How Calendly grew from 0 to $3B in under 10 years

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Calendly: 0 to $3B taking the headaches out of scheduling meetings

Have you ever had 1,000s of users begging to pay you, but couldn’t afford to accept their money?

I’m guessing no (although email me about it if you have!)

Well this is the situation Calendly before they became the $3B giant we know today.

After running out of money for development, Calendly had over 1,000 users but couldn’t pay for payment integrations to be built. And so became Freemium by default.

But hey, rather this than no users - although I can’t imagine Calendly not having any users, it serves such an important purpose in society.

Making scheduling meetings less of a headache.

In just over 10 years, Tope Awotona grew Calendly into a Product-Led Growth Giant. Scaling to over $270M in revenue and a $3B valuation - staying profitable most of the way as well!

This is the story of how Calendly went from Zero to One. 🚀

Calendly’s Growth

Before founding Calendly, Tope was a bit of a serial entrepreneur, with a few failed businesses on his resume - alongside being a really good sales guy.

His role right before founding Calendly was as a national account manager serving Fortune 500 clients and businesses with over $1B in revenue. So we’re talking big-time sales here.

One thing that kept popping up as a challenge was scheduling meetings.

These big companies bring their platoons of security, IT, compliance, accounting, execs. You name it. They bring it. Which made finding the perfect time for a meeting a nightmare.

So one day Tope was trying to set up a meeting for >20 people from 3 different companies (not including himself), and it was just a pain.

John had a Board meeting Wednesday so couldn’t do anything before, Katie had a deadline Friday so was also out then, Ted had his kids baseball game on Tuesday, Robyn had a karaoke day on Wednesday three weeks from now…

And like that, it clicked.

There must be a solution to make this easier.

So Tope went online to find one.

But the problem was there wasn’t a solution.

There were good products, but none that really ticked all the boxes for customer-facing roles - most were designed for the owners of the meetings, not the recipients of the invites.

And so for the next 6 months, Tope signed up for every product on the market solving a similar issue. We’re talking ~30 products.

And he used them religiously.

What he learned was that their customers actually liked their products. But wanted more.

And so Tope decided to go all in. I mean literally all-in.

He withdrew his 401k - paid the penalties as well. He took high-interest loans. Maxed out his credit cards. And found a dev team out in Ukraine to build the MVP for $200k.

2013 came along, the product was ready, and Tope launched it. Calendly was now alive. But completely breathless, without revenue.

The initial plan was for Calendly to be a paid product with a 14-day free trial.

But Tope ran out of money before he could pay for the payment integrations to be built - and it was too late. Calendly had already begun to spread as a free product.

In spring 2014, Tope raised $350k (about 9 months of runway), which allowed him to afford payment integrations. And so in August 2014, Calendly introduced their paid plans.

By September 2014, 15k people had signed up. And by the end of the year, they were making roughly $100k ARR.

And by the end of 2015, they hit profitability and were at ~$1M ARR. Tope and the team then 10xed this over the next two years - reaching $10M in ARR with the introduction of a new pricing tier.

To say Calendly exploded over the next three years would be an understatement.

At the end of 2020, they were at $60M ARR with over 5M active users.

Then after a draught of no outside investment. Calendly raised $350M at a $3B valuation.

As of today, Calendly makes over $270M in ARR with over 10M active users. Making them one of the biggest businesses in the world. So let’s take a deeper look into what drove this success early on.

Key Success Factors (KSFs)

If you’re short on time, here are some actionable takeaways from Calendly, with all the juicy deets below. Enjoy!

🧩 1. Found Founder-Market Fit: Tope knew he wanted to run his own business. So he tried to make it happen - a few times actually. But they all failed. He tried to solve for money by founding a business. Until Calendly that is. When he built a business to solve a problem that he understood.

💌 2. Built an experience everyone loves: Calendly understands that their product isn’t just used by the meeting holder. But by recipients as well. So they focused on building an awesome experience for everyone who would use the product, to create Product-Led Growth.

🧑‍💼 3. Understand who their ideal customer is: Calendly was very specific about who their ideal customer was (someone in a customer-facing role) and built for them. This meant they could prioritize the right features and craft the perfect unique experiences.

🧩 1. Found Founder-Market Fit

As I mentioned earlier, Tope was a bit of a serial entrepreneur before Calendly.

Starting at 17, he registered a provisional patent for a new type of cash register (a typical teenage side hustle).

He got the idea from working at a CVS, so he understood the problem, but didn’t take the business any further because he didn’t feel that he was the right person to solve this problem (awesome self-awareness for a 17-year old).

