Roy Duvall - CTO at Calendly

(Joel Beasley at 00:00:00) Hello, my friends. Today, we are talking to Roy Duvall, the CTO at Calendly, and we discuss challenges faced when dealing with massive scale, how to organize the genius within an organization, and how to use successful thinking patterns of other people to your advantage. All of this right here, right now on the Modern CTO Podcast. Here we go. This is the Modern CTO Podcast.

(Joel Beasley at 00:00:34) Hey, it's Roy.

(Roy Duvall at 00:00:36) Joel, how's it going?

(Joel Beasley at 00:00:38) Amazing. I just got these new AirPod things, and they're weird because they're noise canceling.

(Roy Duvall at 00:00:46) Yeah. I'm an Android phone user, and so it was a little bit sacrilegious for me to buy AirPods, but I love the noise canceling. I ended up getting Jabra, the Jabra Elite, and they're supposed to be the next best thing on the market. And so far, they work pretty well.

(Joel Beasley at 00:01:05) Yeah, you like them?

(Roy Duvall at 00:01:06) Yeah. Yeah.

(Joel Beasley at 00:01:07) That's awesome, man. It's always, like for me, it makes a difference in the workout or the run. Like, when you have the music and it's high quality, it can just take it to the whole next level.

(Roy Duvall at 00:01:18) You got it. You got it. And then they also have the hear-through that you can turn on and off. That's helpful if you're running on the road. I do a little bit of running myself, so it's super important for me too that they stay in and that they work well.

(Joel Beasley at 00:01:31) Oh, yeah. So you like doing some running? You're up in Georgia area, right?

(Roy Duvall at 00:01:35) Yeah, Atlanta, Georgia.

(Joel Beasley at 00:01:37) You got some hills and some nice terrain to run, or you do inside stuff?

(Roy Duvall at 00:01:41) I love trail running. You know, that's my excuse to kind of get out and see nature, just kind of decompress and forget everything and just go along. So I do some distance running here and there.

(Joel Beasley at 00:01:56) Yeah. I think our connection to nature is incredibly important.

(Roy Duvall at 00:02:01) Yeah. Absolutely. You know, it just kind of takes you back to what's important, and you're able to just really decompress and think about things in a whole new way.

(Joel Beasley at 00:02:15) Yeah, it helps that usually when I was stuck on engineering problems, I was like, all right, I'm just gonna go outside. I'm just gonna walk for ten or fifteen minutes. And it's so hard to rip yourself away from the computer and go do it until it becomes a habit. But then once I figured out, like, to separate from the problem, go outside and just get your mind in a different state, then the answers will come to you.

(Roy Duvall at 00:02:37) Yeah. Yeah. You got it. Nothing like a long 50K or a 50-mile run just to think about all the problems. By the time you get to the end—

(Joel Beasley at 00:02:48) Dude, a 50-mile run? Holy crap. You abolish me, man. I do one to three miles a day.

(Roy Duvall at 00:02:54) That's what I do.

(Joel Beasley at 00:02:55) Okay, yeah.

(Roy Duvall at 00:02:56) You know, I think it's part of a personality trait, just going to the extremes. In software, I want to know everything there is to know about software engineering. I want to know development process. I want to know the software as a craft. What's the best pattern? And similar with running, it's like, I started with a 5K, and then it's like, well, I'd like to go a little further and do a 10K. And then got out on the trails, and I see that there's these things called ultra marathons, and it's like, well, how far can you really go? Let's push the envelope. And it turns out most of it's just really about being stubborn and just being unwilling to give up, and just sort of like software, chew on it and keep getting better and better and better. And it's the same thing with long-distance running. You just keep going a little bit further, a little bit further. And I did 72 miles across the North Georgia Mountains a couple years back. And it's just, you know, when you finish that, you think you've solved every problem that you have to that date. And so you go find some more problems to solve and do some more running.

(Joel Beasley at 00:04:00) Was that on the Appalachian Trail area?

(Roy Duvall at 00:04:03) There's a race called the Georgia Death Race, and it comes from Vogel State Park all the way over to Amicalola Falls. So a little bit on Appalachian Trail, but lots of other trails—Duncan Ridge Trail and a few others that are up there that are really challenging, but just super scenic and super fun to do.

(Joel Beasley at 00:04:24) Yeah. My wife and I spend a lot of time up there in the North Georgia tri-state area doing the different mountains and all of that. It was a lot of fun.

(Roy Duvall at 00:04:34) Yeah. Yeah. You know what? Doing that, I've come out to Utah and Bryce Canyon and run there, and it's just an amazing way to see lots of things in a short period of time.

(Joel Beasley at 00:04:47) So what type of shoes do you like?

(Roy Duvall at 00:04:50) All the shoes. All the shoes. I don't know. I guess my favorites are probably Altras. They make a great trail shoe. It's a zero-drop shoe, and they're just super comfortable, nice and lightweight, but just enough support. You can put a rock plate in, and so they support your feet on some of those longer distance runs.

(Joel Beasley at 00:05:10) I love that. I think it says a lot about somebody when you can do that, do the difficult things, take yourself to the extreme. I treat my professionalism almost like an athlete where I feel like I'm training for it constantly, or I'm going to the gym, doing my running. And I did running for several years, one to three miles a day, and then I decided that I wanted to do some more lifting and put on some more muscle, which is actually really hard to do when you're running because the calorie needs are just insane. And so I did a little less running and a little more lifting, and so that's where I'm working on right now. But that mindset, I think, is what you were really hitting on—that mindset to find where your boundary is and say, okay, here's my comfort zone. Let's push it a little bit farther. And I've gone to the point where I've pushed it to unhealthy levels to feel like, what is my ultra 100% maxed out? And then I was like, okay, if I go farther, I will die. Beyond the first time you push it, I'm gonna die, but I push through. And then you're like, I'm gonna die, but you go farther. But then you're like, okay, I will actually die. And you have to take it back a step.

