min read

Calendly vs Chili Piper: Choose your scheduling software smartly

If you’re in the process of evaluating Calendly or Chili Piper and want to find out how they stack up against each other, you’re at the right place. We’ve put together all you need to know about both solutions, including their pros and cons.

Sruthi Srinivasan
June 21, 2023
blog hero image
Table of Contents
Join the Buyer's Journey newsletter
Increase your pipeline conversions
Let's Talk

We know how confusing it can be when you are spoilt for choice. 

Especially when it comes to picking the right scheduling software for your business.

But now that you’ve narrowed it down to Chili Piper and Calendly, we thought it’d be a good idea to help #MakeBuyingSimple for you. 

So we made a pros and cons list. Of both its product capabilities, pricing, support experience, implementation process, integrations, ease of use, and more. 

Ready to take a look?

About Chili Piper

Known as one of the leading inbound conversion platforms in the market, Chili Piper is a scheduling platform designed to help businesses streamline the lead-to-booking process and improve inbound conversion rates. 

It predominantly caters to larger revenue teams with high-volume leads who need automated lead routing and qualification. It has capabilities ranging from scheduling to lead qualification and routing, although they are unbundled and sold as separate products.

  • Instant Booker - To instantly book meetings and update your CRM 
  • Form Concierge - To qualify and route leads from your web form
  • Handoff - To let reps book meetings on behalf of AEs 
  • Distro - To route leads to the right rep 
Chili Piper | Scheduling Software
Source - Chili Piper

About Calendly

On the other hand, Calendly is one of the earliest business scheduling software that has a well-established market presence, brand loyalty, and customer base. Its easy-to-use scheduling automation platform allows individuals to quickly and conveniently book meetings with each other. 

As a value prop, Calendly’s solution caters to all teams across the organization, be it sales, marketing, RevOps, customer success, IT, and recruiting to ensure no team is working in silos. It has a far larger user base that is spread across businesses of all sizes with different pricing plans tailored to fit the needs of each. 

Beyond its primary meeting scheduler functionality, it also offers features such as routing leads, embedding meeting links, setting up custom workflows, and integrating with over 100 apps across multiple categories.

Calendly | Scheduling Software
Source - Calendly

Chili Piper vs Calendly: Pricing

“How expensive of a software does our budget accommodate?” 

“Does it give a good ROI?” 

“Is there a free trial available?”

“How flexible and fair is the pricing plan for our use cases?”

“Will I get the flexibility of monthly billing options?”

“Are there any hidden costs?”

If you have asked all these questions, you’re already making great progress. And to make things easier, we’ll break down the different pricing packages of both Chili Piper and Calendly along with what each one offers. 

Chili Piper’s pricing package 

To begin with, Chili Piper has 4 different products (Instant Booker, Form Concierge, Handoff, and Distro) that you can either buy individually or bundle together as per your needs. But there’s more than what meets the eye. Let’s take a better look at the pricing plans they offer. 

Chili Piper’s Pricing Plans
Source - Chili Piper Product Pricing

For yearly subscriptions: 

  1. Instant Booker: Starts at $15 per user per month
  2. Handoff: Starts at $25 per user per month
  3. Form Concierge: Starts at $30 per user per month, plus a Tiered Platform Fee*
  4. Distro: Starts at $20 per user per month

For monthly subscriptions: 

  1. Instant Booker: Starts at $22.5 per user per month
  2. Handoff: Starts at $37.5 per user per month
  3. Form Concierge: Starts at $45 per user per month, plus a Tiered Platform Fee*
  4. Distro: Starts at $45 per user per month

*Chili Piper charges a Tiered Platform Fee which is calculated based on how many leads are submitted per month.

If you submit up to 100 leads, the platform fee is $225. For up to 1000 leads the fee is $600 and for more than 100 leads you are charged a fee of $1500. 

