Calendly vs Chili Piper: Which scheduling tool should you buy?

Almost every software today claims that it helps you save time and improve productivity—a sign that product differentiation is getting trickier by the day.

Since you are here, I believe you are evaluating Calendly vs Chili Piper to narrow your search for the best scheduling app with lead routing and handoff capabilities. While it may seem like the differentiation between these two scheduling products is blurry, there are nuances that can help you arrive at an informed decision.

And that’s exactly what this blog aims to do.

In the sections below, let’s look through the similarities and differences between Calendly’s and Chili Piper’s market positioning, ease of use, product capabilities, and pricing plans. We will also dig deeper into their integration options and scalability to see how they stack against each other.

But first…a quick word on how we have approached this comparison.

Our approach to make this an objective comparison

As a SaaS business ourselves, we at Avoma believe in being helpful to the SaaS community. Every time we compare two or more software, we base the comparisons on our first-hand evaluation.

To that end, here’s the 6-step process we follow to arrive at an unbiased conclusion:

• We surveyed different people at Avoma who have used one of these two scheduling apps.
• Used the free version of the software to get a feel of it—if they offer one. 
• Refer to our internal notes on why people use or don’t use these apps.
• Reach out to a few of the existing and past users of both scheduling tools to understand their first-hand experience.
• Interview the current and past users to understand the nitty-gritty of the features that are a must-have, good-to-have, and what’s missing.
• Aggregate customer reviews across G2, GetApp, TrustRadius, TrustPilot, SoftwareAdvice, and all relevant SaaS review sites to understand the customer sentiment at scale.

Now that it’s clear how we have approached the research, let’s start scratching the surface by understanding how Calendly and Chili Piper position themselves in the market.

The key differences between Calendly and Chili Piper

Both Calendly and Chili Piper are front-runners in the meeting scheduling software category. As scheduling apps, their core functionalities allow you to book meetings with ease—saving you the hassles of sending multiple emails back and forth, mistakenly booking two meetings in the same time slot, or fumbling over time zone differences.

Calendly has been around in the software category for ‘business scheduling’ for a long time and enjoys a much better brand recall than Chili Piper, as is evident in this G2 Grid for Business Scheduling.

Calendly is ranked second in the “Leaders” category (second only to HubSpot) while Chili Piper is an up-and-coming player in the “High Performers” category. Both Calendly and Chili Piper are ahead of the curve when it comes to the “Satisfaction” and “Market Presence” scales, but between the two, Chili Piper has a lot of catching up to do.

Customer reviews tell a slightly different story. With a common score of 4.7 out of 5, both Calendly and Chili Piper customers peg the two tools similarly when it comes to meeting their requirements, ease of use, and quality of support.

Drawing from those observations, the biggest difference between Calendly and Chili Piper is perhaps their positioning.

Calendly: Best for all business sizes and functions

At a glance, Calendly comes across as a scheduling tool mostly for small businesses. Calendly’s forever free plan, affordable pricing, and customer reviews on sites like G2 are a testament to its small business-friendliness.

But it would be a mistake to say Calendly is only for small businesses. A closer look at its functionalities and current customers gives us a better understanding.

Calendly’s user base is spread across all business sizes—small, medium, and large enterprises. It offers pricing plans that are attractive for small businesses but it also offers subscriptions and features that are suitable for larger teams.

Calendly also claims that it has four times more enterprise users than Chili Piper including some globally renowned names like Dropbox, Lyft, eBay, and Visa.

All in all, Calendly is a flexible scheduling software with a broader market positioning. You can use its free plan or choose from one of its paid pricing tiers. You can either use it as a standalone calendar tool or go for its advanced features to manage complex workflows. And you can use it either for internal meetings across any function in your organization or as a scheduling interface to let your prospects book meetings with you.

Chili Piper: Positioned primarily for inbound demand generation

One thing that differentiates Chili Piper from Calendly—and other scheduling apps—is its laser-focused product positioning. Chilipiper currently positions itself as a Demand Conversion platform, i.e., the platform that offers a set of tools to turn initial interest into a sales opportunity.

From the moment you land on Chili Piper’s website, it becomes very clear that it specifically solves the pain points of sales and marketing teams and helps them “double their inbound conversions,” create “more pipeline,” or “fix leaky funnel.”

The only exceptions are its Form Concierge feature—which Chili Piper claims is “made specifically for marketers”—and a page where they talk about catering to customer success teams. These pages feel like namesake in comparison to Chili Piper’s product functionalities that are majorly aimed at sales.

