Ryan Aylward - CTO of Glassdoor

(Joel Beasley at 00:00:00) Hello, my friends. A quick update on Leaderbits. We are just wrapping up our first round of funding so that we can expand and help as many technologists as possible. I'm so excited with how this has all come about and what I get to wake up and do each day with my life. We are helping individual contributors become team leaders.

(Joel Beasley at 00:00:18) We are helping new CTOs become seasoned CTOs. And if you want to improve yourself or your team as a technology leader, we can help at leaderbits.io. I recommend you try it for three months so that you can see the results for yourself. Now I am really excited because today we are talking to Ryan, the CTO of Glassdoor, and we discuss learning other dimensions outside of technology, why trust is one of the most important things at the senior level, and how Ryan spends his day empowering people, gathering information, and getting something done for himself. All of this right here, right now on the Modern CTO podcast.

(Joel Beasley at 00:00:56) Here we go. This is the Modern CTO podcast. And now we're here today talking.

(Ryan Bonnici (CTO of Glassdoor) at 00:01:10) Brings us here.

(Joel Beasley at 00:01:11) That's why we're here. So how does your day start? What does your day look like?

(Ryan Bonnici (CTO of Glassdoor) at 00:01:16) My day, I try hard to make sure my day starts with thirty minutes on my own so that I can kind of do a quick catch-up looking at some metrics for the day to see how the performance of the site and the business is. I also, I'm a big organizer of my day, so I start by looking at my to-do list. So every morning, I kind of map out what I'm trying to get done. I look at my calendar and see how much time I have, and then I try to come up with my goals of what I really feel like I'll be able to get done independent of the meetings where I'm mostly focused on supporting other people.

(Ryan Bonnici (CTO of Glassdoor) at 00:01:46) So I kind of start with that and then just check through any urgent emails that I need to get to.

(Joel Beasley at 00:01:50) I love it. I have the same similar philosophy. I call owning my morning. So I usually start my morning with a run, and then I list out exactly what I want to accomplish today, and then I figure out how to get that done in between the schedule that's already there. Like, I've got all my normal stuff, but then what's the one thing that I'm going to do today that's going to drive myself and the business forward that's aside from all the other stuff that I have to do?

(Ryan Bonnici (CTO of Glassdoor) at 00:02:16) Exactly. Yep. That's very similar to strategy. And I actually usually have two to-do lists. I have my strategic to-do list, which are often a little more lofty and longer-term kind of things I want to get done over the next, not super long-term, like over the next week too.

(Ryan Bonnici (CTO of Glassdoor) at 00:02:27) And then I have, I translate those into, like, these are the things I'm actually going to try to get done today.

(Joel Beasley at 00:02:32) And so has this served you well? Is this something that's more recent, or have you had this all the way back in 2007 when you first started?

(Ryan Bonnici (CTO of Glassdoor) at 00:02:39) No, I've had it for a long time. I mean, it started off in the early days with sticky notes all around my window, and I would organize them every morning, and then to Notepad and then to Evernote. So the technology has evolved as I have adapted, but the strategy overall has stayed the same.

(Joel Beasley at 00:02:54) You're, I'm a fan of Evernote too. That's what I use. When did the sticky notes start?

(Ryan Bonnici (CTO of Glassdoor) at 00:02:59) It started, my first job in the Bay Area was at Hotwire, a travel company, and it started then. It started, you know, and I felt like I had several things going on at one time, and so trying to keep it all straight in my own head was probably harder to do. And so, you know, to get organized and stay structured, that was my path.

(Joel Beasley at 00:03:19) Awesome. So you start your day, you organize. If you were to take a pie chart of how you spend the day, like the three big areas that you focus on, what would that look like?

(Ryan Bonnici (CTO of Glassdoor) at 00:03:32) Think for a moment on that. Certainly, one part of it is empowering other people. So I kind of look at my day and think about, like, these are meetings that I'm there to help. You know, I've been at Glassdoor for a long time, so I have deep domain knowledge about how our product works, how our technology works. I'm a decision-maker to help empower teams.

(Ryan Bonnici (CTO of Glassdoor) at 00:03:51) So that's a big chunk of it, I'd say, is looking at my day in meetings and that, like, my role in that meeting is to help empower those people to go off and get the things done that they need to get done for the day. The second thing is information gathering. It probably goes in the other direction. It's about me trying to make sure I understand the health of our business, our organization, our technology stack, you know, different components. So it's me trying to stay connected and informed enough so that I am able to make those decisions.

(Ryan Bonnici (CTO of Glassdoor) at 00:04:19) And the third part is probably, you know, the part where I try to kind of hold for myself, which is trying to get something done, and that something done could be, you know, that we're doing performance reviews. It could be that I need to spend time on. It could be that I've got to think about a strategy about how we're advancing our machine learning organization. It could be whatever that something is that I'm trying to think about for myself because that's kind of my own time. So I think those would be the three pieces.

