 Hello, everybody. Hello, Tope. Hello. Welcome to Helsinki. Thanks. Tope just landed 15 minutes ago from Atlanta, so he's still acclimating to the dark and the cold. But great to have you here. It's great to be here. My first time in Helsinki. So I'll give a quick personal intro. So I'm one of the partners at Iconic. I joined a couple of years ago to launch our office in London. For those of you who don't know Iconic, we're a global growth fund. Our differentiation is really that we have a very unique network of founders, families, and CEOs on behalf of whom we invest in the next generation of founders. And we've been over the last 10 years have invested and partnered with some of the most impactful software companies of last decade, companies like Aiden and Miro and Snowflake and GitLab, Procore, and many others. We've also invested in a number of companies that started out with a viral product-led growth motion and then subsequently added on more of a sales-led motion to expand beyond individuals, to tackle teams, and companies of all sizes. And that's really the crux of our conversation today. We've worked with companies like Datadog and Airtable and OnePassword that have all done that well. And of course, Calendly. And so I'm really glad that Tope agreed to do this. He's someone that we've long admired, even before formally partnering with him a few years ago, not only because of what he built Calendly into today, but he's also incredibly thoughtful and articulate about the journey. So I know we're going to learn a lot in this session. Rather than me giving a long-winded intro of you, why don't you introduce yourself, share a little bit about your personal background and what Calendly is? I will do that. My name is Tope Allatana, founder and CEO of Calendly. Started Calendly 10 years ago out of a very simple frustration of, you know, I was a sales rep. I spent, you know, a lot of my work was, you know, trying to get me with our customers and prospects. And this one particular meeting was just too, took too many weeks and too many emails back and forth to get it scheduled. I thought they had to be a better way and decided to start Calendly. And fast forward to now, we started from this simple scheduling product to, you know, a true platform that supports individuals and small teams and even large organizations all across the globe. That's what we do. It's great and Tope is unfailingly humble, so, but I would add that Calendly is now used by over 20 million people, 100,000 plus companies and as you said, all over the world, 200 plus countries. So it's truly a household name within productivity software. So really incredible what you have built. I'd like to spend most of the time on the more recent history in Calendly, but I think just for context and to help frame sort of how you've thought about building the company, let's rewind a bit and start with a bit more of the founding story. And you mentioned that you were an enterprise sales rep, felt the pain point of scheduling firsthand before starting Calendly, but what ultimately compelled you to quit your job and, you know, go all in? Yeah, so before I started Calendly, I was a serial entrepreneur, so I was lucky to work for a number of companies that I'd learned a lot from. I started at IBM, you know, the 800 pound gorilla in tech at the time and they're still a dominant company today. And then from there I went to a startup and during my time at that startup, I really learned the founding story of that business and I got inspired by it. And so I decided that I too wanted to be an entrepreneur. I had a lot of business ideas that I threw out there to the world. Ultimately, I had about four and I shut all of them down. So I was undeterred all the same. And one of the things I realized after those failures is that I was pursuing these business ideas because I wanted to pursue a business, not because I actually really had a unique problem, a unique solution that I wanted to bring to the world. And so I decided I was gonna take a hiatus from, from, you know, just taking staffs in the dark and really try to find something that I was passionate about solving. And then it just fell in my lap, this problem with scheduling. And given sort of like my, you know, my struggles with the previous businesses, I actually did not start this as one, I didn't go into this, wanted to start a business. I went into this looking to learn about the space and the challenges. And the more I learned, the more excited I became about the problem. What I saw was that, you know, scheduling is a massive problem in the sense that, especially the types of meetings that currently schedule today, those meetings have an outsized impact on the success of a company. The average knowledge worker spends over 50% of their time in meetings, which is, you know, it translates to about 1,000 meetings a year. And if you multiply that by a billion workers, a billion knowledge workers globally, that's like trillion meetings on an annual basis. And so you begin to see the size of the opportunity. If you can optimize just a little bit of those meetings, there's a lot of productivity to be had and there's a lot of improved business outcomes to be had. And that's really what got me fascinated about the problem. It's a pain point. I'm sure we can all appreciate ourselves. I think one of the unique things about how you started Calendly was that you didn't raise much outside capital, certainly not the beginning. I've heard that you invested all your life savings and then some and it took out some personal loans. What was it like to bootstrap in those early days? What were the pros and cons of doing that? And, you know, how did that really shape how you thought about building Calendly from there? Yeah, I mean, I had the idea for Calendly and I just knew that I needed to get started as soon