CTO Wisdom with Asanka Jayasuriya | Beyond the Program

Tim Winkler: 00:00:00

Hey, listeners, Tim Winkler here, your host of The Pair Program. We've got exciting news introducing our latest partner series Beyond the Program. In these special episodes, we're passing the mic to some of our savvy former guests who are returning as guest hosts, get ready for unfiltered conversations, exclusive insights, and unexpected twist as our alumni pair up with their chosen guest. Each guest host is a trailblazing expert in a unique technical field. Think data, product management, and engineering, all with a keen focus on startups and career growth. Look out for these bonus episodes dropping every other week, bridging the gaps between our traditional pair program episodes. So buckle up and get ready to venture Beyond the Program. Enjoy.

Eric Brooke: 00:00:53

Welcome to CTO Wisdom. My name is Eric Brooke. This series will talk to leaders of technology at organizations. We'll understand their career, what was successful, and what was not, and what they learned along the way. We'll also look at what the tech market is doing today. We'll understand where they gather their intelligence so they can grow and scale with their organizations. Um, today I'm going to talk to Asanka and we're going to talk about, um, his leadership through technology and his, um, winding career journey and all of the things he's learned. Asanka, welcome. Good to be here. Could you give me the elevator pitch of yourself and what you're up

Asanka Jayasuriya: 00:01:43

to? Sure. I've spent, uh, getting close to 25 years. It's a long time of my career in software, uh, and roles starting as an engineer, as an intern, working my way up through management, uh, to exec roles, but always basically in cloud software, enterprise SAS, uh, e commerce, uh, security, and more recently, uh, in a venture firm as a portfolio CTO. Thanks. A lot of, a lot of different roles, a lot of different industries over the last 25 years. Awesome.

Eric Brooke: 00:02:16

Um, could you tell us a bit about your journey into technology?

Asanka Jayasuriya: 00:02:21

Sure. Um, so I kind of did not start on a path, uh, straight into tech, um, growing up as a Southeast, uh, Asian, uh, kid, uh, you know, being a doctor is kind of a. Principle journey that a lot of us get put on and I think I was told from a very young age that was the path and kind of working my way almost without thinking towards that all through school entered university studying molecular genetics as a kind of precursor towards medicine. But once, uh, after my first year, I spent the summer, uh, in Sri Lanka and got a chance to volunteer a little bit, uh, with my uncle, spent some time, uh, with him as a, he's a doctor there and kind of realized, like, this is not a, this is not a job for me. Um, you know, your, your good days as a doctor are good, but your bad days can be. Really bad. I mean, obviously it's, it's, I think one of the most important professions and obviously it comes with a lot of weight. Um, I just didn't think that was for me, but the whole time, you know, I'd always been playing and tinkering around with computers since I got my Radio Shack, you know, handy XT computer back when I was in grade eight. And, you know, someone said, why don't you start setting time with that? So I switched over to computer science. And from there, I just fell in love with it, fell in love with building, fell in love with, uh, writing code, quickly realized in computer science that I did not love any of the math or formal proof sides of computer science, but was just in love with software, software engineering side, and that's sort of how I indexed my time, uh, and focused on that and moved into, you know, loving computers and building. Cool.

Eric Brooke: 00:04:00

So, um, when you, you started in science, were there aspects of science that you found helpful when you got to kind of like computers?

Asanka Jayasuriya: 00:04:09

I would definitely say the quantitative side of it. So your physics, chemistry, um, and calculus, obviously, subjects like that are very across all those subjects. Having that background is helpful, uh, because ultimately, you know, computers are quantitative in, in a way. So I found that was generally helpful. I feel like the subjects that were. Less helpful biology and things like that, which are a little bit more about memorization, even genetics. Uh, those courses weren't particularly helpful, but I would say the quantitative classes were definitely useful once I moved over. Oh,

Eric Brooke: 00:04:43

so then tell us about your journey. Now you're into kind of software engineering and technology. Um, what was that like for you? Yeah. So

Asanka Jayasuriya: 00:04:52

I was very fortunate in that the university of Toronto, where I went to school had what was called a professional experience year program. So you got to a 12 or 16 month internship. And so in 2000, I started an internship with a Canadian, um, software startup, uh, called Janus Systems that was doing web based, uh, CRM. I want to say web based, intranet based, so this is well before SaaS was a thing, but it was revolutionary because it's deployed in the browser. Customers didn't have to install, you know, windows clients on across thousands of desktops. Uh, I got very lucky for a couple of reasons. So this was may 2000. I was starting and just kind of right at the tipping point of stuff starting to break in the dot com bust. And you don't have offers from general IBM. And, uh, Cisco systems and, you know, a lot of my friends were pushing to go take IBM and Cisco, but this is, you know, the startup environment. And I guess it's, it's a very different world back then. I think today everyone knows all about startups knows what it's like and exciting. But back in 2000, it was not nearly the same level of excitement or celebration around startups and everyone was pushing me towards going IBM. Uh, I ultimately turned IBM down, worked out really well. And I got super lucky because, you know, six months later, IBM, Cisco, and all those big companies, they were letting go their interns. They were downsizing. Uh, sometimes you get, you get really lucky in your career and Jenna went incredibly well. We got acquired by Siebel systems, which was the largest CRM vendor, uh, in the world at the time. And I got to kind of continue my career there to, you know, now at Silicon Valley owned company. Progressing my career and, uh, it was, it was, it was challenging, especially, uh, in about 2002 salesforce. com really came to market. And for those who are familiar, they were really the 1st cloud company, in my opinion, of any real scale, delivering real software over the Internet. And Siebel being the incumbent on premise, uh, you know, it got quite heated that competition and they decided they had this team that they'd acquired our team in Toronto and they're like, why don't you guys figure out how to do this cloud thing? And it's 1 of those interesting things where again, you get lucky in your career. I didn't get put on the most important project at the time. Everybody thought cloud was not really going to be a big deal. It's like a fad. It's for small businesses. No enterprises are going to want this. But I got to start figuring out cloud stuff, you know, back in 2002, um, before any of this stuff happened and just really, really lucky, uh, to get that opportunity. What happened next? So after that, um, you know, kind of progressed up as an engineer, eventually reaching the level of a principal engineer, um, at Siebel, we got acquired by Oracle. So it's like a small fish that got swallowed by a bigger fish that got swallowed by I guess the biggest fish. Uh, and no one was going to, I think we were, the joke we had was nobody was going to buy us now. We were pretty sure that with Oracle, that was kind of the end of the acquisition chain. But I continue to progress as my career as an engineer. And then about 2007, 2008, um, I made a shift in my career and that's when I first moved into management. Tell