(Roy Duvall at 00:06:22) Nice. That's funny. It sounds like we've done the opposite. I, from 22, 23 to 32, I spent a lot of time in the gym working out and trying to find those limits and trying to get big. I'm a little guy, so spent a lot of time eating and bulking and taking the protein shakes and trying to grow and get large and went to a pretty far level of intensity there. And then, you know, sitting behind a desk every day and only doing those heavy weight workouts, it's like, look up and I'm 32, 33, 34. It's like, if I don't start doing some cardio, we're gonna run into issues. And so then that's where I started dabbling in the running and moving on from there.

(Joel Beasley at 00:07:11) Oh, yeah. The cardio and then the stretching, all of that, it makes noticeable improvements to the quality of life.

(Roy Duvall at 00:07:19) Definitely. Definitely.

(Joel Beasley at 00:07:20) I'm a huge fan, by the way, of Calendly. Yeah, I've been using Calendly since 2017. It's a core part of our business, not gonna go away, which is an infrastructure play, right? That's definitely what you want as a company, a business. And it's just, from the moment I used it, I was like, oh, this solves a problem. And then it became a thing where I would just say, hey, where's your Calendly link? And they're like, what are you talking about? And then eventually, you became a verb or—I'm not sure of the part of speech—but you became a thing, like Zoom. Where's your Calendly link? Where's your Calendly link, or do you have something else similar? And eventually, Google started understanding the word and stopped trying to autocorrect it. When I type Calendly, it would try to change it to calendar. But it's a really sweet service, and it's very, very useful.

(Roy Duvall at 00:08:09) You know, I got so lucky stumbling on Calendly. I was unaware of it. I was unaware it was in Atlanta. It's grown organically. And like you said, you use it, you realize it solves a problem, and all of a sudden, that's the only way to go. And I used it and realized, man, this is something that everyone needs. And I hear what you say over and over and over again from our users. It's like, the day I used it, I realized there's just no going back. This solves a problem for me. And that's what brought me to Calendly—being able to work on a product that people can immediately see the benefit from and it helps connect people in a whole new way and makes things easier.

(Joel Beasley at 00:09:00) So when did you join?

(Roy Duvall at 00:09:02) So I've been at Calendly for about 11 months now. I stumbled on it a little bit. Got lucky, really. They recruited one of my product managers out of my previous employment at Sharecare, where I was VP of Engineering. And, you know, if the recruiter had cold-called me and said, hey, there's this scheduling company called Calendly in Atlanta, and they're looking for a CTO—I was in a super good place, and I would have probably not even taken the call. But it just so happened she had given her notice a week before, and she was in her last week of employment. And the recruiter called me and said, hey, there's this scheduling company in Atlanta. And I was like, is it called Calendly? They said, yeah, how did you know? I was like, well, I need to know more about this company. And I really did it just because I was losing somebody that was great, and I wanted to know why. I thought there was pretty much a 0% chance that I was gonna leave my current employer. I was in a really good place. I'd been there eight years and was growing the team exponentially. And I met Tope, and I saw the passion in his eyes. I used the product and found, oh boy, this is something that users love. Really solves a problem globally. It's in Atlanta. We care about our users. That's the passion of the company. Everything from customer experience to product to engineering, we're all there on Twitter listening to our users, getting feedback, trying to find what the next best thing is for us to build. And it's just growing exponentially in all facets. And so that's what I love to do. It checked every box for me as far as internally having the culture that we need, being passionate about the software, but also giving people room for innovation and growth and that time to build software the right way, and then just really solving a problem for users. And so by the time I had my third interview, I'm like, okay, how do I make these people hire me rather than I'm just going there to waste their time because they stole my product manager? It was an amazing journey for me.

(Joel Beasley at 00:11:28) Yeah. Well, I feel like, as humans, when we see something good, we have this desire to amplify it. We want to be a fan of a product. Every interaction I go into with a brand, it's like, I want this to go good because I want to go around saying that this is the best in the world.

(Roy Duvall at 00:11:44) Exactly. Exactly. And this has utility around the world, and it's just been such a hidden gem because we don't have outbound sales and outbound marketing today. I mean, it's just purely been somebody uses it and they tell somebody else about it. And so we're just super interested in getting the brand out there and letting people know that Calendly is gonna just get exponentially better from here.

(Joel Beasley at 00:12:13) Yeah. That's how we got you on the podcast. I make lists of things I love, and then I give them to my team and I say, go find me the people behind the things that I really like. And they do that, and it's very exciting for me. And I've also seen your growth because I was talking to some of the people in HR a year or two ago. You guys were in our sales pipeline for our leadership product. Somebody had reached out before you even joined. And we were talking with her, and I can't remember exactly her name. But I started following her on LinkedIn. So every day or every week, she's posting faces of your new team members. I'm just like, well, this company is growing like crazy. And then she's moving up into new positions, and I was like, wow, you guys are on fire. And, you know, candidly, I had a couple support things that I asked for—favors, essentially, not bugs or anything. I had some favors I asked for from them, and they did them. And I was blown away by that, right? Because, you know, everyone comes on and says, you know, culture when they're doing interviews or when they're talking. It's a common word that comes up or topic that comes up—culture, culture, culture. But when you get to firsthand interact with a support team and request and actually have it resolved and experience that, that is the true culture test. Does it permeate through every employee?

(Roy Duvall at 00:13:38) You know, and honestly, if there's one thing that keeps me awake about Calendly right now, it's that. Right? It's like, today, it is beautiful. That culture and that collaboration is there. That's something that you can do as a 65-person company by getting everybody in the room and having a super articulate CEO stand up in front of that group of people and just say, here's my vision. Here's what we're trying to do. And everybody can go away and regroup as necessary. We've gone from 65 people at the start of 2019 to we're 150-plus people now, and we're all fully remote to COVID. And so this is something that the leadership team sits and we agonize over. It's like, how do we keep that? How do we keep that culture of collaboration? How do we make sure that we're empowering people? How do we make sure that all of our employees in their situation today are the most effective they can be? But we're also accounting for that this is a very unique situation for everyone and giving them the ability to handle their situation appropriately as well. And so that's another thing that brought me here—it's always forefront of thought. And we're not running so fast that we're not taking that time to take that step back and say, okay, now that we're 150 people, what broke that worked well at 65? Okay, how do we fix that? All right. And then at 200 people, what are we gonna do a little bit differently in order to solve that problem as well?