(Joel Beasley at 00:04:45) Yeah, the thing we were talking about earlier, the one thing you really want to get done.

(Ryan Bonnici (CTO of Glassdoor) at 00:04:48) Exactly. That's awesome.

(Joel Beasley at 00:04:48) That empowering people, that's unique. I haven't had that specific advice given yet or that pie chart slice given yet. I like it too. It really stands out to me.

(Joel Beasley at 00:05:00) So a little bit about your career and how you ended up at Glassdoor. Like, you started at Hotwire, then you were director of engineering, and now you're the CTO of Glassdoor. Tell me a little bit about how that evolved.

(Ryan Bonnici (CTO of Glassdoor) at 00:05:11) Yeah. So kind of stepping back a little further. My first role out of school was at Motorola, which was really interesting. I worked on radio systems for police and firemen.

(Joel Beasley at 00:05:22) Cool. Saving lives.

(Ryan Bonnici (CTO of Glassdoor) at 00:05:23) Saving lives. And so what was really different about that was first, super, super high quality software. Like, bugs mean lives, you know, so you needed it to be super fault tolerant. The second big thing in there, that was a really, really huge company. And so two interesting things to learn from that is I didn't like either of those components, honestly, not that I don't believe in high quality software, but the level of quality that you need to put into something like that versus, you know, web technologies is very different.

(Ryan Bonnici (CTO of Glassdoor) at 00:05:53) And you still, of course, need to focus on quality, but and also the really big company thing felt like I was touching a very small box of the entire infrastructure that we were building, and I didn't really have a, it didn't feel very connected to me. It didn't feel like I actually had an impact in a meaningful way. So which did lead me, I took a year off. I was a volunteer teacher for a year, and then, you know, that was when kind of the dot-com bubble was kind of going up, and I wanted to jump in. And so then I moved to the Bay Area and joined Hotwire.

(Ryan Bonnici (CTO of Glassdoor) at 00:06:21) Hotwire was a really wonderful experience. It was a startup. They hadn't launched when I joined. It was about 30 people when I joined, and, you know, I had the pleasure of kind of going from a pretty entry-level software engineer to leading the team. So it kind of grew along that, in some ways, out of necessity. Like, I kind of got dropped in the deep end, you know, within a few months of being a manager when, you know, I was really early in my career to be stepping into that level, but it was just because it was such a competitive market and I kind of had some of the organizational skills and some of the people skills, I think, to kind of stretch beyond, you know, just writing the software, and I was okay at the software side at least.

(Ryan Bonnici (CTO of Glassdoor) at 00:06:56) So that kind of created the path for me into leadership at Hotwire. But that was a great experience. Expedia is kind of indirect. We got acquired by a company called IAC, but ultimately, Expedia was a part of that Expedia travel business. Robert Hohman was an early engineer at Expedia, and he came down and became the president of Hotwire.

(Ryan Bonnici (CTO of Glassdoor) at 00:07:18) So that relationship with Robert Hohman, who is the CEO of Glassdoor, is kind of what led me to Glassdoor. So Robert and I knew each other from that experience. I had a really great appreciation and respect for him. So when, you know, he came knocking for the opportunity at Glassdoor, it made sense. I had a brief startup in between Hotwire and Glassdoor, but it was not very impactful.

(Ryan Bonnici (CTO of Glassdoor) at 00:07:38) What was it? It was called Easy Rez, and they're still around. They rebranded to Switchfly. They were another travel business. It was interesting, and I learned things in that experience.

(Ryan Bonnici (CTO of Glassdoor) at 00:07:48) Not to be dismissive, but, you know, all of the experience I've gone through, I feel like I learned from, which is important. But it was a travel business that still supports a lot of customers that are white label solutions, so they kind of power other travel websites. So not many people know their brand because they're a behind-the-scenes kind of brand, but it wasn't a good natural fit for me.

(Joel Beasley at 00:08:05) So when you got thrust into leadership out of necessity, but you had some of the skills, what were some of the, or at least one of the big takeaways as a new leader? So you become this leader, you have this path of leadership, and then you instantly, like a child learning to walk, you fall, right, you figure it out. What's one of the lessons that still stays with you from that transition?

(Ryan Bonnici (CTO of Glassdoor) at 00:08:28) Yeah. I think the very first thing that's hard for many leaders, many leaders get put, I think, into the leadership role based on their abilities to be successful as an independent individual contributor, and they're very different, and you can't control it all. You know, the big difference is an individual contributor, you control everything in your purview, you know, completely. And as you start to become a leader, you need to transition that to kind of help figure out, you know, how to give advice and coaching and feedback to someone to do it, but knowing that you've got to give them the ability to do it in their own way and it's not going to be exactly the way that you do it. And I think that was a thing for me, you know, I have a controlling personality, but I kind of had to fight against in that role and I've certainly learned to manage through that.

