Cracking the Viral Loop: Calendly’s Playbook for Freemium Growth

Speaker A: Foreign.

Speaker B: Welcome to the Breakout Growth Podcast, where Sean Ellis and Ethan Garr interview leaders from the world's fastest growing companies to get to the heart of what's really driving their growth. And now, here are your hosts, Sean Ellis and Ethan Garr.

Speaker A: All right, in this week's episode of the Breakout Growth Podcast, Ethan Garr and I chat with Darren Chait, the, the VP of marketing at Calendly, the online scheduling service that I bet everyone listening to has used at some point. It's not too hard to make that bet because with the natural viral loops, the freemium model, all of the pieces that Calendly has, it's really become an everyday part of life for more than 20 million users and 100,000 companies. So even if you don't have an account yourself, the people you're interacting with often do. So Ethan, what stood out for you on this one?

Speaker C: What's that phrase, Sean? Uh, an embarrassment of riches. Right? Uh, when you have so many good things to choose from, it just becomes like, overwhelming. I mean, if you could engineer like the perfect SaaS business to scale, you'd look for virality and product led growth. You know, something with natural viral loops, a freemium model, something that users have a reason to just continue using in perpetuity. Calendly's all of those things. So it was really interesting to hear how Darren approaches growth. When he and the Calendly team have all those tailwinds, they have that embarrassment of riches to support them and help them grow.

Speaker A: Yeah, I mean, it's amazing, but yeah, we take a little bit of a step back. You know, even though Darren, uh, calls himself your title is the VP of marketing, he's actually heading growth. And that was, uh, something we tackled early in the conversation because his description on LinkedIn says that he's heading growth. But then when you, when you actually go down to his title, he's the VP of marketing. But you're right, I mean, when you look at a company like Calendly, it's, uh, you have, you have so much virality that's just natural to it. There's all these kind of things that you feel like it could, could just grow on its own. But when, when you talk to Darren, it's clear that's not the case. You know, Calendly is, uh, is, is very focused. They don't just take these things, uh, this kind of, these growth levers for granted.

Speaker C: It comes never that easy.

Speaker A: No, no. And it comes down to the fundamentals. I mean, the fundamentals are always important with growth. And that embarrassment of riches that you mentioned, like Calendly, they have to listen to customers. Cross functional collaboration is absolutely essential. They want to be data informed in everything they're doing. That's the recipe for success. And so even if you don't have all of the things that Calendly has, you can focus on the fundamentals and really maximize the opportunity that you're in.

Speaker C: Yeah, I mean, Darren says growth requires this mix of creativity, strategy and what he was humorously calling fifth grade math. And that feels pretty accurate to me. I mean, I loved when he said cross functional collaboration doesn't mean we agree on everything. It means that we agree on what success looks like. I thought that was just a great way of framing things. And it's key for startups that are looking to get everyone pulling in the same direction.

Speaker A: Yeah, there are so many, ah, good nuggets in this one. And of course we talked about AI. It's such a hot topic in growth and marketing these days. Our last episode obviously was a, ah, deep dive with an AI expert and it was really cool to, to get Darren's take on this as well. And um, you know, he had one quote that just, yes, stood stuck with me for like a day or two after our call. And uh, I want to get the exact wording right, but he says if you're spending your day doing the same tasks that you were doing a year or two ago, you're not taking advantage of what's out there and what's available to you. And I just think that's such a great perspective. AI is, is changing everything. It's giving us so many more capabilities. So your workflow, even if you've got 20 years of growth or marketing, if you're doing the same things you were a couple of years ago, you got to take a step back and revisit it. And so there's a lot of nuggets like that in there. So we should probably, uh, dig into this one.

Speaker C: Yeah, let's get to it.

Speaker A: All right, let's go. Hey Darren. Welcome to the Breakout Growth podcast.

Speaker D: Thanks, Sean. Thanks Ethan. Great to be here.

Speaker A: Yeah, absolutely. As you mentioned, Ethan is here as well. My co host. Uh, hey, Ethan.

Speaker C: Hey Sean. Hey Darren. Good to meet you, Darren. And yeah, excited to chat with you.

Speaker D: Likewise. Longtime fan of both of your work.

Speaker A: I'm a longtime user of Calendly and fan of Calendly. In fact, we use Calendly for booking our, uh, podcast. I recently took on our pack of sessions. I recently took on an assistant and was mortified when she did not send you the Calendly link to book, uh, the meeting. If anyone needs the Calendly link, it's you. That's right. That's right.

Speaker D: Well, we caught up, especially with time zones. It was nice and easy to get this booked.

Speaker A: Yeah. Um, well, so one of the things, and I gave you a little bit of a heads up on some of these questions ahead of time, but one of the things that I found really interesting on your LinkedIn profile is that in your summary you talk about being leading growth at Calendly, but then, uh, in your job title is VP of Marketing. So I was just curious if you see a distinction there and maybe what you see as the difference between marketing and growth of anything.