(Joel Beasley at 00:15:17) Yeah. Actually, I might be able to help too, if you would like. I've got a number of connections. Specifically, you know, TripActions. They went to a couple hundred people, and then the next year, a thousand people, and then, like, three thousand. They just kept exponentially growing over the past two or three years. And so got some connections there.

(Joel Beasley at 00:15:35) And then also at Datadog. Are you familiar with them?

(Roy Duvall at 00:15:38) Oh, yeah. Absolutely.

(Joel Beasley at 00:15:40) Yeah. I mean, I like that as an engineer. I'm a fan of them. But yeah, they grew really fast too and I've got some connections over there. So, you know, maybe after the show, if you're interested, I'll connect you with some of those people if you've got those questions. I mean, I'm sure that the team is incredibly competent. You guys have got it down, but it always kind of helps to have a person who's done it before and bounce ideas off them if you'd like.

(Roy Duvall at 00:16:02) Always. I always want to bounce my ideas off someone else and learn from other people. We have a great community here in Atlanta of CTOs that we get together and just talk about solutions. But yeah, would love to make more connections and learn from additional people. So please, yeah, let's touch base.

(Joel Beasley at 00:16:26) Yeah. It's pretty cool because last year I got to travel around all over the world and talk to different CTO groups. And it's really interesting, there's just different styles of people in different areas. And I know that Atlanta has one of the largest groups because I was actually booked to speak at one of the Atlanta CTO things, but the coronavirus happened. And so everything got canceled. But you guys have a really large community. I mean, Atlanta does, and then there's a very large community in Canada, and then you've got, you know, some Denver and San Francisco. Just some of the groups that I follow personally.

(Roy Duvall at 00:17:03) Yeah. Yeah. Absolutely. It is a great culture in Atlanta of CTOs that just want to learn from each other, but also reaching out to other avenues for finding those CTOs that are amazing, like Plato, reaching out through them and their mentorship programs.

(Joel Beasley at 00:17:25) Yep.

(Roy Duvall at 00:17:26) And just having conversations there to learn from each other. That's more of a worldwide play so that you can touch base with somebody that you may have never come in contact with and kind of learn those different strategies that people are employing around the world.

(Joel Beasley at 00:17:39) Oh, yeah. And I was curious. You said, did you say his name was Tope? You said the guy you talked to that shared his vision, that's the CEO or the founder?

(Roy Duvall at 00:17:46) Yeah. That's our founder CEO, Tope Awotona.

(Joel Beasley at 00:17:50) So what was that first conversation like?

(Roy Duvall at 00:17:53) That first conversation, like I said, I came in with, honestly, with a little bit of arrogance and low expectations and just was like, you know, you hear the startup culture theme all the time, right? We got the perks, we bring in the breakfast, we've got the unlimited PTO. We're growing exponentially, and it's usually because we've got a ton of venture capital backing money that's really helping us grow and expand. And I sat down with Tope, and, you know, he said those things, but then he said, you know, and we're doing total rewards. And part of total rewards is our unlimited PTO is backed with a thousand-dollar stipend. You only get your thousand-dollar stipend if you take your PTO. And, you know, we're looking at how we do laddering. At 65 people, how do we do laddering and career paths so that we're setting people up for success from day one? And, oh, yeah. By the way, we're a profitable company. We're not taking any investment. We don't want investment because we grew this organically, and the snowball has hit that point where it's just rolling downhill faster and faster and faster because people know about us and have learned about us organically.

(Roy Duvall at 00:19:11) And so we don't have people that are asking for return on their investment. You know? He owns this company, and we have some support through OpenView and people, but what we don't have is a need for additional infusion or anything. And then beyond that, it was his vision of the leadership team and what we're there to do and how we're there to empower our employees and make sure that we know it's organized genius. Like, our job is to give them the strategy and the vision and set this platform and let all of these brilliant people solve problems for us and continue to have that focus on the user. And yeah, that first conversation was when the light bulb started turning on for me of, like, oh, boy. I have stumbled on something that is unique. It isn't brochureware of, like, hey, we've got all the buzzwords for a startup in Atlanta. We live and breathe that as the culture and as the values of what Calendly strives to achieve.

(Joel Beasley at 00:20:15) Yeah. What did you end up doing? Well, first of all, I fully agree with your concept of organizing the genius because that's actually quite a hard thing to do. Right? The default is to get in there and want to do the work, to be the contributor. The default is to get in there and do it and then to be able to step back and put somebody and tell the right person, put the right type of genius in that role, ensure that they're... and then take care of that, manage that relationship and build that trust in that relationship, and then to let them operate autonomously and do their thing and coach them through that. That's actually... it sounds easier than it is.

(Roy Duvall at 00:20:57) Well, and that's funny because, you know, Tope admitted that immediately. Right? This is his baby. He's the founder. He's the guy that rolled up his sleeves and walked in and said, hey. This is what we're going to build. He got this thing started. And he was the first person to say, it's like, it's at a point now where I need experts that have done this at a bigger scale than me. And I need to figure out that way to step back and let people and empower people to do their job because they're going to go deeper. They've grown things larger than I have, and it's what's best for Calendly. And so, yeah, I think he struggles with this on a day-to-day basis. He always wants to ask questions. He always wants to understand and be involved, which is, you know, essential for a CEO anyway. But being able to kind of extract himself from the very specific user experience of how we do rolling calendar days versus business days. So...

(Joel Beasley at 00:22:02) How did you end up solving the, you know, ladder, career paths?