(Ryan Bonnici (CTO of Glassdoor) at 00:09:10) But, you know, that ability to allow for someone to take a different approach that you may not even think is as good, but that's kind of allowing that person to learn through their process, I think is really important. And sometimes they turn out to be a better solution than, you know, what you had in mind. So you kind of got to give people that room. That was a hard thing, though, for someone that's got a controlling personality.

(Joel Beasley at 00:09:29) Right? It's like we sit there all day and we command the machine to do as we say, and then we have to go interact with humans. It's like, it's a, we developed—

(Ryan Bonnici (CTO of Glassdoor) at 00:09:40) They don't work that way.

(Joel Beasley at 00:09:40) No. They do not. My wife could tell you about that. Yeah.

(Ryan Bonnici (CTO of Glassdoor) at 00:09:44) Yes. Well, certainly, as a parent, I can tell you about that with your children. You know? You learn it in much more significant ways.

(Joel Beasley at 00:09:50) Oh, yeah. Right now, I've got an 11-month-old that's, she's in the walker, and so she's running around making the, like, go, chasing the dogs, and she'll, you know, ram my feet or the wall or whatever. And I'm just like, you're this machine learning algorithm that's very new. In this very V1 AI type situation. I'm like, I know you love me, but I can't wait for you to make the connection between the pain you caused me ramming into my ankle and the fact that you love me.

(Ryan Bonnici (CTO of Glassdoor) at 00:10:21) But it's a pretty amazing process to go through. My kids are 8 and 10 now, and it's a joy and challenging and all at the same time.

(Joel Beasley at 00:10:28) What's the popular game? Like, what's going on with the technology around that age?

(Ryan Bonnici (CTO of Glassdoor) at 00:10:34) Oh, the big fight in my house right now is my son is 10, and he is desperate to get Fortnite. And we're not quite ready to give our kid a game that is, you know, ultimately about survival and killing other people. So we haven't, that's the main fight in our house. He, what he really likes that he plays is Roblox.

(Ryan Bonnici (CTO of Glassdoor) at 00:10:52) Roblox is cool because you can actually create your own games. So he went to camp and actually was coding and building his own games. And it's very engaging with friends. So it's not a fun game to play by yourself so much, but if you engage with your friends, it's pretty fun.

(Joel Beasley at 00:11:04) Yeah. I was driving up to another city, and I saw a banner outside of this, you know, convention center that said, like, Fortnite competition, you know, and it looked like a video game character almost. And so I looked it up, and I just learned about Fortnite existing a week ago. Yeah.

(Ryan Bonnici (CTO of Glassdoor) at 00:11:22) Yeah. Well, it's really taken off. And I have a cousin staying with us for the summer, and he plays it downstairs. So it's kind of unleashed that onto my son who would love to be a part of it.

(Joel Beasley at 00:11:35) He's sneaking downstairs to look over the couch and watch him play it. Oh, man.

(Ryan Bonnici (CTO of Glassdoor) at 00:11:39) Yeah.

(Joel Beasley at 00:11:40) But that's really cool to hear about the Roblox, you said, camp. They learn to make their own video game and customize it. That is awesome. That type of stuff was definitely not around in the, you know, early nineties, late eighties when I was, you know, coming about. And so that's really cool to hear that it's so accessible now.

(Ryan Bonnici (CTO of Glassdoor) at 00:11:57) It is. And, you know, they're doing it in ways that is fun to them, you know, so they're kind of learning, like, you know, you don't tell him that he's learning in the process. He's learning in the process, but he's having fun with it the whole way through.

(Joel Beasley at 00:12:09) Right. So what were the early days like at Glassdoor? You said, or you didn't say. I know that you're there early. Right?

(Joel Beasley at 00:12:18) And what, about three people when you started?

(Ryan Bonnici (CTO of Glassdoor) at 00:12:21) Yep. Yeah. It was from the very beginning.

(Joel Beasley at 00:12:23) And now how many?

(Ryan Bonnici (CTO of Glassdoor) at 00:12:25) We're about, I think about 750, I believe.

(Joel Beasley at 00:12:29) So what's that, what's that been like?

(Ryan Bonnici (CTO of Glassdoor) at 00:12:30) Yeah. You know, I kind of think of Glassdoor as kind of going through a few phases. You know, there were the super early days where it was all about kind of making sure we built a product that actually fit. You know, it actually did something and met the need of a user. We weren't focused on monetization. We really focused on the user-generated content of Glassdoor. We have reviews and salaries and interviews and photos and benefits information, all that rich content that helps somebody really understand what it's like at a company. You know, it was making sure that that was the right information, that actually was helpful to people as they're in their job seeking experience. So that product fit was the very first phase.