Speaker D: Totally. Um, you're straight on it. Um, I was very impressed with picking that one up. And it's very current for us. It's a thought experiment and approach that we're talking about a lot right now. So in general, um, you know, my background originally was as a corporate attorney. Got into startups. I was doing what I realized afterwards was, was growth. Um, I love to write, you know, I have the legal background, whatever, but I never really saw myself as a marketer. And when I, you know, sort of, you know, grew through the marketing ranks here, I had this imposter syndrome of being a VP of marketing. Um, so it's quite a funny topic now. What's the difference? Well, I can ask you. I, um, mean, obviously Sean, uh, in particular, you've, you've written the book on growth and growth hacking. But, um, I'll tell you how we view things here at Calendly. Um, we originally, um, viewed growth as the job of product and marketing. Here we have a plg, product growth, uh, company, which we should talk about a bit later. And it's a job that we both, we both contribute to. As we improve the product, we create greater and greater viral opportunities, viral loops, and we figure out how best to message the right thing to the right audience at the right time to help us grow our business. And we sort of share that nicely. Uh, now what we've kind of learned is that Calendly has an extraordinary brand. Um, it's one of the key drivers of our growth. Every month, millions and millions and millions of people are signing up for Calendly. We're scheduling millions of meetings a week. Um, all the things are happening off the back of the brand. The way we tell our story, our view of the world, um, the way we articulate features, value propositions. Our value proposition is Very related. So where we're actually heading is we're going to split our. We've split our go to Market Org, our marketing Org into product marketing and brand and growth.

Speaker A: Okay.

Speaker D: And Tope, our CEO describes it as the left brain and the right brain.

Speaker A: Yeah.

Speaker D: Um, so I'm the left brain kind of guy. I'm there at the numbers, the levers, um, looking at how we optimize and PMM and brand is all about very tactically, but the story we tell to who, why and how we have the creative around that. So all of that is to say that it's very tightly coupled marketing, uh, and growth for us. Um, but we're really thinking about things with a left and a right brain approach moving forward.

Speaker A: Awesome. Ah, you know what's actually really funny is that I actually kind of stumbled into the VP of marketing role, uh, as well early in my career when, uh, I never took a marketing course in school. And um, I joined a startup early enough where it was like, you know, I'll tackle that, you know, trying to get some, some users on this product. And um, and the next thing you knew, I got promoted to VP of marketing. And I was like, man, I better go take a marketing class if I'm going to be a VP of marketing. And uh, went to New York University, took a strategic marketing management course, aced it, and then got way worse at my job when I was suddenly trying to do it like the textbook instead of being very like, you know, what actually drives growth in this business? And so it took me a little while to forget the things that I had learned.

Speaker D: Seriously, it depends on the business. As you said, I talk to colleagues all the time, you know, in CMO or VP roles and they do something that it looks nothing like my job if I'm running an enterprise sales business. It's all about pipeline, Legion, webinar, sales enablement that my job couldn't be further from that. But um, we have the same title, right? So it's just a, it's just the naming thing, really.

Speaker C: Yeah, I think, Yeah, I think in SaaS business it's definitely like the lines just keep getting blurry and blurrier and blurrier between uh, between growth, marketing, product. I mean, uh, yeah, I mean I'm working with companies and I'm like, am I a growth guy? Am I a product guy? Who cares? Like at the end of the day it's like at the end of the day it's how are you bringing value to the organization? So I think, um, it's probably good that it's ill defined for you or interestingly defined. Um, but yeah, I think you've already touched on it. But one of the, um, Calendly has got to be the ultimate viral growth model, right, Ethan?

Speaker A: Even before we kind of dig into the growth side of things, just in case people, I mean if someone's been under a rock for the last 10 years and doesn't know what calendly is, maybe we zoom back out for a second and just make sure that that's uh, a good idea. A quick sentence or two on what calendly is.

Speaker D: Sure, totally. And often I've heard us described as like the Kleenex of scheduling. Even if it's not calendly, it's a calendly link. But what we do, Calendly helps individuals, teams and orgs automate the meeting lifecycle by removing the back and forth while scheduling. So, um, we help automate scheduling workflows. I can send you a link with my availability and the workflows behind that often will drive group availability, round robins, routing and sort of complex logic behind how we schedule. Um, and it helps you really create better customer experience, um, and support the external meetings that you're having, whether that's with candidates, you're recruiting partners, clients, customers, whatever it may be, and saves yourself

Speaker A: a lot of time as well. With all that back and forth.

Speaker D: We say seven emails on average, right.

Speaker A: To schedule a meeting.

Speaker D: Um, typically it's crazy.

Speaker A: In fact, Ethan and I were just talking before this call where he was just like, I have wasted so many like minutes or hours, whatever it ended up being, just trying to get one meeting booked with one group of people and that's expensive time.

Speaker C: Uh, and for the record, that company doesn't use Calendly, which is killing me. Um, but that actually sort of leads to the question I was starting to ask, which is the amazing thing about this product is its natural built in viral growth loop, right? It's I send the first time I need to schedule a meeting and I send that invite out. The person on the other end, if they have been living under a rock and have not been exposed to calendly, now they know what it is and it's pretty immediately obvious like, well, that would make my life better too, I guess. How do you look at that from the perspective of like, how do you leverage, um, that viral growth loop, you know, for organic growth when it's the central point of the whole business?

