CTO Wisdom with Asanka Jayasuriya | Beyond the Program

Feb 13, 2024

CTO Wisdom with Asanka Jayasuriya | Beyond the Program

Welcome to CTO Wisdom. In this series, we interview technical leaders who have stepped into executive positions.

Today’s guest host, Eric Brooke, speaks with Asanka Jayasuriya, CTO at 8VC, where he works on their Build program, which incubates several new companies a year. In today’s episode, they discuss:

  • Asanka’s career journey through big and medium tech
  • Setting others up for success
  • The importance of Developing Leaders and ideas (and how to do this!)
  • The transition when your peers become stakeholders at the Executive level (and how to manage through the transition)
  • The difference of a Private vs. Public board and its impact on technology
  • What it’s like to be a portfolio CTO role

About today’s guest: As CTO at 8VC, Asanka Jayasuriya helps startups with product and engineering strategy, particularly as they scale. He also works extensively on 8VCs Build program that incubates several new companies a year. A software engineer by training, Asanka has nearly 25 years of experience building products across enterprise saas, e-commerce, collaboration software, and security products. He’s worked for industry leading companies like Oracle, Amazon, Atlassian and SailPoint.

About today’s host: Eric Brooke has a rich and varied leadership career – leading up to 21,000 people and Billions in revenue, throughout 14 countries. In their career, they have been an Executive six times (e.g. President, CEO, CMO, and CTO) and a Board member of multiple organisations. Eric has been a CTO of scaling startups from 0 to 120 engineers. As an adviser and mentor, they have helped multiple other startups scale both in Canada and the US. As well as supporting multiple startup incubators such as 1871 in Chicago and TechStars.

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Transcript
Tim Winkler:

Hey, listeners, Tim Winkler here, your host of The Pair Program.

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We've got exciting news introducing our

latest partner series Beyond the Program.

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In these special episodes, we're

passing the mic to some of our savvy

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former guests who are returning as

guest hosts, get ready for unfiltered

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conversations, exclusive insights,

and unexpected twist as our alumni

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pair up with their chosen guest.

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Each guest host is a trailblazing

expert in a unique technical field.

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Think data, product management,

and engineering, all with a keen

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focus on startups and career growth.

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Look out for these bonus episodes

dropping every other week,

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bridging the gaps between our

traditional pair program episodes.

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So buckle up and get ready to

venture Beyond the Program.

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Enjoy.

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Eric Brooke: Welcome to CTO Wisdom.

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My name is Eric Brooke.

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This series will talk to leaders

of technology at organizations.

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We'll understand their career, what

was successful, and what was not,

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and what they learned along the way.

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We'll also look at what the

tech market is doing today.

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We'll understand where they gather

their intelligence so they can grow

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and scale with their organizations.

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Um, today I'm going to talk to Asanka

and we're going to talk about, um,

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his leadership through technology

and his, um, winding career journey

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and all of the things he's learned.

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Asanka, welcome.

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Good to be here.

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Could you give me the elevator

pitch of yourself and what you're up

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Asanka Jayasuriya: to?

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Sure.

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I've spent, uh, getting close to 25 years.

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It's a long time of my career in

software, uh, and roles starting as

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an engineer, as an intern, working my

way up through management, uh, to exec

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roles, but always basically in cloud

software, enterprise SAS, uh, e commerce,

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uh, security, and more recently, uh,

in a venture firm as a portfolio CTO.

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Thanks.

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A lot of, a lot of different

roles, a lot of different

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industries over the last 25 years.

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Awesome.

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Eric Brooke: Um, could you tell us a

bit about your journey into technology?

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Asanka Jayasuriya: Sure.

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Um, so I kind of did not start on a path,

uh, straight into tech, um, growing up

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as a Southeast, uh, Asian, uh, kid, uh,

you know, being a doctor is kind of a.

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Principle journey that a lot of us get

put on and I think I was told from a very

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young age that was the path and kind of

working my way almost without thinking

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towards that all through school entered

university studying molecular genetics

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as a kind of precursor towards medicine.

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But once, uh, after my first year,

I spent the summer, uh, in Sri Lanka

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and got a chance to volunteer a little

bit, uh, with my uncle, spent some

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time, uh, with him as a, he's a doctor

there and kind of realized, like, this

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is not a, this is not a job for me.

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Um, you know, your, your good days as a

doctor are good, but your bad days can be.

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Really bad.

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I mean, obviously it's, it's, I think

one of the most important professions and

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obviously it comes with a lot of weight.

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Um, I just didn't think that was for

me, but the whole time, you know,

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I'd always been playing and tinkering

around with computers since I got

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my Radio Shack, you know, handy XT

computer back when I was in grade eight.

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And, you know, someone said, why don't

you start setting time with that?