(Ryan Bonnici (CTO of Glassdoor) at 00:13:08) And because we weren't a monetization engine at that point, we had to stay really lean and small to make sure we were being cost effective as a business. So there was a long period of that. I think once we established the fact that we had found product fit, phase two was scale and monetize. You know, scale in terms of the product offering to consumers and continue to make sure that we're evolving and innovating, but also make sure we layer in the monetization engine into that. And that was really a very difficult thing.

(Ryan Bonnici (CTO of Glassdoor) at 00:13:37) When you go through the life of a company, I think, especially with successful startups, the kind of people you need there are often more "storm the beach" kind of personalities. And as you transition, the personality types change. You know, I don't quite love this analogy, but it becomes a little bit more policemen than the soldiers kind of attacking the beach, that there's got to be a lot more structure and rigor to make sure that you're creating the right end results. And so we went through that phase, and I feel like what I'm really excited about is we're going through the third phase of Glassdoor right now, which is, you know, we recently got acquired by Recruit. We now have a great partnership with another great job site, Indeed, that we're working closely with. And I'm really excited about where that's positioning us for the future and that it's really setting us up to be empowered to innovate and to grow the business with the support of the larger company around us.

(Joel Beasley at 00:14:29) So does Recruit own—did they, you said they bought you?

(Ryan Bonnici (CTO of Glassdoor) at 00:14:34) Yes.

(Joel Beasley at 00:14:34) Yeah. So do they also own Indeed?

(Ryan Bonnici (CTO of Glassdoor) at 00:14:36) They do. So Recruit is this very large Japanese holding company that owns several hundred businesses. One of the largest of which is Indeed. And so Indeed for us has always been one of the big competitors that we've been fighting to eventually hopefully catch and beat. And now it's transitioned to them being a partner, which is really fascinating.

(Joel Beasley at 00:14:57) I actually have a job posted on Indeed. I have two jobs posted on Indeed right now. I see those emails come through all the time.

(Ryan Bonnici (CTO of Glassdoor) at 00:15:03) Post them on Glassdoor as well.

(Joel Beasley at 00:15:06) So I'll post them on Glassdoor as well. So tell me a little bit—and here's one of the reasons why I'm really excited to be talking to you—because in my mind, I didn't know Glassdoor was jobs. I knew Glassdoor is the place I go if I want to sneak a peek on some salaries and see some reviews. So were you always jobs? Is jobs something new? Can you give me some insight to that?

(Ryan Bonnici (CTO of Glassdoor) at 00:15:27) Yeah. So in the very early days, we didn't have jobs to begin with. We were pretty confident that at some point, jobs would be a big part of the monetization engine. The users that we were trying to attract were job seekers that really wanted to understand what it was like to work at a company, so that they could make an informed decision about whether they wanted to join that company. So pretty natural extension that, you know, not just having the user-generated content, but actually having the job opportunities and being able to—the thing that we're really focused on now is being able to marry these two assets together.

(Ryan Bonnici (CTO of Glassdoor) at 00:15:56) So we have a great amount of jobs inventory. We crawl the entire internet to have as many jobs as we can possibly find to make it so it's easy for a single user to find any job that they would possibly want. And then we marry that together with our user-generated content. So a job seeker doesn't just have to look at a pretty flat job description and kind of make a guess whether they should apply or not. They can be a really informed candidate that really understands, you know, this is the kind of company, the culture. This is what's going to pay what I need to be successful in my life that way. It's got the career opportunities or whatever things matter to you. You can understand that by merging those two assets together.

(Joel Beasley at 00:16:31) Oh, man. I love it. I'm going to spend some more time on Glassdoor this afternoon.

(Ryan Bonnici (CTO of Glassdoor) at 00:16:36) Sounds good.

(Joel Beasley at 00:16:37) You guys must have some crazy traffic and some unbelievable challenges with engineering early on as you scaled and grew and started to get all this attention. And you were right there at the forefront of that, right?

(Ryan Bonnici (CTO of Glassdoor) at 00:16:51) Yep.

(Joel Beasley at 00:16:52) Yeah. So give me an idea of how many requests are coming. Is it mind-boggling amounts?

(Ryan Bonnici (CTO of Glassdoor) at 00:16:59) Oh, wow. We don't actually look at the individual HTTP request level, so I don't know if I could tell you. I mean, I know the numbers. We have about 60 million active users that come to Glassdoor every month.

(Joel Beasley at 00:17:10) That's a lot.

(Ryan Bonnici (CTO of Glassdoor) at 00:17:11) It's an estimated number, more than half a billion page views a month. I know it's more than that, but I don't want to give a false number. So I think it's a lot of traffic.

(Joel Beasley at 00:17:22) That's unbelievable, man. Well, congratulations. That's so cool if you go back and talk to yourself years ago.

(Ryan Bonnici (CTO of Glassdoor) at 00:17:29) It's funny to think of the reports I've got. You know, some of the reports I've literally been getting for a decade. And so the same reports where I look at visit numbers from the early days to the visit numbers now, and a big day then versus a big day now. It's exciting.

