Cyrus Mistry, GoGuardian COO on Google to Startup Jump

Michael Koenig: Hello and welcome to Between Two COOs, where phenomenal chief operating officers come to share their knowledge, advice, and at the very end, a crazy story. I'm your host, Michael Koenig, and I'm excited to welcome our guest, Cyrus Mistri, chief operating officer at GoGuardian, an edtech platform used by 22 million students in more than 10,000 schools. Helping over 500,000 educators manage all of the computers in the classroom and improve student safety. And with those types of numbers, it's no wonder how they raised $200 million from Tiger Global Management just this past August at a valuation of well over a billion dollars. Cyrus has spent the past 20 years helping people and businesses be more efficient. Prior to GoGuardian, Cyrus was the Director of Product Management at Google, responsible for education and SMB platforms and ecosystems. And if you aren't picking up on the education trend here, Cyrus holds 4 degrees, not 1, but 4 degrees from Johns Hopkins with postgraduate work in natural language processing and machine learning and AI. Welcome Cyrus. Thanks for being here. I'm excited to have you on.

Cyrus Mistry: It's a pleasure. Thank you so much.

Michael Koenig: Okay, so let's talk 4 degrees. What happened to the 5th?

Cyrus Mistry: I do have a minor in applied mathematics. It was kind of 4.5. That's as much as I could do.

Michael Koenig: Okay, fair enough. I want to note that your technical degrees in computer science, engineering, and your post-grad work, with all of that, you're one of the most technically minded chief operating officers that's joined us. And it's a bit of an unusual background for a COO. What was your path?

Cyrus Mistry: I think that's right. I think graduating, I— definitely had a strong technical background. I was a developer. In fact, my first job, I had a big developer computer on there and I went to, 3 weeks in, I went to present my development project, what I had coded. And they saw me present it and they said, wait a second, you can actually stand up and talk. Not that developers can't, but that I actually had a penchant for it and actually enjoyed it. And so they said, I think you should do something more like technical sales. I think you should be kind of out there, but you have the technical background and that's actually a really great role, right? It's one of the most important roles in enterprise software. So, I actually did that for a few years, but then the company was more of a sell, design, build. It was kind of backwards. So, after we would sell it, they would want someone to go build it. And so then I moved into product management shortly thereafter. And so, I was actually a product manager for a very, the majority of my 25 years working, I would say. And only recently, as I was part of the CPO role, did it get expanded to a COO.

Michael Koenig: Now the pieces are coming together. Can you tell us a bit more about GoGuardian? What do you all do and how have you carved out the COO role there? What are your areas of responsibility?

Cyrus Mistry: Yeah, it's a great question. So GoGuardian is one of the largest edtech companies in the world, phenomenally successful, really great company. Their mission is to keep kids safe in schools and have them learn more effectively as a result of that. And so we have really— you can think of our products in those two areas, right? We have a bunch of products that make sure kids are safe and then a bunch of products that make sure that they're learning more effectively. And some do both, right? Some products actually help with both. For example, there's a teacher product where the teacher can interact with the students, can chat, can make sure that they're staying on task, but also gets them to be more productive and learn more effectively because, for instance, hey, all of you should go look at this, and it just immediately gets sent to all of their screens at the exact same time. So, there are products like that.

Michael Koenig: So— And in terms of the COO role, how have you carved that out?

Cyrus Mistry: Yeah, that's right. So, So what they were looking for at the time, they had great products, and I think they were looking for someone to kind of scale it to the next level. And as such, they wanted me to come in and run product. As part of that, you know, would I also run engineering? And as they thought about what I had done in the past, they said it'd be really great if you can also think about how to scale the company in general. And so would you also look after, you know, strat ops, which is strategy and operations, the BI team, uh, the research organization at the time, uh, and so it became kind of wider in scope. They didn't have a COO, and so this was kind of a very, um, natural next step.

Michael Koenig: Just when you joined GoGuardian, they had closed this monster round of funding from Tiger. What was it like to come into a company at that time with that type of funding event? And once you started, what did you do? How did you go about the task of being a COO at a company that's clearly doing a lot of things right?