Regardless of whether it is qualified, unqualified, or even junk, you end up paying for every form submitted. This can quickly become expensive by making you opt for the higher tier and at the same time impact your ROI.

Point to note here Chili Piper does not offer a free trial. You’ll have to pay a 1-month minimum subscription to test drive their product. Or so we’ve heard. 

We also have strong reasons to believe that Chili Piper’s pricing can eventually end up costing you a whole lot more. Here’s why: 

  • You need to get your Admins a license for each product they manage.
  • There’s a minimum license requirement for all their products. 
  • Implementing Chili Piper can take up to 6 weeks and requires a significant amount of developer assistance, costing you a huge time and effort.
  • And lastly, customizing the platform and its components is quite a task and cannot be done without custom coding. All in all, the dependency on your developer would be really high.  

Find a detailed breakdown of Chili Piper’s pricing plans here. 

Calendly’s pricing plan

Next up, let’s have a look at Calendly’s pricing plan which is said to be more friendly and flexible. Catering to businesses of all sizes, its plan can accommodate single-person-run business needs as well as enterprise-level requirements of added control, security, and support. There are 5 different pricing plans for you to choose from in Calendly.

Calendly’s Pricing Plans
Calendly’s Enterprise Pricing Plan
 Source - Calendly's Pricing Plans

For yearly subscriptions: 

  1. Basic: Can be used free of cost 
  2. Essentials: Starts at $8 per seat
  3. Professional: Starts at $12/seat/month
  4. Teams: Starts at $16/seat/month
  5. Enterprise: Custom plan for which you’ll have to get in touch with their sales team

For monthly subscriptions: 

  1. Basic: Can be used free of cost 
  2. Essentials: Starts at $10 per seat
  3. Professional: Starts at $15 per seat
  4. Teams: Starts at $20 per seat
  5. Enterprise: Custom plan for which you’ll have to get in touch with their sales team

The good news with Calendly is they offer a free 14-day trial. At the end of your trial, you'll automatically be downgraded to the Free plan. If you decide to upgrade to any of their paid plans, it can be done from the billing page in your account. 

Next up, we want to touch upon the aspect of Calendly’s CRM integrations and being able to route off any form. 

While Professional plans and higher allow you to connect to HubSpot CRM, only Teams and Enterprise plan subscribers can route using HubSpot forms. And if you want to look up your CRM and make sure you route the lead to an existing owner, that’s not possible. 

Similarly, Teams and Enterprise subscribers can connect to Salesforce CRM, but only if you’re on the Enterprise plan can you look up your Salesforce CRM for existing owners and route leads to the same owner. This is critical especially if you’ve got leads already in an email/social media conversation with your sales rep. When these leads decide to book a demo, you don’t want them getting routed to somebody else, right?

But if you’re using Calendly forms, you can route leads using it, as long as you are on the Professional and above plans. 

 Calendly’s Pricing Plans | CRM integrations and routing
 Source - Calendly's Pricing Plans

We also have to think that it’s important to read through Calendly’s pricing page thoroughly, multiple times. Cause here’s what we found:

  • If you are looking to upgrade to the Enterprise plan and make use of the features it offers, you should probably know that it comes at a cost. We’ve heard that you are required to pay for everyone in your entire organization and can’t implement it for just your revenue teams.
  • Dedicated and fast support is offered only to the Enterprise plan subscribers. This includes having a Calendly account partner, onboarding and implementation, adoption guidance, and security & legal reviews. Not having access to this in the other plans can end up costing you more indirectly.
  • Customization of the Calendly scheduling pages can be done if you have opted for the Professional, Teams, or Enterprise plan. Although, you can only customize your team name, team page link, welcome message, team avatar, and time zone. The level of customization possible needs to be kept in mind as you cannot tweak the page to reflect your brand’s design, style, or experience.  

Chili Piper vs Calendly: What are their pros?

