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Calendly—The Viral Freemium Product with a $3B Valuation

Free Content

Have you ever been so sure of a gap in the SaaS market that you were willing to empty all your bank accounts to fund the product yourself? (Me neither.)

Thankfully, Tope Awotona was back in 2013.

After going through a particularly horrible experience trying to schedule a meeting, he poured all his resources into a novel solution, banking on the fact that most people have similar experiences.  

Well, almost 10 years later, it turns out Forbes, OpenView, and thousands of enterprise businesses agree with him. They’ve all contributed to the hype train surrounding the latest darling of the product-led growth movement: 

Calendly — the schedule automation platform. 

Since its 2013 inception by Founder-CEO Awotona, Calendly has built up quite an impressive resume, including: 

  • 10M users and a presence in 50,000 companies
  • A $350M Series B funding round lead by OpenView Venture Partners
  • A $3-billion overall valuation in 2022
  • The #21 spot on this year’s Forbes Cloud 100 List
  • De facto status as the top meeting scheduler software 
  • A total of 811M backlinks earned all time

The catalyst behind all this success is Calendy’s efforts to save one of the most vital resources for enterprise companies—time.

Best part? They do it across numerous verticals. They’re a horizontal platform. One that’s useful for virtually every department within the modern enterprise, from SDRs to customer success to marketing to product. And they’ve parlayed successful product-led growth into content marketing success quite effectively. Just take a look for yourself:

search scorecard for calendly

In this case study, we’re going to explore how the product-led growth model built the foundation for Calendly’s assent, as well as the way their marketing team builds off this growth framework to ensure the company is positioned for success well into the future. We’ll dive into: 

  • The popular growth strategy that positioned Calendly’s product for success
  • How links and exposure virality play a central role in their rapid ascent
  • A simple content marketing strategy built to supplement new user capture 
  • Their social strategy that targets the segments of their user base most likely to scale use

Alright then, let’s get into it. 

The Secret to Calendly’s Success? Product-Led Growth 

Plenty of SaaS Unicorns owe their success to the product-led growth model.

Slack, Atlassian, and Zoom, among many others, all sell a core product that is designed to acquire, convert, retain, and expand users efficiently — all while providing an unparalleled user experience. Even cloud infrastructure companies like Hashicorp are getting in on the PLG action

The streamlined development process allows startups to bootstrap and saves major marketing, sales, and customer success investment until they have reached a critical mass of users and capital. 

Initially skeptical (and most likely feeling threatened), many marketers and sales teams have come around to see the product-led model for what it is — the best way to satisfy the end user.

Naturally, this strategy is working out quite well for the companies that adopt the model as well. Ditto for those who invest in them. 

According to OpenView Partners’ 2022  Product Benchmark report, product-led companies are twice as likely as sales-led companies to achieve 100% year-over-year revenue growth

Companies that adopt the “freemium” product-led growth strategy, like Calendly, are particularly well positioned for success. 

Awotona’s meeting scheduling software is free for anyone to use and, since basically every company in every industry holds meetings, they have a massive horizontal market. From multinational pharmaceutical companies to mid-market consulting firms and even solopreneurs, everyone has meetings. 

Ipso facto: everyone needs Calendly

Conventional wisdom says that a massive market like this is difficult to attain (“if you sell to everyone, you’re selling to no one,” and all that). But Calendly has been able to successfully spread across industries thanks to two key components of their product: 

Simplicity and Virality.

Simple UX, Powerful Impact

Calendly’s value proposition is simple: take back your valuable time (and reduce a few headaches) by automating the meeting scheduling process.

It all hinges on the use of a virtual calendar that users share with their network through a link. The Calendly user, aka the inviter, shares a link in email signatures and documents or embeds it on a website. For example: 

calendly link in the signature of someone's email

From there, clients, prospects, or team members — aka the invitee(s) — follow the link to a calendar that looks more or less like this:

reggie peterson calendly page

Once the date and time are selected, the invitee is then sent a meeting link for Zoom, Meets, Teams, iCloud, or whatever other meeting platform the inviter specifies.  

Pretty easy, right? But there are two powerful outcomes to the use of this simple scheduling tool:

  • The pesky scheduling experience is drastically improved for the invitee, setting the meet-up for success
  • The inviter is able to drastically reduce the amount of time (and resources) they spend scheduling meetings each week 

They may seem small, but these outcomes are a major reason why Calendly is dominating the scheduling software niche and, more importantly, the overall SaaS market. 