(Roy Duvall at 00:22:08) So this is a consistent work in progress. Right? So the first thing to do is to start defining our just basic organizational structure. How is it going to scale? When I arrived at Calendly, it was engineer, engineering manager, and QA. And that's the entire engineering organization. You don't need anything besides that. Right? And so, you know, this is where I started coming up with, well, we probably need some site reliability engineers, and we probably want to think about architecture in a different way as a discipline. And so really just kind of laying out what is our viewpoint of an enterprise-sized engineering organization.

(Roy Duvall at 00:22:52) From there, it's, okay, understanding that, now let's start breaking that down into job roles and responsibilities. And so really spending the time to write out those job descriptions, creating the scorecards. And so, you know, what we want to do is we want to make sure we don't fall into the pitfall of, you know, we've got a great engineer. The only way for that engineer to grow is to move over into a management path and start taking on management responsibilities. Some people are great engineers and should be lifelong engineers. Right? And so defining a technical career path for engineers that goes all the way up to principal engineer, starting at junior and then going all the way up to level six for what a principal engineer looks like at Calendly. And then doing that for each role in each definition, site reliability engineer. What's it look like at an entry level? How does it grow? How do you become, you know, world-class guru of infrastructure at Calendly? And so for each one of those roles starting to lay out what's that career progression look like and at each level, what are those responsibilities? You know, what are the core responsibilities? Where do you start? And how do you evolve along that spectrum in order to start moving towards that next level?

(Roy Duvall at 00:24:08) You know, this is something that they had started when I got here, and I just worked to embellish it and make sure that we had special disciplines where that was necessary. But from there, it becomes more of a lattice. Right? So it's not only vertical scale inside engineering, how do we move for one role either laterally or vertically? But what about CX? Is there a path for customer experience to move into engineering? And so now we start to take not only just vertical ladders and horizontal movements inside engineering, we talk about opportunities across the company. It's the greatest thing about exponential scale and exponential growth internally is that there are constant opportunities for people to branch out and learn and pick up another discipline and grow into that discipline and continue to evolve as a person and in the kind of path that they want along their journey.

(Joel Beasley at 00:25:06) How would they access this information? Is this something that's, like, it's a PDF in Dropbox and it shows the things for each role? Like, how do they stay... Obviously, the rules will change and so the needs will change, but, like, how do they visualize it and interact with it?

(Roy Duvall at 00:25:21) Well, so this is a, you know, this is an important thing for us. Right? It's go slow to go fast. It's not just, hey, I need a senior SRE. Let's open that position and get it hired. It's what's that ladder look like? How is it defined? And we create this. This is a readily available document inside Calendly of what are those career progressions? What are the scorecards? How do you move back and forth? What are the open positions today? Right? Because it's not just, hey, this is defined. There has to be that business need as well. We're super transparent in all of this. I think that's essential to continuing to have that culture and that collaboration that we want, right, as everybody needs to know the why and the how and the what. And so all of these documents are published so that people understand what are those opportunities. All of our open positions are published, so people understand, oh, there is something there for me to strive for. And then, you know, from there we actually use a combination of Small Improvements for just kind of having that career progression defined between a manager and that individual and Confluence Wiki page for what's the overall view of that ladder and career growth pattern for people.

(Joel Beasley at 00:26:42) Well, that's really exciting. And because it's very clear for them when they can visualize... A lot of people will talk about it. I'm always curious what it looks like. I hadn't asked yet. And so it's like a Confluence, like, Wiki-type page and you have a visualization and then they just constantly check it. Because I found that if you create an environment for productive, hungry, successful people to thrive in where they can see where the needs are, then they can self-organize and deliver results easier.

(Roy Duvall at 00:27:13) Yeah. I mean, that's what it's all about, is it comes back to that concept of organizing genius. Right? It's like, if you could give the strategy, if you can give the perspective, if you can set goalposts and then get out of the way, then you're so much better off than, you know, having to come back in and do everything by word of mouth and meetings and one-on-one management.

(Joel Beasley at 00:27:35) Now do you nerd out with, like, the OpenAI or SpaceX or anything like that?

(Roy Duvall at 00:27:41) Yeah. I mean, I'm a nerd through and through. I definitely watched a couple scrubbed launches and then the final ultimate successful launch on Saturday. I was super excited about that and just amazing what's being done there. I also geek out on things that maybe even other traditional engineers might not, software development process itself. Like, what's the easiest, most pragmatic way to have enough process and structure so there is transparency, but not so much process that it's like, oh, I've got to jump through all of these hoops to solve a problem. I spend a lot of time researching best process and development strategies. But yeah. Yeah. Definitely all the facets of engineering are super interesting to me.

(Joel Beasley at 00:28:32) Yeah. It's hard because it's like when people are talking about it or you're reading it and you're gaining experience, it's like everyone describing, you know, how to draw a certain type of face. Right? But then as you do it, it's its own unique representation. So there's not a perfect cookie-cutter way to answer all the questions. And it's hard because, like we were talking about earlier, it's like physics. Right? Things have different principles at different levels of scale. Right? So what works at 50 won't necessarily work at 150. And so you're in this constant evolution. And to me, the growth, that evolution is the most fascinating thing in the world to me because you can... if you like learning new things and you're curious, you will never be bored.

(Roy Duvall at 00:29:23) Well, I think you said it. It's about that continuous improvement. You know? We start out with one thing, everything from our career ladder. Right? It's like we started out defining what the engineer's progression is from P1 to P6. We define the manager path and the architectural path and what a site reliability engineer can grow to be. But then, you know, DevSecOps comes up, you know, as we continue to grow and scale, new disciplines come on. And so it's never a stagnant thing. You've never solved the problem. So everything from career laddering to software development process, which was very much just a product manager and a set of engineers solving problems, becomes user research and upfront content with a voice of Calendly, and then going into user experience and design and then going into product and then product marketing. And so, you know, as we continue to grow and scale and build out these disciplines, continuing to look at that process and making sure that all along the way, we're incorporating new and best and more specific practices and keeping the speed and agility that we have in delivering that software.