2 well-renowned products that have some great features to solve your scheduling needs and help eliminate the multiple back-and-forths, avoid double-booking, and reduce no-shows. Plus they also claim to drive more pipeline, increase speed to lead, and bring in more revenue. 

But before we jump into what differentiates them and find out why they are so loved, let’s see what functionalities are common between them. 

  • Automate meeting scheduling, reminders, and follow-ups
  • Integrate with calendar apps such as Google Calendar and Office 365/Outlook 
  • Sync with email platforms including Gmail and Microsoft Exchange 
  • Integrate video conferencing platforms including Zoom, Microsoft Teams, and Webex
  • Customize your booking links
  • Embed the calendar link onto your website
  • Integrate with CRMs including Salesforce to auto sync records and meeting info
  • Qualify, route, and book meetings with prospects instantly using existing web forms
  • Distribute meetings to sales reps in real-time via round-robin
  • Customize and automate workflows using Zapier apps 
  • Provide analytics to help you identify actionable insights

    And now on to the detailed breakdown of the high-rated features of Chili Piper and Calendly.

Pros of Chili Piper 

Did someone ask for 8 of the hottest Chili Piper features at the moment?

Here you have it:

  1. Get a bi-directional CRM sync when you integrate with Salesforce or HubSpot CRM. 
  2. Provide a one-click booking experience via email to your customers. You can do this by embedding suggested times and smart signatures using which customers can schedule meetings.
  3. Qualify leads before routing and distributing them to your sales reps.
  4. Route leads based on account owner, geography, industry, company size, or any other custom routing rules your business requires.
  5. Distribute warm leads to the appropriate rep based on trigger events, such as reaching the lead score threshold, and field updates in Salesforce amongst others.
  6. Manage meeting outcomes via the CRM or calendar platform.
  7. Compatible with Sales Engagement Platforms such as Outreach, SalesLoft, and High Velocity Sales.
  8. Send customizable SMS and email reminders to increase meeting show rates. 

And to vouch for it, let’s also show you some customer reviews that Chili Piper has received about its product capabilities. 

Chili Piper Reviews
Source - Chili Piper

Pros of Calendly 

Next up, we have the 8 most-loved features of Calendly that make a strong case for it being the forerunner. 

  1. Compatible with Apple iCloud Calendar and iCloud Mail.
  2. Has built-in forms, so if you don’t already have an online form provider, you don’t have to buy one to benefit from Calendly's routing.
  3. Has department-specific functionalities to help all the teams achieve their goals, be it closing deals or reducing time-to-hire.
  4. Central governance to instantly distribute critical updates and make sure everyone stays up-to-date and on-brand. Admins can create, assign, and templatize the types of meetings teams use. 
  5. Enables you to collect payments via payment processing apps such as Stripe, PayPal, and Stax at the time of booking.
  6. Lets people vote on dates and times to find the best meeting time for a large group using the Meeting Polls feature.
  7. Qualify leads in real-time using existing marketing forms in Marketo or HubSpot, or new forms that you can build in Calendly.
  8. Automatic lead routing by Salesforce ownership, or by Calendly’s native routing logic that is specifically built for the Salesforce CRM. 

    You know a product is good when you have rave customer reviews backing it up. 
Calendly Reviews
Source - Calendly

Chili Piper vs Calendly: What are their cons? 

Now, onto the part that you probably are the most curious about. And want to spend more time understanding.

Let’s dive right into finding out the areas where Chili Piper and Calendly fall short. What are the main reasons why customers evaluate alternatives and look to switch? And why it is crucial to know of this before you get into an annual contract. 