Speaker D: Yeah, um, we're very lucky, number one, I think, you know, you can design virality as much as you want, your product has to be inherently viral. And a meeting is the definition of reality, right? It involves two people or more. So much like what Zoom saw during, you know, Covid and so on. Not every product, even with the best execution, has the benefit of virality. So I want to call that out for us. I think the, the other thing that's unique to why we're so viral is you see the value of Calendly, um, by scheduling. So very often you'll have a viral loop in your product, a share behavior and the like. But by using the product being on the other side of it, I don't necessarily see the value. So let me give you an example. Let's take mailchimp, right? Many small businesses run on mailchimp, and at a certain tier, you see at the bottom of the email, um, powered by mailchimp. Now that's great marketing. I'm sure they have a large proportion that click through, but really, I've received an email. What I didn't know the value of mailchimp and how effective, how easy it was for me as the email sender to find a template, create the content, get analytics on opens, monitor my customer base and subscriber base and so on. Um, and the value of mailchimp. All I've got was a nice email that was interesting. The thing about product like Calendly or Zoom and a few others is you get to the end, you know, with the scheduling workflow, and I've had the aha moment. I've seen the value on the scheduler side. I'm like, oh, my God, done booked. I don't have to have six more emails with Ethan or with Sean. Um, and that's, you know, that's very lucky for us. And then our job as growth folks is to, is to refine that funnel. So how do we maximize the proportion of folks that book meetings to sign up, to activate, to convert to, you know, have a lot of success? Um, and that's what we do day in, day out.

Speaker C: You know, it's interesting. I would even say, like, you make a really good point, that part of the habit around it is that as a, as the end user or the new user, you're instantly engaged in the experience. And it reminds me, we always talk about Nerial's book Hooked. Like a big part of the Hooked model is that investment moment where you have to do some work. Um, and once you do that now, you're invested and actually going through the process of scheduling is part of that investment. So I think it's, I think that adds. When I think about the habit building, it's like Calendly is like instantly habit building, um, through that model.

Speaker A: Especially if you end up setting up a bunch of different kind of Calendly links and you end up investing more and more in the product for sure.

Speaker D: That's right. That's a big drive for us. Um, event types, which is the Calendly links with the different schedules and rules and the like, the more of them you create, the more invested you are, the more you're going to activate, convert, retain, so on. So it's spot on.

Speaker A: So Darren, how long have you been with Calendly now?

Speaker D: Yeah, so I've been with Calendly for about two and a half years. I joined through an acquisition actually. I co founded a startup, um, named Hugo. Um, we were in the Bay Area and we were in the meeting space also meeting workflows, um, a lot around, ah, note taking and actions. Um, and we joined Ken Calendly through that over the summer of 22.

Speaker A: Okay, I'm curious then, when you joined, how much time did you spend? Really kind of like study. I mean obviously there's some obvious parts of the viral loop, but how much time did you spend like making sure it's a product that has grown to be so popular over time that uh, before you can improve something you need to deeply understand it. And so I'm, I'm curious like how you went about trying to understand how is this thing really growing, uh, and then from there you can start trying to improve it. But I'm curious how you get your head around that.

Speaker D: I spend a lot of time um, really understanding the numbers. I think what's a challenge but an opportunity with Calendly is we have a very, um, heterogeneous user base, right? So we have palm readers, dog walkers, and we have Fortune 500 companies. And they all act differently, they do different things, they buy for different, different reasons and so on. So it's not a simplified, it's not a very, you know, simplistic funnel. Um, so I spent a lot of time sort of slaving over those numbers and I still do. I'm truly understanding each part. Um, you know, I got some great advice actually. Our new president go to market here, um, Shane Murphy Reuter, um, he was previously the CMO of webflow and he's one of the best advice, bits of advice he gave me is any great growth leader should be able to be the CM CFO of the company. He's like, I'M not talking about going to school for finance. And you know, I'm saying that business, but you need to have such a strong understanding of the numbers, um, to be, to be, to be effective, to understand where the leverage is, what's going to drive return and so on. And I still spend a lot of time learning and trying to go deeper there.

Speaker A: Um, do you feel like freemium is an important part of making that viral loop work? If you didn't have a free version, would it, would it work nearly as well?

Speaker D: Yep. So remember, right, we have, we have millions of active free users. They're scheduling meetings, right? They're scheduling meetings with other folks who have never heard of Calendly. Many of those folks are going to sign up and pay. So very, very critical, um, to our business growing, number one. Number two, with a true free trial model, at least for our business and many that have been involved in over the years, your relationship would end at the end of the trial.

Speaker A: Yeah.

Speaker D: So 14 days, which is our current free trial for most plans, if that at 14 days, you're not hooked. There may be many reasons why, right? You've, you're, you sign up, you go on vacation, you're in, uh, a certain segment or industry, it's the wrong time of year, it's a quiet time, whatever the reason is.

Speaker A: Like the holidays that we just passed, maybe you didn't have a single meeting scale for two weeks and then, and

Speaker D: then it's see you later, we're done. Whereas this way we can nurture you forever. We can expose different features, we can try different things, we can have a long term view on our relationship. Um, so we don't want to close the door. So for both of those reasons, the viral loop and the future value of the relationship, freemium is really important to us. But we have freemium free trial, right. So you get basically a full feature set for the trial and then reverts back to freemium.

Speaker A: And then are there other elements of the product led growth model that are important to your growth?

Speaker D: Uh, yeah. So Calendly can obviously add value to individuals, but we have a lot of value for teams as well. So you can have like introverts into company growth. Um, so it's very important to us too, to give you a reason to invite teammates and collaborate, to combine schedules for group scheduling, to round robin between you, to analytics, to see the meetings, your team's booking and so on. So that's a different kind of growth funnel for us and one that's very important as well. Um, naturally as you've probably seen in all the various businesses that you're involved in over the years, larger teams retain better. They obviously make more money that way. Um, so we like teams. Um, but so for those reasons, um, that's a different growth funnel and both of them, um, drive the rally of our product. Cool.