As a relatively new entrant in the scheduling niche, Chili Piper’s strategy to go after a specified niche is understandable—and commendable. The company also boasts of a great line-up of marquee customers such as Workplace by Facebook, Salesloft, PandaDoc, Shopify, Gong, Monday.com, and Airbnb.

In short, Chili Piper aspires to be the red hot scheduling app for high-growth revenue teams and this reflects in their subscription plans. Chili Piper buckets its offerings in different pricing tiers—making it flexible for you to pay for what you use. We will talk more elaborately about the pricing nuances of both tools later.

I'm sure, by this time, you're also wondering:

• Is it just about positioning for different audiences?
• Do you need to buy additional tools and modules for lead routing and qualification?
• Which one offers better value?

If you have these questions on your mind, you’re not alone. That's why we have written this article to help you get answers to those questions and get clarity to decide which tool is the best fit for your needs.

Let's first understand where a scheduling tool fits into your meeting lifecycle.

The role of scheduling tools in the meeting lifecycle

Booking meetings is an inescapable part of remote work. And of course, a lot of us use scheduling tools to book meetings. But for a moment, let’s look at what a meeting lifecycle looks like.

Most meetings have a three-stage lifecycle that spans many tools and processes—namely, the activities that occur before, during, and after the meeting.

Scheduling tools simplify and automate the ‘before’ stage of the meetings by:

• Automating meeting bookings
• Sending reminders to the recipients to reduce no-shows
• Capturing agendas to ensure alignment between both the parties

With this as a base, let’s get back to evaluating Calendly and Chili Piper.

Choosing between Calendly and Chili Piper

When you are comparing two or more SaaS products, we recommend you evaluate them from four critical lenses.

Key factors for evaluation:

1. Ease of use

The ease of using a scheduling tool is an important factor to consider since it determines how well you, your team, or the external collaborators will adopt the product and the full range of its functionalities.

Questions to ask:

• How hard or easy is it to set up and implement the app?
• Do you need a dedicated person to administer the tool?
• Can you trial the tool by yourself?
• How complex is the user interface for you to start using the tool?

2. Product capabilities

Supposing the scheduling app passes the test of user-friendliness, your next criteria for evaluation should be the range of features and benefits it offers.

Questions to ask:

• How comprehensive is the software in terms of its feature offerings?
• Are its functionalities out-of-the-box or customizable?
• What integrations does it support?
• Does it support native integrations or via some third-party API connectors?

3. Pricing

You need to justify the return on investment (ROI) for any software you buy—and scheduling software is no different. Actually, the ROI of buying a scheduling tool should be immediately clear given that it stands to solve the measurable problems related to time management.

Therefore, pricing is an important component to consider in regard to your team size, budget, and goals you expect to achieve by using the tool.

Questions to ask:

• Does the app offer a free trial or freemium subscription?
• Is the pricing affordable, flexible, and fair for your business use cases?
• Does it have flexible monthly billing options or does it force you to sign annual contracts?
• Are there any hidden costs?

4. Scalability

When you are buying a piece of software, you're not just buying to solve your current pressing needs today but also looking to use it for your future needs. It’s best to invest in a tool that grows along with your growing needs.

Questions to ask:

• How easy and affordable is it to add more users to the platform?
• Does it offer enterprise-level features?
• Can the platform support you across your growing use cases and maturity phases?

Calendly vs Chili Piper: head-to-head comparison

The TL;DR version

1. Ease of use

Calendly

Calendly is a poster child of product-led growth (PLG) strategy—and its clean user interface (UI) has a big role to play in making it one of the rapidly-grown PLG brands. Calendly’s UI is almost Zen-like: super-clean with lots of white space, so easy that even a fifth-grader can navigate, and without any unnecessary distractions. Long story short, using Calendly doesn’t feel like you are using software—and that’s due to its simplified UI design.

Its UI is the reason why G2 users rate Calendly 9.4/10 on the ‘ease of use’ scale and use phrases like “The Queen of Calendars" to describe their experience with the tool.

It also integrates with email apps like Microsoft Outlook and Gmail so that you can book meetings with just a single click from within your inbox without having to open a new tab.

I've been using Calendly ever since I started in tech going on 5 years ago, and I can't imagine scheduling meetings with anything different. I mean, I can, because I've used other schedulers... but none are simple and feel as clean as Calendly does. I love that I can drop the link anywhere I talk with people and it's the same experience as if I emailed it.
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- Sheridan Lintz, Recruiter, ex-BombBomb

Chili Piper

Chili Piper is intuitive too and its dashboard feels like many of the UIs you might have seen in other software before. That kind of familiarity flattens the learning curve and helps you adopt its features and functionalities with ease.

