Using Calendly

Using Calendly

Calendly vs. Chili Piper: Which solution is better for you?


Sarah Henning

Sarah Henning
Jan. 11, 2022

Calendly vs Chili Piper blog header

To make the most of your time, you need good scheduling software. It reduces no-shows, prevents time zone mistakes, and most importantly, eliminates all the annoying back-and-forth emails involved in scheduling meetings.

Two of the most popular automated solutions are Calendly and Chili Piper. Here, you can compare these two apps including features, pricing, integrations, and ease of use.

Calendly vs. Chili Piper: A quick breakdown

Calendly and Chili Piper are both scheduling tools aimed at businesses. Users can hold multiple types of meetings via video conference, program in their availability so they never double-book, and more. Automated text and email reminders mean your prospects are less likely to miss their initial meeting. 

Since Calendly is more established, it has a larger customer base across many industries, so it’s going to feel more familiar to your employees and customers — especially those in recruiting, sales, customer success, and marketing. The newer Chili Piper is specialized for sales teams. However, some features may duplicate what already exists in CRMs, like Salesforce Lead Assignment, or in your tech stack if you use tools like LeanData or RingLead.

According to G2, Calendly’s users are spread out between enterprises, mid-sized businesses, and small businesses. Chili Piper’s user base is mostly mid-sized businesses with 500 to 999 employees. Due to Calendly’s robust teams functionality and Enterprise offerings, it has nearly 4 times more enterprise users than Chili Piper. Larger organizations like Lyft, Visa, Dropbox, and Ebay all count on Calendly's enterprise platform to automate processes and save time.


**Note: Be wary of comparisons on Chili Piper’s website, as they often fail to account for all the new features Calendly launched in recent years, many geared toward using Calendly on teams across entire organizations.** 

Features they share

Chili Piper breaks out its scheduling software separately and calls it Instant Booker. Both the Instant Booker and Calendly scheduling tools have robust feature sets. Let’s compare their most similar plans: Calendly’s Teams plan ($16 per seat) vs. the Instant Booker Hot plan ($25 per seat). Both allow users to: 

  • Automate meeting scheduling, notifications, and follow ups

  • Sync with calendar apps

  • Integrate with email platforms

  • Incorporate video conferencing platforms, such as Zoom, Google Meet, Microsoft Teams, and Webex

  • Connect to CRMs including Salesforce and Hubspot

  • Use APIs and web forms

  • Both companies offer browser extensions (Chrome and Firefox) and have web-based apps: Calendly has a mobile app (iOS or Android), as well. 

How Calendly and Chili Piper differ

Pricing comparison

Calendly and Chili Piper are both competitively priced. Calendly has always offered a free version with basic features, as well as a free trial of its paid plans. Chili Piper offers a free trial, but no free plans. 

Calendly’s pricing structure

  • Free plan: $0 per user, per month

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

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

  • Teams: $16 per user, per month when billed annually

  • Enterprise: varies, contact sales team

Here’s Calendly’s pricing table which details features available at each level. 

Chili Piper's pricing structure

You can purchase Chili Piper’s scheduling solution, called Instant Booker, separately or bundled with its additional sales tools. These are the prices just for Instant Booker:

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

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

  • Enterprise: varies, contact sales team

 Here’s Chili Piper’s pricing table which details features available at each level.

Tweet: "Please tell me why @chilipiper is soooooo much more expensive than @Calendly? Man $38 per month ... I thought @NetflixFR was expensive"

You’ll notice Chili Piper advertises advanced sales features like sophisticated lead routing and qualification. Those don’t live in Instant Booker. Those live in Chili Piper’s other modules like Concierge, which are separate purchases requiring a platform fee on top of higher fees per user. Even when you bundle, to get all the sales features Chili Piper advertises including Instant Booker’s functionality, the cost is at least $150 per month plus $40 per user per month. And that bundle doesn’t work unless you have Salesforce. Which takes us to our next major difference…

Why silo your sales team? 

Chili Piper has made a name for itself in the sales space, so most of its premium features were engineered for that field. The complication here is that many of Chili Piper’s advanced features only work in tandem with Salesforce. Where does that leave your employees who aren’t on revenue teams and don’t have Salesforce accounts? 

Calendly, however, was designed to work across the entire company, regardless of department or job function. Staff working on your other teams like accounting or engineering will find Calendly just as helpful.

Yes, Calendly has integrations including Salesforce, Hubspot, MailChimp, and Intercom, so it’s a great tool for sales, marketing, recruiting, and customer success and service teams. Calendly’s sales and marketing solutions let you contact leads quickly, making it more likely 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. 

When you look at Chili Piper’s list of integrations and Calendly’s lists of integrations, you’ll see Calendly integrates with 19 CRMs, while Chili Piper only integrates with 2 CRMs. Calendly also integrates with a longer list of apps used across your business, from Typeform to Pendo to Slack.  

What are customers saying? 

Looking at the data from sites like GetApp and G2, Calendly’s users 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. 

Tweet: "My god @Calendly where have you been all my life?! I might have been too proud in the past to admit it but my schedule mgmt needed help!"

Capterra gives Calendly a 4.7 with 1,730 reviews, as well as top performer and emerging favorite badges for scheduling software. The same site gives Chili Piper a 4.4 with only 87 reviews

Reviewers on both sites preferred doing business with Calendly overall. They also found Calendly easier to use, set up, and administer.

Ease of use

Reading customer reviews, it’s clear that adopting Chili Piper is more complex, which is possibly why the company offers extra customer service. One of the things customers praise the most about Calendly is its ease of use. 

One reviewer on TrustRadius, small business owner Dennis Normile, said he doesn’t know how he’d run his business without Calendly: 

User review: "I don't know how anyone that has appointments as a large part of their work could be efficient without Calendly."

Features: Pros and cons

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 and building in buffers mean you won’t overbook, and it can instantly sync with whatever calendar app you’re using, from Google to Outlook.


Chili Piper’s Instant Booker meeting scheduler features are similar to Calendly, with automatic scheduling and meeting links that prospects can use to set their meeting time. Some Chili Piper users have 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. Here are some other capability differences that may affect your decision: 

  • Apple compatibility: Both companies integrate with Google Calendar, Office 365, and Outlook, but only Calendly integrates with iCloud. Calendly also has built an iOS app

  • In-app payments: Because of its integrations with Stripe and PayPal, Calendly users can accept payment through the app. 

  • Room booking: Only Chili Piper allows you to book a physical room.

  • Polls: Calendly allows invitees to vote on the best meeting times.

Which is better for you? 

Both of these programs are powerful scheduling tools that help users reduce busywork and get their time back. 

With security measures just as strong as Chili Piper’s Instant Booking, essentially the same functionality, a lower price point, and more integrations, Calendly comes out on top in this comparison of scheduling software. 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.

The bottom line

You shouldn’t use Chili Piper’s Instant Booker 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 tons of calendars, email providers, and apps.

  • You don’t use Salesforce as your CRM.

And you shouldn’t use Calendly if:

  • You’re looking for scheduling software that will only be used by a large sales department that requires advanced lead routing.

  • You’re OK with committing to Chili Piper for the long haul. (Once you set up routing with them, it’s not portable. If you want to switch software, you’ll need to rebuild from scratch.)

  • Budget isn’t a concern.

  • Everyone in your company who needs automated scheduling software already has a Salesforce seat

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Sarah Henning

Sarah Henning

Sarah is a Managing Editor at Calendly, the perfect home for her obsession with words and compulsion to organize. Hobbies include spoiling her rescue dog and soaking up Nashville's live music scene.


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