Then after working for a few years, he got into ecom - selling projectors.

But $20k and 6 months later he shut it down. Why? Margins were too thin and people who want to buy projectors also want to be educated on them.

Tope knew nothing about projectors. Nor did he want to learn about them.

With his next business he tackled the margins of the projectors, now selling gardening equipment.

But the same problem stuck. People wanted to be educated on the best products to buy. And Tope couldn’t care less about which lawnmower cut finer grass. And so the business only lasted a few months before also shutting down.

You see Founder-Market Fit can also be asked as: “Are you the right person to solve this problem?”

There are 3 main questions to ask to figure this out. Let’s go through them, using Tope and his journey with Calendly to highlight the difference.

1. Are you obsessed with solving this problem? 🤓

This is arguably the most important question to ask yourself.

If we look at Tope’s previous businesses, there’s a consistent theme to why they failed. Tope didn’t care about the problem he was solving.

Building a business is hard. It’s even harder when you don’t like working on the problem you’re solving and with the people you’re solving it for.

If your business takes off, this could be a 5-year, 10-year, or even longer journey. So if you can’t stand the thought of working with lawyers, don’t build a legal-tech business.

Let’s take Calendly for example. Tope was passionate about solving the problem of taking the work out of scheduling meetings. He knew the pain and wanted to solve it.

2. Do you have the expertise to solve this problem? 📚

Straight away you can see that Tope had the expertise to solve his problem. He had been in sales for years and had been trying to schedule meetings for years.

Importantly, he also understood both the perspective of the salesperson and the recipient of a sales call - something which the other tools at the time lacked.

There are a few ways you can build the expertise to solve a problem:

• You’ve worked on a similar problem before.

• You’ve worked in the industry or a similar industry before.

• You have the technical or soft skills needed.

• You’re the ideal customer for this problem.

There’s no one-size-fits-all way to have the expertise to solve a problem. But the more you can tick the better (take Tope, he ticks all the bottom three points above).

3. Do you have a story that resonates with your customers? 📖

The simplest way to answer this is: Are you relatable to your customers?

Especially early on in a business, your story is important to winning customers. They need to believe the two points above - that you care about them and their problem and have the expertise to solve it.

Imagine you’re a salesperson who came across Calendly back in 2014.

You’re undecided. You’ve tried 10 different tools already and none quite met your needs. Why should you try another?

Then you read Tope’s story. He’s just like you. A salesperson. He was facing the same pains as you. He needed a solution just like you do. And so he built Calendly.

Now do you have more belief that the product will meet your needs better than all the others you’ve tried?

That’s the power of a story. (Assuming you said yes 😂)

💌 2. Built an experience everyone loves

One of Calendly’s most important unique value propositions when it launched was its user experience. But importantly not just for the owner of the meeting - but also for the people booking meetings.

Of all the tools that existed at the time when Calendly launched, none created an enjoyable experience for everyone. So they changed that.

When you’re doing sales and a prospect clicks a link to book a meeting with you, you don’t want them to drop off because they get confused or put off by the bookings page.

You’ve done the hard work to get them here - Calendly’s positioning for salespeople was that they get prospects over this last hurdle and onto a call with you without any hiccups.

Now this is just a sales example. The same applies to any customer-facing role (Calendly’s ICP).

Once people have shown intent to book a meeting, you don’t want to lose them because of an unfriendly scheduling product.

But this tactic didn’t only improve booking rates. It was also Calendly’s biggest driver for user growth.

Calendly was one of the pioneers of Product-Led Growth. But how did this work practically for them?

Well, let’s go back to the beginning of Calendly to see:

Calendly had yet to launch publicly when their development team in Ukraine shared the product with another one of their clients - a B2B SaaS in San Francisco, specifically serving school teachers.

Once the school teachers saw the product and booked meetings on it, they loved it. And started using it to book parent-teacher conferences. It worked like a charm.

They loved it. The parents loved it. And it decreased admin time and increased show-up rates.

Word spread quickly and soon hundreds of teachers and schools were using Calendly - without Calendly lifting a finger. In fact the product wasn’t quite ready to launch, but it was too late. Word had spread and it wasn’t going to stop.

Soon Calendly spread beyond teachers. Parents who were salespeople or customer success managers saw how easy it was for them to book a meeting and wanted to use it for themselves.

Because Calendly had focused on giving everyone who came into contact with the product a great user experience, it spread organically - people loved receiving Calendly’s, so they wanted to send them too.