For instance: once you log in to Chili Piper, you can find everything in its menu listed in the collapsible navigation drawer to the left. It’s a bit cluttered for most people’s taste and you can find a few people in G2 offering feedback to improve Chili Piper’s overwhelming UI.

The good news is that the brand seems to be aware of its flaws and they are soon rolling out a new ‘Fire UI’ upgrade to notch up their UI/UX. As of this writing, Chili Piper has a rating of 9.1/10 on G2 for its ease of use.

Chili Piper makes management and automation of your inbound leads so easy. The UI/UX could be a little more intuitive and visually appealing. I hear that they are working on these elements and at the end of the day they don't impact functionality. But still not the easiest UI to use sometimes.
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- Jason Hubbard, VP of Partnerships and Alliances at SalesIntel.io

2. Product capabilities

Calendly

The best thing about Calendly is that it makes your scheduling tasks no-nonsense with its one-click meeting booking from within your inbox—including LinkedIn and Twitter DMs.

The tool syncs with the most common business apps that you use to manage your meetings (e.g., calendars, video conferencing, email, CRM, and even payment apps) to help you manage your time more efficiently.

Once you configure Calendly to your preferred settings, you can embed your personal Calendly link to one of the many customer touchpoints such as website, email, social media, or Slack for people to book meetings for you—but on your own terms.

Calendly organizes all its product capabilities under six different categories. Let’s take a look at them thoroughly.

Availability Preferences

Calendly lets you choose the best times for your meetings, allowing you to take control of your time. And while you share your meeting links with customers or other people from within your organization—giving them an impression that they are in control of picking an optimum time—it’s actually you who controls when the meetings happen on your calendar (and time zone).

This also lets you create a buffer time between multiple meetings, avoid last-minute surprise bookings, and eliminate the chances of overbooking your calendar.

Team Scheduling

With Calendly, you are not limited to creating a meeting link just for yourself—you can have a team page to offer your customers a broader time range to choose from. You can set a round-robin rule to assign one of your team members to the meeting based on their availability.

Team Scheduling also lets you define the nature of meetings for customers to choose from so that you can assign the right experts to the meeting.

Embeds

As the name suggests, this Calendly function lets you “embed” your Calendly page in different formats on your website. You can either have the calendar interface appear as an inline element, pop-up widget, or pop-up text.

Regardless of the format you choose to display the calendar widget, this functionality allows your prospects to book meetings with you (or your team) in a single click without leaving the browser tab.

Calendar Connections

Calendly integrates with up to five personal calendars—Google Calendar, Exchange Calendar, iCloud Calendar, Office 365, and Outlook Desktop—making it easy for you to check your availability across all calendars and avoid double booking.

Calendly also integrates with video conferencing platforms like Zoom, Webex, and GoTo Meeting so that the conference details automatically get populated in your meeting invite without any added steps.

Routing Forms

This functionality routes and assigns the right person to a meeting based on the information that prospects request on your website’s calendar widget.

For instance—if you embedded a Calendly link on your pricing page for prospects to request a sales demo, the sales team can qualify the person based on the details they input in the demo request form and schedule a high-touch demo call on priority.

Meeting Polls

Polls are the most recent addition to Calendly’s features list and it allows meeting invitees to vote on the most preferred times—based on the majority. You can schedule webinars, internal board meetings, company-wide all-hands, or other large events to get consensus on the optimum times for running an event.

Chili Piper

All of Chili Piper’s product functionalities are optimized for pre-meeting sales workflows.

Although it’s a scheduling point solution, Chili Piper has a diverse range of features that helps revenue teams boost inbound lead conversions, improve customer satisfaction, and increase productivity.

My team and I have had nothing but great experiences with the folks over at Chili Piper. The product itself has removed the barriers to book and it has created the path of least resistance to get a meeting on the calendar.
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- Gabriela Kressley, Sales Operations Analyst, Electric

One major difference between Calendly and Chili Piper is that the latter has zero functionalities that support internal meetings and collaborations—such as 1:1s or corporate meetings. And it seems that the company wants to keep it that way; nothing in its marketing communication hints that the brand plans to add anything in its roadmap to facilitate internal meetings.

If you're evaluating Chili Piper or its alternatives for your sales use cases, the following functionalities can be highly beneficial.

Instant Booker

Instant Booker is Chili Piper’s scheduling capability that helps you automate the meeting scheduling process. Much like Calendly, you can embed a Chili Piper widget on your website or email to let prospects book meetings in a single click.