Eric Brooke: 00:08:11

us what that was like. Oh, yeah. So

Asanka Jayasuriya: 00:08:15

a couple of things that really drove that for me. One is, well, I was a really good engineer. And when I was younger, I thought I was a great engineer, but then you kind of You learn by meeting really great engineers where you actually sit in, uh, in the ranking of things. And at Oracle, um, I got to interact with some just people that made me realize. As good as I was, like, there was just no path for me to operate the level that they operate. It's just, you know, sometimes people you meet in your career and they just have a different gear and that's not necessarily a bad thing. Um, I just realized, like, 1, I was never going to achieve that level of technical contribution. But the other thing I also realized was. It was increasingly not the part of the job I loved the most. I loved leading projects. I love mentoring are more junior developers. Uh, and so, uh, my one of my mentors at the time suggested I make this switch into management. And that's really what kind of made me, uh, make that transition.

Eric Brooke: 00:09:16

So your manager, were there things that, um, as a software engineer were really helpful, but got in the way of you when you were actually a manager, um, in that transition?

Asanka Jayasuriya: 00:09:28

Absolutely. I think that was actually probably the hardest part is often. And I think this is actually something we do very poorly in the industry. It's your best engineers who end up becoming managers, which is interesting because there's not, there's not a lot that's related in that skill set of being an extremely strong technical person and being a good manager. And I've, you know, one of the big reasons is being a strong engineer, you have your team for the first time, you have a tendency to want to really. Do a lot of showing through code and fixing things and keeping your teams from making mistakes, which is good to a point, but it's very easy to cross over that line where your team isn't really learning and growing on their own anymore. And they're basically just doing what you tell you're jumping in and dealing, doing, solving the hardest problems. And I had a good talking to you from one of my mentors who kind of noticed that and said, like, you're just not going to be able to scale and your teams are not going to like working for you if you're always the smartest engineer on the project as well. And that was something I took to heart to really start creating some more space and giving my team some more room to operate, even if things were not necessarily the way that I would have preferred them to be done.

Eric Brooke: 00:10:44

Yeah. So you got out of your own way. So that you could scale

Asanka Jayasuriya: 00:10:49

out of my own way and got out of my team's way, right? It's, I mean, nobody, nobody wants to work in a good people want to have a degree of autonomy. They want to feel like they can explore a path. They want to feel, you know, that they can invent and they can make mistakes in a supportive environment. And I wasn't really doing that as a, as a first time manager.

Eric Brooke: 00:11:09

Um, so how did your management career progress after that?

Asanka Jayasuriya: 00:11:14

So I stayed at, uh, my first three years were Oracle as a manager. Um, I had a very, very brief detour, uh, a large Canadian bank, um, they'd hired me to be part of their renaissance or their technical revolution program. And, uh, it was, it was 1 of those situations where the, the bill, uh, the, you know, the posted that role was very different than reality. Um, I, you know, I remember coming home after my 1st week and telling my wife, like, this is just not going to work. And the main reason was. I'd been in the profit center, right? Technology as the profit center technology as the defining factor of success for the business. And despite their desire to change in that bank, it's clear that technology was a cost center. All I was really doing was managing budgets, managing vendors, like what I wasn't building. But fortunately, uh, one of my friends who was at Amazon at the time reached out and said, Hey, like Amazon's building a Toronto office. You want to do this and help build it from scratch and I interviewed with Amazon and took a role as one of their first hires in Canada, helping to build out, uh, the Toronto, uh, Amazon engineering site.

Eric Brooke: 00:12:29

Very exciting. Um, what was your journey like with Amazon and what were the, some of the leading principles that you stepped away from that organization

