Marketo forms, or Calendly's own form.

This means, if your websites/landing pages use any form other than the ones mentioned above, Calendly's routing is an automatic no-go.

Chili Piper’s form integrations

Chili Piper integrates into a variety of forms, and in several cases where their script doesn’t work out of the box, their team offers Github repositories that your web developers can use to integrate into. This makes Chili Piper the workable choice of the two, if you're one of the many GTM orgs that uses one of the hundreds of other form providers out there.

How easy and simple it is to get a working integration of Chili Piper's router and your web form depends on your level of access to and bandwidth of your web developers. The more the better.

Distribution/Routing Capabilities in Calendly and Chili Piper

Calendly's distribution methods

Calendly has multiple event types that determines how meetings are distributed:

  1. Optimize for Strict Round Robin
    1. Meetings are distributed equally within a team in round robin to ensure that every user in the team gets the same number of meetings.
  2. Optimize for Availability
    1. Calendly displays the availability of everyone in the team to the prospects. The meeting distribution is based on the time slot that is chosen, and the distribution happens based on who is free at that time, and who has the least number of meetings assigned.
  3. Collective round robin
    1. This is used to assign meetings to multiple users at once, at times where both or all selected users are free. In an inbound sense, this is typically used in cases where companies need users from more than one team to be available for the first call.


Things to watch out for in Calendly when it comes routing

The major drawback with Calendly's distribution setup is that the round robin doesn't consider cancellations, and no-shows resulting in sales reps not getting a fair number of meetings.

The lack of calibration essentially makes the round robin a surface level setting that doesn't work for sales teams with deal values where every no-show has a significant impact on the sales rep's ability to hit quota.

Chili Piper's distribution methods

Chili Piper's distribution is based on different types of queues:

  1. Queues based on round robin
    1. Chili Piper's round robin queues for your inbound meetings are by default set to optimize for availability.
  2. Queues based on ownership
    1. Chili Piper's ownership based queues can be configured to look up ownership of existing records in Salesforce and compare them with a list of email addresses added to the queue.
  3. Queues based on Groups
    1. Chili Piper allows hand raisers to book meetings on multiple user's calendars at once but doesn’t take into consideration the availability of all the users.


Data Management in Chili Piper and Calendly

When you automate the scheduling process, you also want to ensure that you have visibility into how effective that automation is, and where there is scope for improvement. We’ll look at how Calendly and Chili Piper handle this, for you to have enough data to get the visibility you need. 

Calendly's data handling in CRM

  • Logs a meeting activity against the lead/contact record in the CRM when a meeting is booked.

  • The Salesforce integration works through a Salesforce flow that automates meeting logging and updates the activity if the meeting is canceled.

  • The Hubspot integration works natively and logs the meeting, and the activity gets updated if meetings are canceled.

Things to watch out

  • Duplicate events when your sales team has their Calendar integration enabled with the CRM
  • Meeting completion statuses dependent on manual updates by the Salesfolks, resulting in stale data and follow ups

Chili Piper's data handling in CRM

  • Meeting activities are automatically logged against the contact/lead in Hubspot and Salesforce. 
  • Logs a reschedule count in Salesforce.
  • Meeting cancellations are automatically logged as a meeting outcome.

Things to watch out

  • Similar to Calendly, Chili Piper users also face the issue of duplicate meeting records in your CRM.
  • Sales reps have to manually mark meetings as completed resutling in inaccurate data around how many meetings got booked vs how many completed at any point in time.


White Labeling for Chili Piper and Calendly

Depending on your industry, company size, brand recall value, and several other criteria, your decision to choose a customer facing product might sway based on the level of customisation that the product allows in terms of branding. Let’s look at how Calendly and Chili Piper work with this.

We’re going to split this into two sections to cover colors and branding (scheduler experience) and the more nuanced domain customisation (communication sent from product).

Colors and branding in Chili Piper and Calendly

Calendly widget customization

  • Allows uploading organization logo and removing the "Powered By Calendly" label.
  • Allows choosing colors on the widget to match your brand with a simple pick list.

Chili Piper widget customization

  • No option to truly and entirely remove Chili Piper's branding in the scheduling experiences.
  • Allows uploading company logos.
  • Color customisation requires editing CSS code.

Domain customization in Chili Piper and Calendly

Domain options in Calendly 

  • Notifications sent from notifications@calendly.com
  • Any follow up meeting links need to be sent with the Calendly.com domain in the URL.

Domain options in Chili Piper

  • Notifications sent from notificaitons@chilipiper.com
  • Any follow up meeting links need to be sent with the Chili Piper domain.


In this aspect, both products don’t offer much in terms of making the experience feel native to the brand that uses them.

Scalability in Chili Piper and Calendly

If you’re at a stage where automating this process is a real problem worth spending time and budget solving, you should choose a product that you know has potential to scale pretty quickly, so you’re not evaluating vendors every year. 

Scaling teams with Calendly

  • Allows adding or removing users at any point in time. This might seem like a “Duh!” moment, but you’d be surprised at the number of products that make you jump through hoops for this.

  • Removing users is frictionless, but there's no consideration of the impact on existing routing logic. When you remove a user in Calendly, you have no idea about which of your automated routing flows might be sending your prospects to a broken experience. 

