Calendly vs Chili Piper: Which One Is Better?

Calendly vs Chili Piper: Which One Is Better?

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Calendly and Chili Piper are business scheduling tools. Making a comparison of them is not as easy as it seems.

Both are outstanding schedulers with excellent features. They are very similar but there are slight differences.

Chili Piper’s design is especially useful for sales teams.

Calendly is a multipurpose scheduler and is also useful for commercial businesses. Calendly’s flexibility makes it attractive for a wider audience.

Below you will find a more detailed look into this comparison of Calendly vs Chili Piper.

Calendly vs Chili Piper – A Brief Overview



The Calendly scheduling software is perfect for organizing and managing meetings and appointments.

The design works great for individuals and multi-person organizations. Users can display their availability and manage recurring tasks.

Calendly no longer uses email and phone tags to schedule appointments, interviews, calls. Instead, customers can log in right away.

The setup of Calendly is very straightforward. Make an account from your browser and link a third-party calendar.


This platform supports Google Calendar, iCloud, Office 365, and Outlook.

The free plan allows you to set up one event type. To set up multiple event types you will have to purchase a paid plan.

Calendly has an automatic reminder and confirmation function. Guests will receive these reminders to maximize retention.

There is a version for desktop computers, tablets, and smartphones.

Chili Piper

Chili Piper

The second scheduling software, Chili Piper, aids users in making and managing appointments. It uses inbound lead conversations to extract incoming appointments.

You can schedule appointments from chats, emails, Microsoft Teams, web forms, and more.

This robust platform takes many scheduling tasks off your hands. It also works well in a variety of circumstances.

This shows that it is much more than a calendar or scheduler.

Chili Piper supports B2B companies and sales teams, helping them to improve customer satisfaction. This has a beneficial effect on conversion rates and team productivity.

It allows users to review their appointments and also to start phone calls right from the app. Based on predefined settings, it reviews and assigns leads to different team members.

It also has more common features, like calendar management, meeting room booking, and online booking.

User Base

User base is the first point of comparison in this Calendly vs Chili Piper review.


User Base - calendly

Calendly has users from many different backgrounds. They range from students to local businesses and consultants.

The platform helps to organize individual calendars. It further enables small teams to work together.

Users can apply Calendly in a variety of industries:

  • Computer software
  • Education
  • Marketing and advertising
  • IT

Within those industries, it is useful for those in consultancy, customer service, and human resources.

It seems that a wider variety of people use Calendly than Chili Piper. They find that Calendly improves their workflow and makes it more efficient.

Chili Piper

User Base - Chilli Piper

Chili Piper, has a more focused user base, mainly in sales and revenue teams.

A notable feature is the scheduling of mass meetings with potential leads. It works fast and seamlessly.

The majority of the sales and revenue teams are in:

  • Internet technology
  • IT
  • Software

Chili Piper’s features are most useful for those that schedule recurring meetings. It helps them to be ready for their meetings and avoid wasting time.

Chili Piper offers subscriptions at the business level. Calendly only has individual subscriptions.


An important consideration when comparing Calendly vs Chili Piper is pricing.

Calendly offers a free plan and includes a free trial with its paid options. However, both platforms offer attractive pricing plans.

Calendly’s pricing structure

Calendly’s pricing structure

Calendly’s premium plans are a little cheaper than Chili Piper and other scheduling options. There are free plans available and the paid plans have attractive pricing.

Their main selling point is the low prices rather than the features.

  • Free plan. $0 per month per user
  • Premium. $8 per month per user when billed annually
  • Pro. $12 per month per user when billed annually

The Enterprise plan has a per-person rate. It includes advanced control, advanced security, and technical support.

Chili Piper’s pricing structure

Chili Piper’s pricing structure

At this moment, Chili Piper has two plans. Billing is either monthly or annually, with the annual price being cheaper.

Chili Piper’s plans each offer a monthly and annual price. Chili Piper’s pricing is based on the platform fee and a base user fee.

  • Spicy plan: $15 monthly per user when billed annually
  • Hot plan: $25 monthly per user when billed annually


For some, this section may be the most important part of the Calendly vs Chili Piper comparison.


Calendly is a simple, straightforward scheduling tool with the most important features. Users value the quality of service and the free features it offers.