Instant Booker updates the status of no-show, rescheduled, or canceled meetings automatically to your CRM so that you don’t have to manually enter those details in the CRM.

Form Concierge

Form Concierge is one of Chili Piper’s more popular functionalities because it lets you qualify, disqualify, and route meetings to the right individuals or teams. It’s a lead qualification tool that you can embed on your website as an online form.

Chili Piper claims that Form Concierge helps businesses double their inbound conversions by speeding up their demo response rates. It has plenty of customer stories on its website to back up the claim.

Distro

Distro is short for ‘distribution’ (or so we suppose), which allows you to automatically distribute a lead to the right rep.

Going by their individual feature pages, it’s hard to tell the difference between Form Concierge and Distro since both functionalities claim to help you assign the right rep to the right leads.

Our conclusion is that the concierge functionality helps mostly with lead qualification while Distro handles the distribution after the qualification is done. But that’s where it gets tricky because Chili Piper’s next functionality also offers a strikingly similar benefit.

Handoff

“Ditch your lead routing spreadsheet…automate your handoff process with Chili Piper” is how the opening paragraph describes the Handoff functionality in one of Chili Piper’s product pages.

But…isn’t that just another way of saying automatic lead distribution—something that the Distro functionality already solves?

Perhaps the company means that Distro helps you assign the right reps to the right account while Handoff specifically helps with the ‘handing over’ aspect from one rep to another—if there’s a need for it.

In any case, it feels that Chili Piper could have bundled three of its functionalities (Form Concierge, Distro, and Handoff) in the same bucket or articulated their different benefits more clearly in its feature pages because right now they all sound like automations for the same workflow.

3. Pricing

Calendly

Pricing is yet another area where Calendly outshines Chili Piper. The app has a free forever plan that comes with basic functionalities like scheduling unlimited one-off meetings and customizable booking links. The free plan is also what explains how Calendly earned a massive 10 million users across the globe.

Calendly’s paid plan starts at $10/seat/month for individuals and goes up to $16/seat/month for teams. It also offers an enterprise plan for companies that want to purchase 30+ seats with added control, security, and support.

Here’s a look at its pricing page:

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Calendly objectively has one of the best pricing plans in the scheduling app category even when you peg it with other leading players like HubSpot, MixMax, or Doodle.

The only thing that I don't like about Calendly is the fact that in the free version, you can only have 1 type of event so if you want to have a shared meeting with a member of your team, you can only give that link and not one for another meeting just by yourself.
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- Nicolás González Casabianca, Sr. Global Expansion Consultant, Ontop

Chili Piper

Chili Piper’s pricing plans are very simple and relatively affordable in comparison to other SaaS apps in general. But it pales in contrast to Calendly’s plans and the value each of them offers.

Chili Piper has subscription plans based on its product functionalities, i.e. Instant Booker, Handoff, Form Concierge, and Distro. Calendly offers most of these functionalities across most (if not all) of its paid plans—rationed proportionately to the pricing tier.

If you go by Chili Piper’s website, it doesn’t offer a free trial or freemium option. The only way for you to get a feel of the product is to book a demo with their sales team. But there are confusing sources that contradict this information.

Thankfully, there’s no such confusion with its paid plans. Its pricing tier starts at $15/user/month if you are just using scheduling links. It’s also important to note that its best plan (i.e. Form Concierge) comes at $30 per user per month with an additional ‘platform fee’ that Chili Piper discloses upfront on its pricing page.

Take a look at Chili Piper’s pricing page:

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At a glance, it looks like Chili Piper doesn’t offer an enterprise plan—but a closer look at its top nav bar (third from left menu option) tells a different story. Instead of listing its enterprise options on the pricing page, Chili Piper has that information published on a separate page.

Its customized solutions for larger teams extend the product’s offerings across sales, marketing, customer success, or other revenue teams. Other benefits of using Chili Piper’s enterprise solution include better privacy and security, assured compliance, and free-of-cost SSO/SAML authentication.

4. Scalability

Calendly

Point solutions extend the scope of their functionalities by increasing their integration options with other tools adjacent to their niche. As such, Calendly integrates with 70 different apps across nine different categories. Besides, you can also use Calendly API to build your own integrations.

Calendly also has Google Chrome and Firefox extensions that allow you to quickly access your calendar events, access Calendly from your Gmail/LinkedIn/Sales Navigator/Recruiter interfaces, save favorite events, and add notes to calendar events—all without having to leave your browser tab.

However, these integrations still fall short of extending Calendly’s capabilities to other areas of managing meeting workflows beyond scheduling. We will talk about this shortcoming in more detail in just a minute.