Speaker A: Cool. Yeah. So, um, obviously just getting people to try, it's one thing, uh, actually being able to build a healthy business means you gotta keep them retained. Uh, Ethan, probably a good area for you to dig into.

Speaker C: Yeah. So I had uh, sort of the standard question about what retention strategies do you work. But I guess kind of a good question maybe for calendly. You've described sort of this natural way that it becomes part of your. It's this built in, part of your process. It goes every, you know, every day, make, you know, scheduling meetings, being scheduled for meetings. I guess another question would be what is the enemy of retention for you? Like what drive what, what do you have to fight against to keep people, to keep people coming back every day?

Speaker D: Uh, lots of things. Uh, retention is always every B2B SaaS companies and B2C software companies challenge. Um, for us here, there's lots of different buckets. Why people don't retain. In many cases it's a failure to create that habit. It's like we were talking about with, uh, hooked, um, if you get going, but it's not part of your process, your habit, um, you're not going to retain. And we can keep you on life support for a few weeks by nurturing the hell out of you and trying to get you back. But unless you're part of my business process, we're not getting anywhere. So that's probably one of the bigger issues. Um, in general use case, obviously folks sign up. Um, I remember during the pandemic there were some customers that were using calendly for scheduling vaccines. Um, obviously people who get vaccinated against Covid aren't necessarily great calendar customers, but a lot of them thought this was really cool and they signed up. They just didn't have a use case. So they're obviously not going to retain, um, amongst others. Um, and uh, then of course there's environmental and uh, frictional reasons for lack of retention. Small businesses, they contract, they grow, they change over time, they cease to exist. Sometimes, unfortunately, seasonal type use cases, we see huge education. I touched on before in certain times of the year and then not many meetings are scheduled over the summer naturally with colleges and schools and districts and the like. So lots of different reasons and what we have to do to address that is just split them all up and treat each cohort, each reason, each objection or challenge with its own strategy.

Speaker C: So do you have sort of your own sort of definition and measurement for retention? Um, kind of unique to calendly?

Speaker D: Yeah, I don't think it's unique to Calendly. Um, we ultimately look at gross dollar retention, um, and we, sorry, a level above that. We split into usage and revenue retention. Both are important. We obviously care a lot about our free customer customers as well. Um, and we want to make sure that they continue to use it. We look a lot at meeting intensity and things like that. How are they, like what volume and rate are they scheduling meetings? How's that changing over time? What's in character, out of character for them? So there's a usage side and then on the retention, sorry, on the revenue side, um, very traditional gross dollar retention and then net dollar retention. Because we have expansion opportunities too. So both of those things. Um, ah, the way we think about retention here.

Speaker A: Yeah. One of the things I find interesting with calendly is, um, because I avoided for a really long time bringing on, uh, a personal assistant. And as I mentioned, she helped to book this meeting. And I was under the impression maybe that if I had an assistant who was helping me book meetings that I wouldn't want to keep calendly. But the funny thing for me is that even though I use it a lot less now that I have her booking the meetings, when she's off the clock, it's, you know, if there's an important meeting to book, it's just so easy for me still to send that link out. So even with a lot less frequent, uh, kind of usage of calendly, I still find it indispensable. And so it's kind of interesting. Like, I wonder what I would look at, look like on your end. Like, oh, am I, uh, am I a high risk customer because I'm using it less? But I, you know, even if it looks like that in the data, I can tell you that I'm not a high risk customer, that I actually value Calendly a lot even though I use it less now.

Speaker D: There you go. And I guess that comes down to how you measure value, right? You know, like if there was one really complex meeting that was so critical to your business with lots of different folks, or one regular meeting, but just one a week where you have to coordinate a few people together, that could well be worth the revenue. Right. For others, they need to be scheduling 50 meetings a week. To see that value. Um, so it's like anything there. And by the way, the executive assistant use case is one we hear a lot. We actually have some features around that schedule on behalf of and the like to allow EAs to be more productive because their time also costs money. Right, Cool.

Speaker A: Yeah. How do you. How would you kind of get the word out about that functionality? Because that's something that I think probably would have been pretty helpful for me to uh, have her read or even for me to read. How would you normally kind of use that or get that content in front of the right people who could benefit from it?

Speaker D: Um, yeah, it's tough. I think we need to, um. Again, it comes down to segmentation of our customer base and then how do we market parts of the product to the right segments? Um, that's for a solopreneur send on. Sorry. Schedule on behalf of as a feature is just not relevant. I don't have anyone who's using who's scheduling from my calendar. Um, in a bigger business where you have folks who are helping you be productive like EAs and the like, that's critical. So maybe we need to do a better job if you want to cross that feature in that area. Uh, but we really try with product marketing and releases, we really try cut up our customer base. So we're marketing what's actually helpful for the way they work and the way they schedule.

Speaker A: Awesome. Awesome. Yeah, go ahead, Ethan.

Speaker C: I was going to say do you find that with like a big challenge for calendly as a whole is just avoiding feature creep in that you've got. There's all these millions of things you can do. But like what you just described, there's only a small segment that can get or it may not be a small segment, but there's only a segment that can get value from it and the other segment can get distracted by it. Right. So you're always, uh, to me there's always this challenge, but it seems like for calendly maybe a really big challenge. And I'm curious if so. And how do you guys deal with it?