Cons of Chili Piper 

If you’ve been exploring Chili Piper’s competitors, we believe you would have faced one or more of these challenges:

  1. Need we even mention how deep of a hole Chili Piper can burn in your budget? Their products are bundled and sold separately, making sure you buy more than 1 to accommodate your advanced routing needs. Plus, the tiered platform fees, admin licenses, and hidden costs like minimum licenses make it more expensive than it could be. You can find a detailed analysis of Chili Piper’s pricing plans here.
  2. Though it is a flexible product that offers the ability to customize components to your brand’s style, the main drawback here is you require significant developer assistance, time, and effort to do so.
  3. Chili Piper’s widget load time is said to take its own sweet time to load. Depending on the complexity of the rules, this can be anywhere from 8 to 13 seconds. It takes a toll on the end-user experience and causes a high drop-off rate between form fill and booking a meeting.  
  4. Chili Piper is primarily built to be a Salesforce-first solution for scheduling and routing. So, customers who use HubSpot CRM or other CRMs find the integrations to not be up to the mark. And not having that strong 2-way sync is a sure-shot recipe for a leaky funnel.
  5. When it comes to looking up account ownership in your CRM, Chili Piper does not let you dynamically check and match leads with the right account owner. You’ll need a lot of admin work to get it right. Plus, it does not let you distribute your leads via a strict round-robin. 
  6. Lastly, we’ve also heard that when it comes to implementation you might have to wait for days or even weeks for the team at Chili Piper to get back and resolve your query. Correct us, if we are wrong. 
Chili Piper’s Customer Reviews on G2
Source - G2

Cons of Calendly

Similarly, if you’ve been meaning to switch over from Calendly, we believe you would have faced one or more of these challenges:

  1. While Calendly integrates with a whole bunch of CRM software, it comes with pricing restrictions. Only Professional plans and higher customers can connect to HubSpot CRM, while Teams and Enterprise can integrate with Salesforce CRM.
  2. Routing leads on Calendly is a relatively new feature that comes with its own set of challenges. Only customers on the Teams and Enterprise plan can route using HubSpot forms. And if you’re on the Professional plan and above, you can route leads using Calendly’s native forms.
  3. The next tricky bit in Calendly is routing leads via ownership. If you want to look up your CRM for existing leads in order to show their account owners’ calendars, there are 2 roadblocks in your way. One, you need to have Salesforce CRM to do this. For HubSpot CRM users, this functionality is out of the question. Two, you need to upgrade to the Enterprise plan to be able to do so. You know what that means - getting an enterprise license for your entire organization, irrespective of how many people are actually going to use it. 
  4. Strict round-robin is impossible on Calendly since it works on showing the entire team's calendar and not bringing a person's calendar in rotation.
  5. Since the platform is built as a calendar that contains rules and not the other way around, setting up meeting types and distribution rules can be difficult. For every team, you have to set up a meeting type and rules of distribution. 
  6. But what you can’t do with Calendly is redistribute a lead, if they submit a form but do not book a meeting. This means more headache for sales ops and sales managers.
  7. Calendly is in the same boat as Chili Piper when it comes to customer support. Only customers on the Enterprise plan get a dedicated Calendly account partner, onboarding and implementation assistance, adoption guidance, and security & legal reviews. 
Calendly’s Customer Reviews on G2
Source - G2

The smart choice in scheduling software

We hope that covered just about everything that you’d want to know about Chili Piper and Calendly as you’re evaluating both solutions. 

I’m biased here but I think it would be a disservice to you if I didn’t mention RevenueHero - an easier and more efficient way to #MakeBuyingSimple. 

An inbound revenue acceleration platform, RevenueHero is designed to help businesses accelerate and improve the B2B buying experience. It enables marketing, sales, and revenue teams to book more qualified meetings, connect high-intent website visitors to the right rep instantly, reduce the sales cycle, and drive more pipeline without hurting budgets. 

And let’s address the elephants in the room straight up. 

