How Does Calendly Make Money? Business Model of Calendly

Calendly is a web-based meeting scheduler that helps you and your client schedule meetings at the times that suit them best.

But how does Caledndy make money? It is an obvious question and needs to be addressed. In this article, I’ll delve into Calendly’s revenue stream and discover how they generate its income. Let’s begin!

Calendly offers a freemium business model where it provides its service for free but charges for its subscription services.

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About Calendly

Calendly is a scheduling app that uses artificial intelligence to perfect the meeting experience. Its true secret lies in its innovative upside-down funnel and the unique marketing approach that turns every meeting into an ad for itself.

Calendly makes scheduling events easy for everyone, whether they’re managing a small group of 10 or a large group of 10,000. It allows you to easily set up recurring events, so you don’t miss any important dates.

Business Model of Calendly

Business Model of Calendly

Calendly has a “freemium” (free) pricing structure for its service. It also uses founder Tope Awotana’s upside-down marketing strategy, which we’ll discuss in more detail later. Other competitors include:

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

Many people use Calendly for scheduling appointments and managing their billings. Time and customer goodwill are wasted when there’s friction and back-and-forth between parties involved in arranging meetings.

The truth is, that every successful CRM must require multiple contacts with each client. The effort required to maintain these contacts takes away from other important activities, so outsourcing this activity to a smart SaaS makes sense.


Calendly is an online booking platform for meetings and events. It uses artificial intelligence (AI) to find just the right timeslots and reduces friction.

Basically, Calendar has mastered the art of making meeting bookings as easy as possible. Applications of this software include:

  • Sales
  • Customer Success
  • Recruiting

On their website, statistics include:

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

Calendly, which has been praised for its great user experience, offers seamless integration with Google Calendar, Outlook calendar, and iCalendar. It also supports multiple devices including iOS, Android, Windows Phone, BlackBerry, and Nokia S40.

  • Office 365
  • Google
  • Outlook
  • PayPal
  • Stripe


The marketing aspect is when the freemium business strategy is most useful.

As long as you’re not paying for Calendly, you’re still advertising Calendly every time you schedule a calendar event. If someone else schedules an appointment using Calendly, he/she will be able to view the available timeslots as shown by Calendly.

If Calendly works well, then each Calendly appointment booking is also an ad for Calendly. So every time someone books a meeting through Calendly, they’re advertising their own business.

Calendly also offers its own blog and partners with users as direct marketers with incentive programs that offer commissions.

  • Tech Partners
  • Affiliate Partners
  • Strategic Partners


Calendly has never had to worry about paying rent, utilities, taxes, etc., so they’ve been able to keep their overhead low by staying lean and agile. With any SaaS, there are technical costs involved, but Calendly doesn’t need to spend a ton of cash on them since they don’t operate out of physical locations.

We could expect other SaaS-based expenses for Calendly including:

  • Hosting
  • Payroll for development

Plan for Profit

Calendly cofounder Tope Awotona plans to use his company’s profits to create an “upside-down” sales channel.

The idea is that he wants to prioritize customer relationship management (CRM) over selling and advertising, with the idea that happy customers would lead to word-of-mouth referrals and repeated business.

When Calendly started out, Owatonna focused on the first 1,000 users before expanding his business. He now realizes that focusing on the first 1,001 users would be better for him.

Anyway, he has incorporated his freemium business strategy into his premium subscriptions. The challenge will be keeping people from trying out his services by offering them some sort of incentive.

Calendly has stolen market shares from its competition by offering an easy-to-use service. It’s hard to believe that something so simple could be successful when there were giants like Google and Microsoft competing against them.

However, once they’ve adapted to any tricks that smaller competitors have been able to pull off for a couple of months, they’ll be able to create their own scheduling system.

Owatonna, though, has one advantage against the juggernaut companies: he keeps his expenses low and profits high. By maintaining low expenses and high profits, he can keep his high-profit margin even when his revenue rises.

How Does Calendly Make Money?

Calendly is an online scheduling tool for freelancers and small business owners. It allows them to schedule meetings with clients and manages their projects.

