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

To achieve your goals and make the most of your time, your company needs good scheduling software that automatically sends inbound leads to the right sales reps. 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.

The biggest difference between Calendly and Chili Piper? Known for its easy user experience, Calendly is designed for your entire company. Chili Piper is used primarily by revenue teams.

Calendly vs. Chili Piper: A quick comparison

Calendly and Chili Piper aren’t just booking links. They’re scheduling automation tools that help streamline processes for large, global companies. Example: For enterprise sales and marketing teams, both tools can integrate with website forms to qualify, route, and schedule sales meetings with high-value prospects instantly.

At the most basic level, appointment scheduling software helps users remove the back-and-forth from scheduling meetings. Scheduling automation should work with your existing tech stack so you can quickly book meetings from anywhere, avoid double-booking, reduce no-shows, and more.

Both of these companies have the basics down. But the differences become clear when you need to scale scheduling automation across your organization.

Calendly has nearly double the integrations, and they’re spread across a wider range of tools. Those integrations help you qualify leads faster, close more deals, retain more customers, hire top talent, and hit organizational growth goals.

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.

Since Calendly is more established, it has a larger customer base across many industries, so it’s going to feel more familiar to your team members and customers — especially those in recruiting, sales, customer support, marketing, and IT. 

The younger Chili Piper is specialized for revenue teams (sales and marketing) and customer success. But what about all those everyday scenarios where other teams are involved? Although Chili Piper now offers a ChiliCal Teams product that seems like it could be used by various teams across your org, it’s still very tailored towards revenue teams and described on their website as “smart scheduling links for revenue reps.”

So what happens in a scenario where your recruiting team needs to set up an interview with a job candidate that includes people from sales, HR, and product? Your recruiting team might end up buying a separate scheduling solution that better supports their needs and integrates with their ATS system, or they end up scheduling people manually.  Sounds like a costly and inefficient solution right? 

Scheduling platforms exist to bring people together faster, so before you buy, really think about who can benefit from time savings — just your revenue team, or the entire business? 

“When we presented [scheduling platform] options, Calendly was the one that was simultaneously the easiest to use and the friendliest. It had the best UX, but also, it was the thing that resonated with people the most: 'I like to work in this application.'”

Zlatko Unger

IT Director at Alation, Inc.

Features for individuals and small teams

If you’re a small business owner, both Calendly and Chili Piper have features to ease your day-to-day workload and help you get faster results. You can:  

• Automate meeting scheduling, notifications, and follow ups

• Sync with calendar apps such as Google Calendar and Office 365/Outlook

• Integrate with email platforms including Gmail and Microsoft Exchange

• Incorporate video conferencing platforms including Zoom, Microsoft Teams, and Webex

• Customize your booking links

• Embed your calendar link on your website

• Automatically detect your invitee's time zone, so the event added to their calendar reflects the correct time zone on your calendar and theirs

Calendly also lets you collect payments via Stripe or PayPal at the time of booking, and includes Meeting Polls, a feature similar to Doodle, that lets people vote on dates and times to find the best meeting time for a large group. Chili Piper doesn’t offer either. 

“Compared to our previous scheduling automation solution, Calendly’s user interface was a breath of fresh air. Calendly made it possible for us to shorten onboarding time for new team members to 30 minutes or less. It helps a new team member feel as if onboarding is not a burden.”

Cody Cooley

Manager, Customer Success at Criteria Corp

Features for sales and marketing teams

Calendly and Chili Piper have the potential to drive more pipeline, increase speed to lead, improve conversion rates, and ultimately bring in more revenue. Both allow users to: 

• Integrate with CRMs like Salesforce and HubSpot to autosync records, meeting info, and follow ups (including matching HubSpot contacts to account owners directly from lead routing forms)

• Instantly qualify, route, and book prospect meetings using your existing web forms in HubSpot, Marketo, and Pardot

• Shorten forms with Clearbit or ZoomInfo enrichment data

• Distribute meetings to sales reps in real time via round-robin scheduling, based on first available, equal distribution, or customized priority

• Keep your data secure and your organization compliant with enterprise-grade security features like SSO and SCIM

• Use APIs and connector tools like Zapier to further customize and automate your workflows

• Centralize billing and user management with customizable administrator features

• Identify actionable insights with scheduling analytics

“Within the first month of using Calendly, we jumped from 30% to 61% of leads scheduling a call.”

Sean McVey

Director of Demand Generation at Virtru

A quick note about routing: Chili Piper's routing features require that you create and connect third-party marketing forms. Calendly lets you create your own routing forms quickly and easily within Calendly — a great option for businesses that don't want to pay for third-party forms or need a quick way to create a landing page form with lead qualification, account matching, and scheduling.

Qualify, Route, and Book Sales Meetings Instantly

Fill pipeline faster and drive more revenue using scheduling automation.

Read the guide

What are the differences between Calendly and Chili Piper?

Functionality-wise, both platforms give you essentially the same features to automate processes for large revenue teams. The main differences?  Departmental solutions, integrations, and pricing. 