Cyrus Mistry: Yeah, that's right. So I'm in a very fortunate position because the people are amazing, the company is really, really great, um, so there's a tremendous amount of tailwinds. And of course, what's happening with education technology, uh, we, we couldn't be at a better place and time. So yes, you're right. And the Tiger deal actually closed within weeks, literally weeks of me joining, as in 3 or 4, not 20 weeks. So that did have an influence, to be honest. It had an influence on me from the sense that if you think about it, whenever you get to ride on the diligence and work of someone else, it's always really good, right? This is one of the people, one of the reasons companies love to recruit Googlers or

Michael Koenig: If it's good enough for Tiger, it's good enough for Cyrus.

Cyrus Mistry: Yes, that is right. That is right. Fantastic.

Michael Koenig: You mentioned Google. You moved from a global behemoth of a company of over 130,000 employees to obviously a much smaller one, though it's growing tremendously quickly. What drove you to that decision, and how has your entry been?

Cyrus Mistry: Um, you know, uh, I, I knew a good amount about the company, so I was in a little bit of a fortunate situation since I, um I was the one that brought Chromebooks to education. I was the first product manager to, you know, decide that I think Chromebooks will do well in schools and businesses. And so that's actually what I did. And I was— by the time I left, I was the longest-running product manager on Chrome OS. So I'd just been on that team a very long time. But as part of that, I had met the founders of GoGuardian very early on, probably within their first year, to be honest, first year or two. And so I talked to them and I knew that they were executing extremely well. They were hitting on a very good part of the market. So yes, while they were several hundred people instead of several hundred thousand people, very different in scale, I knew what the potential was. So that was a big part of the decision is I knew what's ahead for them. It was also a fantastic opportunity to, to run an entire organization is great. I mean, Google is a fantastic company, but there's a lot of people that want to know everything that's going on. Even when you're— I was an executive there, right? Even when you're a director, there were a lot of people, even within Chrome OS, right? There's a lot of senior directors and VPs. So I think it is really awesome to be able to move quickly the way that we do now. And so that was another big factor. A third factor is just, You know, to be honest, it was more of a personal thing. Just the 15 years at one company, 11 of which are on one product, you're really excited to do something different. I mean, I did the math. I mean, I was what, 44? And I'd spent 11 years on Chrome OS. I mean, one-fourth of my life was working on one product, meaning one out of four waking days of my life was working on one product. So, you know. Uh, I think I did my time. Yes. Yeah.

Michael Koenig: Yeah. That definitely puts it in perspective, doesn't it? What have you found to be different in the COO role from your role as a product manager of Chrome, ChromeOS, and Ed at Google? What, what's been different about it? And what have you had to learn at GoGuardian along the way?

Cyrus Mistry: Yeah. That's right. I love this. It's a very good question. So I'll start with a cheat. I'll start with saying what's very similar. I think being a lead of a product area, and I ran all of Chromebooks for commercial from a product management perspective, is you have to be what's called the general manager of the product, right? You have to think about it like you are a general manager, like you are running the P&L for that product and everything about it, the success for it, customer satisfaction of it, the growth rate of it, the innovation within it. The COO, at least when you also have product and engineering, like I think both of us do as COOs, you have to do all of that as well. You have to still feel like you are the owner. It is on your shoulders. You're the general manager. So that is actually very similar. And I think strong generalists that have strong business background and can be general managers, are very well suited for a COO position. But I think the new stuff that comes, of course, even as a lead of product, you're going to get escalations and emergencies and fires, which people in operations are very used to dealing with. But I think what was very different that I had to learn a lot of that I did not expect would be as much. And I still tell this to people today. I tell it to my CEO. I was telling it to my CFO just yesterday. We were joking on Slack about this. And I said, If you had told me when I joined that 80% of my work would be people stuff, I would have said, there's no way, I don't believe it. Won't I be doing product strategy the whole time and just fantastic execution? They're like, no, I am dealing with this person wants a promotion, that person's leaving, who are you backfilling, where are you hiring, why is the hiring velocity not right? Every single thing is about people. And granted, I have a few hundred people just in my organization, but It is an— and I'm glad, to be honest, that's actually a very good thing. If I can just make sure that the people are the right people, the right leaders in place, people are excited, they're happy, we're doing the right DEI things. But I had no idea the percentage of time that probably most CEOs spend just on people things.

Michael Koenig: It gives you a whole new appreciation of HR, doesn't it?

Cyrus Mistry: Yeah, that's right.

