Calendly's Charismatic Climb!

Calendly's revenue growth, viral marketing strategy & founders's productivity hack

Jan 03, 2024

Hello everyone 👋🏼

Every New Year, we all want to get a better version of ourselves. The one way to get there is by doing more than we did the previous year. It all boils down to better productivity. Multiple tools, multiple hacks–– all trying to make us manage our time better.

Speaking of time, I just wanna block the next 13 minutes on your calendar so you can read the next part of this captivating journey we're on together 😊. Now, in a world without scheduling apps, that could mean a bunch of back-and-forths, time zone mix-ups, and potential scheduling chaos. But we are in luck, because a visionary called Tope Awotona had this lightbulb moment, and bam! Calendly was born—a scheduling wizard for over 20 million users worldwide.

Our next story is on Calendly, which is a game-changer in the world of appointments, meetings, and collaborations. No more endless email back-and-forths just to nail down a time. With Calendly, you can smoothly toss your availability out there, and others can also choose a time on your calendar that works for them.

So, instead of hitting you up with an email marathon to set our 13-minute date, I’m just basking in the wonder of how Calendly has shaken up the way we handle our schedules. Ready? Let’s dive in and talk about how Calendly is raking in the big bucks because, well, numbers speak volumes.

It's not just about making meetings a walk in the park; there's a genius strategy at play here, bringing in the cash while keeping customers grinning ear to ear. So, let’s decode the secrets behind Calendly's revenue model and get a sneak peek into the minds of these industry leaders as they craft their winning strategy.

Calendly’s Business Blueprint!

Calendly is a scheduling platform, helping teams to simplify the way they plan, prepare, and follow up on meetings. It was founded by Tope Awotona in 2013 and headquartered in Atlanta, Georgia. With over 20 million users worldwide, Calendly has redefined the art of scheduling, making it a breeze for individuals and teams alike.

It operates on a freemium model, offering both B2B and B2C users a scheduling software with a free plan and three premium subscription plans. The freemium approach is particularly effective in marketing because even non-paying users act as promoters when scheduling meetings. Each time a user books a meeting using Calendly, their counterparts see the available time slots, essentially turning every appointment into a Calendly advertisement.

Calendly generates revenue through subscriptions to its premium plans, which offer additional features beyond the free version. The company also engages in partnerships, including tech, affiliate, and strategic partnerships, providing incentives such as commissions to direct marketers.

Being a bootstrapped operation, Calendly has been able to keep costs down, focusing on essential expenses like technically skilled staff, energy, and equipment maintenance.

Tope, follows an "upside-down sales funnel" strategy, prioritizing customer relationship management (CRM) over traditional sales and marketing. Satisfied customers lead to referrals and repeat business.

(Image courtesy: https://www.autopilothq.com/blog/claire-suellentrop/)

Tope's plan for profit involves continually adding new features to the premium subscription packages, motivating clients to opt for paid plans over free ones. While competitors like Google and Microsoft may pose challenges, Calendly's emphasis on low costs and the freemium model contributes to its success. The company's revenue streams include the Premium Plan, Pro Plan, and Enterprise Plan, reflecting different levels of subscription packages. It's the Calendly way – making meetings smoother, one plan at a time. 😎

Since we've checked out how Calendly makes money, let's dig into the numbers that tell the real story of their success. We're talking about growth, acquisitions, and all the digits that highlight Calendly's impressive journey. Facts and figures, these are the 2Fs that best illustrate the story of any company’s remarkable rise.

Give Me My Time, Take My Money!

Calendly's been on a money-making spree, and it's not just chump change.

In 2020, they cashed in $70 million.

The next year, they cranked it up a notch, almost hitting the $100 million mark.

In 2022, they practically made it rain with a jaw-dropping $181.5 million in revenue.

In 2023 it hit $276.1 million in revenue. Now that’s called progress.

Talking numbers, they've got 2 million folks paying up for that premium Calendly experience in 2022. That's a lot of people saying, "Take my money, Calendly!" And it's not just regular folks. Over 57K businesses have jumped on the Calendly train at the end of 2022. They're scheduling meetings, making moves, and keeping things organized – all thanks to Calendly.

An Investment that has paid off

Calendly has raked in $350.6 million from two exhilarating funding rounds. The recent one went down on January 26, 2021, marking their Series B round. The big guns, ICONIQ Capital and OpenView, were throwing their weight behind Calendly.

Not just about the money, Calendly's been making strategic moves. They acquired Prelude on September 27, 2022, joining forces to conquer the scheduling world. This is their most recent acquisition.

Talking market share, Calendly's no underdog. As of 2023, they hold a hefty 32.28% slice of the scheduling service pie.

