How Does Calendly Make Money? Business Model of Calendly

How Does Calendly Make Money

Calendly is an online scheduling tool that helps you and your clients to easily coordinate meetings and appointments at the time most convenient for everyone without any hassles of back and forth emails. 

But how does Calendly make money? It is a logical question and needs to be answered. In this article, we’ll dive into Calendly’s business model and find out how Calenly generates its revenue. So, let’s get started.

Calendly operates on a freemium model as a SaaS for both B2B and B2C. It makes money through subscriptions of its scheduling software that are offered in three types of premium plans in addition to the free plan.

About Calendly

Calendly is an AI enhanced scheduling software that has perfected the art of the meeting. The real secret to its success, however, is founder Tope Awotona’s innovative upside-down sales funnel and its unique marketing strategy that turns every meeting into a Calendly advertisement.

Calendly helps people schedule appointments and meetings with their clients, employees, and groups. Whether you manage a team of 10 or 10,000 people, the Calendly tool will help you improve your productivity, reduce meeting no-shows and spend more time doing the things you really want to do.


Business Model of Calendly

Calendly has a freemium business model as a SaaS. This scheduling software also employs founder Tope Awotona’s upside-down sales funnel, which will be discussed in more detail later. Competitors include:

  • HubSpot Sales Hub
  • TimeTap
  • Setmore
  • Picktime
  • Doodle
  • Acuity Scheduling
  • Chili Piper

For many, Calendly functions as a personal assistant and billing assistant. So much time, and possibly customer goodwill, is lost due to friction and back-and-forth related to setting up meetings.

The truth is, any customer success program requires multiple incidents of contact, what in real estate is referred to as “20 touches”. The time commitment to maintaining this contact takes away from other important tasks, so if this can be outsourced to some smart SaaS, all the better.



Calendly is scheduling software, offered as a SaaS in both B2B and B2C. What makes Calendly special is that it employs AI to find just the right time-slots and reduce friction.

Basically, Calendly has mastered the art of booking meetings with as little friction as possible. Popular applications of this SaaS include:

  • Sales
  • Customer Success
  • Recruiting

Statistics on Calendly’s website include:

  • 45% faster meeting scheduling
  • 25% more revenue per lead
  • 100% more candidate screens

Calendly, known for its great integration, mobile support, and usability, checks all calendars to avoid schedule conflicts or double-booking and seamlessly integrates with the following:

  • Office 365
  • Google
  • Outlook
  • PayPal
  • Stripe



The marketing aspect is where the freemium model is really helpful.

Since Calendly is a scheduling software, even non-paying users are marketing Calendly every time they schedule a meeting. If a user tries to book a meeting with some counterpart, the counterpart will see the available time slots as displayed by Calendly.

If Calendly does its job right, that counterpart will want Calendly for himself or herself. Therefore, every Calendly appointment booking is also a Calendly advertisement!

Calendly also has its own blog. In addition, Calendly offers partnerships to users as direct marketers with incentives that include commissions. These partnerships include:

  • Tech Partners
  • Affiliate Partners
  • Strategic Partners



Calendly has always been a bootstrapped operation. They have been able to get away with that because they are not really a brick-and-mortar business and, therefore, save on a lot of costs. As with any SaaS, Calendly needs to pay for technically skilled staff, their energy expenses, and the maintenance of their equipment.

Other SaaS related expenses we could expect for Calendly include:

  • Hosting
  • Payroll for development
  • Sales
  • Marketing


Plan for Profit

Calendly founder Tope Awotona’s plan for profit is what he has described as an upside-down sales funnel.

The idea is that Awotona wants to prioritize CRM over sales and marketing, with the idea that satisfied customers would lead to referrals and repeat business.

During the earlier stages of Calendly, Awotona had decided to focus on the first 1000 customers before expanding his business. Now that Calendly has mushroomed into a four-billion dollar unicorn, he cannot focus on the first 1000 customers anymore.

Regardless, his freemium model is still incorporated into Calendly’s subscription packages. The challenge will be to keep adding new features to the premium subscription packages that will motivate clients to pay rather than try to get something for free.

To date, Calendly has been able to steal market share from its competitors through its ease of use. The fact that this has been able to happen in the past decade when there have been juggernauts like Google and Microsoft roaming the earth going up against some guy with $200,000 defies comprehension.

That kind of good fortune, however, cannot last forever. Super-competitors like the ones mentioned will eventually adapt to any tricks a smaller competitor has been able to get away with for a couple of years and create their own scheduling software.

Awotona, however, has one thing on his side against the juggernauts, low costs. He has never strayed too far from his bootstrap roots, so by keeping costs down and revenues up, the high profit margins he has been able to “rake-in” during his rise to unicorn status, can still be maintained, if not necessarily at the same exponential proportions.


How Does Calendly Make Money?

Calendly is a freemium SaaS. Based on Awotona’s upside-down sales funnel, he uses the freemium model to attract new customers and then focuses on CRM to sell those existing customers on premium SaaS subscriptions.