Michael Koenig: 100%. As you've alluded to, Google is an operational marvel. How have you approached adopting some of those operational efficiencies that you've seen and experienced over your 15 years there and putting them to work at a smaller company like GoGuardian? Certainly there were some elements that you left behind and said good riddance to, but perhaps there are some that you took with you.

Cyrus Mistry: I'm trying to be very careful about what I bring versus what we don't. And luckily, Jenny, who just joined as a CTO, a press release for her just went out today. She's phenomenal. She was a senior director of engineering that is now my CTO. She runs all of engineering now at GoGuardian. She ran Google Beijing. She ran Google Pay engineering. Phenomenal leader. She and I joke about this, but there are certain things that Google did right. No doubt. No doubt. Phenomenal company. Certain things that we do not want to bring over, right? The legacy stuff that has dragged them down. I'll give you an example, right? The way they handle promotions at the company is notoriously across the board one of the least rated things by employees there. So, we want to make sure we don't bring that process over, right? And so, doing it thoughtfully, carefully, bringing over the right pieces. You know, it's funny, if we talk about operations for a moment, there are companies where the center of the mass of the company is truly operations. If you think of the most famous example is of course airlines, right? Airline operations, you know, University of Michigan, their IOE group right there, Industrial Operations and Engineering, I mean, there are books and like literally movies written on the opera. Literally, there are actually movies written on the operations of just an airport. Forget an airline, forget coordinating crew being in the right place and weather events and boarding, like it's in baggage. It's unbelievable how they can turn around an aircraft in 20 minutes and get it back out. So, um, that's an example. Another one, I worked at Disney for many years and, and looking at their operations arm, right? 80% of the company reported into the CEO. Oh, right, the operations was the park operations, hotel operations, F&B operations from the resorts, the hotels, the theme parks, all report into the COO. So every single thing about growing that group and where we need them and when we need them as operations. When you think about a software company, it's actually usually not a massive operations role. And what I mean by that is a cloud provider is different. So Google is not just a software company, that is a portion of it, but it's also an enormous cloud provider for the world, similar to Amazon, Azure. That is a massive operation. You're talking about data center operations. Like that is an actual operations role. There's people have to be there and things have to be ready and you have to have parts in Kanban and just in time, all of the stuff that you would think about has to be ready. But software engineering is actually runs on a little bit of a different cadence, if that makes sense, until it actually gets up into an operation like Gmail, then moves into an operations group, looks after it. So I don't know if that— I didn't need to go into that whole thing, but what I wanted to say was, when you think about software engineering, when you think about a COO in software engineering, it is not similar to a COO of park operations at Disney or the COO of American Airlines. It's a very different level of operations headaches that we have to deal with, fortunately. Right.

Michael Koenig: So, so that's interesting to have been at a company like Disney, seeing all of the operations that go into making Disney magical, if I can be cute there, I guess. And then also looking at the operations of one of the seminal tech companies in history. You mentioned promotions, which are interesting in a smaller company because it can take time for companies to hit that stage of growth. Where they start expanding teams and opportunities for promotions become available. How do you think about that? Taking what you've learned from Google and what you don't want to do, and how do you think about that and design for that at GoGuardian?

Cyrus Mistry: You know, it's a good point. I think speaking about people in general, people want fulfillment, they want psychological safety, they want to feel like they're growing and they're moving. I think one of the problems that Google had, probably many companies, is people don't have a good sense, and you'll hear this all the time, what is it exactly that I need to do to get this promotion? Or why did Jane get it but not Jackie? Like that kind of thing should not become, you know, a growing problem at your company. And so one of the big projects that we're going to do actually, we're kicking off in January, is kind of looking at the ladders and making them much more clear and making the lines much more clear so that people say, you know what, I am at this. And then we can say, yes, you are. That's phenomenal. You should get the promotion versus so subjective. And it also, we want to remove bias from the equation. We don't want any type of bias. You know, the manager just loves them. And so they promote them. That is the wrong thing. One thing Google, I think, tried to do, they didn't do that well, was this concept of promotion committees, which was a centralized committee that did not include your manager at all. And they would look at your packet and everything that you've done and the level that you're at and the level that you want to go to. And they would make a third-party determination. The downside of this was they had no context. And so there was so much bias brought in. You'd have someone coming in from Search, they would, change the shade of blue for the ad and it would generate about $190 million within 5 days. But you have some other person that's been working for 7 years on the product, so excited they launched and they got $20 million. And so that search person comes in thinking, well, this person hasn't added much value to the company. And so, you know, you have these kinds of things going on. So there are pros and cons to a separate promotion committee, but it should be looked at very carefully how you want to handle promotions and career movements in general, by the way.