Asanka Jayasuriya: 00:12:36

with? Yeah, I, I would say Amazon was probably the most transformative part of my career. And I think you'll find a lot of people who will say that, and there's a couple of reasons for that. So almost immediately when I started, we were in what was called a Regis is a real estate company that runs temporary office space, uh, before we worked somehow made that a tech problem, which I don't quite understand how that happened. You know, we were in a temporary space in a mall, uh, with, you know, next door to us and there was a massage of people running a massage studio. It was a really interesting space. But Amazon, you know, they threw us in there and I kind of quickly realized like, okay, what's the plan to building this out? I was kind of waiting for like the directives to come down like an Oracle. Like, okay, this is what you're doing. Here are the rules. But what I realized is there were no rules. There were no directives because Amazon pushes ownership down very deep in the company. Okay. And expect you to execute and figure things out. Um, there can be a very stressful environment from that perspective, but for the right type of person, it's just incredibly empowering. Like they really give you a lot of autonomy and a lot of ownership. And. You know, for all the negatives that people hear about working to Amazon, and I wouldn't dispute any of the stories that you hear about people crying at their desks or any of that. It highly depends on the group that you work at there, because it is so much a collection of small companies that anyone that you can work for can, you can have a radically different experience. I happen to work for a great, uh, general manager who is running my business and it was a fantastic environment and I just got the opportunity to help grow that team in Toronto, eventually expanding into, uh, Seattle, uh, taking on teams in Seattle. And the big part for me, there was the core values that the company used were really operationalized. I think every company has core values that are probably written down on a memo, like a brochure or something that you join to see them and you probably never, ever see them or hear them again after that first day. Amazon operationalize their values into every part of the business, whether it was promotions or how you're thinking about a business idea and those core values I actually took with me for the rest of my career and still to this day, really. Push them and implement them and how I have executed. I've actually directly brought variations of those values to new organizations. I've been at the other area. I would say that Amazon really changed me is being an operational leader before my career. We had ops teams. You know, we would build software. There'd be a huge ops organization. They would run it. Amazon was you build it, you run it, which I'm a huge proponent of, and having operational ownership for software, understanding how to do that at scale and with quality was just an incredible experience to get.

Eric Brooke: 00:15:35

Cool. There's kind of two parts I'd love to dig into. Could you give an example, one of the Amazon principles beyond the operization and the pushing down ownership? I'd love to hear that. Um, but give me one of those kind of like principles or two that you really do embody now.

Asanka Jayasuriya: 00:15:51

So one is customer obsession. Amazon really starts from the perspective of if you do what is best for the customer, even if the, in the short term, that may not make sense in the long term, you will win. And you can see that through so many different parts of the business, you know, from a consumer perspective, you think about same day shipping, right. Or next day, building the infrastructure for that was billions of dollars in fulfillment network capacity. A huge loss leader for a long time. However, can anyone live without that today? Like no one competes with Amazon on that, right? Like everyone loves that capability. Um, so customer obsession and just that focus on if you solve the customer's need, you will, you will win as a company, um, is one of the cores. Another one is hire and develop the best. Uh, when I was there, Amazon wasn't a relentless growth pace, but they intend, they kept a very, very high bar for talent. And uh, there was a program called bar raisers where after you'd done a certain number of interviews, you became a bar raiser and a bunch of trials. And the goal was. In every interview loop, there would be one of these bar raisers on the loop, and the bar raiser always came from a different organization, so they had no skin in the game to the hire. Like, they weren't under pressure, like, hey, we have to fill this role, and the goal was always to ensure that every person that you hired into the company was better than half of the people in that role. And if you stop and think about for a second, what that means is if you do that for long enough, your team is just getting better and better and better. It doesn't mean that the bottom 50 percent aren't good employees, but they're saying everyone you bring in, you want to be better than half the company so that they can keep pushing that bar higher. And there was just a relentless focus on one hiring from that perspective, but also developing again, if you're in the right organization. And they saw your potential, like you would get invested in to get the right opportunities, the, you know, more autonomy, more scope and more responsibility. It was a lot of fun, but like I said, in the five, five ish years I was there, I felt like I did 10 years of work. Right.

Eric Brooke: 00:18:00

Good to know. Thank you. Um, so carrying on with your journey, um, you're now at Amazon building, um, at the Toronto office, you're at management at a higher level. Tell us about the continuation of that journey.

Asanka Jayasuriya: 00:18:15

Yeah, so I was a senior manager at Amazon. Uh, I think my organization was probably around 250 ish people across Seattle and, uh, Toronto. And Amazon has, uh, at the time anyway, I don't know if this has changed, it had a bit of a glass ceiling. If you weren't in HQ, like, if I wanted to make that next step to my career at Amazon, it was, you know, my, my leaders told me, it's like, should think about getting you to, uh, Seattle. So me and my family were kind of going through that process of relocation and kind of getting that figured out. And I was going to join the last mile engineering group at Amazon, uh, to lead a lot of that. And that's the Amazon delivery network, which at the time was just getting off the ground. But in the middle of that, uh, Atlassian reached out about running Jira cloud in Sydney. And, you know, I've always loved Atlassian. Uh, everyone's kind of aware of their culture developer focus. So my wife said, if we're moving, we might as well. Go down there and check it out. So flew down to Sydney, uh, met with the founders of Atlassian, a lot of the leadership and absolutely fell in love with the company, but me and my wife on that trip also realized like it was just not practical for us to move to Australia. Cause once you get on that plane from Toronto and you fly to Vancouver and you will have layover and then you fly to, you kind of realize, wait. Every single vacation we have is going to be flying back to visit family, so that's all we would do, but kind of from a more career perspective, the thing that became clear to me is that I could probably have a great four to five year run at Atlassian, but there was no other opportunity in Australia. Like, it was really clear, right? Like, there's Atlassian at that time, and there was really nobody else at any scale, um, solving hard computer science problems, uh, to work for. And I'd be in a situation to go in there for 4 or 5 years. My kids would be getting to high school and then we'd probably have to rip them out and at that time and bring them back to Canada. And that's something we wanted to do. But when I turned down the role, uh, the CTO, uh, there, uh, Sri, who's still one of the mentors and someone I talk to regularly. Uh, he said, well, why don't you take over our Austin engineering instead? Uh, and he couldn't caution me. He's like, there's a lot of problems over there, you know, and it's going to be a bit of a fixing situation. And I've always actually kind of liked fixing things. So I was like, yeah. And we loved Austin. So we made the journey, made the, uh, change and moved to Austin in 2016.

Eric Brooke: 00:20:44

Awesome. And so describe this role. You've, you had like 200 plus people in like Amazon and you've got this role here. Um, have you got to, I'm guessing you're managing managers at this point as well?