(Joel Beasley at 00:17:41) No, I feel that same way with the podcast, watching the listeners grow. I was at a stadium or a concert, and I Googled real quick about how many—it was a big stadium, and I Googled real quick to see how many people could fit in there. And it was about 70,000. And I said to my wife, I said, "You won't believe this. You see how many people are here right now watching this? I was like, this is how many people listen to the show. If we put them in a stadium, this is what it would look like." And it is just mind-boggling, right? Like, to be able to see them all.

(Ryan Bonnici (CTO of Glassdoor) at 00:18:13) And to have that impact. You know, I mean, one of the things I get most excited about and one of the reasons that brought me to Glassdoor and keeps me here is that we're having—I believe and hope we're having—a very positive impact on people's lives in terms of helping them find, you know, for you, hopefully career advice or help get better understanding of how to be successful in the role. For us, actually helping people find the right job opportunity. But I feel really excited to be a part of a company that's trying to really help people in a meaningful way.

(Joel Beasley at 00:18:38) One of the questions that I did get from the audience was about prioritizing product roadmap, right? So a lot of our listeners are either CTOs—new, existing CTOs, enterprise—and then, let's say, about 60% of our audience is engineers, leaders, lead developers that want to move up higher in the management technology chain. So prioritizing roadmap is obviously something you have to do in order to have success and to get to where you are. Can you speak a little bit about that?

(Ryan Bonnici (CTO of Glassdoor) at 00:19:07) Yeah. I think one of the things that, depending on the phase of the company, evolves—but by and large, one thing that holds almost always true—is focus. You know, make sure you make big bets. What's really easy, I think, to happen is that you see, "Well, I need to do this thing over here, I need to do this other thing, I need to do this other thing, I need to do this other thing," and you've got 10 different things that you're trying to accomplish all at once, and so you're doing none of those 10 things particularly well. So really trying to create the focus on what's the one, two, or three things that you really need to do to make your business, your users successful. Trying to create that is probably one of the most important things. The second thing is evolve the technology at the right pace. You know, I'm not a believer in over-engineering. I think we made a lot of choices early on in Glassdoor to make sure that we didn't overinvest in the technology. But as we evolved, we needed to start to make those investments to make sure that we were scaling with the business and make sure you advocate to make sure that that technology evolution is happening along with the business evolution and don't let either one lag too much. Everyone knows the term tech debt. You know, don't allow that tech debt to build by focusing too much in one direction or the other.

(Joel Beasley at 00:20:19) I like that. I like the first part. It was summarized like "less is more," right? Let's take away the total number of objects and instead just condense our focus down on these one or two things that are going to push the business forward. That'll be the theme of this chat, right?

(Ryan Bonnici (CTO of Glassdoor) at 00:20:36) I think, ultimately, particularly if you're really early stage, there's usually one or two things that is really the differentiator for what's making your product stand out against the market, and you've got to find those things quickly and then exploit it by investing heavily in it.

(Joel Beasley at 00:20:48) Oh, I love it. I see when I added you on LinkedIn right before the show—so I'm not upset that you didn't accept. I'm joking. So when I did click on you because I like to see the face of the person I'm talking to, I was like, "Oh, this guy looks awesome. Real cool person." And so I saw that in your signature, you know, "We're hiring," right? So we're always of the hiring mentality. And I noticed that some of the best companies always have that, right? Because they're always attracting great talent, because they're always growing, because they're always doing the right things. And then I also checked out a YouTube talk about mistakes when hiring engineers. And so I was curious about what you look for when you're hiring engineers, and then any advice you have on developing a culture of quality.

(Ryan Bonnici (CTO of Glassdoor) at 00:21:35) So first and foremost, just some raw smarts. I mean, you know, it's easy to look in different directions and think about the other aspects that matter, but there's nothing that addresses just raw horsepower and ability to create results for your business by being a smart engineer. So that is probably the hardest thing. The second thing, though, that I think stands out really close to it is making sure it's a collaborative, team-oriented, can-work-well-with-others kind of personality. And I imagine I said this—and I recall that talk, but I don't remember when I said it—but I imagine I said, you know, a common mistake for us has been hiring really, really smart people that just can't interact and play well with others. You know, whether that be an ego thing or just be that they just can't relate very well with other people, but that is a really common thing. So focusing on that very heavily, I think, matters. And focusing on someone that has passion. You know, that passion can come in different ways. It could be passion about technology. It could be passion about what the product offering is, maybe both ideally. That'd be great. But they just need to have something that they've got to have their own internal drive and excitement that kind of keeps them going. It is my job. It's our leadership's job to create a vision and inspire and motivate people, but there's only so much we can do if it doesn't kind of burn deep within you on its own. So I'd say those are kind of the three things I focus on.

(Joel Beasley at 00:23:02) Got the fire in the belly. Yeah.

(Ryan Bonnici (CTO of Glassdoor) at 00:23:04) That's right.