as I could. And rather than waiting on trying to raise money, trying to find a technical co-founder, I basically emptied my 401k and my savings and even took out some loans to solve the problem because I was that convinced that there was a big problem here and I could play a part in solving it. Unfortunately, I was not really good at, it was tough for me to raise money for a number of different reasons. One, I did not exactly have a strong track record as an entrepreneur with four field businesses. I did, the space itself was not a space, there were no major successes in the calendar scheduling space. So for all those reasons, it was tough to raise money. And so I really had a bootstrap in. I ended up flying to Ukraine and hiring a team of engineers who built the initial version of the product and that probably began to take off. But soon enough, I ran out of money. But after a lot of pitches, I ended up meeting a man by the name of David Cummins, serial entrepreneur, very, very successful entrepreneur and investor in Atlanta. He invested $350,000 in 2014 and we took that $350,000 and really, it's really essentially what's killed the business even till today. Yes, we've raised some money in institutional capital from you and a few others in the last few years. But really, those are just dollars hidden in our balance sheet. They haven't really gone into the operations of the business. But back to the pros and cons of bootstrap in, when you don't have to worry about, when you know you can't raise money, it forces you to really go win with customers, right? And so what Cal landed up doing is we became uniquely focused on the problem we were trying to solve and we had to monetize early. And because we had to monetize early, allowed us to really understand where we had the strongest product market fit. Like what were the cohort of customers that our product really resonated with and had the strongest ROI, the most compelling ROI with our product? So I would say that the challenges of fundraising meant that we had to really win with our customers and it forced us to be focused in what we built and who we built it for. Yeah. No, it makes a lot of sense. I think I heard that you ran out of money just before launching a paywall. And so a lot of the early users were passionate about the product and using it, but you weren't able to monetize until afterwards. But clearly something, you were able to win the hearts and minds of those users. What was the moment where that flywheel got spinning? Like how did you actually get that going in the beginning? Was that something deliberate that you did or did it kind of, was it more accidental? Yeah, it's a combination of a lot of different things. It was definitely an iterative process. I think the first part of it is luck, right? In the sense that we happen to pick a problem that's viral by nature, right? So there's no way to use currently without introducing other people to it. So we got lucky there. The second part is that dressable market is large, right? There are lots of products in which as you use it, you introduce other people to it, but you don't really get that flywheel going because ultimately the dressable market of that product is small, so you don't get this vicious, this virtuous cycle of I discover the product, I turn around and begin using it for myself. So the other part of that was, sorry, the large addressable market. And then pricing and packaging played a role. The product started initially as free because I ran out of money, but in doing that, what that allowed us to do is it just reduced the barriers to use the product. So I guess I'll say the first thing is the free plan, having a free product allowed us to really increase the total number of people active on the platform. So increase weekly average active users. And the second thing we began to then focus on is how do you improve the quality of that active usage? And so one metric that we pay a lot of attention to a currently is median intensity, which is the average number of meetings booked by a currently user in a given period. And so we began to implement a series of product improvements that would improve that median intensity. And then the third thing we then began to do is began to execute against a product strategy that really allowed us to capture as much of that addressable market. So you had this virtual cycle of people discover the product, they use it, the quality of their usage increases, which means they're scheduling more and more meetings. And then we began to serve not just individuals in SMB, but for teams and mid-market customers in a lot of different industries and all those things just really contributed back to the creator of that flywheel as you described it. Makes a ton of sense and then at what point did you sort of layer on the more sales led motion to augment kind of that viral product-like growth that you've had? Yeah, we tried to not ever have a sales team, but it failed miserably and I'm glad I failed. You know, I came from a background in enterprise sales and frankly I got tired of that and the reason I got tired of that is I see the future as given buyers the choice instead of hiding your product behind a lead form and people have to talk to you to find out the price. I think you should just let the product do the selling and create a product that's so compelling and so easy to use that customers can realize value without any human assistance. And by the way, we would have never gotten to where we got, to where we were if we needed a sales team because we were very lightly capitalized. So being able to build a self-serve business meant that in the early days of the business it grew very slowly but very, very efficiently. But fast forward to the sales team, what we saw was that our customers were really pulling us, telling us, asking us to do more. So