(Joel Beasley at 00:30:42) I love it. Oh, man. It's been a while since I've been... it's been... I haven't been writing software for, like, a year now. So I did it for, like, seventeen years. And then this past year, I haven't been doing it hands-on as much just because of the podcast and the leadership company, but I need to get back into it. I was thinking about... I'm waiting for my kids to get to that age where I could, you know, teach them some little programming stuff. I was teaching my daughter, who's three, how to type her name on the keyboard the other day. But I'm looking forward to getting the Raspberry Pis and maybe a rocket kit and then using the Raspberry Pi to ignite the rocket. You know, do something simple. That would be like a weekend project or something really easy to do. But are you playing around with any future technologies right now that you like?

(Roy Duvall at 00:31:26) You know, I have dabbled in a large number of languages over my career. And it just so happens I bounced into a company that is a Rails shop, and I am not a Ruby on Rails expert. But I'm like, that's not okay for me. So I've been spending a lot of time just getting into Ruby and Rails and understanding that technology stack. Lots of background in .NET and then C and all the way down to assembly, and all the way up to Java and Spring. And so it's, you know, at some point, picking up another language becomes syntax and understanding the patterns of that language.

(Roy Duvall at 00:32:12) So just spending time on some of the magic that Rails brings to the table and understanding that. One of the problems with convention over configuration is that in convention, you just gotta know the tricks. And so that's very much Rails versus, like, Spring. In Spring, I could just go in and understand Java and how it was configured and reverse engineer everything. In Rails, I need to understand more about what are those tricks, what are those conventions that happen under the covers that create that magic.

(Roy Duvall at 00:32:46) So spending more time understanding the things that are gonna help me at Calendly rather than dabbling in next gen AI and machine learning, which is also super interesting to me, and I'd love to spend some more time there. I'll get to do that as we start building in that intelligence and automation into our software stack. But for now, it's, you know, and that's part of what we're doing at Calendly. It's like everybody that is in engineering is an engineer. Like, we love software.

(Roy Duvall at 00:33:18) I write software. I don't wanna get away from that. I refuse to be, you know, ivory tower architect or whiteboard guru. I wanna be able to get in there and understand our software just as well as the next person. So yeah, I've kind of similar to you where the podcast took over and you have gotten away from coding.

(Roy Duvall at 00:33:41) I had to table some of my side projects in Kotlin and Swift and some of the dabbling that I was doing in AI in order to kind of come back and make sure that I can just speak on the same level with the engineers at Calendly about our Rails application.

(Joel Beasley at 00:33:58) Yeah. That was, like, my last seven, eight years was Rails programming.

(Roy Duvall at 00:34:02) Yeah. Yeah. Well, we need to connect there too. You can just give me the cliff notes version, and I won't have to do all this book reading.

(Joel Beasley at 00:34:10) Yeah. But I've actually learned some of my best programming concepts from, like, Martin Fowler. And I don't even think he gives, like, Rails examples. I think they're all Java examples, if I'm right.

(Roy Duvall at 00:34:21) Yeah. I love Martin. Yeah.

(Joel Beasley at 00:34:21) Yeah. And it's really what I get out of them. There's different modes of my learning. Like, okay. I wanna learn how to perform this specific technique, trying to accomplish some very specific results. But then, you know, that's pretty narrow, and that's usually solved not through reading a whole lot. I find what I, the biggest benefit I get from reading those types of people is understanding how they think about creating the software. And through watching them come up with their examples and then explain them, I can, it's like if you have a friend, you could emulate their thinking patterns. Well, you can do that same, like, if you think of a character, like, maybe, like, Michael Scott from The Office. Like, you could start thinking, like, what decisions they would make. And I personally, I like to, I bring this up a lot, by the way. And the reason I do is because I believe it's very under discussed. Like, for example, I've never heard anybody else talk about this. So I talk about it a lot because I wanna hear it out there in the world because it really is this untapped superpower that humans have.

(Joel Beasley at 00:35:25) And it's interesting as I watch different organizations and I get to go visit a lot of companies, so I get to see a lot of different cultures. And it's so interesting how it's 100% this behavior and everything is 100% infectious. Like, the people just mold to the behavior of the leadership. Like, whether they like it or not, it's just they start orbiting that. But yeah, this ability to have good influences and then those thoughts and those thinking patterns become contagious and spread throughout the organization. That's an incredibly valuable tool.

(Roy Duvall at 00:35:57) Yeah. That's what it's about. Right? Like, learn from the best, understand how the best think, come up with those patterns, and just, you know, don't reinvent the wheel. They're out there. There are some amazing creative thinkers out there that you can learn from and spend a lot of time reading and trying to do that. Martin Fowler is a great example of somebody that helps us in the Java world. But like you said, it's a pattern of thinking that's super important.

(Joel Beasley at 00:36:26) I think Sandi Metz is pretty good in Rails too.

(Roy Duvall at 00:36:29) Okay. So this is not what I'm familiar with, but I had to check that out.

(Joel Beasley at 00:36:32) Oh, yeah. So she gives a lot of her examples, like, with bicycling. Like, she does a lot of road biking. She's pretty cool.

(Joel Beasley at 00:36:39) I'm sorry I cut you off. I just wanted to get that out there because you were talking about, like, authors and Rails and stuff. And I actually have a, I actually have a page. I was doing some mentoring on, have you ever heard of CodeMentor?

(Roy Duvall at 00:36:49) Yeah.

(Joel Beasley at 00:36:50) Yeah. So for, like, a year or two, just for fun to, like, know more people, I was mentoring students coming out of code schools and Rails. And basically, I just kept referring. I was like, okay. If you just go read these four or five books, I had to get down to that. You will be in a much better position. And I ended up, I think the website's like abetterdeveloper.com, but it has, like, four or five of these books that are, like, essential for programming and specifically, I think some of them were, like, three or three out of five of them were for Rails specifically.

