How Calendly Reached 4 Million Monthly Users and a $3 Billion Valuation with $70M Revenue (Interview with Founder and CEO Tope Awotona)

Tope Awotona Introduces Calendly and Its Core Value Proposition

Tope Awotona

00:06I'm Toba Owatana. I'm the founder and CEO of Calendly. And Calendly is a platform that helps to schedule meetings and also powers meeting workflows. So what that means is we eliminate the back and forth of scheduling instead of sending four or five emails to get a meeting scheduled we help you get that done in one interaction. And in addition to that we power meeting workflows so after the meeting is scheduled we can help you distribute the

Monthly Active Users and Enterprise Customers

Tope Awotona

00:27meetings between team members, we can help you send out reminders so that invitees show up on time and are well prepared, we can update your CRM, your applicant tracking system. Those are just some of the workflows that we power. We've been in business for six years now. About 4,000,000 people use the app on a monthly basis and our customers range from individuals to small teams to large enterprises like Zillow, Zendesk and Marketo.

The Origin Story: Frustration with Scheduling

Tope Awotona

00:55The idea of came to me when I went to schedule a meeting. Before I started Calendly, I was an enterprise software sales. I spent a lot of my time scheduling meetings with people. One day I was looking to schedule a meeting and it took way too many emails to get it done and I became frustrated I and was hoping I could just go to some website and sign up for a product that would make scheduling easier

01:17for me. Instead of finding that I found a lot of tools in the market that were difficult to use, were clunky, they were vertical specific, they worked really well for people in the health and beauty space, but they didn't really work well for a business professional. Seeing, you know, that the world desperately needed a scheduling tool that worked really well for everybody, I became obsessed with the problem. And I studied it and spent a lot of

01:43time really developing an idea of what would make a world class scheduling platform and I hired a team of engineers to partner with to build it.

Gaps in the Market and Building a World-Class Scheduling Platform

Tope Awotona

01:57Unfortunately I had a lot of really bad businesses before Calendly but they were really instrumental in my learning so before Calendly I started a number of e commerce businesses. I started those businesses because I was looking to start a business not because the world needed another e commerce website and so because of that some of those ideas failed but Calendly was the first business that I did that had major success and we've just doubled down on

02:21the success instead.

Lessons from Failed E-Commerce Businesses Before Calendly

Tope Awotona

02:26One, being a little crazy, I think helped. But some of the things I think helped the most is I was, you know, I spent a lot of my time in my career doing many, many different things. So I've kind of changed. My career has evolved in a lot of different ways and through those evolutions I learned a lot about many different topics and so what I think a founder does what a CEO does is like they're

02:51really very they're very good generalists right and I think that you know, I was able to acquire a lot of varied experience throughout my career. So what I would encourage entrepreneurs to do or as inspired entrepreneurs to do is be very open to learning all kinds of different things. And if you see an idea that you think that you feel incredibly passionate about, go for it.

03:18So some of the lessons that I've learned is first and foremost, it's important to be about the problem that you're looking to solve. If starting a business for you is just about making money it's probably going to be very difficult for you to succeed because you can't fake the passion. If you don't have the passion you will not be motivated to work hard on a problem and without hard work and concentration and focus it's very difficult

Advice for Aspiring Entrepreneurs: Passion and Customer Acquisition

Tope Awotona

03:41to make a business successful. One is passion. Definitely I think it's very important to think about your product and your service along with how you're going to acquire customers in a repeatable way from day one. Some of my previous businesses I thought about the product, thought about the service, but I didn't put enough thought into how I was going to acquire customers in a repeatable and cost efficient way. I spent too much time thinking about the

04:05product and the service and not enough about the customers and what I would do differently. So those are some of the lessons that I've learned from my failures.

04:16Some of the biggest challenges that we have is that we're just growing really fast. So the product is growing, the team is growing. And so how do you make sure that in spite of all that growth, everybody feels like a family, everybody feels a team, everybody really knows how to work together and that we're capturing feedback and we're acting on that feedback in a rapid manner. So those are some of the biggest challenges that we have.