Speaker D: Yeah, it's a challenge. Of course. Um, one of our values and very much part of our ethos here is being incredibly customer centric. Voice of customer plays a big role. It's something Tope, our CEO is talking to customers almost every day, multiple times a week. It's very much part of our culture. So listening to customers is obviously how you drive these requests and ideas. How do you weigh them up and decide what to build? That's where it gets tough. I love the Henry Ford quote. If you ask the people what they want, you would have got faster horses. It's true. Um, but I also think that comes down to your ability to research and talk to customers. I don't want solutions from customers. Right. I want problems. If I'm a product manager, it's my job to come up with the. The solutions. So we really try and listen to customers, but not necessarily give them what they asked for, but give them what they need or what they'll get value from. Um, but no silver bullet there. It continues to be a challenge all the time. Um, for us.

Speaker A: Yeah. And I do think. I mean, that's one of the things we face at Dropbox, too. It's like part of the elegance of the product is its simplicity. And when you start to add too much to it. Yeah. You lose, really, like the key thing that makes it so great. So it's a struggle to stay true to a very, um, straightforward, simple product. I mean, at least that's from the outside. That's what my assumption is. Um, so. Yeah, go ahead.

Speaker C: I just want to say. And I think that's also exacerbated when you are a market leader, like. Like a calendly. A lot of times the people who are trying to impinge on your space, um, what they're doing is creating features that you have to then decide, like, is that a feature we want to bring into our fold to combat that, or is it a good. Like a few years ago, I remember there was a product that came out and it was, um, some sort of calendly competitor. And I remember they had sort of one key feature that they were, um, they were suggesting makes this better than calendly. I don't exactly remember what it was, but something so that you didn't have to look at your own calendar or something. I don't know. Um, but I was thinking for a calendly, that must be the challenge is that there are always going to be things coming out in the world around you, and you have to decide whether those are real threats or not to. And that influences feature decision as well.

Speaker D: It does. It absolutely does. And the other thing to remember is who is your customer, you know? Right. Like, if we built for, uh. It's funny, when we used to raise money at Hugo and spend a lot of time with VCs, VCs, you know, often are full of product feedback for you. Um, with the greatest of respect, they want to. They want to help you. Right. They have views, they want they want return on their investment and they want to help the founder. Now when I think about VC as a use case, that's a very niche kind of use case for things. And take Getting feedback from VCs unless you're building product for VCs is not helpful. And I think about that quite often too. Right. If you look at a competitor who might have some killer feature and everyone's talking about it, but that might not be relevant if it's not for who we serve and who our main customer is. Or maybe it is and we're late to the eight ball and we have to compete. So you got to just assess case by case.

Speaker A: Right. So one of the things that we've talked about, uh, obviously why we were so excited to get you onto the podcast was just the viral story of, of Calendly and this product led motion. It's like so many of the things that are really cool about Calendly, um, uh, are some things that make it kind of unique and challenging as well. And so kind of coming back to this, um, growth versus marketing versus product versus data. And when you have something that is driven by a product led motion and virality, it is the intersection of so many teams working together that makes it work. So I'm curious, um, one, how you guys effectively kind of manage that and coordinate your efforts and then two, uh, that cross functional challenge marketing is a function. And when marketing is in your title, do you ever find that you're limited uh, in your ability to reach to other functions and work well with them when you are also uh, in a function yourself?

Speaker D: Yep, um, great question. So we're always iterating on these models and I talk to peers and growth roles and other companies in that like us and it's, there's no, there's no uh, there's no, you know, ah, simple answer to this. Um, the way we operate here is we run cross functional growth squads and we group them and align them by stage of funnel or and goal essentially. So if I work on a um, expansion squad, my job obviously is to drive folks to spend more money with Cali to get more value from Calendly and then they'll spend more money from calendar and um, there's lots of ways we can do that and the ways we do that are really just channels. Is it a part of the product that's going to do that, um, where I can expose some other relevant bit of value that you weren't aware of in app? Is it an email nurture sequence? Is it retargeted ads. Is it a brand campaign where you didn't realize accountant did so much more? And all of these things have that same, um, expansion goal. But we operate as a squad where we're looking at that goal. We have a roadmap, a backlog, and everyone's hitting it with their different channels. So that's, that's how we, that's how we approach it here. Cross functionally. Um, having marketing in my title and really marketing, you know, as one of the key growth drivers. Uh, no, look, I mean I think you've got to have the right folks where people genuinely want to move the needle and solve a problem. Most of the time the best answers, the best, uh, solutions are um, where. Cross functional, where we hit it from every angle. We've been doing some work recently around churn and retention and there's a product change, an email ad, you know, whatever, everything all happening together. And that's amazing where I'm an engineer, where I'm like, well I've built this front end thing. How awesome if we could hit them when they're out of product tomorrow with this message and you know, bring it together. And that's the magic. And that excites people about what working together. Um, but at the same time I don't think it makes sense to have engineers reporting to a marketer because yes, there's alignment, but you miss out on the technical mentorship and development and so on. So you need dotted lines and some sort of cross functional coordination in my view.

Speaker B: Cool.

Speaker A: So it sounds like it works and that marketing, the title has not really been uh, ah, a hindrance for you.

Speaker D: Not if you got the right people, which I'm glad to say it seems like we do here.

Speaker A: That's great. That's great,

Speaker C: son. You got another one?

Speaker A: Uh, yeah, that was the main one there. I mean obviously, uh, I think there's an interesting area to explore which is AI is kind of changing everything right now. So uh, maybe we could dig into that a bit. You want to take that, Ethan?