Michael Koenig: Getting back to your engineering roots and experience at Google, how do you think about the scale-up and organizational design of an engineering department that needs to happen in order for GoGuardian to grow quickly?

Cyrus Mistry: I think that's right. I think, I think, I think one of the biggest things we want to do with our engineering department is make sure we have the right level of management in place to scale, right? You can't scale. Imagine if there was only one strong leader on top, you wouldn't be able to scale, right? Because everyone can't report to them directly, right? Jenny is amazing, but she would probably come after me and say, this is crazy. So I think Jenny is putting in place, you know, making sure she has, and there are some amazing leaders already there in engineering that she can tap into, luckily. And a lot of them have been growing well, right? As you grow, you naturally learn how to manage larger teams and whatnot. And so I think that is exactly right. I think the best way to scale is to make sure you have the right middle set of people that are strong. They're A, you've heard the whole, you know, A's hire B's, B's hire C's or what, right? And so you want to make sure you are keeping the bar high. Tech is a very interesting place right now because the supply demand has still not worked itself out even after 20 years of people knowing that computer science is the the hottest thing. It's still to this day extraordinary pay for tech talent because of this supply and demand issue. Every single job is, you know, needs tech and is moving to tech, and every company has tech or has a website. Dorada has an IT department. So there is— it is just that hard to get good tech talent, and the most easy thing to fall back on is just lower the bar. Right? Well, we gotta just get, get, get, get a person in seat. And so I think holding that bar and instead deciding to just pay enough for the absolute top talent, that's usually the better call if you can do it.

Michael Koenig: It's a job seeker's market right now. There's no question about it. And that top dollar that you're talking about is going higher and higher and higher every single day. At what point do you say, okay, this is a little crazy?

Cyrus Mistry: Yeah, there will be a point. We're not quite there yet, but I know I look at, I look at what tech talent costs and my first thing is to make sure that our team is commiserately paid so that they don't all want to leave, right? And because everyone's looking and everyone knows now what everyone makes. So you want to make sure your team that is already here and is loyal and knows the product is not, right? You don't, we don't want regretted attrition. And so that's the first thing. And so what keeps me up is almost less recruiting. It's more making sure our team is happy and excited. And so we are doing that. We're doing, you know, we are working on making sure that everyone is going to be very well taken care of.

Michael Koenig: That's fantastic to hear. Okay, switching gears. $200 million of fresh funding in the war chest. How do you all think about deploying that capital and putting it to work to grow?

Cyrus Mistry: You know, there's a variety of things, right? There's of course organic growth, which is just growing the product teams. That's what you've been talking about, growing the teams. There's inorganic growth, which is, you know, of course M&A or other types of things we might do. Um, you know, we want to be strategic about it. We want to be smart in how we grow. I think the good news is there's so much upside to this company on such an incredibly tiny engineering team. They have created incredible penetration in K-12. And so assuming we can accelerate that by just giving the engineering team more people, right, instead of being able to turn out 3, 4 features, they can turn out 40 and 50, right? Imagine what we could to do. So that's what I'm most excited about, to be honest.

Michael Koenig: Having that kind of capital does open up all sorts of M&A opportunities, as you mentioned. How do you approach that and evaluate inorganic growth opportunities?

Cyrus Mistry: Yeah, you know, there are a variety of— there are a variety of reasons that you acquire a company, right? So one is for the people. A second is for the resources that they have. And this can be anything actually, right? This can be capital equipment they have. It can be customers. You could almost think of as maybe that's a third. And revenue, right, is another one, right? So you want to be able to get into a whole new area and bring the revenue along with it. IP, right? There's a variety of reasons that you would go after a company, right? And IP meaning all of their code, and that can accelerate what you're doing. Ideally, it checks more than one box, right? If you're just bringing them over for a quick way to hire, sometimes that's actually not a bad idea because you're not just bringing on people very quickly, but you're bringing on the skillset that you want. So if you do it smart, that's not a horrible thing. But if you can bring on software that you love and you get great people with it, and by the way, you also get customers and you also get revenue, that's a four-way win, right? And I think that is why we're being very careful in what we do. Yeah.