Asanka Jayasuriya: 00:20:59

Yeah. Uh, Amazon was the first time I started managing, uh, other leaders.

Eric Brooke: 00:21:04

And so the transition from being a manager to managing managers, what was that like? What kind of changes did you have to make in yourself?

Asanka Jayasuriya: 00:21:15

I think the biggest thing that you do as you kind of make the steps is you have to as a leader start designing mechanisms to give structure to your organization and give you visibility so you understand what's happening in your org. And I kind of realized that. You do have to be structured about it because you wanna give your teams kind of operating structure as well. Like if we're gonna do a regular weekly metrics review, or if we're gonna do a, you know, quarterly planning, like building those structures out so that you understand what your teams are doing, you understand what their challenges are, where you can help unblock them. But you also at the same time don't want so much visibility all the time, such that, you know, you're in the weeds of all your teams. And again, kind of similar to my earlier transition to being a manager, you want to give managers a lot of scope to run their team, right? And evaluate them based on that. And it can be hard to do if you do too much of the managing for them. Um, so really building out those structures, you know, how often should you do skip levels, right? Arranging that so you understand. The people dynamics in the different subteams, so as you scale, you just need to build more and more mechanisms, I think, into how you operate and manage your team. Would

Eric Brooke: 00:22:28

you have, like, so, um, like, we talked about visibility. Could you give us an example of visibility that was really helpful to help your managers, but also help you to stay connected to the your wider

Asanka Jayasuriya: 00:22:42

team? Yeah, so I think 1 of the big things is project progress, right? Like, status reporting is. Kind of the least favorite thing I think anybody has to do, um, but at the same time, you know, I need to be in a position where if I'm talking to an executive and they have a question about what a key project that one of my teams is doing, like, what is happening? So we built a, you know, a regular, like, monthly kind of status reporting framework, a template for how projects can be reported on. We tried to keep it as lightweight as possible. You know, when I'm managing managers, I was less interested in like sprint metrics and velocity and stuff like that, because I truly believe those are the metrics that belong to the team and the manager for it to optimize. And I, but my mechanism is much more around business impact, delivery, key highlights. Um, I just didn't want my team spending a lot of time, you know, just reporting status effectively. So they liked it because it was lightweight and they weren't constantly reporting on a whole bunch of, you know, things instead of investing in building software and building product.

Eric Brooke: 00:23:46

And then for, that's process. What about leadership development? How did you grow your managers? Were there common patterns or things that you didn't see to begin with, but you learned later? And to help your leaders grow as well, that

Asanka Jayasuriya: 00:24:00

that was always been and remains a favorite part of my career has been developing other leaders. Um, I'm a position now. We're seeing multiple of the folks who've worked for me become vice presidents of engineering at different organizations. Um, 1 is becoming a CTO of a series B company in the next couple of weeks. So I'm really excited and kind of proud. About as well to see her making that step in her career, but the things that I always did was look for opportunities to push my managers, right? And I always, you know, because because people have done this to me is, you know, when their plate is full. No, giving them just a little bit more just to push him a little bit past that limit of like, yeah, this is going to be hard, but it's going to force you to create your own mechanism. It's going to force you to think about how you delegate within your teams. But it's always, I think, you know, finding the right opportunity for growth. And I think as a leader, your biggest responsibility is doing just that. Because if you create the right opportunities, the stretch goals, stretch opportunities for your team that allow them to grow their career, it's That means your organization is going to be successful because if, especially if you tie those things to milestones that align to the business.

Eric Brooke: 00:25:14

Cool. Thank you very much. Okay. So, um, you're at Atlassian in Atlanta. Um, where, where in Austin, thank you. Um, where did you get to, um, winter is an exec

Asanka Jayasuriya: 00:25:28

role. So that I would really consider Atlassian kind of my first exact type role because I reported directly to the CTO and there were only 5 of us reporting to the CTO who ran all of engineering for Atlassian. Um, I would say that that was actually 1 of the most fun parts of my career for a couple of reasons. One was I got to take all the practices I learned from Amazon and apply them in a new environment that hadn't seen them before. Um, at the time Atlassian was really making a hard pivot from its on premise, uh, roots to cloud. Uh, that was the mandate of the new CTO, uh, who was there and the reason I was hired as well. I was hired into, um, the hip chat organization, which I don't know if anyone remembers hip chat. It was the, uh, predecessor to slack and things at the time were not going well, uh, slack and immersion, the market chat had had some high profile outages and they were in the middle of a full rebuild, a full rebuild of the hip chat product. And that was not going well either. Um, there was no head of engineering at the time. And so I kind of stepped into a difficult situation. Yeah. I got to one, earn the trust of team, start implementing some of these processes. It was really exciting to see. Some of the processes that we implemented around technical operations in particular get pushed to all of Atlassian, um, and help just transform how Atlassian did cloud, but it was, it was a, it was a hard 2. 5 years, but also incredibly fun because the team was very motivated. Um, you know, we had this. Goal that no one thought we could accomplish even inside it last year. No one thought we'd be able to get this done. Ultimately, we did get it done. It did not end up mattering because as Microsoft was coming to the market at the time, the company kind of realized that this isn't going to be a market that there's going to be a lot of revenue to be made in. It's probably going to end up being free, which is. Exactly what has happened. And, you know, no one pays for this stuff with office. And I think it's one of the reasons why Slack got sold to sales forces. They saw their growth opportunities kind of limited in the future, but it was kind of a exciting journey to be on a building, not only building the new product, but also bringing a lot of the cloud practices I've learned at Amazon, uh, to Atlassian. Awesome.