(Joel Beasley at 00:23:05) I'm the tech person that I don't know why I'm so pumped up and motivated to do something, but I just am.

(Ryan Bonnici (CTO of Glassdoor) at 00:23:12) But isn't it fun to work with other people that are like that too? I mean, besides it being good because they create results, but it just creates energy and you want to work with people that kind of bring that energy into the office. So when you get there, you're like, "Man, today I'm a little bit tired, but that dude next to me is fired up," and he's kind of bringing that over to me. It's, you know, bringing that over to me.

(Joel Beasley at 00:23:28) Yes. And you diversify your energetic balance—that was a weird phrase—but if you have a bunch of people who have that fire in them, and then one can be down and have an off day, and you're going to be way up versus if you've got six people who are low and that one person's always drained because they're always trying to pull everyone else up. Yep. I know that experience. So you guys have an excellent culture because you have awareness of that, so you obviously are looking for that. And so you'd say that you've done a great job of finding those people, those passionate individuals?

(Ryan Bonnici (CTO of Glassdoor) at 00:24:03) We've certainly tried. We worked hard, and I do think we have a really talented group that I'm really proud of. And it makes—you know, there's lots of things that make me motivated to want to be a part of Glassdoor for a decade. Certainly, really high up there is that I work with a bunch of people that I enjoy and feel good to learn from and grow from.

(Joel Beasley at 00:24:18) So when we talked earlier about your first venture into leadership, right, becoming—going from individual contributor to team lead—when they make that transition at Glassdoor, how do you resource them? How does that process take place?

(Ryan Bonnici (CTO of Glassdoor) at 00:24:34) You know, I mean, one of the things that we always try to do is we promote people and grow people, regardless of the level, is kind of make sure that we're setting them up for success. And a part of that is first, honestly, making sure that they're almost doing the job before we promote them into it. You know, it seems in some ways you could say it's almost unfair because we're not promoting them any time, but it's like, I'm totally confident when we put someone into that next level that they're more or less doing that job already because—and we do that by continuing to give people challenges. You know, any level, any company you're in, regardless of the role, I feel like it's really important to always be challenging yourself. You know, that'd be another piece of advice I would give anyone. You've always got to make sure that you're being challenged and growing. And so we try to make sure we're doing that with engineers as they're progressing, and so we're challenging them into that next level already before they even step into it, and so then you're really confident. So that's the first part. The second part, of course, is making sure that they've got a good mentor. You know, anytime you're taking on new challenges, you're not going to be perfectly successful, and so you need to have someone that's there to help catch you when you make a mistake or to give you the advice you need to kind of get you ready for it.

(Joel Beasley at 00:25:38) So when you're looking at, let's say, your whole organization, right, because you're a senior leader there, and you have, you know, maybe a direct team, but you're interacting organizationally wide, right? So what is one thing that would stand out to you that someone would be, you know, exceptional or high potential, that you would flag them mentally as showing signs of good leadership qualities? What's one thing that would jump out to you?

(Ryan Bonnici (CTO of Glassdoor) at 00:26:08) I think probably the first thing that comes to mind is influence. You know, the ability to create results through influence. So it doesn't mean that a leader is an authoritarian person that comes in and says, like, "Hey, well, I'm the boss, so you've gotta do these things because I said so." A leader is someone that creates in different dimensions. It could be because they're so strong technically that people around them want to learn from them and grow from them, and so they start to create influence that way.

(Ryan Bonnici (CTO of Glassdoor) at 00:26:38) It could be because they're just really inspiring, motivating people that are always have that positive energy we're referring to that people gel around. It could be because they have great product insights and they have great thoughts about where to help take the product, and so they're influencing the product team. But having some way to influence beyond just, you know, "Here's the box that I need to—here's the piece that I need to code today to build my part," but they're starting to drive influence beyond themselves. That's, I think, probably the most clear attribute to identify leaders.

(Joel Beasley at 00:27:06) I love it. Right? Because I like how you addressed the influence and the concept that it's not a negative word. Right? And so often people say, "Oh, influence," and a lot of people have a negative association with it, but it's not.

(Joel Beasley at 00:27:21) It's your ability to communicate effectively and sell your vision on how you see the world and then getting people to buy into that vision.

(Ryan Bonnici (CTO of Glassdoor) at 00:27:29) Yep. Exactly.

(Joel Beasley at 00:27:31) So for new CTOs, one of the common questions I get is about interacting with their peers at the C-level because there's not a whole lot of content on CTOs in technology leadership in general. There's even less content about the part that people don't talk about in writings in public, and that's interacting with your peers. So what sort of lessons or insight do you have as far as interacting with your CEOs, CFOs, those peers?

(Ryan Bonnici (CTO of Glassdoor) at 00:28:01) I think a couple of things come to mind. First, you know, as I talk about—I've alluded to, like, always be learning. One of those things you have to learn is to learn other dimensions outside of technology. So don't exclusively be focused on learning technology. For me, that came up as I was evolving into a director role.