Chili Piper

Chili Piper has over 50 integrations across nine different app categories—that mostly cater to sales and marketing use cases. If you want more options, you can also leverage websites like Zapier, Tray.io, Workato, or Chili Piper’s own API and Connectors to integrate with more tools.

Chili Piper offers two extensions—Google Chrome plugin and Outlook Add-In—that you can use to book meetings easily, keep a tab on upcoming meetings, and access your Chili Piper settings.

Like Calendly, Chili Piper also hasn’t thought through the entire spectrum of the meeting lifecycle—which is why its scope of scalability is limited. 

What are Calendly and Chili Piper missing?

Both Calendly and Chili Piper are great tools for the variety of features and benefits they offer, but as we discussed earlier, they both are point solutions that enable only the ‘before’ stage of the meeting lifecycle.

Scheduling is just one of the many workflows in the long course of a meeting lifecycle. Calendly and Chili Piper solve for most pre-meeting use cases like creating scheduling pages, sending meeting links, and routing events based on rules. They don’t solve for the broader spectrum of workflows that take place during and after the meeting.

Imagine this scenario:

You either use Calendly or Chili Piper to get your meetings booked. It then automatically sends reminders to reduce no-shows or options to reschedule meetings.
You still have to use a meeting assistant tool to record and transcribe your meetings so that you don’t miss out on key information.

You take notes during the meetings, which then needs to be transferred to a CRM to ensure that the information is available to everyone for access. And you need to do this manually for every call. It becomes very stressful when you have 10-15 meetings a day.

On top of this, if you’re using conversation intelligence and revenue intelligence software to ensure you don’t let deals slip through the cracks—then you’ve more tools to cobble together.

If you’re looking for a scheduling app that extends its capabilities with your rapidly-scaling teams and processes—both Calendly and Chili Paper fall short of those expectations.

Even if you play the devil’s advocate and consider their integrations with CRM as a post-meeting capability, it’s incomplete without the full context of meetings. 

Both the tools try to compensate for this lack of conversation intelligence capability by integrating with tools like Gong.io and Fireflies.ai respectively, but that only leads to more licensing of seats, more administrative hassles, and increased total cost of ownership.

If you are familiar with the hassles of integrations, you probably know that too many app integrations often feel like herding cats. It’s a security hazard and adds to the list of complexities you might already have managing your SaaS techstack.

This is where Avoma comes in handy.

Avoma Scheduler helps you:

• Create as many scheduling links as you want for different purposes
• Create group scheduling links
• Create round-robin scheduling links to manage distribution of meeting for sales, customer success, support and other high-traffic functions
• Route the inbound leads and customers to the right rep in real time based on rules, opportunity type, territory assignments, CRM account ownership
• Book meetings during a call on the fly and handoff to your AE seamlessly
• Reduce no-shows with automatic reminders and rescheduling options

And because Scheduler is part of Avoma, it enables you across the entire meeting lifecycle by:

• Automating note-taking for your meetings and update it to the CRM 
• Recording the audio and video of your meetings
• Giving you actionable conversation and revenue insights

All this in one place, not all over the place.

To be fair, Calendly does offer its solutions for a wider range of business functions, but its capabilities stop at just scheduling and nothing beyond that. On the other hand, Chili Piper is hyper-focused on solving the scheduling problems mostly for sales—implying that other go-to-market teams don’t have a deeper need for simplifying their scheduling woes.

As a result, both these tools create silos—instead of encouraging company-wide collaboration—mostly because their i) core offerings are limited to scheduling, or ii) narrow focus on the sales team.

Our final verdict

Like we stated at the beginning of this blog, the differences between Calendly and Chili Piper are mostly blurry if you compare their core features and functionalities. But Calendly seems to have a clear edge over Chili Piper on most fronts like brand recall, ease of use, and pricing. While they both are great at what they do, they solve only a small aspect of your meeting lifecycle problem. 

So which one should you go for?

• If you are looking for a flexible scheduling solution only for your revenue team, go with Chili Piper’s Instant Booker plan or upgrade to its more expensive plans for advanced routing requirements.
• If you are looking for a scheduling software that caters to individuals, all business teams, and internal use cases—start with Calendly’s Basic or Essential plan for its easy pricing.
• If you want to simplify and automate your entire meeting lifecycle starting from scheduling (without compromising on any of the scheduling aspects such as round-robin or lead routing) to getting revenue insights (including deal risks and forecasts) from your meetings—give Avoma a try . Avoma offers flexible pricing based on your current needs and can scale as you grow.