That is why the Basic Plan is still available, to draw people into the funnel. Even though the Basic Plan is not a revenue stream, it is part of the subscription model and the subscription model is the source of Calendly’s three revenue streams:

  • Premium Plan
  • Pro Plan
  • Enterprise Plan


Basic Plan

In keeping with the spirit of the freemium model, the Basic Plan is always free. Basic Plan Core features include:

  • Calendar connections per user (1)
  • Personalized booking link
  • Web, iOS, and Android apps
  • Scheduled meetings
  • Active Event Types (1)
  • One-off meetings
  • Meeting notifications
  • One-on-One event type

In addition to Core features, the Basic Plan has a Customization feature, Embed options.

Furthermore, in addition to Core features and a Customization feature, the Basic Plan has the following Integrations features:

  • Connect to Google, Office 365, Outlook, and iCloud calendars
  • Connect to Zoom, Microsoft Teams, Google Meet, and GoToMeeting
  • Connect to Slack and Intercom

The Basic Plan also has the following Support Features:

  • Self-serve help center
  • Email support (standard)


Premium Plan

The Premium Plan costs $8 per user per month. In addition to all of the Core features of the Basic Plan, the Premium Plan includes:

  • Calendar connections per user (2)
  • Active Event Types (unlimited)
  • Group, collective, and round robin event types

In addition to the Embed options Customization feature, the Premium Plan has the following Customization features:

  • Custom email notifications
  • Hide Calendly branding
  • Custom branded pages

In addition to all of the Integrations features of the Basic Plan, the Premium Plan includes:

  • Webhooks
  • Over 700 app integrations with Zapier

In addition to all of the Support features of the Basic Plan, the Premium Plan includes:

  • Email support (3 hours)
  • Live chat support (10+ users)


Pro Plan

The Pro Plan is $12 per user per month. In addition to all of the Core features of the Premium Plan, the Pro Plan includes:

  • Calendar connections per user (6)
  • Team pages
  • Workflows

In addition to all of the Customization features of the Premium Plan, the Pro Plan includes:

  • Custom SMS notifications
  • Expanded color options
  • Redirect invitees

In addition to all of the Integrations features of the Premium Plan, the Pro Plan includes:

  • Connect to Salesforce
  • Connect to HubSpot and Mailchimp
  • Collect payments with Stripe and PayPal
  • Track with Google Analytics and Facebook Pixel

The Pro Plan has all of the Support features of the Premium Plan.


Enterprise Plan

The Enterprise Plan is priced on a per seat basis and the interested user needs to contact the Sales Team to learn more about pricing. The Enterprise Plan has all of the Core features, Customization features, and Integrations features of the Pro Plan.

The Enterprise Plan has all of the Support features of the Pro Plan but the Email support is expedited and there are the following additional features:

  • Phone support
  • Designated customer success
  • Individualized onboarding and training

Only the Enterprise Plan is in possession of Admin features, which includes the following:

  • SAML-based single sign-on (SSO)
  • SCIM provisioning (Beta)
  • User groups (Beta)
  • Security review and MSA support


Calendly Funding, Valuation, & Revenue

What founder Tope Awotona has accomplished is remarkable. With a few hundred thousand dollars of seed money, he has been able to acquire hundreds of millions in funding over the course of a single year.

According to Fortune, Accel, Iconiq, and Sequoia have courted Calendly.

Up to 2020$550 K
2021$350 M

What began as a bootstrapped startup with $200,000 of Axatona’s savings has blossomed into a four-billion dollar unicorn.

2020$3 B
2021$4 B

The rise of Calendly’s revenues has been nothing short of meteoric! From 2014-2015, Calendly went 10x. From 2015-2016, it quadrupled. Then, it more than doubled the following year. Finally, over a three-year period from 2017-2020 it did a 6x.

YearRevenue (ARR)
2014$100 K
2015$1 M
2016$4 M
2017$10 M
2020$60 M

Is Calendly Profitable?

Calendly, a leading scheduling software startup is profitable and growing rapidly. The revenue is being used to accelerate product development and enhance the team to further scale the company’s mission of helping people schedule meetings. 

The goal of the company is to create an easy way for people to schedule meetings so they can focus on the content of the meeting. The team has worked hard to build the most seamless, easy-to-use meeting scheduling solution available.

When Calendly’s revenues (ARR) did a 10x in 2015, they reached profitability according to

According to GetLatka, automation was the real secret behind their road to profitability. Improvements from this automation included:

  • Easier purchasing
  • Easier upgrades
  • Ease of switching accounts
  • Reduction of friction points within the SaaS
  • Segmentation based on users’ behaviors and requests

Therefore, the answer is yes. Calendly is definitely profitable.


Conclusion: How Does Calendly Make Money?

So there you have it; a guide to the business model of Calendly and how the company makes money. We hope you found the information useful and if you would like more information on Calendly, you can visit their official website (

Thank you for reading this blog post. We hope this article was able to shed some light on the revenue sources of Calendly. If you have any questions or comments on the topic, feel free to write us an email.

Remember to keep learning and stay curious 🙂

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