Calendly features

  • Most important features included in the free version
  • Full version for $12 per month
  • Sales and marketing solutions help to contact leads fast. That ensures that you are able to book meetings with them and convert them into customers
  • Meeting reminders for participants
  • Customizable branding. Users can add their company’s logo and design to emails
  • Personal booking links for users

Calendly paypal integration

  • Integration with PayPal and Stripe. Users can receive payments through the app
  • Detailed reporting features
  • The many other integrations allow for full customization to fit your needs. There are more than 80 integrations with other applications

Calendly buffer

  • Rescheduling and reassignment by meeting participants
  • Set buffers between meetings to assign time for other tasks
  • Assignment of date ranges and time frames for meetings


Calendly attendance

  • Calendly doesn’t have data reporting on meeting attendance and conversion rates. Most sales teams will find this a gap in the features it offers
  • The round-robin routing is too simple. It does not take ownership, cancellations, vacations, seniority, etcetera into account
  • Double forms. Before creating a form in Calendly many teams have to make a separate form. That results in loss of time and, potentially, leads

Chili Piper

Chili Piper meeting

Chili Piper’s features focus on the needs of marketing and sales teams. This scheduling software has gained a lot of popularity in these fields.

It is a robust tool but it is still easy to use. It will find particular use in large teams and complex organizations.

Chili Piper asks for more technical skills when it comes to integrations.

The scheduling abilities of Chili Piper are very similar to Calendly’s. Users can activate the automated scheduling feature.

Your clients will receive personal meeting links. Using these they can add the event to their personal calendars.


Chili Piper tracking

  • Sales protect tracking. Other lead management features are call reporting and routing
  • Full automation
  • Shown to accelerate revenues under varying circumstances
  • Automatic qualification of meetings and inbound leads. The user can set and customize qualification criteria

Chili Piper time booking

  • Customizable lead routing and booking. The configuration works in real-time
  • Prospects can schedule meetings with a single click. That starts a sequence of reminder emails right until the start of the meeting

Chili Piper salesforce integration

  • Integration with Salesforces and many other applications
  • Fortune 100 corporations are among Chili Piper’s satisfied customers
  • The price levels make it accessible for startups and other companies with a tight budget


Chili Piper cons

  • No feature that prevents you from overbooking your calendar
  • Easy integration, but startup takes a long time
  • Calendar syncing is not always accurate. Users need to manually verify that all appointments are transferred correctly.


Next in this comparison of Calendly vs Chili Piper is a closer look at the security of these platforms. Now that so much of our work takes place online, it is important to know whether our data is safe.

Both Chili Piper and Calendly have security measures that ensure that online interactions are private.


calendly security

Calendly has several features that ensure secure working.

  • Zero knowledge. It does not save any identifiable personal information from the associated calendars. It does not store contact details and it does not record meeting participants.
  • Secure authorization. It uses a secure OAuth connection for syncing calendars. One aspect of this security measure is that it never saves or reads password information.

Calendly encrypts connections with iCloud Calendar.

  • Zero email access. Calendly never accesses personal emails or address books. Only the designated recipients will read the emails sent and received through Calendly.
  • Encryption. Calendly encrypts all the data that it handles. That is true for information that it sends, receives, and stores.

It employs TLS SHA-256 with RSA encryption for data traffic between the browser and the platform server. Calendly uses HTTPS for all data transactions.

Chili Piper

chillipiper security

Chili Piper, too, uses current data security measures to protect information. It uses a secure OAuth connection to interact with Google Calendar and others.

Like Calendly, all data that Chili Piper handles is encrypted. That is true for information that it sends, receives, and stores.

It employs TLS SHA-256 with RSA encryption for data traffic between the browser and the Chili Piper platform server. Chili Piper uses HTTPS for all data transactions.

This scheduling software hosts information in secure databases and offers additional privacy options.

The Chili Piper website has a special security section. This section shows in detail what Chili Piper’s security measures are and how they work.

Final thoughts on Calendly vs Chili Piper

Chili Piper and Calendly are both robust and modern scheduling tools. Both save time, increase productivity, and improve other aspects of work culture.

The Calendly vs Chili Piper comparison has been challenging because of their similarities. Both Calendly and Chili Piper are highly recommended as calendar tools.

Calendly is most suited for individual users and Chili Piper is best for teams. Chili Piper focuses on sales teams that handle many meetings with potential leads.

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If you enjoyed reading this article with Calendly vs Chili Piper, you should read this one on Calendly alternatives.

We also wrote about a few related subjects like Appointy vs Acuity, alternatives to Doodle, Doodle reviews, Honeybook reviews, Thryv reviews, Acuity Scheduling reviews, and Housecall Pro reviews.

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Milos Timotic
Milos Timotic

Technical Lead