How Calendly CEO Tope Awotona grew Calendly to $276.1M revenue and 10M customers in 2023.

[Music] I'm Toba Anna I'm the founder and CEO of calendly and Callaway is a platform that helps to schedule mediums and also powers medium workflows so what that means is we eliminate the back-and-forth of scheduling this Ted ever said in four or five emails to get a meeting scheduled we help you get that done and one interaction and in addition to that we power meeting workflows so after the meeting is scheduled we can help you distribute the meetings between team members we can help you send our reminders about your invitees show up on time on a wall prepared we can update your CRM your applicant tracking system those are just some of the workflow that we power we've been in business for six years now over for about four million 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 so the idea calendar came to me when I went to schedule early needed alright so before I started counting Li I was an enterprise software sales so I spent a lot of my time scheduling meetings with people right and one day I was looking to schedule a meeting and they took way too many emails to get it done and I became frustrated and I was hoping I could just go to some website and sign up for a product that would make scheduling easier for me instead of finding that I found a lot of tools in the market that were difficult to use they 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 and 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 and spending a lot of time really developing an idea of what would make a world class scheduling platform and I had a team of engineers to partner with to build it unfortunately I had a lot of really bad businesses before calendly but they were really instrumental in my learning so before countly I started a number of ecommerce businesses I started those businesses because I was looking to start a business not because the world needed another ecommerce website and so because of that some of those ideas filled but calendly was the first business that I did that had major success and we've just double down on the success in step one being a little crazy I think helped but some of the things I think helped the most is I I was a you know I spent a lot of my time in my carrier doing many many different different things I've kind of changed my career's 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 was a CEO does is like they're really very they're very good generalists right and I think that you know I was a bit acquire a lot of varied experience through my career and so what I would encourage entrepreneurs to do or aspiring entrepreneurs to do is be be very open to learning all kinds of different bands and if you see an idea that you think that you feel incredibly passionate about go for it so some of the lessons that I've learned is first and foremost it's important to be passionate about the problem that you're looking to solve if starting a business for you it's just about making money it's probably gonna be very difficult for you to to signal to succeed because you can't fake the passion if you don't have the passion you will not be motivated to work really hard on the problem and without hard-working concentration and focus it's very difficult to make a business successful so one is passion definitely I think it's very important to think about your product and your service along with how you're gonna acquire customers in a repeatable way from day one some of my previous business is I thought about the product I thought about the service but I didn't put enough thought into how I was gonna acquire customers and in repeatable and cost-efficient way I spent too much time thinking about the product in 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 failing some 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 like 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 another 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 and 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 the business so those are some of the things that are top of mind for me right now I find inspiration from a lot of things so one of the things that I like to do is I'd 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 I go somewhere and I have a really good experience whether it's another product company whether it's a commune oh it's a retailer or 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 it touches me I want to make sure that we're not creating those have bad experiences from for our customers for our employees so that's how I get a lot of my inspirations it could be from sometimes it from product companies from sometimes it's retailers sometimes it's services businesses yeah so when I first started the company I bootstrap there with my mind so the idea of you know what we now call calendly was so I was so excited about it that I took every single adela that I never 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 continue to grow the product in containers for 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 is raised so raising very a little bit of money and that they made the difference in their early days to continue to build upon of the product yeah so I have two investors that they're aligned Adventures and open B ventures so these companies they've invested in lots of successful companies what I would advise the entrepreneurs is that if they're thinking about bringing on investors is I think first and foremost before you bring investors I think it's good for you to build and develop your idea as much as possible so that way your raise them later on in the in the lifecycle and what that means is you can you can raise and give a very little viewer your ownership stake in the business right so there 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 might be my first advice to entrepreneurs the second advice is as you're raising money there are lots of people out there who if you have a really good idea and they're 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 that will help you solve difficult problems that will come along the way it might be an international expansion it might be people and culture it might be product it could be any kind any kind of thing but 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 altogether we have about 80 people 70 of those are in the States and then we have 10 people from our technical partner in rails where so we started with rails where they were the initial people who helped us to get the product of the ground over time we've added people in the states we've added them in all kinds of function so sales and product and engineering but we still continue to work with rails we're and we've expanded that relationship but since we started working with them in 2013 so my current my current role we today we have a really strong management team so just really all functions within within the company we're 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 to be a glue for them to finance their ideas and also be a cheerleader and taught them to get those ideas done yes my job has changed so much since 2013 and it will it will continue to change some of the big changes were in 2013 I was essentially the only person on the business side right so we you know work with the engineers from rails when...