(Roy Duvall at 00:37:21) Nice. I will definitely check that out. I was just gonna say, we actually hired a couple of teachers out of the code schools and brought them to Calendly because, like you said, like, it's about those patterns and it's something that we foster inside the organization is that mentorship programs. And so not only are we in the Atlanta ecosystem where we're trying to reach out and we actually host a lot of the Rails meetups and present at those for best practices, but we take that externally and internally for that mentorship and growth and just try to ingrain the culture of learning and, you know. And so for me, that that means being out in front and being a public persona. And, you know, I think this opportunity to be with you and listen to a bunch of podcasts, you've had a few people on there that I've worked with before, Bryson Koller.

(Joel Beasley at 00:38:20) Oh, really? You've got to work with him?

(Roy Duvall at 00:38:22) Bryson's a great leader, man.

(Roy Duvall at 00:38:23) Yeah. Overlap at the Weather Channel. You know, and just an opportunity to tell people about what we're doing, and I couldn't pass it up. So yeah, I will, I'll write something down. Cool guy for me to collaborate with, and I'll send that over to you so that you have it retroactively.

(Joel Beasley at 00:38:43) So my background, you know, was the engineering and, you know, you talked to me three years ago and I was shy and hadn't didn't know anybody really. And one of the things that I've gotten to experience after going out there and speaking and getting to speak at conferences and meet people in their companies is that there are some real legitimate business reasons to do the speaking and to be out there. And I think the one, because I'm so nerdy and try to be, like, pretty exact, sometimes to a fault. But one of the, like, really tangible ones you can hold on to is recruiting. So finding good people.

(Joel Beasley at 00:39:20) Back to that point earlier, like, when you go and you speak at a conference or when you're here talking on the podcast about the product and why you love it and that you like running and that, you know, you're in Georgia, people are identifying with that, and they're saying, wow. Now I heard it from Roy. Like, now I understand the culture. I understand how this guy thinks. I would like to go work with him, or I'd like to go work on that team. Right? I like Calendly. I wanna go do good things with them. And that is a really important benefit too, especially as your company is growing. You guys aren't just gonna stop at, like, one fifty. You're gonna go to the moon. Right?

(Roy Duvall at 00:39:57) You got it. Yeah. Our growth plans are exponential, and we will be a worldwide known name. You know? And so that's exactly why I'm here is, I don't wanna have to get lucky. You know, how I arrived at Calendly is, you know, I got lucky. I don't wanna have to get lucky with that next brilliant engineer. I want people to know, like, this is an amazing place. It's an amazing product. You wanna work here because your ability to affect a software solution that solves real world problems for a huge number of people, it's unparalleled.

(Joel Beasley at 00:40:37) Well, this whole podcast, by the way, hundreds of guests, the first people for a long time, it was just, you know, me and coordinating with people and sending emails, like, hey. Will you come talk to me before we built up a whole team? And Calendly was, like, critical to my success there because it maximized my available time. And so I was, like, so grateful that that tool existed. On the company, like, LinkedIn page or the company bio, it says that you guys take time to celebrate your accomplishments. Can you tell me a little bit about that?

(Roy Duvall at 00:41:13) Yeah. Absolutely. You know, and I think that goes back to Tope and what really sold me about this company is, let's take COVID for an instance. Right? Like, the first thing we did, we were one of the first companies in Atlanta to say, like, look. Stay home. Let's go fully remote. We weren't versed in being a remote first company, but we'll figure this out. And by the way, we know your kids are at home too, and we know that, like, everybody's having that unique experience right now. And we want you to understand, like, if you're not working forty hours this week, that's okay.

(Roy Duvall at 00:41:51) Like, take the time you need to solve the problems that you're facing today. That's just one of the greatest things about Calendly is we are passionate about building the software and building a product that people love, but we also know, like, if you don't have your work, your home life, and your family, and if that's not in order for you and you don't have the time and the space to be able to be immersed and present in that, then Calendly won't be great either. And so, even as that's going on, what happened great at Calendly today? Right? That's taking that time to say, like, hey.

(Roy Duvall at 00:42:30) You know, we're talking to the sales engineer. They tweeted about Calendly, and it goes public on Slack. Right? And everybody's super engaged and interested in knowing what our last customer success was or customer experience gets feedback, you know, all the time for going above and beyond, like, you know, solving users problems. They write in, they have a problem, and just taking the time, solve it thoroughly, spend the time that's necessary, and make sure that person moves on their way no matter if it's a single user or part of a 100,000 person account that we have.

(Roy Duvall at 00:43:12) We'd like to spend that time and make sure that we solve it, solve it well, and then, and then celebrate it, you know, and make sure that that transparency is there.

(Joel Beasley at 00:43:22) And during this whole COVID thing, I know you guys have an office in Atlanta, so, like, you're just remote now. But did you have kids? Like, do you have to deal with that as well or just some of your team members?

(Roy Duvall at 00:43:35) Yeah. I have a four year old girl, Emerson, and a six year old boy son, Nolan, and wife. I'm super lucky. My wife is a stay at home mom, and she's taken on the educator role and the entertainer role and the summer camp role and the chef role and the house queen role and, like, just, you know, kind of clears the plate and lets me focus. Not everybody has that luxury, but, man, she is, you know, she's the workhorse of this family, definitely, and empowering me to just kind of focus on Calendly and be there for our employees. And so, yeah.

(Joel Beasley at 00:44:16) Shout out to the wife. Yeah. When I watch my wife operate because I have a girl that's three and then a boy that's 1.5. And so, like, when I watch how she handles all of that, like, getting up and taking care of them, like, what we did was we sat down and we decided, like, essentially, like, business partners, like, what our roles and responsibilities would be so that we didn't, you know, cross over and that everything was really clear for both of us to be, you know, strong team players. And so, like, I've got, you know, my list of responsibilities. She has hers. But when I get to watch her, like, enact those responsibilities, it, there's, like, a bit of admiration there. Right? Because it's different. It's like, what I do is difficult. What she does is difficult, but it's different, and I can see that happening. But she doesn't get to see my difficult as much because I go away to the office. Right? But I get to see hers, like, in the morning and then in the evening. And so it's, it is really great to have a strong team player.