in the beginning when I thought about currently and scheduling meetings, I was really thinking about the friction of getting that meeting on the books but it turns out that meetings in a lot of ways are sort of the atomic unit of business, right? So acquiring a customer, a new customer starts with scheduling a meeting with them, acquiring a candidate starts with scheduling that first interview and so meetings end up triggering all these different processes and these processes involve integrating into other systems, pulling, you know, bringing additional people onto the platform. And as we just followed our customers down that path of it's great that you scheduled a meeting with me but really what I don't want to just schedule a meeting, what my ultimate goal is to convert a prospect to a customer, to do that I need to trigger all these different processes. Point is like, you know, it just became, it became more complex over time. And even though it's possible for our users to be able to do all those things themselves, ultimately they wanted to talk to somebody on the phone to really understand how they could use the product and get a little, and get some consultative advice. We were hesitant to do that initially but what we found was a couple of things. One, we discovered that the LTV of every single customer was not the same, right? The kind of customers who wanted to talk to us on the phone, when we did talk to them on the phone, like a perfect example was this, we had this bookkeeping service, they wanted to initially start with 10 users and they want to talk to us on the phone, we didn't think that really needed a conversation but we did talk to them, they started with those 10 users and it's based on six months, it grew to 120 users, right? So there are all these anecdotal stories of when we gave, provided a medium touch experience, not only did we acquire those customers, those types of customers grew over time. So what we began to do is really try to understand like what are the signals that predict the customers, whose lifetime value is worth, a higher customer acquisition cost for, and that was sort of the genesis of our sales team. So it started as just a series of product experts just talking to the customers on the phone and then it became more consultative sales reps but that's sort of the evolution. Yeah, it makes a ton of sense. I think when we started working with Iconic, the enterprise sales motion was relatively nascent, you know, fast forward a few years, it's, I think you've, I think I read recently that you have like 86% of the Fortune 500 are Calendly customers. What, when you think about kind of working with the larger enterprises, what were some of the challenges that you encountered both on the product and the sales side? Yeah, so I think even with, even though we have a sales team now, 90% of our customers on our revenue still really starts with our initial footprint in a company is usually through the self-serve channel, right? So what ends up happening is an individual user in their large company uses the product, they wanna introduce it to their team or they start spreading it in the company and then IT finds out about it, they wanna roll it out on a wider basis and then they begin to have a lot of questions, right? Some of the things they care about, they care about security, they care about compliance in highly regulated industries like financial services and healthcare, they care about, you know, purchasing, you know, procurement flexibility, like they don't want just a, maybe they want a three-year agreement, for example. Sure. So essentially what we ended up doing is it became a company-wide effort over time. It started with sales, like I said, but over time it also became marketing and we began to think about messaging and positioning and attending conferences and lead routing. Those are things we didn't really think about before because we're sending it right to the self-serve channel. On the product side, we began to introduce capabilities that address those security concerns and granular permissions, for example. And then on the GNA side, we started redlining agreements, which are things that we didn't do before. We began to do security reviews and stood up an entire team that handled that efficiently. And then on the price and then package inside, we began to introduce an enterprise plan that sort of wrapped up all the capabilities that those enterprise customers. Yeah. When you think, I mean, the breadth of customers by segment, the use cases, you know, the sectors that you're addressing is incredibly broad. How do you find focus, you know, and within that opportunity and make sure that you don't leave anybody behind and that you're kind of serving all these customers so well? Yeah. I mean, I think the diversity of our customers is one of the most exciting things about the business. It's also very intellectually stimulating. It's also very, very, very tough. So yeah, I can't say that we've perfectly balanced it, but I think that the times in which we've been, we've made the best decisions are those in which we've truly understood like the relative view of different customer cohorts. Initially, we sort of served a very, very wide audience of anybody who needed a schedule a meeting whether internal or external. And then we introduced a paywall, you know, in 2014. And what we found was we had stronger product market fit with people looking to schedule external meetings. The ROI of those meetings were just higher for them. And then gradually over time, we did a much more rigorous analysis over the next few years and we realized that sales, customer success and recruiting and executives were much higher LTV for different reasons. For sales meetings, ultimately, those were directly tied to revenue. For customer success, there was a correlation