04:38Another challenge that we have is just because of the growth that we're having and also the, you know, the strength of the economy. It's a very tough environment to recruit talent and also attract talent. One of the things that we want to do very well is continue to invest in our culture, our people culture, more so than we've ever done in the life of business. So, these are some of the things that are top of mind

05:00for me right now.

05:05I find inspiration from a lot of things. So, one of the things that I like to do is I like to take ideas that work in other businesses and think about why they can't work in your business. Right? So if you look all around you, every time you go to buy coffee and you go to Starbucks, even though it's in a completely different business from you and it has a completely different distribution model from you, anytime

Biggest Challenges: Rapid Growth and Talent Recruitment

Tope Awotona

05:24I go somewhere and I have a really good experience, whether it's another product company, whether it's a, you know, it's a retailer, whatever maybe, I think about how we can learn, how we can take lessons from some of those ideas. Conversely, every time I have a bad experience, I want to make sure that, you know, it touches me. Want to make sure that we're not creating those bad experiences for our customers, for our employees. So that's

05:48how I get a lot of my inspirations. It could be from, sometimes from product companies, sometimes it's retailers, sometimes it's services businesses.

Bootstrapping with Personal Savings and the 2014 Seed Round

Tope Awotona

05:59Yeah. So when I first started the company, I bootstrapped it with my money. So the idea of, you know, what we now call Calendly was so I was so excited about it that I took every single dollar that I ever made all my savings all my retirement money I took all of that and I invested it into Calendly over time after we built the MVP I needed additional funds to continue to grow the product and continue

06:23to serve our customers. And after that, I decided to raise a seed round in 2014. And that's really most of the money that the company has raised. So, we raised a little bit of money and it made the difference in the early days to continue to build upon the product.

Investor Selection: Atlanta Ventures and OpenView Ventures

Tope Awotona

06:44Yeah, so I have two investors, they're Atlanta Ventures and OpenView Ventures. So these companies, they've invested in lots of successful companies. What I would advise entrepreneurs is that if they're thinking about bringing on investors is I think first and foremost before you bring investors, think it's good for you to build and develop your idea as much as possible. So that way you're raising later on in the in the life cycle and what that means is you

07:06can can raise and give up very little of your your ownership stake in the business right so the later you are by the time you decide to raise the more of the company you can retain not only just in terms of equity but also in terms of control. So that might be my first advice to entrepreneurs. The second advice is as you're raising money there are lots of people out there who could if you have a

07:26really good idea and a really good business there are lots of people who are dying to give you money for it but not everyone is a good advisor. Right? So what I would also encourage people to think about is not just who has the money, but who has the networks that will help you grow, will help you solve difficult problems that will come along the way. It might be international expansion.

07:44It might be product, it could be any kind of thing, I would encourage entrepreneurs to raise money from those people who can help them solve difficult problems that they will undoubtedly encounter as they grow their businesses.

Team Size: 80 People Including Railsware Partnership

Tope Awotona

08:01Altogether we have about 80 people, 70 of those are in The States, and then we have 10 people from our technical partner Railsware. So we started with Railsware, they were the initial people who helped us to get the product off the ground. Over time we've added people in The States, we've added them in all kinds of functions, sales and product and engineering, but we still continue to work with Railsware and we've expanded that relationship since we

08:24started working with them in 2013.

08:29So my current my current role, today we have a really strong management team. So just really all functions within the within the company are being led by other people that are way smarter than me and way better at what they do. And so my job these days is just to to be the glue for those people, right? So I with in conjunction with them, I set the strategy for the business. And so my goal is just

How the CEO Role Has Evolved Since 2013

Tope Awotona

08:51to be a glue for them to finance their ideas and also be a cheerleader and to help them to get those ideas done. Yes,

09:04my job has changed so much since 2013 and it will continue to change. Some of the big changes were in 2013 I was essentially the only person on the business side, so we you know work with engineers from Railsware and I was the only person. I was support, was sales, I was product manager, I was a designer in some ways, just I spent time with the customers but today much other people do those things and also

09:32today compared to six years ago, six years ago, the strategy and the vision for the company resided in just my head. Fast forward to six years later, when you have 80 people working together to launch this idea, it's a lot more important that communication is improved, that the strategy and the vision is clear to everybody. And so that's how my role is changed now. Spend more of my time really thinking about the vision and the strategy

09:58and communicating that to the team than actually maybe doing the work myself.

