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Calendly vs. Chili Piper

Ty Collins, September 02, 2020

Whether you’re a freelancer, a recruiter, or simply need to book regular appointments, good scheduling software can make your life a lot easier.

Since you’re likely shopping around for scheduling solutions before you commit (as you should), you’ll have noticed that two of the most popular scheduling tools are Calendly and Chili Piper. 

This guide will help you understand the features of each app so you can pick the right one for your business.

Calendly vs. Chili Piper: quick breakdown

Calendly and Chili Piper are both scheduling tools aimed at businesses. Their feature sets are similar, although Chili Piper is designed to be used by sales teams. Calendly can be used for that purpose, but it’s adaptability makes it accessible to a wide range of users beyond the sales department. 

According to G2, most of Calendly’s users are spread out between small businesses, mid-sized businesses, and enterprises, with most of the users being in the small business category. Chili Piper’s user base is mostly mid-sized businesses with between 500 and 1,000 employees. Calendly appears to have more enterprise level users than Chili Piper, according to G2’s data


Both of these scheduling tools have robust feature sets. Calendly and Chili Piper allow users to: 

  • Utilize APIs

  • Use automated scheduling

  • Get automatic notifications

  • Sync with other calendar apps like Google Calendar

  • Get mobile alerts

  • Integrate their scheduling with email

  • Use web forms

All of these features are useful, but there are areas where Calendly provides a little extra. 


While it originally focused on functions aimed at streamlining interview bookings, Calendly has grown into a powerful tool for a variety of other purposes. Users can hold multiple types of meetings via video conference, program in their availability so they never double-book, and more. 

Calendly’s sales and marketing solutions, for example, let you contact leads quickly, making it more likely that you’ll book meetings with your leads and convert those leads into customers. Embedded scheduling links in your emails let prospects easily schedule the meeting time that works best for them. 

Calendly offers customizable branding so businesses can add polish to their emails and unify their brand persona across communication channels. Automated text and email reminders mean your prospects are less likely to miss their initial meeting, making the onboarding process easier for everyone. 

Because of its integrations with Stripe and PayPal, Calendly users can accept payment through the app. Calendly also gives users access to detailed reporting features. 

Dozens of other app integrations make for a variety of customization options to fit your team’s needs. Calendly integrates with over 80 other apps, including: 

  • Gmail

  • Freshbooks

  • Salesforce

  • PayPal

  • Zoom

  • Hubspot CRM

  • HoneyBook

  • Stripe

  • Outlook

  • MailChimp

Calendly’s strength is in its scheduler. Embedded website or email links make it easy for people to pick their appointment time. Programming in your availability means you won’t overbook, and it can instantly sync with whatever calendar app you’re using, from Google to Outlook.

You can even set a buffer between meetings or establish specific date ranges and time frames in which individual meetings can occur in order to save time for other tasks. 

Chili Piper

Chili Piper has made a name for themselves in the marketing space, and most of their features revolve around that field. For example, Chili Piper gives users a few different lead management features to track sales prospects. The app also gives users access to call reporting and routing.

Some of Chili Piper's other useful features include:

  • Booking management

  • Email marketing management

  • Room booking 

  • Sales integration

  • Automatic lead distribution

Chili Piper’s meeting scheduler features are similar to Calendly’s, with automatic scheduling and meeting links that prospects can use to set their meeting time. It does not appear, however, that Chili Piper has any features in place to prevent overbooking. 

Some Chili Pepper users have also noted that calendar syncing isn’t always accurate, so keep that in mind if you’re looking for a scheduling solution that’ll help you easily sync your calendar across devices. 


Both Calendly and Chili Piper are competitively priced. Calendly has always had a free plan and free trial of its paid features available, and Chili Piper recently introduced the same options for its users.

Calendly’s pricing structure
  • Free plan: $0 per user, per month

  • Premium: $8 per user, per month when billed annually

  • Pro: $12 per user, per month when billed annually

Chili Piper’s pricing structure
  • Free plan: $0 per user, per month

  • Spicy plan: $15 per user, per month when billed annually

  • Hot plan: $25 per user, per month when billed annually

Overall, Chili Piper is more expensive than Calendly. While it’s not by a large margin, it’s still something to consider if you’re on a budget. 