Looking at this G2 performance grid, it’s easy to see that Calendly is a dominant player in the business scheduling space. Considering HubSpot Sales Hub is not exclusively a scheduling software, Calendly has a significant hold on the market. 

capterra ranking

Image source: 

So, you’ve got a good grasp on how this simple tool is perfectly positioned for product-led growth, but the question still remains:

How did they actually achieve it?

Scaling an “Accidental Freemium” Product with Links and Virality

It’s funny to think that all of Calendly’s success is attributable to a lack of capital during a critical growth stage. 

In a conversation with Forbes, Tope Awotona talks about how he wanted to make Calendly a paid product, but the company was strapped for cash at the time and opted for the freemium approach. 

It turns out that was a huge blessing for the company (and all of us). 

See, Calendly works through links, and as a free product with a horizontal product-market fit, it’s an incredibly easy product to spread among — and across — professional networks. 

How easy is it? According to their homepage, it takes just 3 steps:

calendly get started

In other words, Calendly’s growth model helps them achieve the same type of viral popularity that you see from other product-led companies like Loom. 

Users and product enthusiasts actively spread products like Loom and Calendly to their professional network in order to reap the benefits of their features. In the case of Loom, by providing async video communication and, for Calendly, by automating an inefficient and frustrating scheduling process. 

It’s a process that OpenView calls exposure virality — where user sharing is built into the product’s main function — and it’s an incredibly effective avenue for rapid product-led growth. Here’s how it works for Calendly:

  1. Director A sets up Calendly profile (free or paid)
  2. Salesperson B requests to meet with Director A, is referred to a Calendly page through the link
  3. Salesperson B saves time (and stress) by using Calendly 
  4. Salesperson B sets up free Calendly account
  5. Rinse and repeat 

It’s this type of growth that’s helped this PLG giant achieve a high branded search volume and near 70% direct search rate.

Oh, speaking of viral, let’s take a quick second to appreciate this notorious Twitter beef involving Tope Awotona that helped expand the product’s user base. 

Here’s the TL;DR:

  • Facebook’s Ex-VP of Product posts that Calendly is inherently rude and a “naked” display of workplace power inequities
  • The post, unsurprisingly, goes viral and activates Calendly enthusiasts
  • Tope responds, thanking the critic for the “huge spike in signups” 
  • Ex-VP comments (tongue in cheek) that he deserves an affiliate code from Awotona

As you can see, there’s more than one way for a SaaS brand to go viral (although I’d bank more on the product-led growth part if I were you).

Okay, now back to our regularly scheduled programming. 

Capturing Users With Conversion-Drive Pages and Blog Posts

Following the formula of their product-led growth strategy, Calendly’s marketing team succeeds by creating its content according to the principles of product-led growth. 

That means: 

1. Capturing user interest

calendly outperform the competition with fast frictionless interactions

2. Inspiring immediate conversion

calendly helping millions schedule better

3. Reducing barriers to sign-up

calendly freemium signup box

Essentially — they want their web content to keep the user on the page, provide a compelling reason to join, and make the signup process as frictionless as possible.

Since its inception, Calendly has strived to make this transition from discovery to conversion smooth. Even way back in 2015, Calendly placed conversion at the front and center of their marketing efforts (and landing page): 

calendly's 2015 landing page

Of course, the design leaves a lot to be desired and it’s not the most compelling call to action, but conversion is, quite literally, the central focus of the page. 

Fast forward to today and you find that Calendly is deploying a similar concept, one that’s fully optimized for conversion: 

calendly's 2022 landing page

Bells and whistles aren’t necessary when you’re providing immediate value, zero-friction signup, and sleek design. 

From first glance, Calendly’s marketing team has created a homepage providing everything they need to convert new users:

  • A straightforward tagline
  • A concise explanation of their value prop
  • An immediate CTA for email signup 
  • A disclaimer about the freemium nature of the offering

Given that nearly 70% of their total traffic comes via direct search, the lead section of their homepage is incredibly valuable. Their marketers take all the necessary steps to ensure conversion by placing potential users right at the very bottom of their acquisition funnel.

Calendly supplements new user capture for the remaining 30% of their organic traffic with blog pages. And they’re certainly no slouches in the content department. All of Calendly’s content is designed to compel and direct potential users toward secondary sign-ups.

Every month their blog brings in over 260K in organic traffic, valued at over $200K.

That’s another quarter of a million people coming into the Calendly sphere of influence, potentially those without direct exposure to the product. 