(Ryan Bonnici (CTO of Glassdoor) at 00:28:17) I took a couple business classes. I took an accounting class and I took a marketing class. And I can't say I connected as much with the marketing material. The accounting stuff was, you know, more engineering-minded kind of stuff, so I connected with it. But that stuff pays dividends.

(Ryan Bonnici (CTO of Glassdoor) at 00:28:32) I still feel the benefit that as we're looking at our business results as a company, I understand all the terminology that's being used when we talk about EBITDA and we're talking about net revenue and all sorts of terminology that people don't connect with. That's just one example, but, you know, starting to broaden yourself so you have an understanding of the other disciplines in some way so you can relate to those people. Like, I don't have a deep understanding of sales, but I need to know enough of that so that when I'm interacting with our sales leader, I can have a reasonable conversation. We can get aligned on each other. And if we're speaking different languages, that's hard to do.

(Ryan Bonnici (CTO of Glassdoor) at 00:29:05) So that's probably the first thing. And that's one of the things I coach, you know, especially my senior leaders are getting ready to have to play a broader impact across the organization where they're not just looking at their domain and their product partners. And then the other thing is obviously communication. You know, you have to be open, honest, transparent communication. Trust at the senior leadership level is one of the most important things, I think, for a company to be successful. If you don't have good trust across the leadership teams, then that creates tension across those teams and that permeates all the way through the organization very quickly. So, working to build that trust with people—and that's something we're very conscious about to trying to do as a leadership team.

(Joel Beasley at 00:29:50) And then I found that when building trust, one of the foundational elements of it is just saying you're going to do something, then doing it, and then communicating it back that it's done. I don't know if you have anything to add to that, but for me, I found that that is almost like a formula for trust. Right? If I say, "I'm going to do this," and then I go do it and then I come back and I communicate that I did it, people now see me as the individual that I do what I say I'm going to do.

(Ryan Bonnici (CTO of Glassdoor) at 00:30:19) I certainly agree with that. I think that's an important part. But I think it goes in another dimension to add to that, I think, is I've gotta really know and understand, you know, our head of marketing. Like, I've gotta know and understand that when he says something, not just that he's gonna do it, but that his intent is something that I get where it's coming from, and I get that he's doing it for the best intentions for making Glassdoor successful. And it's not that he's got some special agenda. And I have that relationship with our head of marketing. So I think it's having a deep enough relationship to really understand that so there isn't any level of suspicion.

(Ryan Bonnici (CTO of Glassdoor) at 00:30:57) Like, one of the things we talk about is that it's easy for you to create stories in your head that you may not even be conscious of, that you don't verbalize, but you start to create these stories of like, "Why is this guy asking for this one thing? And what is he doing?" And so our challenge to ourselves is when you start to feel that story, ask. Like, you know, be straightforward and ask that person. Like, "Hey, you know, I just want to make sure this is why you're doing this," and just be really open and transparent so that that creates that deep level of trust, and that deep level of trust then forms a foundation to make good decisions and there's never hidden agendas for people.

(Joel Beasley at 00:31:32) I love it. That's an extra dimension that I think is beautiful. And I also really enjoyed how you said you took the other classes. I had heard once a story of a CEO taking a coding boot camp so that then he could then communicate with his CTO better. And I was like, "That is brilliant."

(Joel Beasley at 00:31:49) Right? And then I went myself and started taking, like, purchasing sales courses to learn sales, taking marketing courses to learn, and not like the old stuff either. I was taking like the recent stuff and it wasn't that I was doing it, but at least I learned the landscape, the terminology, and some of the core pillars of the areas of knowledge so that I could, you know, it's awesome when you're a CTO and your CFO can maybe ask you a question that's in your own domain, like, with your own words. Right? It makes you feel a little less alone, a little more connected.

(Joel Beasley at 00:32:27) So—

(Ryan Bonnici (CTO of Glassdoor) at 00:32:28) Absolutely.

(Joel Beasley at 00:32:29) I love it. What are you most excited about at Glassdoor today? Like, what's getting you out of bed in the morning?

(Ryan Bonnici (CTO of Glassdoor) at 00:32:36) You know what? I'm most excited about, honestly, is kind of where this acquisition has positioned us. I feel like there were two paths for Glassdoor. One of them was to be a public company, and one of them was to be acquired. And I think there's pros and cons to both, but for us, I feel personally that the acquisition was a really great outcome as a step along the journey because it is empowering us to not have to focus on necessarily just what are the results going to be next quarter that our shareholders and our public market is going to hold us accountable to.