That is why the basic plan is still available even though it is not a revenue stream. It is part of the subscription model and the subscription mode is the source of calendula’s 3 revenue sources:

  • Premium Plan
  • Pro Plan
  • Enterprise Plan

Paid Subscriptions

Basic Plan

With the Basic plan, you get everything for free. You just need to pay for Premium features.

  • Number of calendar connections for each user (1)
  • Personalized booking link
  • Web, iOS, Android Apps
  • Scheduled meetings
  • Active Event Types (1)
  • One-off meetings
  • Meeting notifications
  • One-on-One event type

It includes core functionality plus customization options, embeds, etc.

Furthermore, in addition, to core features and a customization option, the basic plan has the following integrations options:

  • Connect to Google, Microsoft Exchange, Outlook, and iCloud calendar accounts
  • You can connect to these services from within Slack.
  • Connect to Slack and SendGrid

The Basic plan includes these additional features:

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

The Premium plan costs $8 per user each month. It includes all of the core functions of the basic plan plus these additional premium services:

  • A number of calendar connections per user (2).
  • Active Event Types (unlimited)
  • Event type: group, collective, or round-robin

With the Premium plan, you get these additional customization options:

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

The Premium plan includes additional integrations beyond the basic plan.

  • Webhooks
  • More than 700 apps integrate with Zapier

With the Premium plan, you get all of the support features of the basic plan plus these additional features:

  • Email support (3 hours)
  • Live chat support for 10 or more users

The Pro Plan costs $12 per month for each additional person who uses your app. It includes all of the core features of the Premium plan plus these extra features:

  • 6 calendar connections per user
  • Team Pages
  • Workflows

With the Premium plan, you get access to all of the customization options for both the free version and the pro version. You also get access to all of these customizations for the pro version:

  • Custom SMS notifications
  • Expanded color options
  • Redirect invitees

With the Pro Plan, you get access to all of the integrations available for the Premium plan plus:

  • Connect to Salesforce
  • Connect to and
  • Use Stripe and Paypal for online payment processing
  • Use Google Analytics and Facebook Pixel for tracking conversions.

The Pro Plan includes all of the features of the Premium Plan plus some extra ones.

The Enterprise plan costs per seat and the interested user needs to contact sales to get pricing details. It includes all core, customization, and integration functionality of the pro plan.

With the Enterprise plan, you get all of the features of the Professional plan plus email support is expedited and you get the following additional features:

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

Only the Enterprise plan has admin features including the ability to create new accounts, change account settings, etc.

  • SAML-based single sign-on (SSO)
  • SCIM provisioning (Beta)
  • User groups (Beta)
  • Security reviews and MSAs (maintenance services agreements)

Calendly Funding, Valuation, & Revenue

His accomplishment was remarkable. With just a few hundred thousand dollars in seed money, he acquired hundreds of millions in financing within one single calendar year.

According to Fortune, the companies Accel, Iconiq, and Sequoia Capital have invested in Calendly.

What started out as a bootstrapped company with $200,000 worth of its founders’ savings has turned into a four-billion-dollar company.

The rise of Caledndly’s revenues has been nothing short of meteoric! From 2014 -2015, Calendly goed10x. From 2015 – 2016, it quadrupled. Next, it more than doubled in the following two years. Finally, over a 3-yr span from 2017 – 2020, it did a 6X.

Is Calendly Profitable?

Calendly, an online meeting scheduler, is profitable and growing quickly. It uses its revenues to develop new products and improve the team.

The goal of the business is to create a simple, easy-to-use meeting scheduler. They’ve put a lot of effort into building the best one available.

Calendly was profitable when its revenue grew by 10 times in 2015.

Automation was the real secret behind the company’s success. Improvements include:

  • Easier purchasing
  • Easier upgrades
  • Ease of switching accounts
  • Reducing friction points between salespeople and their clients
  • Segmentation based on users’ behaviors and requests

So, the answer is yes, but not necessarily for everyone.

Conclusion: How Does Calendly Make Money?

Here’s a quick overview of how Calendly makes its income. If you’d like more information on Calendar, you can check out their official site.

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About Robby Khattak