Scaling teams with Chili Piper

  • Adding users typically requires an email to be sent to the sales rep to get an additional license before you can add them and start getting meetings sent their way.

  • Removing users is seamless, but the impact on routing logic is not considered. This means, any time you remove a user, you run the risk of sending prospects to a broken scheduling experience or sending them to the wrong calendar. 

Territory management in Chili Piper vs Calendly

We’re looking at territory management as a representative example of a use case that involves pretty frequent based on dynamic data which is just a common reality in growing sales orgs. 

Calendly’s Territory Management

  • Dynamic list based routing is currently not possible without multiple rules for every single condition, making it difficult to manage constructs like territories or custom values for routing.

Chili Piper’s Territory Management

  • List based routing requires manual input of each item separated by commas, making territory management manual and cumbersome to manage and scale.
  • Any time updates are needed your admins need to go through a long winding process to keep your routing logic up to date. 

Pricing Comparison of Calendly vs Chili Piper

Calendly Pricing (Team and Enterprise Plans)

Calendly offers a straightforward pricing structure with flexible options depending on team size and the level of feature customization required for scheduling.

The Team and Enterprise plans are the only two plans that offer Calendly’s routing capabilities. 


  1. Team Plan: Targeted toward smaller teams and offers collaborative features.
    1. Price: Starts at $16 per user per month (billed annually).
    2. Features:
      • Unlimited active event types.
      • Collective and round-robin event types for team scheduling.
      • Analytics and reporting for tracking meeting metrics.
      • Hubspot ownership based routing
      • Salesforce basic integration
      • Customizable branding, automated reminders, and workflows to streamline scheduling.

  2. Enterprise Plan: This plan is designed for large organizations with advanced security and customization needs
    1. Price: Custom pricing based on team size and requirements.
    2. Features:
      • Everything in the Team plan, plus advanced security and compliance features (e.g., Single Sign-On (SSO), SCIM provisioning).
      • VIP support and onboarding assistance.
      • API access for deeper integrations and custom workflows.
      • Hubspot ownership based routing
      • Enhanced admin control and centralized billing.

Chili Piper’s Pricing (Concierge)

Chili Piper's pricing is more focused on specific use cases, particularly inbound lead scheduling and routing through their Concierge product.

Concierge is positioned as a more specialized tool for teams that prioritize lead response time and conversion, and its pricing reflects a focus on sales teams with high inbound lead volume.

Chili Piper has one product aimed at inbound scheduling and routing and covers all the features discussed in this article. 

  • Price: Starts at $30 per user per month (billed annually).
  • Platform fees: Starts at $150 up to 100 leads, and $1000 when your form fills are more than 1000 per month (includes junk, invalid, disqualified form fills)

If you’re curious, here’s more information on what Chili Piper’s pricing will eventually cost you in the long run.

What do revenue leaders end up choosing?

The choice between the two will ultimately depend on your existing tech stack stage complexity of routing requirements and the necessary sophistication levels.

Consider the integration capabilities, distribution methods, data handling, customization options, and scalability features when making your decision.

While Calendly and Chili Piper have built the brand that led you here, over 250 plus revenue leaders from modern marketing, ops, and sales organizations have chosen RevenueHero over Calendly and Chili Piper in the last 1.5 years.

If you’re looking for an inbound scheduling product that goes beyond just calendaring and surface level CRM integrations, here are some reasons customers choose RevenueHero over the other two in the space:

  1. RevenueHero offers the best CRM integration available in the space today. What does this mean?
    1. Matching based on any account/contact/lead property and not just email domains.
    2. Automated meeting statuses that auto-update meeting completions and incentivises sales reps to mark no-shows. (1-click from slack/calendar)
    3. Automatic deduplication of meeting activity record allowing for accurate data for marketers, while sales reps get to keep their CRM <> Calendar integrations on.
    4. Intelligent retries based on CRM record creation delays to keep the chances of data anomalies as close to none as possible.
  2. The most advanced routing capabilities available in the space. Why does this matter to you as a marketer/sales rep?
    1. Depending on your preference, you can set up RevenueHero to round robin meetings on a truly strict round robin basis, or optimize for availability.
    2. Collective round robin by RevenueHero allows your prospects to book times where multiple members have common availability to ensure an effective first meeting.
    3. Meeting outcomes automatically calibrate the position of sales reps in the queue (No-shows, Cancellations)
    4. Flexibility in deciding which meeting outcomes should affect calibration between no-shows and cancellations.
  3. Easiest to build, maintain, and scale.
    1. RevenueHero’s dynamic matching lets you set up ownership lookups without the hassle of maintaining a manual list of owners to check against.
    2. The intelligent user removal flow prompts you with all the impacted areas with quick access to each one, allowing you to fix and update each one before you remove the user. Built with safety and customer experience in mind.
    3. Custom lists in RevenueHero provide centralized management for any collection of custom values, making routing based on territories, domain based blacklisting, or any collection based routing logic a breeze.
  4. Completely white labeled experience
    1. Colors, logo, and scheduling experience can be completely customized to match your brand.
    2. Any communication sent, can be sent from your own domain.
    3. All links can be customized to use your own domain with no mention of RevenueHero.
  5. Fixed, predictable pricing
    1. RevenueHero’s platform fee is fixed, allowing you to know exactly what

Here is a quick sneak peak of RevenueHero, for you to make an informed decision:

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