Speaker C: Yeah, I guess just with AI doing just that, like changing how we think, how we approach. How do you, how are you guys approaching integrating AI into the calendly experience? And like, where does that start? I mean we talked a little bit about like feature creep, but how do you, how do you, how do you approach this now?

Speaker D: Totally. So we, we have, we have very much an applied AI view of the world. Um, you know, the buzzword and the, the sexiness of AI, you know, through the um, hype cycle. Bull Wayne Right. We could have said the same thing about being cloud based not too long ago. Um, so in other words AI is a critical part of how we operate and how we're going to and what we're building. Um, but the fact that it uses AI isn't the value.

Speaker C: Right.

Speaker D: Um, what are we using AI for? Well today, um, as you know we support people in external facing roles. So sales folks, customer success professionals, recruiters, you know, consultants, business owners and the like. Um, and the meetings they hold ultimately drive revenue directly or indirectly. Um, so if we can make those meetings more effective, if we can you know, um, increase the value of those meetings, we're creating tremendous value for our customers. Um, scheduling is one piece of that. But you know, the interactions um, that you have and through a relationship, an external relationship over time, um, has a lot more opportunity. So all of that is to say stay tuned. We're absolutely building and releasing a ton um, you know, later this year and uh, and leveraging AI to do that. And at the same time, you know, calendar side, um, we, you uh, know we're being the. I think I've been the most effective in my career leveraging AI. We've built a ton of custom bots. It supports the way we write, it helps with analyzing data, looking for trends, um, modeling out um, churn and churn prediction, modeling out expansion opportunity, trying to find um, figure out the best next action that we can do to support our customers. All AI solutions that are in play with us now. So we're sort of hitting it internally and externally but it's without a doubt the most sort of uh, critical. Uh, it's definitely a huge milestone in my career without a doubt. Right. It's changing the way that we operate. Um,

Speaker A: yeah, I'm really glad that you. Sorry, we're having a little bit of uh, connectivity issues here so I apologize if m. I'm talking over you. But um, yeah, I'm really glad that you went into the direction of not just AI, kind of to drive features within the product or the experience within the product, but also how you as a team are using AI to do your jobs better. And uh, that was really cool. Thank you for touching on that.

Speaker C: Yeah, we actually ah, just today uh, in terms of when we're recording this, we just released an episode uh, with a really an AI prompting expert. And I think that we. A big part of what Sean and I have been talking about is that AI as part of the growth leaders workflow is super important. And um, yeah it's not just about the the, the outputs of AI, you know, to your customer base like that are going to be impactful. It's also about using AI daily just to gain the, you know, the benefits of it. It's great like when you give it the specific, specificity and context to help you grow, um, it speeds up growth. So I think, um, yeah, it is really interesting to hear you say there's two sides of it. It's not just the forward facing part of what it does for Calendly, it's what we're doing to make calendly better every day. So um, one thing I want you is um. Oh, sorry, go ahead.

Speaker D: I was gonna say I think a good heuristic for people in many roles, especially in growth and or marketing. If you're spending your day doing the same tasks that you were doing a year or two ago, you're not taking advantage of what's, what's out there and what's available to you. Um, there's so many lower order tasks or tasks where I, I didn't have the brain power to analyze, to realize trends, to try alternatives that now I'm outsourcing obviously to you know, to AI power solutions. So look back, think about the way you spent your days and if it's the same, I'd be asking yourself what am I not adopting? What should I be trying? What should I be experimenting with?

Speaker A: That's a great point. Like my, yeah, my day to day has changed so much now because of AI compared compared to a year ago. M like everything. My first instinct is how can AI help me do this faster or better? It's super cool.

Speaker D: Go ahead.

Speaker C: Yeah, I was curious, is there a uh, like a single defining metric that your teams but really all of calendly looks to as the driving force for the company?

Speaker D: Um, yes and no. Uh, when I think about growth, I think about incremental, um, revenue incremental acv, or ARR. Um because that takes into account obviously top of funnel growth, expansion and, and then churn and contraction. So that's if you had to ask me as a growth leader, like what, what is. If I had to limit to one metric and we were impacting that and knew nothing else, like that's, that's success. Um, but from there it really splits out and I think that's the magic of the model I spoke about earlier where it's really hard to stay up at night or you know, have those thoughts in the shower and be thinking about 12 different metrics because there's just so many different directions I can Go in for growth if I really try and specialize our team. So all I'm thinking about is expansion or retention or net new acquisition or whatever it is. And I can go deep and I can think about that. So yes, I think about the, uh, net new acv. But, um, I really encourage the team to stay more focused.

Speaker A: Do you guys use a North Star metric or are you familiar with that concept?

Speaker D: Yep, yep, yep. So, uh, it's sort of set by team for us, um, but as a company, um, it would ultimately be, um, an incremental revenue, um, North Star.

Speaker A: Cool. But yeah, it feels like, um, from more of like a mission perspective that you could have something like weekly meetings booked or something that, uh, because earlier you had talked about, you sort of have revenue goals and usage goals. Um, and that usage, uh, is often like a leading, uh, indicator for revenue.

Speaker D: Totally. And there's a handful of those too. Daily meetings book, uh, meeting intensity, which is meeting per active user. There's a handful of North Stars there. Obviously. Look at engagement and activity amongst our entire customer base, not just, not just revenue. So each sort of area of our product or business has a handful of North Stars as well.

