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Calendly vs. Chili Piper

If you’re in the market for scheduling software, you may be considering Calendly vs. Chili Piper. 

This comprehensive comparison guide will tell you everything you need to know in order to confidently make the best decision.

If you’re interested in skipping the article and simply scheduling a demo call, you can do so quickly and easily here

Calendly vs. Chili Piper: 1 Minute Summary

Calendly and Chili Piper are both scheduling tools with similar core features. 

  • Calendly is ideal for individual users who want a simple tool for scheduling calendar appointments. 
  • Chili Piper is best for teams, especially sales teams and success teams, who want to convert leads into meetings instantly using high-powered automation and qualification rules. 

To restate: 

  • If you’re a single user who wants a simple calendar scheduling tool, Calendly is a good option.
  • If you’re part of a team who wants a scheduling tool that is ultra-powerful, robust, and feature-rich, Chili Piper is your best option.

If you are considering Calendly vs. Chili Piper your next step should be scheduling  a demo with a Chili Piper rep. It’s quick, easy, and will help you answer all the questions that are specific to your business, your situation, and your needs. 

Go ahead and schedule your demo now. 

For a deeper dive, here are the details.

Calendly vs. Chili Piper: What Are the Main Differences? 

There are a few other products that users might consider in addition to Calendly.

You can read about them here.

However, Calendly is the most widely used schedule tool according to our research.

  • Calendly is a simple, basic tool for calendar scheduling. Some of its features are free. 
  • Chili Piper is an easy-to-use but high powered scheduling tool that can support large teams, complex routing solutions, and sophisticated integrations. 

Let’s walk through the main differences. 

Here’s What You Need to Know about Calendly

Calendly is one of the most well-known scheduling tools — like Taylor Swift, or Beyoncé are in music. They were an early solution in the space, and have carved out a large brand presence for themselves. 


calendly vs. chili piper

Calendly’s User Base

According to market research, Calendly’s user base consists of the following:

  1. Individuals — consultants, students, part of a business that doesn’t have a company-wide calendar solution
  2. Small teams — often it’s a few sales reps or even an individual sales rep who has used the basic free version of Calendly 

Calendly also appears to be targeting the following verticals:

  • Education
  • Human resources (recruiting)
  • Customer success
  • Consultants

Calendly is Cheap

Calendly competes on price rather than features.

  1. They have a very basic version (free)
  2. Premium version: $8/month
  3. Pro version: $12/month 

What are Calendly’s Main Features?

Good Features of Calendly

  • Bare-bones basic version at no cost. $12 for the full-feature version. 
  • Allows for round-robin meeting distribution
  • Users receive personal booking links
  • The platform sends reminders to meeting participants
  • Meeting participants can reschedule and reassign 
  • Payment processor integrations to collect payment up front

Negative Features of Calendly

  • Can only push data from Calendly to Salesforce, not vice versa
  • Does not provide data reporting on conversion rates or meeting attendance, which is essential for a high-functioning sales team
  • Simplistic round-robin routing. Cannot account for ownership, vacation, cancellation, lead scoring, seniority, etc. 
  • Double forms — Teams implementing Calendly often have to create a form before the Calendly form, creating massive friction and losing a high percentage of potential leads
  • Any website visitor can book – Calendly cannot qualify inbound prospects in real-time, so anyone can book a meeting on your website, even if they’re a bad fit 
  • Calendly does not support recurring meetings

What are Chili Piper’s Main Features?