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So I switched over to computer science.

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And from there, I just fell in love

with it, fell in love with building,

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fell in love with, uh, writing code,

quickly realized in computer science

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that I did not love any of the math or

formal proof sides of computer science,

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but was just in love with software,

software engineering side, and that's

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sort of how I indexed my time, uh, and

focused on that and moved into, you

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know, loving computers and building.

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Cool.

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Eric Brooke: So, um, when you, you

started in science, were there aspects

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of science that you found helpful when

you got to kind of like computers?

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Asanka Jayasuriya: I would definitely

say the quantitative side of it.

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So your physics, chemistry, um, and

calculus, obviously, subjects like that

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are very across all those subjects.

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Having that background is helpful,

uh, because ultimately, you know,

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computers are quantitative in, in a way.

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So I found that was generally helpful.

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I feel like the subjects that were.

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Less helpful biology and things like

that, which are a little bit more

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about memorization, even genetics.

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Uh, those courses weren't

particularly helpful, but I would

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say the quantitative classes were

definitely useful once I moved over.

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Oh,

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Eric Brooke: so then tell

us about your journey.

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Now you're into kind of software

engineering and technology.

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Um, what was that like for you?

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Yeah.

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So

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Asanka Jayasuriya: I was very fortunate

in that the university of Toronto, where

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I went to school had what was called a

professional experience year program.

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So you got to a 12 or 16 month internship.

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with a Canadian, um, software

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startup, uh, called Janus Systems

that was doing web based, uh, CRM.

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I want to say web based, intranet

based, so this is well before SaaS

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was a thing, but it was revolutionary

because it's deployed in the browser.

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Customers didn't have to install,

you know, windows clients on

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across thousands of desktops.

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Uh, I got very lucky

for a couple of reasons.

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I was starting and just kind of

right at the tipping point of stuff

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starting to break in the dot com bust.

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And you don't have

offers from general IBM.

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And, uh, Cisco systems and, you know,

a lot of my friends were pushing to

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go take IBM and Cisco, but this is,

you know, the startup environment.

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And I guess it's, it's a very

different world back then.

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I think today everyone knows

all about startups knows

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what it's like and exciting.

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the same level of excitement or

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celebration around startups and everyone

was pushing me towards going IBM.

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Uh, I ultimately turned IBM

down, worked out really well.

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And I got super lucky because, you

know, six months later, IBM, Cisco,

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and all those big companies, they

were letting go their interns.

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They were downsizing.

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Uh, sometimes you get, you get

really lucky in your career

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and Jenna went incredibly well.

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We got acquired by Siebel systems,

which was the largest CRM vendor,

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uh, in the world at the time.

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And I got to kind of continue my

career there to, you know, now

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at Silicon Valley owned company.

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Progressing my career and, uh, it

was, it was, it was challenging,

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:especially, uh, in about:

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com really came to market.

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And for those who are familiar, they

were really the 1st cloud company, in my

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opinion, of any real scale, delivering

real software over the Internet.

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And Siebel being the incumbent on

premise, uh, you know, it got quite

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heated that competition and they

decided they had this team that

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they'd acquired our team in Toronto

and they're like, why don't you guys

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figure out how to do this cloud thing?

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And it's 1 of those interesting things

where again, you get lucky in your career.

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I didn't get put on the most

important project at the time.

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Everybody thought cloud was not

really going to be a big deal.

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It's like a fad.

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It's for small businesses.

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No enterprises are going to want this.

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But I got to start figuring out

cloud stuff, you know, back in

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happened and just really, really

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lucky, uh, to get that opportunity.

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What happened next?

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So after that, um, you know, kind

of progressed up as an engineer,

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eventually reaching the level

of a principal engineer, um, at

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Siebel, we got acquired by Oracle.

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So it's like a small fish that got

swallowed by a bigger fish that got

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swallowed by I guess the biggest fish.

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Uh, and no one was going to, I

think we were, the joke we had was

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nobody was going to buy us now.

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We were pretty sure that with

Oracle, that was kind of the

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end of the acquisition chain.

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But I continue to progress

as my career as an engineer.

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:And then about:

made a shift in my career and that's

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when I first moved into management.

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Tell

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Eric Brooke: us what that was like.

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Oh, yeah.

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So

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Asanka Jayasuriya: a couple of

things that really drove that for me.

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One is, well, I was a

really good engineer.

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And when I was younger, I thought I

was a great engineer, but then you

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kind of You learn by meeting really

great engineers where you actually

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sit in, uh, in the ranking of things.

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And at Oracle, um, I got to interact with

some just people that made me realize.

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As good as I was, like, there was

just no path for me to operate

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the level that they operate.

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It's just, you know, sometimes

people you meet in your career and

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they just have a different gear and

that's not necessarily a bad thing.