Eric Brooke: 00:27:51

Thank you. Um, so continue your journey. What happens next? So,

Asanka Jayasuriya: 00:27:58

after we, at the end, towards the end of my Atlassian career, I was managing, uh, Stride, Hitchat, and Trello. I'd also taken ownership over the Trello product. But I kind of knew that there was no real next opportunity for me there. I was reporting into the CTO and like, there was no real clear next step. And I got the opportunity to work for, uh, envision as their CTO. And when they approached me about the role, you know, I, first I wasn't sure, but as I dug more into it, I kind of realized that one, they were a thousand person remote company. And today that sounds like no big deal, but back in 2018. They were the largest doing that in the world, and very few companies were remote, uh, back then, at least at scale. And so I wanted to understand, you know, how can you do that? Because the biggest challenge to any engineering that has is finding great talent. And when you're constrained to geographies, that makes it that much harder. So I wanted to understand, like, can this actually work? And as well, they were, uh, you know, a unicorn, they just take an evaluation at 2 billion, I think. So, uh, you know, closing in on a hundred million in ARR seemed like a great time to join. I joined and as always, as you learn is like, things are never quite what they seem at any company. And I think everyone always goes through, I think you start and you're super excited and there's this kind of trough of disillusionment that you go through and then you come out the other side and realize that, you know, just because you can. Hire anywhere doesn't mean you should hire anywhere, uh, and they hadn't really maintained us high bar, I think, for how quickly they had hired an account. And so it was the largest kind of transformation I had to make in terms of raising the bar on hiring on talent while executing on a product roadmap. That was just too full. There were too many priorities. And it was really, really challenging to move that forward. And ultimately, I don't know if you saw, Envision officially announced their shutdown a few weeks ago, which is I think the first of many broken unicorns that we're going to see. I learned a lot about focus there and about, you know, being realistic about where you're, where you are. Um, And we just couldn't quite make that last pivot and roadmap that we had to as Figma was, you know, basically just emerging and everyone knows how quickly Figma kind of took over and learned a lot about, uh, what it means to be a fully vertically integrated solution like Figma versus a piece of an ecosystem like Envision was, uh, which made it vulnerable. But incredible opportunity to learn what it means to be in the CTO seat, where you learn for the first time that You really don't have fears anymore. You know, at Atlassian points, the CTO, I have good friends and who made my good friends, who are my peers, who ran the other engineering groups in your first leadership seat, you realize, you know, you have your CRO, your chief people officer, chief product officer, head of marketing is peers, but you're not really a team in the same way. You're really all stakeholders in each other's worlds and you need things from each other. But I kind of realized that there's a little bit of loneliness that job because you have people below you who rely on you and you provide leadership to you and your peers who need things from you, but you don't really have teammates in the same way. And it gets, it can was surprisingly a little bit more lonely than I expected it would be.

Eric Brooke: 00:31:29

Cool. That's a great point. So let's dig into that a little bit when you say. So, in a sense, what I heard was like you had collaborators who are on your side, helping you be successful, kind of probably being critical friends when needed. And then you have stakeholders. What does that feel like? What's the difference between stakeholder?

Asanka Jayasuriya: 00:31:53

So I think one of the key differences is that, you know, when I had my peers at the last thing, we could just go have a beer and talk about, you know, whatever, even if it's talk about the dumb thing we think our boss did, right? Or, or, or, or everybody does that. And I'm sure all, all my directs have done the same and gone out for a beer and talked about some dumb thing that I said or dumb thing I told them to do, right? That kind of comes with the job. But when you're an exec, every interaction almost feel can feel like an evaluation to a certain extent, right? Because if you're meeting with the CRO and the CRO needs a future shift or needs your understanding to make a customer happy, like, you know, that's part of it. And. It, it just, it creates that sense of, you know, you're not necessarily just buddies, right? You're, you need things from each other. You need to deliver for them. And that's kind of, I think, where that sense of loneliness comes from a little bit. And at that point, my career is also when I realized I had to lean much more into building my network of those people who I'd worked with, who were my friends and partners. I advocate that strongly today to anyone in leadership is like, keep in touch with the good people you work with. Like, you know, go back to them. You know, once you haven't talked to someone in 6 to 9 months, set up a zoom, like, just check in. And 1, it's just great to maintain relationships. I believe, especially in this industry and both from a personal perspective. But also for your career, uh, you would not believe if you how powerful a tool it is to look at your network, see it, all the great places that are adding like, oh, I have a question about so and so company and. You know, I talked to so and so last year, but I should reach out to them because I have a question about this company. So that's something I think as we as engineers in particular aren't great at. I think people in the sales, marketing organizations are so much better at it. And I think it is a superpower for engineering leaders to really invest in building and maintaining a network.

Eric Brooke: 00:33:51

Awesome. Asanka. In terms of you being in a C suite role, were there other dimensions at this point that you needed to understand that you didn't need to say in the last lesson? that you're now having to learn or that will be helpful for others

Asanka Jayasuriya: 00:34:06

to know about? Yeah, definitely. I mean, as an engineering leader before, it's all about just shipping and delivering products. Um, you know, you have a budget around headcount and stuff like that. Once you're the leader of a business unit, it becomes a lot more, right? You have to understand, really understand the revenue organization, really understand marketing, understand the customers much more deeply. Like, even though you have a product partner, like It's not sufficient for me to be the engineering leader who's building stuff. You really have to understand how your company works, the financial goals. You know, when are you raising money? What does your runway look like? What does your burn look like? All these things that I didn't really, where I've never really concerned for me as a, um, just an engineering leader right now became front and center, uh, just understanding the business at a much deeper level

Eric Brooke: 00:35:03

and in terms of like working with the board, um, how does that change the game? It's