Michael Koenig: Okay. Last question for you, and it's my favorite. We've all had those moments where you have a new problem and you've thought, just, wow, I never thought I'd see that. Do you have one that comes to mind that you can share with us?

Cyrus Mistry: Uh, a problem that I thought, my gosh, I'd never expected to see this. I'm trying to think. I think, you know, you know this, right? In the COO world, or even I guess general manager of a product line, you see every single thing. I'll tell you a fun one. I'll give you a very fun one. I don't actually take vacations almost ever, sadly, because I always take my laptop with me. So it's almost like, okay, I guess I'm just working from somewhere else. This is really depressing. And it's not good. I do not want this to be a model for my team at all. I am working hard on fully disconnecting and not having FOMO over my email or Slack. But I decided I had won a cruise to the Bahamas, and it was— so my wife and I decided to go. And I'm out there in the middle of the ocean. Luckily, I had bought the internet plan, and I promised I wouldn't really go on the laptop. I said, no, honey, we're going to just enjoy, go to dinners, go to dances. And I see an email. Of course, I'm checking on my phone. I see a work email that says, "Hey, we have a problem with the Chromebooks." I said, "Okay, well, not a big deal. Bugs happen." They said, "Some push we pushed out broke Wi-Fi on some huge number of millions of Chromebooks." And so at first I thought, "Okay, well, push a fix." They said, "We can't push a fix because the device can't get it." And so this is one of those— and now, and this was day 2 of my 7-day cruise. And I'm thinking, you've got to be kidding me. This is all— and this is K-12. These are students that— and it wasn't all of them, fortunately. It wasn't the 40 million or whatever that were out there, but it was like 3 million, 2 million. I can't even remember, but that's a lot of Chromebooks on it. So now I'm sitting there staying up nights. Like my wife is sleeping. I would go up to the Royal Caribbean library and I'm literally sitting on video calls trying to figure out how do we get communication and how do we even know which ones are no longer— we have to guess which ones aren't talking back. But this is kind of one of those fun intersections of product management and operations and escalations that I will never forget. We did come out of it, fortunately, but, uh, there was a good postmortem write-up on that one, I can assure you.

Michael Koenig: Holy smokes, how did you get out of that? How do you push an update over the internet to computers that aren't connected to the internet?

Cyrus Mistry: Yeah, and then we used to— yeah, we used to say they're bricked, right? They they're kind of off the grid. Bricked is worse. Bricked is when it's like completely, you can't do anything with it. You might as well throw it out the window. No, so to be honest, I have to remember what we did. We had very, very smart engineers and some very creative things that we did. We told them if they can at least get onto any guest network, so manually have the kids get to a guest network, the computers will go check for an update. The update did come down and would solve it. And actually put them back on the correct Wi-Fi network. So the problem is a lot of schools didn't have a guest network. They had to set one up, or they had to use, like, a teacher's hotspot or something like that. But they did get it back, and amazingly, many schools had figured this out on their own and did it very quickly. So a lot— it actually became just a big communications project more than a technical project. But anyway, yeah. Amazing. That was fun.

Michael Koenig: Okay, I lied. Last question. This is the last one.

Cyrus Mistry: How many—

Michael Koenig: 10 years, you said, I think, working on ChromeOS?

Cyrus Mistry: Yeah, 11 years. Yeah. 11 years. I still— this device literally is a Chromebook right here.

Michael Koenig: How about that?

Cyrus Mistry: Yeah. An Acer Chromebox. It's a really good one too. So yeah, I still use it. I still love it. It's still a very, very easy, lightweight OS. And 99% of what I'm doing is on the web. Right? This company that I'm currently at ironically doesn't hand out Chromebooks. They hand out the, you know, the other fruit computer, which I've used for years. So I don't mind that either. I had used it before I joined the Chrome OS team. So yeah.

Michael Koenig: You can't even say the name. You have to refer to it as the fruit computer.

Cyrus Mistry: That's because that's my training from my Chromebook days. Yeah, there it is.

Michael Koenig: Well, Cyrus, thanks so much for coming on the podcast.

Cyrus Mistry: Where can people go to keep up with you? Oh yeah, good question. I mean, find me on LinkedIn by all means and message me or say hi. Yeah, yeah.