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 appropriate 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 was built only for revenue teams, which silos them from the rest of your organization.

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? 

For example, you might need to set up an interview with a job candidate that includes people from sales, HR, and product. So then what happens? You buy separate scheduling solutions tailored for other teams, or end up scheduling people manually. Managers know all too well that team silos lead to inefficiencies and miscommunications that cost the company ROI.

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.

Calendly vs. Chili Piper: Features for individuals and small teams

Keep in mind Chili Piper has a minimum license requirement for each of its plans. For example, you must buy at least five licenses to use their most basic Instant Booker plan. That immediately rules out Chili Piper for individuals and solopreneurs like consultants and lawyers.

But 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, including: 

• 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 (Calendly also has iCloud Mail)

• Incorporate video conferencing platforms including Zoom, Microsoft Teams, and Webex (Calendly has Google Meet, Chili Piper has Google Hangouts)

• 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

Calendly vs. Chili Piper: Features for enterprise and revenue 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, based on first available, equal distribution, or customized priority

• Ensure security with 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

• Provide analytics to help you identify actionable insights

“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

Functionality-wise, both platforms give you essentially the same features to automate processes for large revenue teams. The main difference for revenue teams? Integrations.

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.

Both Calendly and Chili Piper offer native integrations with marketing industry leaders, Marketo, HubSpot and Pardot, if you already use those platforms. Both integrate with Salesforce, but Chili Piper is the only option for Salesloft users.

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

Qualify, route, and book sales meetings instantly

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How Calendly and Chili Piper differ

When each team uses a different combination of tools, information gets siloed, and costs add up fast. 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 closing high-value deals to reducing time-to-hire — while delighting customers and candidates. Here are some examples that go beyond Chili Piper’s purview of sales and marketing.

Recruiting: Increase candidate pipeline, book more interviews, and fill roles faster

Both Calendly and Chili Piper can offer your recruiting team basic automations for setting up interviews. But only Calendly is built to solve complex scheduling puzzles unique to recruiters, such as building multi-day person and multi-day interview schedules. 

Through integrations with ATS and tools like Greenhouse, JazzHR, and RoboRecruiter, you can manage candidate and interviewer data, and use load balancing to distribute workload evenly. And thanks to Calendly’s Linkedin Messaging integration, you can schedule candidate meetings or follow ups without leaving LinkedIn. A study conducted by Forrester Consulting found that recruiting teams achieved a 26% shorter recruiting cycle with Calendly.

Customer success: Improve customer retention, growth, and satisfaction

Use team pages to empower customers to select from several options to meet with CS, whether they need tech assistance, have a pricing question, or want to schedule user training.

Calendly’s workflows help automate, standardize, and manage communications before and after meetings. Plus, you can automatically update customer records with meeting info using CRM integrations, including Salesforce, HubSpot ActiveCampaign, and Close. 

The results? Higher customer satisfaction, more retention, and less churn. A report on the Total Economic Impact of Calendly found that Calendly drove a 1.5% increase in customer renewal rates, boosting annual profits by $180,000.

With Calendly, HackerOne’s customer success team realized 169% ROI, booked 114% more meetings, and saved 588 hours on scheduling in a 12-month period. The CS team uses that reclaimed time to deliver more enablement training and collaborate better with cross-functional teams.

The Total Economic Impact™ of Calendly

A study conducted by Forrester Consulting found that Calendly provided customers a 318% ROI over three years. Read the full study for real customer insights about the benefits of using Calendly.

Financial services

When employees use software to interact with prospects and customers, companies don’t always have easy access to that communications data. This is a special concern for sectors like financial services, which 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 are audit-ready and can stay compliant with SEC and FINRA recordkeeping requirements for client communications. Calendly follows FINRA and GLBA guidelines, and meets the compliance needs of trusted financial service companies such as Modern Woodmen of America, CI Assante Wealth Management and Buckingham Wealth Partners.

Pricing comparison

Most SaaS companies don’t publish their enterprise pricing because every enterprise plan needs to be tailored to an organization’s needs: Calendly is different, and publishes a baseline price for Enterprise. If you need advanced features or are buying dozens of seats, definitely talk to a sales rep. But still read this section, because it reflects how the companies think about pricing. 

Calendly has always offered a “free forever” version with basic features, as well as a free 14-day trial of its paid plans. Chili Piper offers a free trial, but no free plans. 

Both Calendly and Chili Piper have a tiered pricing model, where each level offers additional features for a gradually increasing price per seat.

Here’s Calendly’s pricing table:

• Free version: $0 per user, per month

• Standard: $10 per user, per month (billed annually)

• Teams: $16 per user, per month (billed annually)

• Enterprise: Starts at $15,000 per year

Here’s Chili Piper’s pricing table:

• Instant Booker: $15 per user, per month when billed annually

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

• Form Concierge: $30 per user, per month when billed annually

• Form Concierge + Concierge Live: $60 per user, per month when billed annually

• Distro: $30 per user, per month when billed annually (note: you must purchase one of the plans above to add on Distro)

Here’s Chili Piper’s pricing table:

• Instant Booker: $15 per user, per month when billed annually

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

• Form Concierge: $30 per user, per month when billed annually

• Form Concierge + Concierge Live: $60 per user, per month when billed annually

• Distro: $30 per user, per month when billed annually (note: you must purchase one of the plans above to add on Distro)

What are the big pricing differences?

Think of Chili Piper like a discount airline: The flight price might look OK at first, but that’s before you add in fees for luggage, choosing your seat, etc.

Chili Piper tacks on fees for volume: The more people who fill out your online forms, the more “platform fees” you’re charged. You pay whether those leads are qualified, unqualified, or junk. That price could vary wildly depending on your campaigns and seasonality. 

Also, Chili Piper’s Distro tool isn’t included in any plan: It’s an add-on with an additional cost per seat. So if you want to instantly qualify, route, and assign leads, you’ll need to budget for that extra expense. 

With Calendly, 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. 

And Chili Piper doesn’t provide great ROI unless you also pay for 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 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 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. Embedding your availability in your emails lets prospects easily schedule the meeting time that works best for them. Easy scheduling is a major time saver — to the tune of more than 9,000 hours saved on external meeting booking over three years.

When you look at Chili Piper’s list of integrations and Calendly’s lists of integrations, you’ll see Calendly integrates with more CRMs and with a longer list of apps used across your business, including Monday.com, Gong, Typeform, and Notion.

What do customers say about Calendly vs. Chili Piper? 

Looking at data from sites like Capterra, GetApp and G2, Calendly’s users are 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 use Calendly to improve their workflow and get more done, more efficiently. 

Capterra gives Calendly a 4.7 with about 3,500 reviews, as well as top performer and emerging favorite badges for many scheduling software categories. The same site gives Chili Piper a 4.4 with only 120 reviews. It’s an identical story on other software marketplaces with user reviews. 

Reviewers on Capterra, G2, and GetApp 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 that it’s user friendly.

“A good tool is one that’s so simple, sales reps can basically forget about it and let the meetings roll in. That’s what happened when we implemented Calendly.”

Julia Pan

Sales Enablement Manager at SignPost

What solution is better for you? 

Both of these programs 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 Salesloft seat.

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