Asanka Jayasuriya: 00:35:10

really interesting. Um, and I've been at board exposure, both in kind of private world and in the public world. Uh, in the private side, you know, your board is just, uh, effectively the venture firms that have invested, right? That's typically what your board is made up. And, you know, I would say at envision, you know, the board experience. You know, we were constantly, you know, we present our roadmaps and stuff, but I would say the questions were largely to the revenue team. Um, you know, we got some questions about one product and stuff with shit. When I went to the public, uh, world with SailPoint, the role I took after InVision, it was very different because now your board members have significant fiduciary responsibility, obviously, to the public markets, and it's just, the bar is much higher in terms of the questions and expectations they have of you, um, and their responsibility. You also kind of learn that, you know, what is the relationship I'm supposed to have with the board? And it's actually relatively formal, right? You don't go to the board and, Tell them everything that's going wrong with the team or your company or the beers, right? Like, no, it's, it's, it's a very formal relationship. We talk about the goals and the metrics that you have and just learning those interactions is what was great for me. And now I get the chance to be an advisor, not so many boards. 1 of my upcoming career goals is to join more boards and start learning to be what it means to actually be on the board side, which I haven't done yet.

Eric Brooke: 00:36:38

So continue your journey onwards. Um, what's next?

Asanka Jayasuriya: 00:36:45

So after envision, uh, I got kind of, you know, I had a career plan of what I wanted to do. And the next thing was to be the CTO at a public software company. And that's when sale point reached out, um, they are similar to it very similar to last year, best in breed on premise, identity, government software, they had a cloud solution. But they were ready to go all in on cloud and make that big push. And so I joined them to help lead that transformation. It was also interesting because at the time, this is in, uh, December. When T 19 that I'm interviewing with them, I'm like, this is great. And I'm actually looking forward to getting back into an office as well. Uh, cause after being remote for about two years in the vision. And then my start date was April of 2020. And as you can know, obviously I did not get to start, uh, in office. And so it, uh, COVID hit and I joined and they went fully remote. And it actually turned out to be very useful that I had two years of experience leading remote engineering teams, because now I was forced to lead a remote engineering team again. Great, uh, great culture at the company and we really just pushed hard on making that pivot from on premise to cloud. We shifted our hiring strategy, shifted our architecture philosophy about how we're going to invest and just went all in. It was going exceptionally well, uh, so well, in fact, that Toma Bravo noticed and, uh, they, uh, they came in and acquired us, um, in, uh, 2022. Uh, but it was a great journey, grew that business tremendously. Uh, I think we more than doubled ARR, uh, in the time that I was there, I think, and that has continued since and, uh, and then the private world, uh, but it was a great experience to, to lead a engineering at a, at a public software company.

Eric Brooke: 00:38:37

So you mentioned already what you, um, see is the difference in the public. Were there any other changes in terms of, like, yes, you have a formal relationship with the board, you have stakeholders, that's your executive team. From that particular job, were there things that you come away from? I learned that there. It's still

Asanka Jayasuriya: 00:38:57

fine. I think I learned the. Real focus in a public company on quarterly reporting. Um, I mean, when you make commitments and revenue commitments associated with product launches. And that goes to the street and to investors, like that's significant, right? Like, you know, it's, it's very, very different. And so I just learned that that pressure can be pretty significant. And you have to, as a result, be a little bit more conservative in how you plan your roadmaps and what you announce, uh, to both very publicly, because once you announce publicly, like there are revenue implications and, you know, Wall Street, Okay. Implications of what that means. So learning that ability to be a bit more conservative externally, but more aggressive internally was a little bit different.

Eric Brooke: 00:39:47

Okay. And so what's next in your career?

Asanka Jayasuriya: 00:39:51

So after the sale point acquisition, uh, you know, I had a conversation with my leader and, you know, if I wanted to stay on and be in, uh, continue the private equity journey, and it wasn't really for me. Um, I've always been much more of a builder. I like to build and explore and private equity. So much more tends to be much more disciplined, financially driven journey. And it just, it wasn't a path that I wanted. I decided to take, uh, some time off. My goal is to take about a year off. Um, I spent a lot of time riding my bike, uh, went down to Columbia with some good friends of mine, rode bikes in the mountains, went to the Galapagos with my family, uh, traveled around quite a bit, started playing a lot of pickleball. I'm really just kind of unwound for about six to nine months. It's the first, first break in my career. I mean, I started my career when I was 20. Because when I took that internship, I never actually went back to school full time. I just finished my degree part time and stayed working full time. So I had been, you know, 23 years without more than probably 2 weeks off at a time. And I was looking forward to my first career break. And so I really just kind of disconnected from everything for a while. And just a lot of pickleball, a lot of bike riding, a little bit of travel, skiing. Yeah, it was, it was a good, it was a good career break.

Eric Brooke: 00:41:12

Yeah. And this, um, What were the things you would say that you got from a career break? You got to relax. What other things would you say? Um, do you think career breaks are a good thing?

Asanka Jayasuriya: 00:41:25

Oh, I, I, I will caveat this in a couple of different ways. I think they can be a good thing when they come at the right moment in your career. And when I say that, like for me, it's like financially it was in a good position where like, that wasn't really a concern. Um, my kids were at the right age where like, You know, do a bunch more traveling and fun things with Ben. Um, and that was, was great. And it let me really recover. I mean, I, I didn't really realize like how much kind of the pressure of being in these leadership book, uh, you know, successively bigger leadership roles and take it. And I, I didn't realize actually until probably about 6 or 8 weeks into my break about like how tired I actually was. And that I was losing the energy and kind of the excitement around building things. Uh, and so it was perfect from that perspective for me, uh, to get that rejuvenation. I see a lot of things on LinkedIn of folks taking like career breaks in their early 20s. And maybe I'm just like an old cynic now, but I think that's probably a little bit too. Too soon. I think you gotta, you gotta bring some miles first before you, before you do that. Awesome.