🧑‍💼 3. Understand who their ideal customer is

When Tope started building Calendly it was for people like him. Customer-facing roles - think sales, customer success, recruiting.

But soon there was tension.

Calendly could go so much wider than this.

I mean I’m struggling to think about a role that couldn’t get value from Calendly. Everyone hates scheduling meetings.

But only some consistently value it enough to pay for it. And those are people working in customer-facing roles.

Speaking to people is the meat and potatoes of their jobs. So making the meeting process smoother and more effective has a huge impact on their work.

Salespeople can sell more. Customer success managers can retain customers longer. Recruiters can vet and hire more people. Freelancers and consultants can close more projects.

Tope and Calendly understand this.

And so Calendly's messaging and product development was tailored towards this.

Even look at Calendly today. They are telling us who their ICPs are.

And they are showing the benefits to each ICP clearly.

Being clear on their ICP also helped them with their product roadmap. For example, one of their first integrations was with Salesforce. And when we look today, they even have LinkedIn integrations to help salespeople book meetings on the platform.

One example of a feature that didn’t get built but was requested by users who didn’t fit their ICP was a Venmo integration - to accept payments for retail vendors. But this doesn’t fit with who they are building for. So they didn’t build it.

Calendly’s decision on who to focus on was also awesome in that they chose not only the people who needed their product the most - but also the people who could make it the most viral.

Salespeople (often) try to prospect as many decision-makers as possible. Recruiters try to reach out to as many candidates as possible. Their ICPs are users who reach out to many people - creating a win-win for Calendly. If their customers can get in front of more people - so do they (very similar to a strategy used by Flodesk).

Calendly is a great lesson to be clear on who your ideal customer is and to prioritize them.

Tactics to replicate Calendly’s growth

Create persona-specific landing pages and content 📄

We talked above about how Calendly was super clear on their target personas. But what were some tactical ways they got these personas into their product adoption cycle?

Calendly knew that at a high level, someone in a customer-facing role was their ICP. But that could be broken down more specifically (as we talked about above).

So they wanted to make sure they were speaking clearly and in the most effective way to each of these personas. And so they created persona-specific landing pages and blogs.

Each of these landing pages uses language specific to that persona and shows Calendly’s impact for users like them:

Showing relevant features of the product and potential workflows for each ICP, as well as giving them valuable content to help them become better in their jobs.

This hyper-targeted messaging, social proof, and valuable content builds trust and increases adoption of Calendly as well as advocacy.

If you have more than one ICP, you need to differentiate for them.

Create content and landing pages for each.

Then direct traffic, through paid ads, internal linking, and social media directly to the relevant landing page. This will boost your conversion rate significantly.

Understand your competition 🥊

Calendly wasn’t an overnight success.

In fact, Calendly took 6 months to even go from idea to Tope actually building a product.

Tope wanted to be sure he was solving a problem with a product and not building a product to hopefully solve a problem.

He started with the problem first and wanted to fall in love with it.

In all my deep dives this has been a golden thread - Find a problem to fall in love with and solve it in the best way possible.

But I’m getting distracted and you’re probably wondering what this has to do with competition. Sorry, I get excited and easily distracted speaking about product building.

Well you see, Tope’s research was super thorough. Deeper than any company I’ve covered in this newsletter yet.

He bought ~30 similar products to see how they were solving the problem:

• Were they solving the whole problem? (i.e., did he even need to build something else)

• What parts did they not solve?

• What did they do really well?

• What did their customers love?

• What did their customers hate?

• How did they approach customer support?

• How was their onboarding experience?

Tope asked these and a bunch more questions to himself for each product. He became obsessed with the problem.

He spent hours engaging with users in community forums, submitting support tickets, acting as a buyer of the software, and battle-testing each of the products.

These were some of his key learnings:

1. Customers loved the products, but wanted more.

2. Most products only focused on traditional brick-and-mortar businesses.

3. The products only thought about the meeting owners.

4. At a minimum, this was a decent business without changing anything. But there was exponential potential growth to be had if he could lower the barrier to entry and make it appealing to the people booking meetings as well.

After these 6 months, Tope was clear on what the gap was in the market, how to position Calendly to stand out, how to improve the user experience, and how to speak to customers.

Now I’m not saying you need to spend  6 months without building. But the lesson here is to really fall in love with solving a problem. The solution should come from that.

So build early and build fast.

But remember you’re solving a problem and your product needs to be the best solution for that. So speak to customers. Try competitor products. Find who has a deep pain that needs solving and what that solution could look like.

Don’t build blind.

Have a great week, speak soon!

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