(Roy Duvall at 00:45:19) I'd probably say that a little differently for me. Like, I love what I do so much. What I have is, like, I've got the easy game. She's a machine. She's the person that has a difficult job and, like, man, I just can't say enough good things about, you know, about what she does on a daily basis. Just, you know, lucky guy. Definitely lucky guy here.

(Joel Beasley at 00:45:43) We'll send her a link to this clip. Go, Roy.

(Roy Duvall at 00:45:48) Don't tell her. Alright. Don't tell her.

(Joel Beasley at 00:45:52) Jake's drafting the email right now. We got the PR team on it. No. I do know you, you know, you value your privacy. Right? And that's an important thing, and I think that's becoming even more important now, you know, with things. Like, I was reading earlier about, like, the COVID contract tracing and the privacy. And we don't have to, like, talk a whole lot about it, but I've been actually thinking about it here and there for the past couple months about privacy because I have, I think you and I both have a very unique perspective in the sense that we understand, or I won't speak for you. I'll say, I understand as an engineer that, like, I wanna do cool things and bring value to people using the product. I'm excited and energized about this cool look what I could do for you and, like, look, I can connect these pieces of data and here you go. Now you've got this added benefit and we're, like, using, I'm here building technology. I'm in the room. I'm in the furnace. I'm making it happen so that we can make your life easier. But at the same time, you can step back as, like, an individual and a consumer, and you can see some of the things that happen with privacy or data and be like, I don't necessarily want those connected.

(Joel Beasley at 00:46:56) Or so it's a really, it's hard to have a high level conversation about it because it's so nuanced in, like, which specific vertical you're talking about. But I definitely see a trend away from privacy, and that kind of scares me because it's, I feel like we're gonna end up in a future that's, like, really controlled by, really surveilled, highly surveilled.

(Roy Duvall at 00:47:23) Yeah. It's just not okay. You know, trust is a currency. You know, maybe more important than the actual currency. You get one chance to lose trust with your customers. And, you know, if you have that breach or that privacy concern that gets exposed, you're kind of done. And that's the way I look at it in our engineering team is, like, you know, our first thing is, do we need that piece of data? If we don't need that piece of data, we don't store that piece of data. We don't keep something just in case. Our calendar connections are free busy only. We don't pull your information from your calendar. Anything that is on your calendar, that's yours. We just need to know the availability. We just need to know if you're booked or not booked. That's what we store.

(Roy Duvall at 00:48:11) This is busy time. This is free time, and that's what we use to expose availability because we don't want it in our system because we don't want to be responsible for it. At some point, if there's something that we need to do for you with that data in the future, we'll ask you for it. But we definitely are just ultra intent on making sure that we only store what's necessary and that we keep that footprint as small as possible.

(Joel Beasley at 00:48:35) What do you think about the future? Like, what does the future look like for us as consumers? I guess I'm asking you tough questions that we don't, but I'm just curious as a human just trying to form thoughts with other intelligent people. I don't like the feeling of feeling helpless. I don't like the feeling of being a bystander.

(Joel Beasley at 00:48:57) And I see every day we get less privacy. And it's not like they take away a piece of privacy and then you gain something. It's like two steps forward, one step back. It's just like you lose, you lose, you lose, and it's just this continuous pattern forward. And I'm thinking, like, what is it that we can do? Maybe it's just being moral in our products or having a code of ethics in our products and just saying the thing I can do is, as engineering manager, I'm going to focus on we're only going to collect the data we absolutely need. Maybe that's just how you see it, but I'm just curious to know, what are your thoughts?

(Roy Duvall at 00:49:33) That's the start, right? We're going to run our company the way that it should be done because there will be backlash at some point. You know, like you said, every day it's another person that's aggregating your data in a way that you weren't quite aware of, and then it gets exposed.

(Roy Duvall at 00:49:55) And at some point, this will go beyond concern for consumers of, like, I'm a little worried that I don't know what Facebook is tracking today. But tomorrow it will be like, I'm just not going to use that product. Right? It doesn't bring me enough value to eliminate the concern that I have for the privacy that is violated or the data that is collected about me. And so, you know, I think there are just regulation after regulation after regulation.

(Roy Duvall at 00:50:30) CCPA just came out for California. Obviously GDPR came out a few years back. Governments are enforcing that there will be more and more transparency here, and as people realize and understand more and more about what is being tracked and how it's being tracked and how it's being used, I think it's inevitable that things like DuckDuckGo, where they're not tracking you, those tools and the companies that are doing it right and that are super transparent about what they do and don't have will be the ones that rise to the top. And so, you know, I do think it's all about today, it's about maintaining what we do internally. But, you know, because tomorrow the user will be empowered to really understand what's happening and will be a discerning consumer based on that.

(Joel Beasley at 00:51:23) That's why I like the mindset of engineers too and the fact that, you know, we both know a lot of engineers. We typically want things to be right. And there's these core intrinsic human values that I have that I think go beyond our nationality or geography, like things that we believe is right just as a humanity. And so I think there will be more whistleblowers and, you know, I think that'll happen a lot more.

(Joel Beasley at 00:51:48) People will get more comfortable with that. I think people will just direct their products in more professional ways. And then I think there's going to, I hope there's going to be a lot more transparency. Like, it's strange that I want to go Google something and then I think I don't want this in my profile. Like, I don't want this in a record somewhere where I searched it.

(Joel Beasley at 00:52:12) So I'm going to VPN to a DuckDuckGo, and I'm going to ask my question there because I don't want that because all it needs is just, you know, ten years. And I was a bored 13-year-old hacking stuff. I mean, the time's run out on that, so I'm good. But thank you, statute of limitations. But, you know, there's going to be some time where someone gets, we're humans, they're going to get angry, aggravated, or curious. One of those. They may get curious. And that data, it's collected, so it could be exposed. And it's not even embarrassment data or anything like that. It's for me, it's the step farther that concerns me.