Chili Piper also offers extra services at the Hot level — $300 per month and $525 per month for concierge form scheduling and call routing services. To get the most out of their services, you’d have to pay for add-ons and modules.

Customer reviews

On TrustRadius, Calendly received a 9.2/10 and Chili Piper received a 7.9/10. Calendly and Chili Piper both received a 4.5/5 rating on G2, with Calendly exceeding Chili Piper’s score in a variety of online marketing tool ranking criteria, including ease of use. 

Calendly also ranked 4.6/5 on GetApp with over 1,200 reviews, and is a top-rated app on TrustRadius in the appointment scheduling category. One reviewer on TrustRadius, photographer Dawn Rabinowitz, said of Calendly:

“As a small shop operation, I can work as though I have a bigger team. I can be responsive to the needs of my customers with regard to scheduling and the integrations with other application[s] makes all the difference. The mobile app is also easy to use and versatile. For a business that is based on scheduled appointments, this is the go-to app for any company.”


With more and more of our business conducted online, everyone wants to know what measures are being taken to keep their data secure. Both Calendly and Chili Piper implement security measures to keep online interactions safer. 


Some of the steps Calendly takes to keep user data secure include: 

Zero knowledge

Calendly never stores personally identifiable information from your connected calendars. That means no contact information gets stored, and meeting participants don’t get recorded. The notes that meeting participants make also don’t get stored. Calendly only uses data from connected calendars to prevent double booking and determine when you’re available.

Secure authorization

Calendly uses a secure OAuth connection when syncing with your calendars. That means it never stores password information or reads it, and iCloud calendar connection passwords are encrypted. 

Zero email access

Calendly also never accesses your email or address book. Emails you send and receive with Calendly don’t get read by anyone but the people they’re meant for. 

Read more on the detailed measures Calendly takes to protect customer data here

Chili Piper

Chili Piper also uses some of the latest security measures available to protect customer data, including a secure OAuth connection between Chili Piper and connected calendar apps. 

Other steps they take to enhance security include:

  • Hosting data in secure databases

  • Using encryption

  • Offering users privacy options

Chili Piper also has a detailed section on its website breaking down the security measures the company has in place to protect data (though there are no white papers).

Customer base

Calendly’s users, upon looking at the data from sites like GetApp and G2, appear to be spread out over a wider number of industries than Chili Piper’s. Customers ranging from freelancers all the way up to the enterprise-level executives are using Calendly to improve their workflow and get more done, more efficiently. 


Industries Calendly serves according to G2 data include:

  • Computer software

  • Marketing and advertising

  • IT 

  • Education

Calendly’s adaptability makes it an ideal app for professionals in any industry. In fact, more than half of Calendly’s users categorized their industry as “other.”

Chili Piper

G2 found that most of Chili Piper’s users work in the following fields:

  • Computer software 

  • Internet technology

  • IT

Computer software users make up the largest segment of Chili Piper’s user base at just over 41%.

Which is best for you?

Both of these programs are powerful scheduling tools that take security seriously and offer their users options to improve their work. 

With security measures just as strong as Chili Piper’s, the same essential functionality, and many more integrations, Calendly comes out on top in this comparison. A much broader user base for Calendly also means that clients are more likely to be familiar with the platform and have an easier time working with you as a result.

Bottom line: you shouldn’t use Chili Piper if

  • You’re looking for a tool that will be useful for employees and departments outside of your sales team

  • You’re trying to minimize expenses

  • You don’t want to make your clients use an unfamiliar scheduling program

  • You’re looking for a software solution that can easily integrate with other apps

And you shouldn’t use Calendly if

  • You’re looking for scheduling software that will only be used by a large sales department

  • You’re primarily interested in scheduling recurring meetings and don’t need extra features or integrations

If you’re still undecided and want to see Calendly in action, get in touch to schedule a live demo and we’ll show you what our app can do.

Ready to explore what Calendly can do for you? Sign up for free today.

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Ty Collins biography
Ty Collins

Ty is a digital marketing leader, content management expert, and Calendly alum.

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