Eric Brooke: 00:42:37

Thank you. So, Galapagos. Awesome. Um, what was next in your journey?

Asanka Jayasuriya: 00:42:45

So the next, I wasn't, I had no real plan, um, but kind of backed into two different opportunities, uh, through very unlikely paths. So the first was actually through the Galapagos. Um, we were on a On a cruise of the islands there, which I highly recommend to do at some point in your life, the wildlife and it's just incredible, but it was a small boat, probably for 20 people and there was another family on that boat. And the father of that family was managing director at new mountain capital, a private equity company. No, he asked me, Hey, do you have any interest in ever doing stuff with PE? And I said, no, not really. And then, uh, he reached out again later and he's like, why don't you just come meet with us? You know, we, you know, we're not like a typical PE. We, we believe in investing and growing and it was true. And so I joined them as an executive advisor, uh, not really a full time job, but I helped them with due diligence. Uh, technical strategy, product strategy, um, great group to be working with. So I started dipping my toe in with that. The other thing that happened was I was playing a lot of pickleball and two, uh, guys in my neighborhood had built a pickleball court and one of my friends knew them and I was like, I got to. No, these guys, I want to put on their, you know, their private court. And, uh, they introduced me and started playing pickleball with them. And they were two of the founders of ABC who had moved from San Francisco to Austin during the pandemic. Uh, the headquarters of the firm had actually moved here. Uh, so Joe Lonsdale was the, was the GP and founder of the fund and he moved, uh, headquarters to fund here during the pandemic. And after playing with them for a while, they just said, are you going to work again? What are you doing? I'm like, I have no real plans. And so I said, Hey, we could use some help with some advisory stuff for some of our companies. So I started dipping my toe, you know, advising some other companies on portfolio companies on product and engineering. Um, Yeah. Yeah. Yeah. And that kind of has grown slowly until eventually they said, why don't you join as our portfolio CTO? And ultimately I did, uh, even though, you know, what exactly a portfolio CTO remains, a work in progress as we define that. Uh, but the real reason I joined ABC is, you know, they believe in building companies. They actually incubate, you know, seven to 10 companies a year. And just investing was not something I thought would really appeal to me, and it still actually really doesn't. But I really get to get involved with these companies as they're built, help them solve problems, and that's just a lot of fun.

Eric Brooke: 00:45:17

So you're now kind of mentoring multiple CTOs and multiple companies. Are there kind of common patterns that you see that CTOs could either be better at, or that you see CTOs facing? Yeah, so there's 1

Asanka Jayasuriya: 00:45:33

very emergent topic that's across, I think, most of our portfolio companies and actually in my CTO networks is the question that's coming up more and more than ever in my career is how productive is engineering. Uh, you know, when resources were plenty and money was plenty, you know, often you'd see companies evaluating CTOs and how quickly they were hiring engineers. Like, that's the success metric. Like, look at how many engineers we hired last quarter. Well, guess what? That is no longer the success metric, I think, for just about any company in the world. Maybe there's a handful where that's still a success metric. But then the questions really started to come of like, okay, we've grown engineering and product this much. What did we get for it? Like, are we going faster? Are we shipping more customer value? And the thing that everybody is struggling with, I think, is we don't really have good frameworks as engineering leaders to report that stuff. Um, you know, we have sprint metrics, we have velocity. Those are, you know, you can't put that in a board slide and say, look, here's our velocity. It's like, it's like, what does that mean? Like, are we better? Are we good? Is it bad? Like, and that is, I think the, one of the biggest common things I see across our portfolio and other companies, even public companies right now is how do we get better at answering the question? Of how good is engineering how efficient is it what is more dollars into engineering and product mean and value to customers and it can often be difficult because you know when I had CRO partners who have intensely metrics of an organization like look there's my quota metric why don't you give a quota to your engineers well it doesn't really work the same way and you know there's a lot of different reasons but those conversations are becoming more and more real and I see that everywhere right now. Thank

Eric Brooke: 00:47:23

you. Um, so like, I guess that feeds in very well to what are you seeing in the current market? Why do them say your portfolio? But what are you seeing in technology?

Asanka Jayasuriya: 00:47:35

Yeah, I think actually, uh, there's a blog post that a colleague of mine just pushed out on LinkedIn, which I highly recommend just talking about the state of venture and how different it is now than it was. Um, and so when I look broad, I see a few different things happening. One, there is far less funding happening right now for startups. I think it is going to be very challenging for a lot of the later stage, like series B series C's companies that are going out to looking for funding. It's going to be harder to get checks. I think we're going to see many, many more companies disappear and go under for that reason. Same time, I think it's going to be very exciting at the seed stage. There's a lot of activity there and a lot of good founders and so it's a focus now, though. I'm not just, Hey, I have an idea. It's like, I have an idea to build a real business. And I think that's. Honestly, that's just not something that was there over the last 10 years, especially the last few years. I have an idea to do X. Like, I don't know if we'll ever make money. Great. Here's 10 million, right? Like, that's not really happening anymore. Um, so that, that is a big change that I'm seeing kind of broader. And so I think we'll see venture get smaller, uh, in terms of the number of venture firms out there, the number of people employed in venture will get smaller. And I think also just from a product and engineering perspective, I think the valuations for like enterprise software companies, you know, they have come down and people say, oh, they'll go back and like, I'm not so convinced. I actually think that the valuations now are back to normal and back to where they should be. And I'm actually a little bit excited now because it's kind of going back to the roots of when I started my career of like, you don't have abundant resources, you're going to have to scrap and fight for every dollar and making everything work. And it's going to be a little bit more of a grind. But I think from that, we're going to see the true, really good engineering leaders that true companies get born. Um, you know, I was saying, I think it's true that The biggest companies get born during the hardest times, right? Like, if you think about all the juggernauts we have in the industry today, the sales forces service now work day, like all these guys, they all came out of the dot com crash. That's when they all cut their teeth. Um, and then in 2008, 2009, right? Like, that's when they started to have the Googles and all that comes into play. I think that's something I recommend everyone think about is these times when things seem the worst is often when the next wave of biggest things are going to be built. And I'm pretty excited for that.