(Joel Beasley at 00:52:51) It's when people start making decisions based off of you as a collection profile and not as an individual in real time. That bothers me.

(Roy Duvall at 00:53:03) Yeah. Yeah. It's a scary world out there right now. Everything from health information that's passed around to economics or financial information for you to just what did you Google search, or what did Alexa hear you say today? And then the ad you get served tomorrow.

(Joel Beasley at 00:53:29) It's insane. It's funny because, like, you and I were both making technology for a long time. And so when I was first making technology, people were not talking about technology. Like, the people I would be around at school or in life, they were just like, nerd, nerd. Like, you're just like, if you need someone's computer, go talk to Joel or something.

(Joel Beasley at 00:53:51) But now it's like every, I hear my friends talking about it or my non-technical family members talking about how they'll say something and it comes up on an ad. And then I was like, is that for real? Because I've heard this a couple times. So then I researched it, and it is 100% true. Like, you enable your microphone on, like, Facebook asked for microphone access, and it's 100% true. And in their terms of service, they let you know. Like, this is how it's being used. And it's like, whoa.

(Roy Duvall at 00:54:20) Yes. Not okay. Not okay. You should not be recording me and targeting me. You know? That's just, yeah, it's craziness.

(Joel Beasley at 00:54:28) Happened. There was, I saw last night in one of the tech news sites that I follow. There's this $5 billion thing, I think, against, like, Siri was recording clips when it didn't need it before you were activating it. Did you see that headline?

(Roy Duvall at 00:54:45) I didn't see that one. I am not shocked by it, though.

(Joel Beasley at 00:54:48) Yeah. Like, when an engineer came out, there was an engineer contractor and said, hey, I sat there for a year and listened to hundreds of hours of people recording Siri. And then, whoever, I guess it would be Google or Apple. Apple would be Siri. So, and then Apple's like, we didn't do that or we shut down that program.

(Joel Beasley at 00:55:06) But for me, I'm thinking, like, there is no oversight to this. It's just, it's a private company. Like, I own a business. If I was just like, hey, you know, hey, engineering team, just do this. Like, with the exception of the engineer standing up themselves, then no one would know.

(Roy Duvall at 00:55:23) I don't know. You know, there's a lot of inquisitive people out there. There's a lot of white hat security hackers out there that are constantly reviewing things and looking for holes and gaps and identifying patterns that don't make sense. So, yeah, probably the engineer that's sitting there and writing the software is the most prominent and easiest one to identify that will find that. But like I said, there's also a ton of people out there that are awesome. They're looking out for it and willing to make it visible and transparent to everyone. And then beyond that, which is probably the worst or most difficult way for it to come out, is the kind of enforced regulations on that transparency.

(Joel Beasley at 00:56:09) We'll do some more research on this. Why don't I, I should get some, there's got to be some experts out there that talk about this, right? Would that be useful content if we did some episodes on that and I went and got some of the people that maybe do it for the White House or different countries and kind of see what, how they approach privacy or what's going on there. I don't think we've done many privacy episodes. Would that be something you'd like to listen to?

(Roy Duvall at 00:56:33) I'd listen to it. Definitely.

(Joel Beasley at 00:56:35) We'll look into that. Was there anything else that we wanted to raise awareness for or get out about Calendly?

(Roy Duvall at 00:56:45) I think we covered it pretty well. You know, it's an exciting time in Atlanta in software technology and at Calendly itself. So, you know, you'll hear more from us, definitely.

(Joel Beasley at 00:57:01) Nice. Well, I'm a fan. The website is calendly.com, right?

(Roy Duvall at 00:57:05) You got it.

(Joel Beasley at 00:57:06) Yep. And people can hunt you down on LinkedIn or if there's a jobs, careers on the Calendly site, so they can look more about, you know, what positions you guys are hiring and what type of experts you're looking for?

(Roy Duvall at 00:57:18) You got it. Yeah. And we're learning to be remote first, so we'll be opening up positions around the world as we continue to grow and scale as well. So no matter where you're at, this is a great place to be.

(Joel Beasley at 00:57:33) It's exciting. There's probably, like, there's no Calendly in other languages yet, is there?

(Roy Duvall at 00:57:38) Oh, yeah. We're in five languages. About 30% of our audience is international. Yeah. 200 and something countries use us today.

(Joel Beasley at 00:57:51) That is so cool. So, yeah, I was actually, I was having a conversation the other day with, I think it was Stripe, CTO of Stripe, and he was talking about the benefits of as they scaled, putting offices in countries where they had high usage because they would be able to understand that local culture better, and then that actually helped drive the product as well.

(Roy Duvall at 00:58:15) This is our next frontier. We have just begun the conversations of, okay, now how do we start to expand the scope and understand the cultural norms of these countries and make sure that we fit in very well.

(Joel Beasley at 00:58:30) And then Stripe also is making a, they created this blog post that had all their learnings from going remote. So look that up, or we could share it with you after the call. But I just want you to know, between you and me, my friend, if you ever need anything, if you want to bounce any ideas off or got questions or if you're ever like, hey, I'm very curious about this one topic. Do you have anybody in your network? You just let me know. We'll connect you and do whatever we can to help Calendly because we're customers. Love the product. I want to see you guys grow and do well.

(Roy Duvall at 00:59:00) Awesome. No. I really appreciate that. And when I'm in town, maybe we go for a run. We'll keep it short, though.

(Joel Beasley at 00:59:06) Yeah. We'll have to keep it short, but, yeah, I'll go for a run. Sounds good. And I actually will take you up on the run. I've done that once before, like, gone running with somebody from the show. So, yeah, it was really great meeting you and hanging out today, and thank you so much for your time.

(Roy Duvall at 00:59:23) Hey. No. I really appreciate you having me on, and I probably will reach out to you. You're a well-connected guy, and I think we have some mutual friends that are interesting people to know and a great resource. So thank you so much for your time.