Building an Advisor Network

Tope Awotona

10:07Yes, so I have lots of advisors and one of the things I wish I would have done earlier in the life of the business is being more proactive about seeking out advisors but I have all kinds of different advisors. I have an advisor who I lean to for people and culture issues right so as you're growing a company you need to attract people you need to retain them you need to create a culture that makes people

10:29excited about the mission that you're looking to build so I have an advisor for that, I have product advisors, I have engineering advisors and also my management team they function as advisors for me. So in seeking out advisors the recommendation I would I have for every entrepreneur is to to start thinking about it early and also find advisors that complement them in all kinds of different ways and advisors who've solved problems that you haven't solved before.

Choosing Railsware as Technical Partner

Tope Awotona

11:02It was definitely very difficult to choose a vendor. One of the reasons it was very difficult for me was it was the first time I was building something of this magnitude. It was the first time I was committing this much money and this much capital. I was going all in on the idea. And this really, for me, was a very personal thing. I was using all of my life savings to build it. So not only was

11:23I excited about the idea, the risk was also really high. But believed at the time that the world needed another scheduling tool even though it wasn't obvious then I I believe very strongly in the idea and I knew that if we did built a really good product if the execution was really good that we would be very successful. And so when I was thinking about getting a technical partner, I wanted to find somebody who was just

11:45who had a great track record of building great products. And that's how I found Railsware. But to answer your question about what are the what was the process that I went through to pick a vendor? I interviewed a lot of people, people all over the world. And what I found was a lot of people just really cared about how much money I had. They weren't excited about the idea. They it was just another project for them

12:08and they saw an opportunity to make money but there there was no passion in what they were looking to build and so I would encourage entrepreneurs as they're looking for people to partner with I would encourage them to find somebody who's truly a partner somebody who's just as equally excited about your product and your idea as you are right it's a very difficult bar to meet but I would encourage entrepreneurs to find that I'd also encourage

12:31entrepreneurs to find people who have an excellent technical record

12:39So I mentioned some of those before, some of the reasons I went with RealWear was as I interviewed lots of different people, I met with a lot of people who cared about money but not people not many people who are extremely passionate about idea. What also happened at the time I was looking to pick a partner was I spent a lot of time thinking about the product that I wanted to build. I knew exactly what I

12:58wanted to build or at least I thought I did. And so I was just really looking for somebody who was really great at building product and would just build exactly what I wanted. But when I met with Railsware, so when I met with Railsware and when I compare my conversations with Railsware with some of the conversations from the some of the other vendors, Railsware actually they challenged my ideas right and in challenging my ideas they got

Why Railsware Won: Challenging Ideas, Not Just Executing Them

Tope Awotona

13:24me to think about things I hadn't thought about before and in doing so it made my idea much better and till today it's probably the difference between Calendly being successful not being successful. So the reason I went with Railsware is they took my idea the ideas I already had and they challenged it and made it a lot better. I would encourage entrepreneurs to think about people who can execute really well and build great products but also

13:50people who can improve your strategy.

Final Advice: Start Earlier and Pursue Learning Opportunities

Tope Awotona

13:56Entrepreneurs, I did not start to act on my first business idea until I was in my late 20s and knowing what I know now I think I could have started a lot sooner and it's also very inspiring and encouraging for me when I see kids that are fifteen sixteen and they already launched websites that are you know they're collecting some money from one person but and I wish I would have done more of that when I

14:19was 15 or 16. There's nothing I stopped you from doing that a lot a lot earlier. So that would be my advice. If you find something that you think that you're qualified to do or very excited to do, try to get started in any way you can. And also take advantage of any learning opportunities that you have along the way.