Calendly simplifies scheduling for every department, not just sales and marketing

When each team uses a different combination of tools, information gets siloed, and costs add up fast. Between Calendly and Chili Piper, only Calendly provides a single scheduling platform that can standardize and scale across the entire business, so you don't have to manage — or pay for — different apps for each team.

When all users in your organization work from the same platform, admins can align all users with company standards and best practices. Managed Events let admins create, assign, and templatize the meeting types teams use, so everyone stays up-to-date and on-brand. Central governance means you can instantly distribute critical updates.

Plus, Calendly’s department-specific solutions are designed to help teams meet their goals — from revenue teams closing high-value deals to recruiting teams looking to  reduce time-to-hire. Here are some examples that go beyond Chili Piper’s focus on sales and marketing:

• Recruiting: Increase candidate pipeline, book more interviews, and fill roles faster by automating interview scheduling with Calendly. Calendly integrates with recruiting tools like Greenhouse and JazzHR, making it easy to manage and sync candidate info.

• Customer success: Improve customer retention, growth, and satisfaction by empowering customers to self-schedule troubleshooting, training, and contract renewal calls.

• Financial services: Highly regulated sectors like financial services have unique compliance and audit needs. Calendly for Enterprise is one of the only scheduling platforms that can create a trackable, auditable record of all email and SMS communications sent from your account, so you're audit-ready.

Learn more about Calendly’s use cases across industries and departments.

Calendly offers a wider variety of integrations for teams across the business 

Chili Piper has made a name for itself in the sales space, so most of its premium features and integrations are designed 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 don’t have Salesforce accounts? 

Calendly connects with the tools used across your organization — not just on sales and marketing teams. Some of Calendly’s 100+ integrations include:

• Sales and marketing tools (HubSpot, Salesforce, Marketo, Gong)

• Recruiting software and ATSs (Greenhouse and JazzHR)

• Collaboration and project management (Slack and Microsoft Teams chat)

• Payment processing (Stripe and PayPal)

• Workflow automation (Zapier and Microsoft Power Automate)

Here’s a complete list of Calendly integrations and Chili Piper integrations.

Calendly vs. Chili Piper pricing

Another big difference between Calendly and Chili Piper? Pricing. 

Both Calendly and Chili Piper offer a “free forever” version with basic features. Calendly offers a tiered pricing model, where each level offers additional features for a gradually increasing price per seat, as shown below.

Here’s Calendly’s pricing table:

• Free plan: $0/user/month

• Standard: $10/user/month (billed annually)

• Teams: $16/user/month (billed annually)

• Enterprise: Custom pricing starting at $15K per year

On the other hand, Chili Piper’s pricing is a bit more complicated. Chili Piper offers 5 core products: ChiliCal Teams, Concierge, Chat, Distro, and Handoff. 

ChiliCal Teams includes basic scheduling functionality and can be used alone for $15/user/month. In order to leverage any routing functionality, customers must purchase either Concierge, Chat, Distro, or Handoff, depending on their routing needs. 

Each product is $30/user/month — plus a platform fee: 

Here’s Chili Piper’s pricing table:

• Concierge: $30/user/month + platform fee of $150 - $1,000 per month 

• Chat: $30/user/month + platform fee of $1,000 per month 

• Distro: $30/user/month + platform fee of $150 per month 

• Handoff: $30/user/month + platform fee of $150 per month 

So what does this mean? If you’re looking to qualify and route leads coming from your website forms but you also want the ability to book on behalf of other team members, then your team will most likely need to purchase both Concierge and Handoff. 

Chili Piper does offer bundled pricing, which helps bring the price down a bit, and you’ll only pay one platform fee. But here’s the kicker: The highest platform fee is applied and you still have to pay per user per product per month. This means that if you’re team needs access to both Concierge ($25/user/month bundled) and Handoff ($25/user/month bundled), then you pay $50/user/month PLUS the higher platform fee, which could be up to $1,000 per month for Concierge, depending on how many inbound leads you get on your website. 

The other kicker? Some of Chili Piper’s platform fee for Concierge charges based on volume —  the number of inbound leads that are submitted each month via your website. That means that the more people who fill out your online form, the larger the “platform fee” you’re charged (up to $1,000 per month). You pay whether those leads are qualified, unqualified, or junk. That price could vary wildly depending on your campaigns and seasonality. 

Calendly’s pricing is simple: You’re only paying per seat. On the pricing chart, what you see is what you get, and your pricing won’t vary from month-to-month based on your website engagement. 

Which solution is better for you? 

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

With essentially the same functionality, a lower price point, more use cases, and more integrations, Calendly comes out on top in this comparison of scheduling automation software. Unlike Chili Piper, Calendly can be scaled and standardized across your entire organization. And a much broader user base for Calendly means your customers are more likely to be familiar with the platform and, as a result, have an easier time working with you.

You shouldn’t use Chili Piper if:

• You’re looking for a tool that will be useful for employees and departments outside your sales and marketing teams.

• 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 don’t need a scheduling solution that works across teams. 

• 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 or HubSpot seat.

See how more than 100,000 companies simplify scheduling and delight their customers. Request a Calendly demo.