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Um, I just realized, like, 1, I

was never going to achieve that

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level of technical contribution.

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But the other thing I also realized was.

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It was increasingly not the part

of the job I loved the most.

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I loved leading projects.

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I love mentoring are

more junior developers.

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Uh, and so, uh, my one of my

mentors at the time suggested I

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make this switch into management.

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And that's really what kind of

made me, uh, make that transition.

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Eric Brooke: So your manager, were

there things that, um, as a software

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engineer were really helpful, but got

in the way of you when you were actually

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a manager, um, in that transition?

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Asanka Jayasuriya: Absolutely.

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I think that was actually probably

the hardest part is often.

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And I think this is actually something

we do very poorly in the industry.

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It's your best engineers who end up

becoming managers, which is interesting

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because there's not, there's not a lot

that's related in that skill set of

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being an extremely strong technical

person and being a good manager.

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And I've, you know, one of the big

reasons is being a strong engineer,

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you have your team for the first time,

you have a tendency to want to really.

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Do a lot of showing through code and

fixing things and keeping your teams

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from making mistakes, which is good to a

point, but it's very easy to cross over

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that line where your team isn't really

learning and growing on their own anymore.

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And they're basically just doing what

you tell you're jumping in and dealing,

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doing, solving the hardest problems.

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And I had a good talking to you from

one of my mentors who kind of noticed

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that and said, like, you're just not

going to be able to scale and your

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teams are not going to like working

for you if you're always the smartest

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engineer on the project as well.

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And that was something I took to

heart to really start creating some

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more space and giving my team some

more room to operate, even if things

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were not necessarily the way that I

would have preferred them to be done.

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Eric Brooke: Yeah.

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So you got out of your own way.

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So that you could scale

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Asanka Jayasuriya: out of my own way

and got out of my team's way, right?

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It's, I mean, nobody, nobody wants

to work in a good people want

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to have a degree of autonomy.

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They want to feel like

they can explore a path.

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They want to feel, you know, that

they can invent and they can make

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mistakes in a supportive environment.

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And I wasn't really doing that

as a, as a first time manager.

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Eric Brooke: Um, so how did your

management career progress after that?

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Asanka Jayasuriya: So I stayed

at, uh, my first three years

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were Oracle as a manager.

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Um, I had a very, very brief detour,

uh, a large Canadian bank, um, they'd

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hired me to be part of their renaissance

or their technical revolution program.

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And, uh, it was, it was 1 of those

situations where the, the bill, uh,

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the, you know, the posted that role

was very different than reality.

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Um, I, you know, I remember coming home

after my 1st week and telling my wife,

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like, this is just not going to work.

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And the main reason was.

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I'd been in the profit center, right?

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Technology as the profit center

technology as the defining factor

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of success for the business.

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And despite their desire to change

in that bank, it's clear that

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technology was a cost center.

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All I was really doing was

managing budgets, managing vendors,

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like what I wasn't building.

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But fortunately, uh, one of my

friends who was at Amazon at the

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time reached out and said, Hey, like

Amazon's building a Toronto office.

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You want to do this and help build it from

scratch and I interviewed with Amazon and

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took a role as one of their first hires

in Canada, helping to build out, uh, the

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Toronto, uh, Amazon engineering site.

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Eric Brooke: Very exciting.

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Um, what was your journey like with

Amazon and what were the, some of

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the leading principles that you

stepped away from that organization

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Asanka Jayasuriya: with?

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Yeah, I, I would say Amazon was probably

the most transformative part of my career.

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And I think you'll find a lot

of people who will say that, and

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there's a couple of reasons for that.

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So almost immediately when I started,

we were in what was called a Regis is a

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real estate company that runs temporary

office space, uh, before we worked somehow

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made that a tech problem, which I don't

quite understand how that happened.

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You know, we were in a temporary space

in a mall, uh, with, you know, next

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door to us and there was a massage

of people running a massage studio.

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It was a really interesting space.

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But Amazon, you know, they threw

us in there and I kind of quickly

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realized like, okay, what's

the plan to building this out?

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I was kind of waiting for like the

directives to come down like an Oracle.

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Like, okay, this is what you're doing.

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Here are the rules.

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But what I realized is

there were no rules.

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There were no directives because

Amazon pushes ownership down

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very deep in the company.

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Okay.

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And expect you to execute

and figure things out.

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Um, there can be a very stressful

environment from that perspective,

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but for the right type of person,

it's just incredibly empowering.

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Like they really give you a lot of

autonomy and a lot of ownership.

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And.

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You know, for all the negatives that

people hear about working to Amazon,

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and I wouldn't dispute any of the

stories that you hear about people

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crying at their desks or any of that.