  1. RevenueHero’s pricing is designed to be in sync with the value provided to your sales teams — booked meetings. You only get billed for the people who get meetings booked on their calendars. Our platform fee is charged only for customers in the GTM Enterprise plan and is very nominal at $79/month when billed annually. And even more so our license fee doesn't apply to admins.
  2. You get a completely free 14-day trial with a working proof of concept before you decide to pay.
  3. Implementing RevenueHero is quick and easy. We’ll have all hands on deck to get it up and running for your team in less than a couple of days.
  4. While it is built to be self-serve without developer dependency 99% of the time, we are always just a Slack message away in case you require our help with any query or issue.
  5. ‍Whether you’re on Salesforce, Zoho, or HubSpot CRM you’ll have absolutely no hiccup in setting up RevenueHero and syncing the platforms. You can easily connect your forms, look up account ownership in your CRM, and route leads based on it.
  6. RevenueHero also integrates with the other tools in your stack seamlessly. Right from your calendars (Google Calendar, Outlook Calendar) and video conferencing platforms (Zoom, Google Meet, Microsoft Teams) to communication solutions (Slack, Intercom) and form enrichment tools (ZoomInfo, Clearbit).
  7. Lead qualification, routing, and distribution are optimized to ensure your buyers get on the fast lane to talk to your reps. You can prioritize buyers with the most potential as it helps you analyze your form-fills faster and categorize your leads more efficiently. Plus, with smart distribution logic, you’ll be able to automatically match every lead to the right sales rep, close deals faster, and reduce your sales cycle.
  8. Create a unique experience tailor-made for every prospect at every touch point. When sending personal meeting links to a prospect, you can now include targeted messaging that includes embedded recaps, inline collateral, and customized content to increase the success rates of your meetings.
  9. Everything from the interface and brand colors to the greeting text on your widget and the thank you page redirection can be customized easily in a few clicks. No code is needed. Nor a developer’s help.
  10. RevenueHero’s booking widget is optimized to always load in under 1.5 seconds to ensure interested prospects never drop off after a form fill. 

Don’t just take our word for it. Hear what our customers have to say. 

RevenueHero | Chili Piper and Calendly Alternative
Here’s why RevenueHero is a great alternative to Chili Piper and Calendly
Source -


So which solution is the one for you?

Feature RevenueHero Chili Piper Calendly
Lead qualification
Booking page load
time < 1.5 seconds
Lead Routing

Based on:

- Geography, industry, company size

- Any custom logic your sales process requires

Based on:

- Geography, industry, company size

- Any custom routing rules your business requires

Based on:

- Salesforce ownership

- Calendly’s native routing logic
Lead to account matching ⚠️

(Does not dynamically check. Needs a lot of admin work to get it right)

(Only on Salesforce CRM for Enterprise customers)
Lead distribution via round-robin and custom logic ⚠️

(Does not do strict round robin)

(Can’t redistribute leads in case leads fill the form, but do not book a meeting)
Scheduling page customization with zero-developer dependency ⚠️

(Custom coding required)

(Only name, link, and time zone can be customized)
Personal meeting links & share slots in email ⚠️

(Cannot be customized or include any embedded collateral)

(Can only share personal meeting link)
CRM integrations
(Works best only for Salesforce)

(Need to upgrade to the highest tiers)
Tech-stack integrations

(One-click integrations)

(5,000+ apps via Zapier)

(5,000+ apps via Zapier)
Pricing with positive ROI
(Pricing is based on plans that allow scheduling as well as lead routing and distribution)

Starts at $25/user/month

Starts at $30/user/month when billed annually for Form Concierge

(+ Tiered platform fees + minimum license requirements + unbundled product offerings)

Starts at $16/user/month when billed annually

(Advanced routing capabilities available only in the highest tier + requires you to buy it for everyone in your organization)
Free 14-day trial
(With a guided, risk-free proof of concept)
Responsive and reliable support
(Plus, anytime support on Slack connect)

(Available only for the highest tier customers)

(Available only for the highest tier customers)
Quick, easy, and hassle-free implementation ⚠️
(Only for Enterprise customers)

Revenuehero is fast and intuitive, custom-built for modern sales teams.
Request a Demo