Chili Piper vs Calendly: Which Is Better? (2023 Comparison)

chili piper vs calendly

If you want to automate your meeting scheduling and book more meetings, Chili Piper and Calendly are two scheduling solutions that you might consider.

But, despite their surface-level similarities, these two tools are actually quite different. In order to determine which software solution might be right for you, it’s important to have an understanding of what Chili Piper is best for and what Calendly is best for.

Chili Piper vs Calendly: Overview

What Is Chili Piper?

chili piper

Chili Piper is a scheduling and routing software platform built for B2B sales teams to help them book more meetings with qualified prospects.

Chili Piper highlights:

  • Instant Booker feature embeds smart signatures and suggested meeting times in emails
  • Made specifically for sales teams
  • Two-way syncing with CRMs

Chili Piper downsides:

  • Only geared towards sales teams (leaves other teams to look for alternative solutions)
  • Only integrates with four CRMs (Salesforce, HubSpot, Pipedrive, and Microsoft Dynamics 365)

What Is Calendly?


Calendly is a scheduling app designed to eliminate all the back and forth via email when trying to find a time to meet with team members, prospects, clients, or anyone else.

Calendly highlights:

  • Provides scheduling page that can be sent via email or embedded on a site
  • Works for all types of teams
  • Wide range of integrations
  • Meeting polls to find the best time for group meetings

Calendly downsides:

  • Not tailored to a specific use (such as sales funneling)
  • May be overly simple for some types scheduling (like prospecting)

Calendly vs Chili Piper: A Closer Look

For our comparison of Chili Piper and Calendly, we rated the platforms in five categories: features, ease of use, integrations, customer service, and pricing.


Let’s kick off the features comparison of Chili Piper vs Calendly by looking at what they have in common. 

Both of these platforms share a major core functionality: they allow people to automatically book meetings in just a click or two. This is Calendly’s core feature, around which everything else is built.

As we mentioned earlier, Chili Piper is heavily tailored towards sales teams, so it has a lot of other features intended for streamlining sales funnels. 

One of these features is called Form Concierge, which is a tool for qualifying and routing prospects to the right sales reps.

chili piper form concierge

Since Calendly is intended for use by many different types of teams, it doesn’t have sales-specific functionality, but it does have other notable features, such as Meeting Polls. 

Calendly’s Meeting Polls allow multiple people to vote on the best time to meet, making it much easier to schedule team meetings and other kinds of group meetings without endless back and forth in a long email thread.


Winner in features: Tie

It’s too close to call a winner in this category, as both Calendly and Chili Piper have similar base features. Chili Piper may have more robust functionality for sales teams, but Calendly has more all-around-useful features.

Ease of Use

Although Chili Piper is a powerful booking tool, the UI isn’t always the most intuitive. It may take teams a while to get comfortable in the software, especially when using its more robust sales-related features.

Calendly, on the other hand, is incredibly fast to set up and get comfortable with. The user interface is simple and straightforward, and there’s no need to have any technical knowledge to jump right in.

Winner in ease of use: Calendly

Calendly wins in the ease of use category because it’s just so, well, easy to use! Reading other customers’ experiences with Calendly vs Chili Piper, it’s clear that Chili Piper is by far the most complex of the two.


Both Chili Piper and Calendly have many different integrations with everything from CRMs to team chat and email platforms.

What we found surprising was that, despite being a sales-oriented scheduling tool, Chili Piper only has integrations with four CRMs: Salesforce, HubSpot, Pipedrive, and Microsoft Dynamics 365. 

Calendly, which is not targeted only at sales teams, has an impressive 19 integrations with CRMs, including the same ones as Chili Piper and many more.

Winner in integrations: Calendly

Since Calendly and Chili Piper share many of the same integrations, Calendly wins this category simply by having a higher volume of integrations (100+).

Customer Service

Chili Piper and Calendly both have help centers on their respective websites, which are full of tutorials and other information to help users set up and navigate their products.

However, Chili Piper’s help center is equipped with a virtual assistant, making it easier to find what you’re looking for. And, if you can’t, the virtual assistant will connect you with the customer service department.

Calendly’s customer service is much more lacking. In fact, you can only find a support email embedded in the site’s terms of use. The only contact form on the site is for contacting sales, not customer support.

Winner in customer service: Chili Piper

Chili Piper is the definite winner in the customer service category. Chili Piper’s help center is more powerful and it looks easier to get in touch with the customer service team.


Calendly offers an always-free version, as well as various paid plans ranging from $8/seat/month to $16/seat/month. There is also special enterprise pricing available for teams of 30+ people.

Calendly pricing

Chili Piper will set you back $15/user/month for the Instant Booker feature alone. You have to pay for each of the other features, as well. So, for example, if you want access to the Form Concierge tool, you have to pay another $30+/user/month.

Chili Piper pricing

Winner in pricing: Calendly

Calendly beats Chili Piper in the pricing category by a landslide. As you can see from the numbers above, Chili Piper could get very expensive, very fast, especially if you want to give large teams access to all the different sales-related tools.

Chili Piper vs Calendly: Which One to Choose

When should I choose Chili Piper?

If you’re looking for an alternative to Calendly that has more robust functionality for sales-specific meeting scheduling, Chili Piper might be just what you’re looking for.

That being said, you shouldn’t necessarily choose Chili Piper if you’re looking for a scheduling solution that will also work for teams outside of your sales department, if your sales team doesn’t already use one of the supported CRMs, or if you are trying to keep expenses down.

When should I choose Calendly?

You should choose Calendly if you’re looking for a budget-friendly scheduling app that works across departments and is good for scheduling many different types of meetings. 

Keep in mind that you can still use Calendly for scheduling sales meetings and that it has many of the same integrations as Chili Piper, including with CRMs, plus many more.

The Bottom Line

Calendly and Chili Piper are two scheduling software solutions that have received generally positive reviews from users.

For simple meeting scheduling needs, Calendly is the more cost-effective, user-friendly, and versatile choice. 

But, for those with more sales-oriented needs, there’s a lot of additional functionality to be found in Chili Piper.

If you’re looking for something a little different than either of these tools, such as a WordPress booking plugin for a service-based business, we highly recommend trying out WEBBA Booking.

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