Speaker A: Yeah. Um, and then I want to go back to something you've touched on a couple of times is, uh, you know, when we talked about competitors and feature creep and some of these things you keep coming back to, like, ultimately it's customers. Ultimately, what do our customers need? How do we respond to their needs? I'm curious, um, whether. Whether it's in product development or growth and growth initiative ideas, how are you kind of gathering feedback and using that to make better decisions on, on your end?

Speaker D: Yeah, um, usually we have a research team here, so we're looking at it from a qualitative standpoint. Talking to customers every day, um, NPS scoring, feedback, um, research in terms of interviews, focus groups, prototype testing and the like. Um, we then do market research outside that. Looking at the space, the problems we're solving, pricing, monetization, it's really just resourcing for that and focusing on the voice of customer through everything we're doing. So no secret sauce there. Um, I think in my career, one of the things I've learned is magic happens at the intersection of qual and quant, qualitative and quantitative. Where, um, a customer telling me something is insightful. Watching what the customer does in terms of metrics and analytics is insightful. But the magic is hearing them explain what they think they're doing while I see what they're actually doing. Um, and that's where you generate the critical insights.

Speaker A: And are you using that one? Follow up and let you anything. Are you using those insights for like, do you do a lot of experimentation or like, how does experimentation kind of fit into driving improvement in your model?

Speaker C: Yep.

Speaker D: Yeah. Look, we're fortunate to be of a scale where you can run a lot of experiments and get, you know, statistically significant answers quickly. Um, so we do, we test, we test a ton. Again, you've got to be careful about segment. Segmentation. I think, um, making sure you're testing amongst the right folks is very important. And not everything should be experimented. And there's kind of a whole conversation about this. I think as an industry, as a world, we love A B testing and especially early stage companies probably do it too much. There's times where there's conviction in what we need to do and why and we should do it. Um, so not everything is an experiment. Uh, but we do do a lot of experimentation here at Calendly.

Speaker A: Yeah. But even when it's not set up as an experiment, being able to have some kind of data feedback loop that lets you know, have we made a bad decision in what we did and should we reverse course?

Speaker D: That's right.

Speaker C: That's right.

Speaker D: Even to impact what's next. Right. You learn about your customer through that feedback loop. Um, wow, that made them do that. So what if we did this now? What would that make them do? And so on.

Speaker C: So that's true. So I just wanted to go back to that, um, with such great resources for gathering user feedback, customer feedback, and you're talking about qualitative and quantitative, uh, methodologies. How do you make sure that the entire organization has access to that or is getting those learnings and can figure out how to use all that information to make good decision making? Yep.

Speaker D: Um, so we share out as much as we can in every, all hands. There's an element of voice of customer. All the quant stuff gets shared out in Slack channels daily with daily reports for the whole company. We really try and have that culture of um, sharing um, both qual and quant, um, insights there. I think um, the other thing that's interesting is um, there's a risk in only sharing synthesized um, insights. So if you. Every month we have someone from our research team and some from our analytics team stand up and say here's what we learned in three bullet points. You lose a lot of the connection to the voice of customer. Um, so it's really important to hear from customers, to listen to recordings of calls to Attend customer interviews to see raw NPS results coming in. And we've really tried to maintain that here through access to Slack channels, through bringing customers to our off sites. You need a hear it, because the best ideas come from everywhere and the only way we're going to be successful is if everyone has all of those inputs not filtered through one mouthpiece of synthesis.

Speaker C: Well, uh, I think so much of customer feedback can be nuanced even beyond just the words they're using. It's amazing if you're in the same room as a customer to watch their body language, to kind of get those visual cues that connect what they're saying with what they mean too. So. So, yeah, uh, I think it's a really good point. It's not just. If you're just relying on synthesized data, you may be missing out on a lot of opportunity.

Speaker D: That's right. And trends too.

Speaker A: Right?

Speaker D: Um, passing comments that someone may say that you may dismiss. You hear that same passing comment 5 times and all of a sudden you've got something really meaty here as an insight. So you need access to a cross section to learn that.

Speaker A: Yeah, definitely. The patterns emerge when you have enough conversations.

Speaker D: Exactly.

Speaker A: So you mentioned you've been there now, uh, you said two and a half years, is that right?

Speaker D: Yeah, that's right.

Speaker A: Yeah. So, um, I'm just really curious. When you reflect on those two and a half years, is there something that you feel like you've really learned about growth that maybe you didn't really understand as much before? We like to kind of wrap up every, every, uh, conversation with just kind of digging into recent learnings or just like advice for our listeners. With growth, however you want to weave, it would be great.

Speaker D: Sure, tons. Let me give you a couple of bullet points. One, um, unsexy stuff works, right? Um, every channel can be a growth lever. Uh, rates mean, um, compound growth. And what I mean by that is if I can make a tiny tweak to the right rate at which a website visitor signs up or a sign up schedules their first meeting, or their new customer invites a teammate, at scale, um, that is not only material multiplied by a reasonable base or a large base in our case, but it's there forever. Every month that rate, provided nothing else changes, is yours. So these are forever, um, benefits. So all of those things together, looking at what, um, the levers are and what I can do to tweak the levers, the seams, between funnel stages or between, um, steps in the user journey, um, without a doubt is what's made the difference here, um, so that's one, two, stop, um, looking at everyone else. I think there's so much great content out there that scrapes growth marketing and growth ideas from others. And there's tons of um, very specific books on topics out there and the like. It's very insightful to learn what's worked for others. But there's no playbook that's generic. And by the way, even if there was, by the time it goes to print, it's not relevant. Um, you know, I, we talk about, uh, one example here would be webinars. Um, in my last role if I hosted a webinar with 5,000 attendees. It would transform our business. Absolutely transformational. It would be, you know, I'd be the most successful, successful marketer in history and I would literally put up on the map at calendly 5,000 people on a webinar based on our daily meeting and sign up volume. It's, it's borderline waste of time. Um, and uh, but the book, you know, but if I take the growth marketing playbook and throw it in there, um, that's what I'm going to be trying to do because that's what a marketing mix looks like in a B2B SaaS company. So I, um, think it's helpful to, to know what others have done, but don't. The idea of adopting a playbook is fundamentally flawed.