Oh, and this blog content also saves them $2.4M in digital advertising each year.  

search scorecard for calendly's blog page

At first glance, many of the highest-performing content on their blog seems very surface level:

blog pages by traffic for calendly's blog

But all these pages funnel visitors towards free user accounts by offering content that’s useful, full of examples and templates, and light on fluff. Many of the posts are geared towards beginner-intermediate professionals, meaning Calendly is also filling its pipeline with potential long-term users. 

Once these potential users are converted, it’s just a matter of time before they contribute to the backlink strategy that’s baked directly into the Calendly product. 

Calendly’s Baked-in Backlink Success

Calendly’s simple, link-based system isn’t just great for expanding its user base, it’s also helped the company gain a massive amount of link equity and domain authority. Over the past decade, it’s helped them grow to the point where they now have 484K distinct domains referring to their website. 

And that’s just the domains

All told, Calendly has earned over 811M backlinks since its inception and currently boasts over 31M Dofollow links, 128K of which come from high-authority domains.

That’s a lot of quality link equity.

calendly's built-in backlink success

The reason for this backlink success should be obvious now. It’s built into the product itself. 

As exposure virality spreads Calendly to more and more users, more and more of them become users and attach calendar links to a “schedule appointment” or “book a demo” CTA on their own website. 

When these users scale from freemium over to paid they unlock additional benefits, including the ability to embed their Calendly link within a webpage. 

calendly's embedded calendars

These embedded calendars offer another layer of benefit to inviters, invitees, and Calendly’s backlink network. 

Paid users have the opportunity to insert their calendars inline, as a pop-up widget, or as pop-up text — all options that improve the user experience while passing some link equity back to Calendly’s site. 

But making the jump from a freemium to a paid enterprise user is no easy feat. And while Calendly does have a dedicated sales team, they’ve invested in another channel to help drive expansion.

Hitting Their ICP Where They Live (And Work)

As I said earlier, Calendly targets a horizontal market — providing users segments across all industries and job descriptions an equal opportunity to cut down the time they spend scheduling meetings

However, this doesn’t mean that all of these user segments are equally likely to become paying customers or product evangelists. 

For many product-led companies, the ultimate goal of achieving a presence at the enterprise level relies on properly identifying these user segments. This takes a more targeted approach – in terms of both channel and messaging. 

It’s no surprise then that the lion’s share of Calendly’s social referrals come via LinkedIn: 

60.19%, to be exact

That’s more than twice as many web referrals as Calendly gets from the next 4 social platforms combined!

calendly's social referral traffic by channel

Calendly’s social success on this platform makes a lot of sense. SDRs, customer service reps, and recruiters are primary users of both Calendly and LinkedIn. They’re also more likely to be heavy users of both. Calendly’s social team is aware of this and tailors content accordingly.

For instance, out of Calendly’s top 20 current LinkedIn posts, over a third of them are directed towards improving results for SDRs and sales team leaders. 

They cover some pretty juicy topics too, like this:  

calendly linkedin post promoting how sales teams close more deals with their service webinar

Not only does LinkedIn provide the perfect platform to warm up and qualify potential enterprise power users with gated assets like webinars, ebooks, and whitepapers, but it also provides the perfect opportunity for them to announce their latest integrations: 

calendly linkedin post promoting how to automate lead generation with zapier and calendly

Boasting 100 different integrations with some of the biggest names in tech, Calendly posts about these connections through LinkedIn to notify, inform, and activate their current followers. As Calendly’s array of product partnerships and premium features expands, they can easily prime their power user base for expansion with this kind of social content.

It’s a masterful example of complementing a viral product with social marketing that scales users. 

Follow the Pros: Don’t Overthink Product-Led Marketing

I’m sure you’ll agree that a top 25 spot on the Cloud 100 list, 10 million active users across 50,000 businesses, and a $3B valuation is a pretty decent haul for a company that went the freemium route because their CEO (luckily) didn’t have the capital to install a paid membership component. 

Calendly’s success is the perfect model for any product-led company looking to invest in a lean marketing strategy without distracting from the main product. Here’s a recap of how they did it: 

  • Calendly’s product-led strategy helped their product fit into a massive horizontal market
  • Through exposure virality, they turned their freemium user base into a massive sales team
  • Designed their web content to function as a supplementary user conversion engine
  • Amassed over 818M total referrals through their baked-in backlink feature
  • Used LinkedIn content to activate and scale their power user base of SDRs 

Calendly has definitely benefited from some instances of luck and the inspiring determination (and attitude) of Tope Awotona. But make no mistake, this product-led darling follows a blueprint for SaaS success applicable across the tech space. 

Arm yourself with the right strategies and you’ll see firsthand.  

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