When it comes to valuation, they're keeping that a secret. But back in January 2021, they flaunted a $3 billion price tag during their funding round. So, you do the math – it's one valuable scheduling powerhouse!

In the next section, let’s pivot to the driving force of these impressive numbers — the marketing channels that propel this scheduling giant forward. So, how did they strategically reach and captivate their audience? Read on to learn more.

The 70-10 Rule!

Most people find Calendly in two main ways. First up, 7 out of 10 folks just type "Calendly" in their browser or use a bookmark they saved. That's called direct traffic – the straightforward route.

Then, about 1 in 10 folks get here through referrals. That's when someone tells them about Calendly on a blog, social media, or another website. It's like a friend saying, "Try this cool tool!"

So, while most people just type it in, the word-of-mouth crew still brings in some new friends. It's like having a digital hangout – simple and easy!

With this, let’s look into the numbers to see the breakdown right away!

The Tope Awotona Effect!

Time to switch gears and meet the brain behind it all- Tope Awotona.

"Do things the way they should be done, so they can turn out the way they should turn out!"

Have you heard this quote? That's a gem from Tope’s mom, it's a life philosophy he swears by. Tope is the brains behind Calendly and this saying is his absolute favorite. Starting the blog with this quote felt right because now I am about to take you through the inside scoop on how Calendly went from an idea to becoming the world of scheduling. And since we're diving into the growth story of Calendly, one awesome meeting at a time, please! 😊

Before deciphering Calendly, let's decode what this quote truly meant for Tope and how it set the stage for the birth of Calendly. To break it down, his mom's wisdom is all about giving your best effort, no matter the task. Whether it's an easy task or a tricky challenge, the idea is to tackle it with the dedication it deserves. Cutting corners was not in Tope's playbook. His mom's philosophy taught him that when you do things the right way, without shortcuts, the results can be pretty remarkable. So, armed with this mindset, Tope ventured into the creation of Calendly, a platform that reflects this commitment to doing things right from the get-go. Let's see how this idea shaped the start of Calendly.

Tope's journey began in Nigeria, where he was born to ambitious and hardworking parents—his dad, a microbiologist, and his mom, a pharmacist. Moving to the United States at the age of 15 opened up a world of opportunities for Tope. He embraced the challenge, finished high school, and pursued his college education at the University of Georgia.

Tope's early professional life revolved around sales, starting with part-time jobs in high school and college. His resilience and ability to persuade people became evident during his stint at a call center and later selling alarm systems door-to-door. These experiences laid the foundation for a successful sales career, where he dealt with strategic and complex sales for enterprise software.

Despite his success in sales, Tope harbored a deep desire to become a successful entrepreneur. His entrepreneurial journey had its share of false starts—a dating site, an ecommerce venture selling projectors, and another one offering grills. These endeavors, however, lacked a crucial element: passion. Tope realized he needed to solve a problem he was genuinely passionate about.

The turning point came when Tope experienced the frustration of scheduling meetings through endless back-and-forth emails. Despite searching for a solution, existing products fell short of his expectations—slow, clunky, and lacking usability. Recognizing the gap in the market, Tope decided to take matters into his own hands. Armed with his unique blend of sales expertise, technical acumen, and an eye for usability, Tope emptied his bank account to kickstart Calendly. Little did he know that this venture would not only streamline meetings for millions but also redefine how teams across the globe approach their busy schedules. Doing things the right way, that’s what this success is all about.

Serendipity Strikes!

When Calendly first hit the scene, it wasn't a grand plan—it was a bit of an accident. Tope initially launched the scheduling platform as a free service. The original idea was to make it a paid product, but due to budget constraints, they didn't get around to building billing features. As it turns out, this accidental decision to keep it free became one of the best moves they never planned.

The product's virality played a crucial role in attracting its first users. Tope had collaborated with engineers in Ukraine to kickstart Calendly, and those engineers were also working with another company in the Bay Area—Bright Bytes. Through a series of connections, people at Bright Bytes discovered Calendly and became some of its earliest users. Bright Bytes' customer success team started using Calendly for scheduling calls, and then the magic happened. They introduced it to K-12 schools for parent-teacher conferences, creating a viral ripple effect.

The freemium model, accidental as it was, worked wonders for Calendly. The combination of being free and having a product that naturally spread through word of mouth became the foundation for their initial growth. Users, finding the product intuitive and valuable, organically promoted it each time they scheduled a meeting.

But, of course, every success story has its share of lessons, and Tope admits to a mistake. When they eventually decided to start charging in August 2014, they didn't give users enough notice. Looking back in retrospect, it became evident that better communication and possibly allowing existing users to continue using the service for free could have made the process of transitioning from a free to a paid model more seamless and problem-free.