Eric Brooke: 00:50:07

Thank you, Sonka. Is there something that you're working through or digging into and investigating at this time?

Asanka Jayasuriya: 00:50:15

Obviously, this is going to be a huge shocker. It's

Tim Winkler: 00:50:17

AI, right? That is,

Asanka Jayasuriya: 00:50:18

uh, uh, you know, taking everyone's focus. And, you know, for the first time in over 10 years, I'm actually hands on playing with this stuff to learn it. I believe that it is going to be as big as the internet was like that transformation that happened in the late 90s, early 2000s. I believe that's what AI is going to do. I disagree with the time scale that most people think it's going to happen. I think already we're seeing companies raise, you know, nine figure rounds on very little ideas. You know, I think sometimes we don't learn from our mistakes and you see that happening, but I think what is going to happen is. There's this period of what right now I think of extreme hype around AI, going to be followed very quickly by a period of disillusionment of like, oh, this can't do everything. But over the next two to three years, I do expect to change the world. I just think right now everyone's expecting too much of it too soon. But it is going to come. It's, it's very clear that it's going to change how we build software. It's going to change how I think every service gets delivered. It's going to change education. Um, I think it's the most important area to invest in learning and having a foundation right now. Yeah,

Eric Brooke: 00:51:35

I concur. It's um, this is like an industrial revolution for, as you say, moving us to next step. Thank you for sharing your journey. Um, so just checking in. What are the things that have helped you grow or scale as you have? You mentioned earlier that mentors, um, you mentioned kind of community, um, there may be books, podcasts, but what would you recommend to either prospective CTOs or CTOs now as a source or recon of intelligence?

Asanka Jayasuriya: 00:52:10

So again, once you get to the CTO level, I really do believe it's about networking, uh, both. Years, so people who are solving and dealing with similar problems to you, but also maintaining a few people that have gone further than you, that you can go to for advice. And I was really lucky to have kind of those people throughout my career, just a few steps ahead on the path than you. So they can give you that feedback. But I believe as a CTO, that is just absolutely the way you have to do it. You have to invest in building and. Network of people that you can reach out to rely on, but also you have to pay that forward, right? A big part of. My belief is like, anytime somebody asks me for help, I do my best to say yes, because I think that all comes back to you at some point. Like, I don't, that's not why I do it, but I do believe that, you know, doing your best to help people, it ultimately will come back to you, uh, down the road. And so, as much as you look out to build your network, someone reaches out to you to ask you a question for something or some career advice are about the time. You don't know when that pays dividends for you down the road, and you are going to need to do that yourself. guys. Ciao. Awesome.

Eric Brooke: 00:53:23

Thank you, Saka. So you've described a lot of what you've done. What do you do for fun? Um, so I

Asanka Jayasuriya: 00:53:30

have two boys, uh, two teenage boys that keep me pretty busy, but outside of that, uh, pretty athletic, uh, like, you know, weightlifting, running. I was a huge cyclist for a long time. I've been off the bike for a little while, uh, and tendonitis in my elbows, you know, getting old. All these injuries start to creep up a little bit, but I'm a big cyclist, also love snow sports, snowboarding, wake surfing is a big hobby of mine, and then just movies and kind of all the typical stuff. Endurance sports is another one. I did Grand Canyon, the rim to rim hike. It was supposed to be rim to rim to rim, but when we got to the far side, the prospect of going back another 26 miles, we decided we'd rather just go get a beer. Um. But yeah, that's pretty much, uh, what I, what I do for fun.

Eric Brooke: 00:54:20

Is there a movie you're looking forward to?

Asanka Jayasuriya: 00:54:25

You know what, I have been really disappointed in movies lately. I just saw Godzilla Zero. I don't know if you've seen that. It was fantastic. It is, it's, uh, it's hard to describe, but it's like a low budget movie, but Godzilla is in it, but it's not a Godzilla movie. It's more about the Japanese struggle during World War Two. Absolutely fantastic. But in terms of anything coming up, like, I used to be so hyped for all the Marvel stuff. And I don't know if it's just me or like, but we kind of got to this fatigue level where we just kind of all of a sudden stopped watching all of it. Like all the shows on Disney plus, we were like, oh, yeah, we haven't even looked at Disney plus in a while. Like, I think we got the peak marble. But outside of that, I'm trying to think of. And, oh, a Jordan Peele's new movie, uh, Monkey Man, uh, looks really good. It's, um, I think it's an action movie set with, uh, Dev Patel from, uh, Slumdog Millionaire. That one looks pretty good. I am looking forward to that.

Eric Brooke: 00:55:25

Awesome. I'm looking forward to Dune 2. Um, I love expansive science fiction, but Ahsoka, thank you very much for your time today and for sharing your thoughts and your wisdom. Greatly appreciate

Asanka Jayasuriya: 00:55:37

it. Yeah, it was great being here. Thanks for having me.

Tim Winkler: 00:56:00

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