Good Features of Chili Piper

  • The scheduling software is fully automated. Once integrated and set up, Chili Piper manages the entire customer lifecycle. 
  • Inbound leads and meetings are automatically qualified based on criteria that you can create and customize
  • You can configure Chili Piper to qualify, route, and book leads, all in real time. 
  • Prospects can schedule with a single click, automating a sequence of reminders, emails, right up until the meeting starts with an SDR or AE. 
  • Chili Piper integrates with your existing tech stack, starting with Salesforce and dozens more. 
  • Chili Piper’s integration with Salesforce is seamless and powerful, making two-way data transfer between the apps a breeze. You can track and sync every stage of the meeting process – bookings, meetings held, no-shows, reschedules, and cancellations, all safely stored in Salesforce. 
  • While Chili Piper is used by Fortune 100 mega corporations, it has a price point that makes it accessible to lean budget-strapped startups, too.

Other Differences Between Chili Piper and Calendly

  • Chili Piper can accommodate enterprise-level customers, whereas Calendly services individuals and SMBs
  • Chili Piper is a robust revenue acceleration tool with multiple use cases. It’s not just a calendar or meeting scheduling tool.
  • For complicated use cases, routing rules, and multiple integrations, setting up Chili Piper is pretty simple, but can take some initial setup energy.


Chili Piper is a full-orbed solution for revenue teams that want a powerful and seamless tool to book and close leads faster. 

That being said, it’s not for every revenue team, just as Calendly is not a suitable solution for Salesforce powered revenue teams who want to work fast and with power. 

Chili Piper has the highest adoption rate and usefulness for B2B companies, especially businesses that want to increase inbound conversion rates by making it easy for prospects to book meetings directly on their website. 

For the best insight into businesses that have benefitted from Chii Piper, check out these case studies. 

Do NOT use Chili Piper If These Things are True

Bottom Line: Don’t use Chili Piper if you 1) are a single user, 2) looking for a low- or no-budget solution, and 3) you aren’t using Salesforce. 

  • You’re a single user (no team) who just wants to allow meeting scheduling
  • You don’t want to spend money
  • You are not using Salesforce

Do NOT use Calendly if These Things Are True

Bottom Line: Don’t use Calendly if you are 1) using Salesforce, 2) have a sales team, and 3) want power and sophistication with your scheduling software.

Calendly simply can’t keep up. 

Do not use Calendly if…

  • You want to allow users to schedule demos instantly on your website
  • You want to offer a true one-click booking experience, with no unnecessary friction
  • You want to book recurring meetings, like a monthly check-in or training
  • You have more than five sales reps
  • You want to qualify leads as they come in, rather than waste your sales team’s time with unqualified leads
  • You need sophisticated routing, more than a simple round-robin. For example, you want to avoid snafus like a meeting getting scheduled with a rep who’s on vacation. 
  • You want full integration with Salesforce and your calendar solution — both talking to each other. For example, you want to be able to transfer information from SFCD to your scheduling tool and vice versa. 
  • You want to allow handoff meetings, say from an SDR to an AE in real time. These are often hot qualified leads who want to get started

What Do Users Say Who Have Experience Using Both Calendly and Chili Piper?

Ben who works in marketing at Emotive shared with us his experience of trying to use Calendly for their sales and revenue team.

His team was using, or trying to use Calendly to allow sales reps to schedule calls. In Ben’s words, “It was a disaster.”

The source of the frustration was the amount of manual work that it required. Calendly simply isn’t equipped to seamlessly schedule sales demos, especially when the team relies on Salesforce. 

The solution to the frustration was…

  • Discontinuing with Calendly
  • Switching to Chili Piper
  • Using Chili Piper’s instant booking solution 

You can read up on Ben’s story, or just check out the video. It’s very helpful for users who may be considering Calendly vs. Chili Piper.

The net effect of using Chili Piper instead of Calendly was the following:

  • 80% conversion rate from inbound lead to meeting booked. (If you’re not familiar with industry-standard conversion rates, that is huge.)
  • Increased speed to lead by eliminating steps and automation qualification, something that Calendly simply doesn’t allow.


The best way to make the most informed decision regarding Chili Piper is to schedule a demo. If this article has raised detailed questions, our sales team is fully equipped and eager to answer any and all of the questions you may have.

Schedule a demo now.