(Ryan Bonnici (CTO of Glassdoor) at 00:33:08) But what are the things that Glassdoor wants to deliver and accomplish over the next two, three, four, five years? So it's allowing us, I think, to have more long-term thinking, which I think will then drive into a more innovative thinking and approach, which is certainly going to be a lot more fun for engineers and product managers at Glassdoor. So I'm really, really excited that, you know, this is the path that when we got acquired, I felt like that's one of the reasons why that was the path I was hoping for, and I'm feeling like that's coming true. And then there's this other aspect which is, you know, the partnership we have with our new sister company Indeed. You know, it's really fun to sit across the table from someone that's been a competitor for a decade and learn from each other and start exchanging ideas and see the opportunities of things that, you know, we can, at the very least, just exchange ideas and to understand how we can both be stronger and better going forward. So yeah.

(Ryan Bonnici (CTO of Glassdoor) at 00:33:57) Yeah.

(Joel Beasley at 00:33:57) And combine your knowledge bases in order to take on a larger set of competition.

(Ryan Bonnici (CTO of Glassdoor) at 00:34:02) For sure.

(Joel Beasley at 00:34:03) So if you were able to go back and give yourself a piece of advice from your early days, like, when you're back there at Motorola being a cog or feeling like you're a cog in the machine, what piece of advice would you give your previous self back then?

(Ryan Bonnici (CTO of Glassdoor) at 00:34:18) One thing that I think I would give anyone—so I'll broaden this, I guess, not just to myself, I guess, but it's kind of hard to think about. Like, as I think about—I have a conversation later today with some of the interns at Glassdoor, and so these are things that are kind of top of mind for me that some of the things that we talk to them about is, one, is work hard. You know, there is no substitute for hard work. We have a lot of God-given talents and how our abilities and capabilities are, but beyond that, it's hard work that allows you to grow and to learn and to challenge yourself and to do all the things that I think eventually get you to the path that you want to get to. I believe in work-life balance.

(Ryan Bonnici (CTO of Glassdoor) at 00:34:55) You know, I have a family and I, but I still find ways to put enough energy into my work that allows me to be successful. And particularly, you know, early phase of the career, I feel like where everything is a learning opportunity, I think there's no substitute for hard work. The second thing probably is to be humble. You know, you don't know a lot of stuff and I don't know a lot of stuff. You know, I'm still constantly learning, and I think that you're much more open to learning and growing when you're humble. You're more—and you're a better partner and collaborator with other people when you're humble.

(Ryan Bonnici (CTO of Glassdoor) at 00:35:35) So I think that's probably a second really important piece of advice. And then the third one that I've alluded to a whole bunch is just always be learning. Like, there's no—you know, the world—and one of the exciting things about being a technologist, I think, is that it's constantly changing. But just keep up. You know, you have to continue to advance yourself by learning and exposing yourself.

(Joel Beasley at 00:35:57) Yeah. There was—I love that piece of advice too because I was watching a talk the other day and the individual had, you know, a stadium full of people essentially and they were all college graduates and he asked how many of them since graduating have read a business book, like, to raise their hand. And it was, like, virtually none of them, and the point that he was ultimately driving home was that we have this sort of subconscious idea that we go to school to learn, and then we go out in the world to leverage that knowledge and, like, the fact that there's this delineation between our time spent learning and then our time spent earning, like—you don't stop. Like, that's just—you're just learning assistedly for four years. Right?

(Joel Beasley at 00:36:43) With some great content, some great teachers. Now you're prepared to go continue learning by yourself and with your team, with your organization for the rest of your life because things will constantly be evolving and changing.

(Ryan Bonnici (CTO of Glassdoor) at 00:36:55) Absolutely.

(Joel Beasley at 00:36:56) Yeah. Man, we did it. Ryan, we made a podcast, my friend.

(Ryan Bonnici (CTO of Glassdoor) at 00:37:01) We made a podcast.

(Joel Beasley at 00:37:02) We did it. Success. Did you enjoy it?

(Ryan Bonnici (CTO of Glassdoor) at 00:37:04) It was fun. Yeah. I appreciate it, Joel.

(Joel Beasley at 00:37:06) Excellent. And I just sincerely thank you for your time. And are you out in San Francisco?

(Ryan Bonnici (CTO of Glassdoor) at 00:37:12) San Francisco. Yep.

(Joel Beasley at 00:37:13) Oh, excellent. Yeah. So I'll be out there, I think late September meeting with some of the great guests from the show. So maybe if you're around, stop by and say hello.

(Ryan Bonnici (CTO of Glassdoor) at 00:37:21) Happy to meet. Yeah. It's a pleasure. It's nice meeting with you.

(Joel Beasley at 00:37:24) Thank you so much, Ryan. You have a fantastic day.

(Ryan Bonnici (CTO of Glassdoor) at 00:37:26) Thank you. Bye.

(Joel Beasley at 00:37:32) Thank you so much for listening to the Modern CTO podcast. Share this. Get the word out. Thank you guys so much. I couldn't do it without you.

(Joel Beasley at 00:37:38) I appreciate it. You guys are the absolute best.