between that to retention. And then for executives, we found executives to be one of the most important Trojan horses to get into a company. So if the CEO's using the product, it makes it a lot easier for them to send it to the sales team, saying you can be way more efficient. So we went through that analysis and that's really how we've been able to sort of prioritize the customer course we wanted to focus on. And then in addition to that, we did that sequentially. It wasn't, today we serve SMB, mid-market customers and enterprise customers. We didn't always serve those very well on day one. It took every bit of 10 years to do that. And so we just did that sequentially. It's an incredible challenge, but also an incredible opportunity as you said. What are the theme of slash this year's building to last? And when you think about how quickly technology's evolving, especially with the advances in AI and how accessible that's becoming, how do you really foster a culture of innovation within your product teams to kind of stay ahead of the curve and stay ahead of any competitors that may be encroaching on your turf? That is not very hard to do. And the reason it's not hard to do is exactly where you left off. We are in a very, very competitive market. Every single day there's a new calendar competitor that is looking to take a shot at us. And so I think it just forces us to be our best. The second part is it is very difficult to not run into a calendar customer on a given day. So, and our customers are very, very generous with their feedback. So through our great customers who provide us, who are very generous with their feedback and a very, very competitive market, it is very difficult to get complacent. Yep, 100%. When you just kind of staying on the theme of AI for a second, how do you see that sort of playing a role within the product? How have you added it to solving more problems around scheduling and meeting efficiency? Yeah, I mean, I'll maybe step back a little bit and say, we've been doing calendar for 10 years now. And in those 10 years, I don't think there's been as much innovation in meetings and productivity as we've seen in the last three, four years. There's a lot of really exciting things that are happening. And AI is enabling a lot of the things we've thought about for a long time and making them possible. So we see AI as just a great reset in approachability and accessibility of our product. Our product today, we take a lot of effort to make it really simple for a lot of different types of use cases. But there's still a little bit of a berry and a paradigm shift that you have to embrace and maybe to adopt Calendly. And AI provides an opportunity for you not to really understand Calendly lingo, but really just express what you want in simple language and for Calendly to interpret that. So that's an area that we're focused on, is how do we make Calendly that much more accessible and easier to use for people who don't really want to get a Calendly PhD to use the product. So that's one step. The other step is that we see our, we're excited not just to help you schedule your meetings, but really to help you make your meetings productive. I talked early about a trillion meetings happening on an annual basis. The vast majority of those meetings are not run well. And they're not run well because people don't want to. It takes a lot of effort to run a really good meeting. It takes thoughtfulness and a good memory to actually put together an effective agenda. It takes a lot of work to make sure that you follow up effectively on the items that were discussed and that the action items aren't forgotten. And we see an opportunity to help with all of those. And we think AI can play a very, very important role throughout that entire journey of preparation for a meeting, host the meeting effectively, following up effectively, all this, you know, virtual cycle to nurture relationships and drive customer and business outcomes. I've heard you talk about the meeting life cycle management as, you know, part of the evolution for Calendly. Is that what you mean by that? That's exactly what I mean by that, yeah. And to be clear, like we, one of the Calendly today has over 100 integrations. So we don't see ourselves as doing all these things natively, but it's really being that orchestrator of all these important actions and tasks that need to happen for a meeting to be successful. We see ourselves as being the glue and orchestrator for that. Yeah, makes a ton of sense. And really, you know, as Calendly has become synonymous with scheduling automation, a great insertion point from which to kind of expand and own that broader meeting management. Anything on the horizon from a product perspective that you can share with everybody in terms of what you're particularly excited about? Yeah, man, where do I start? So we are working on a number of different AI prototypes. Hope to be able to launch something and make something generally available in the next few months. I think you'll see Calendly become more people-centric in the next few months. So today, sort of like the organizing principle of Calendly is, you know, is meetings and event types, which is a set of rules that govern how you want to accept meetings. But we see an opportunity to actually humanize all of that. And really, like I said, help our customers not just schedule meetings, but really to nurture relationships. This is some of the things that we're working on that we're very excited about. That's amazing. Well, I think we're about out of time, but it's been an incredible decade for Calendly and it's been a lot of fun seeing how the company has just blown everything out of the water in terms of how far you've come and incredibly excited for what's to come. So thank you again for being here and for sharing this door with all of us. Thank you.