Speaker A: Yeah, that mirrors one of my big uh, learnings and almost like oh crap moments is that uh, in some senses when you get really big, it's like the job is fun, but in other senses when you're really big, it's like the things that can move the needle on a big businesses as big as Calendly really do get narrowed down. And so coming back to what you said before, then it's about rates like, but if you can, if you can improve your conversion rate in one area or your share rate or any of those, like, they can have massive impact. So it uh, you know, PLG tends to, tends to work better at scale and virality tends to work better at scale. But external channels like, like a webinar or even like paid marketing or something get harder and harder when you, when you get to the size that a calendly is.

Speaker D: John, our CEO always talks about the metaphor of a really big ship. Right. You know, if I, it's really hard to move a ship as um, you know, um, but if I, if I just, if I can do it one degree to the left or right, that ship is not stoppable. And that's going to look nothing like the trajectory, you know, once we sailed a fair bit. And I think about that metaphor very often for the same reason.

Speaker A: Yeah, another, another thing that I reflect on a bit from this conversation is um, the fact that you came into Calendly, uh, through an acquisition. So you've been a founder. I have this hypothesis that the best growth people have a founder background and part of it is just because you know, found founders have a lot of risk. You know, they're taking a big risk when they start a company. But two, they have to think about the big picture. They have to think about all of the interdependent parts of a business. And um, so when you step into a growth role, those are a couple of the big challenges in a growth role is, you know, growth is in your title. You better make it, ah, you better make it happen. And then secondly, um, yeah, that you're going to have to, you're going to have to get a lot of uh, disparate parts of the company working well together. So I'm curious what your thoughts are on founders as growth leaders, if you agree with that hypothesis or not.

Speaker D: Couldn't agree with you more. And that's really because what is a growth leader or anyone working in growth? You're part time cfo, part time writer, part time analyst, part time creative. You're doing everything. And isn't that the job of what a founder does, being able to do that? So um, understanding the mechanics of a business and then doing what you need to impact them is really the crux of growth.

Speaker A: Absolutely. Ethan, you any big takeaways just going on?

Speaker C: Yeah. With that I would just say like um, I always think of the head of growth role as the step back leader, the person who has to step back in the room and look at that big picture. And I think that feeds very much into what you just described. Um, also just going back to your thoughts on Playbooks, I think it might have been an early growth hackers conference. Someone uh, kept using the phrase, they kept saying this is suggestion, ah, not prescription. And I feel like uh, that often gets overlooked. I mean when someone writes a book, they write a book that by definition it's a playbook, um, in many ways for how you do this. Um, but if you look at that from the perspective of what is the suggestion in that? Not necessarily like what's the, the prescription of it? Um, a lot of times you can get a lot from those without being so prescriptive that you lose the sense of like well this doesn't necessarily apply exactly at my business. So I thought that was interesting. And then like, just the other thing that stood out is you mentioned that, like, how important customer feedback is, which is a theme of every one of our 90 something conversations we've had. Um, but one thing thought that you had, which I thought was helpful is your job is to hear the customer's problems, but not necessarily take their solutions as, uh, it's really about understanding their problems and then it's your job to come up with the solutions. I just thought that was a good way of putting it. You put it much more eloquently than I did. Um, but yeah, this has been great, Darren. I've really enjoyed this.

Speaker A: So, Darren, any last thoughts? Reflections? No.

Speaker D: Um, I know yesterday when we were chatting, the email, um, you asked me what I understand about growth today that I didn't understand a couple of years ago. And I had this funny, like, introspective moment when I'm sort of going back and trying to rewind to where I was. And like, honestly, you know, we spoke about imposter syndrome at the beginning around being a marketing leader without the resume of that and, you know, having not been to school for marketing and the like. What is growth like? Growth? To me, it's fifth grade math. Right. Like pretty straightforward math. Well, it's, it's. I've got. My moldest is in first grade. It's harder than that. She's not multiplying yet. She's still adding and subtracting. But it's certainly not complicated. You know, high school math, it's fifth grade math. Um, on top of like a creative understanding of your customer and their journey. If you understand your customer, you can think creatively and, um, you know, how your funnels work, how the plumbing works. That's all that you need to do with growth, right? So it's a straightforward model. You just have to be in the trenches, in the detail and truly understand your business. And then from there it's fun.

Speaker A: Yeah. That's a perfect note to wrap up on. Well, Darren, thank you so much for taking time out of your busy day to, uh, share your insights and experience with us. Ah. Um, we're so happy to have you on the podcast and for all those tuning in. Thanks for tuning in.

Speaker C: Thank you very much.

Speaker D: Likewise. Thanks for the chat.

Speaker B: Thanks for listening to the Breakout Growth podcast. Please take a moment to leave us a review on your favorite podcast platform. And while you're at it, subscribe so you never miss a show until next week.