In the end, Calendly's journey to its first 1000 customers was a mix of unexpected turns, accidental successes, and the powerful force of a product that people not only used but loved to share. So, freemium model, ease of adoption, virality and word of mouth, and monetization transition — reason for Calendly’s growth — Product-Led growth!

Founders’s Productivity Toolkit!

Tope Awotona, has a set of tools he uses for his work. One of them is, of course, Calendly, the scheduling tool we've been talking about. But there's another cool tool he likes, and it's called Monosnap.

Calendly: Making Schedules Easier

No surprise here – Calendly stands as Tope's go-to scheduling solution. It helps him plan meetings and keep things organized. Tope likes things to run smoothly, and Calendly does just that.

Monosnap: Capturing Ideas Clearly

Monosnap is a tool that helps Tope share pictures of his screen. Sometimes, a picture can explain things better than words. So, when Tope needs to show something to his team, Monosnap lets him take a picture or record a quick video to explain his ideas.

In Tope's own words, "A picture's worth 1000 words, and Monosnap lets me easily share screenshots or record quick videos to communicate with our product team."

Elevating Productivity, One Tool at a Time

Tope's toolbox reflects a strategic blend of efficiency and clarity, where each tool plays a unique role in optimizing his productivity. Calendly keeps the schedules in check, and Monosnap elevates communication to a visual level, ensuring that Tope's ideas are conveyed with precision.

Smart Scheduling!

Calendly is stepping into the world of Artificial Intelligence (AI) to take scheduling to a whole new level. AI, for Calendly, means more than just automating tasks; it's about transforming how humans and systems collaborate. Here's why AI matters to them:

Filling Information Gaps

AI aids in closing information gaps, ensuring accuracy, and minimizing bias.

Creating Richer Experiences

By empowering users to exert greater autonomy and impact in their respective roles.

Calendly, a company that's always open to new ideas, is bringing in AI to match its forward-thinking values. AI won't just make us work faster; it's meant to make our work better overall. In Calendly, AI will:

Decide what tasks are most important based on schedules and business needs.
Improve how we connect at every step of a meeting to make them more effective.
Help us manage our time so we can focus on the things that really matter.

This turns Calendly into a complete system for meetings, making everything from planning to follow-up work as well as possible. The main goal is to make every meeting really count, and maybe even make people like meetings more.

Exciting things are on the horizon! All we have to do is wait and watch, or maybe sign up on their AI with Calendly waiting list.

In essence, Calendly’s journey reflects grit and determination, qualities Tope identifies as essential for successful founders. To him, grit means having the courage to persist in the face of challenges. He personally gave his all to Calendly's plan, fully committed to making it succeed. Even as successful founders like Tope, with minds that never rest, have various ideas brewing, the unwavering commitment to their main plan remains crucial for achieving success.

"There's no reason to have a plan B because it distracts from plan A." - Will Smith

Tope acknowledges that he has a multitude of different ideas, one of which involves a new product in the fitness industry—a fusion of CrossFit with a more accessible and less intimidating approach for the general population. However, he emphasizes that, for now, these ideas will have to wait as Calendly keeps him pretty busy. The lesson here is clear: having multiple ideas is great, but the true key to success lies in staying committed to the main plan, as it keeps the focus intact and ensures continuous progress toward the primary goal.

Growthstore Giveaway: FREE AI scheduler for Social Media 🎁

Imagine if you could take that same smart scheduling approach to your social media game. Picture effortlessly scheduling your posts, crafting content that perfectly suits the moment—crisp, spicy, positive, professional—again, all with a few clicks. I found tools from a startup called Highperformr that makes it happen. This tool looks really promising. It lets you create engaging posts, fix spelling and grammar errors, and even design eye-catching images. You can elevate your social media presence with these tools.

FREE AI Scheduler

In today's digital world, the impact of visual content cannot be overstated. As Tope himself emphasized, 'A picture's worth 1000 words,' highlighting the significance of effective visual communication. Recognizing the importance of understanding your audience's preferences in this visually-driven era, we are thrilled to introduce our latest feature – Media Engagement.

Why Media Engagement Matters

In a world where pictures speak louder than words, Media Engagement equips you with the insights needed to make your visual content truly stand out. Whether you're a seasoned content creator or a marketing enthusiast, this feature provides the key to realizing the full potential of your visual assets.

What You Gain

Media Engagement feature offers a comprehensive analysis of how your visual content has performed over the last 1, 7, or 14 days. This means you get a clear and detailed look at the impact of your images, helping you fine-tune your content strategy for optimal engagement.

Stay ahead of the curve and maximize the effectiveness of your visual content with Highperformr's Media Engagement feature. Your audience is waiting – make every visual count!"

Learn More