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It highly depends on the group that you

work at there, because it is so much

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a collection of small companies that

anyone that you can work for can, you can

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have a radically different experience.

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I happen to work for a great, uh, general

manager who is running my business and it

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was a fantastic environment and I just got

the opportunity to help grow that team in

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Toronto, eventually expanding into, uh,

Seattle, uh, taking on teams in Seattle.

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And the big part for me, there was

the core values that the company

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used were really operationalized.

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I think every company has core values

that are probably written down on a

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memo, like a brochure or something

that you join to see them and you

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probably never, ever see them or

hear them again after that first day.

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Amazon operationalize their values into

every part of the business, whether it was

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promotions or how you're thinking about

a business idea and those core values

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I actually took with me for the rest of

my career and still to this day, really.

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Push them and implement them

and how I have executed.

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I've actually directly brought variations

of those values to new organizations.

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I've been at the other area.

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I would say that Amazon really

changed me is being an operational

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leader before my career.

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We had ops teams.

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You know, we would build software.

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There'd be a huge ops organization.

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They would run it.

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Amazon was you build it, you run

it, which I'm a huge proponent of,

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and having operational ownership for

software, understanding how to do

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that at scale and with quality was

just an incredible experience to get.

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Eric Brooke: Cool.

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There's kind of two parts

I'd love to dig into.

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Could you give an example, one of the

Amazon principles beyond the operization

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and the pushing down ownership?

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I'd love to hear that.

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Um, but give me one of those

kind of like principles or two

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that you really do embody now.

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Asanka Jayasuriya: So one

is customer obsession.

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Amazon really starts from the

perspective of if you do what is

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best for the customer, even if the,

in the short term, that may not make

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sense in the long term, you will win.

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And you can see that through so many

different parts of the business, you

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know, from a consumer perspective, you

think about same day shipping, right.

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Or next day, building the infrastructure

for that was billions of dollars

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in fulfillment network capacity.

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A huge loss leader for a long time.

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However, can anyone

live without that today?

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Like no one competes with

Amazon on that, right?

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Like everyone loves that capability.

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Um, so customer obsession and just that

focus on if you solve the customer's

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need, you will, you will win as a

company, um, is one of the cores.

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Another one is hire and develop the best.

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Uh, when I was there, Amazon

wasn't a relentless growth pace,

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but they intend, they kept a

very, very high bar for talent.

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And uh, there was a program called

bar raisers where after you'd done a

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certain number of interviews, you became

a bar raiser and a bunch of trials.

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And the goal was.

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In every interview loop, there would

be one of these bar raisers on the

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loop, and the bar raiser always came

from a different organization, so they

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had no skin in the game to the hire.

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Like, they weren't under pressure,

like, hey, we have to fill this role,

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and the goal was always to ensure

that every person that you hired

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into the company was better than

half of the people in that role.

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And if you stop and think about for a

second, what that means is if you do

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that for long enough, your team is just

getting better and better and better.

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It doesn't mean that the bottom 50 percent

aren't good employees, but they're saying

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everyone you bring in, you want to be

better than half the company so that

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they can keep pushing that bar higher.

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And there was just a relentless focus

on one hiring from that perspective,

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but also developing again, if

you're in the right organization.

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And they saw your potential, like

you would get invested in to get

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the right opportunities, the,

you know, more autonomy, more

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scope and more responsibility.

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It was a lot of fun, but like I said,

in the five, five ish years I was there,

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I felt like I did 10 years of work.

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Right.

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Eric Brooke: Good to know.

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Thank you.

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Um, so carrying on with your journey,

um, you're now at Amazon building,

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um, at the Toronto office, you're

at management at a higher level.

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Tell us about the

continuation of that journey.

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Asanka Jayasuriya: Yeah, so I

was a senior manager at Amazon.

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Uh, I think my organization was

probably around 250 ish people

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across Seattle and, uh, Toronto.

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And Amazon has, uh, at the time anyway,

I don't know if this has changed,

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it had a bit of a glass ceiling.

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If you weren't in HQ, like, if I wanted

to make that next step to my career

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at Amazon, it was, you know, my, my

leaders told me, it's like, should

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think about getting you to, uh, Seattle.

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So me and my family were kind of going

through that process of relocation

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and kind of getting that figured out.

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And I was going to join the

last mile engineering group at

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Amazon, uh, to lead a lot of that.

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And that's the Amazon delivery

network, which at the time was

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just getting off the ground.

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But in the middle of that, uh,

Atlassian reached out about

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running Jira cloud in Sydney.

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And, you know, I've

always loved Atlassian.

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Uh, everyone's kind of aware of

their culture developer focus.

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So my wife said, if we're

moving, we might as well.

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Go down there and check it out.

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:

So flew down to Sydney, uh, met with

the founders of Atlassian, a lot of the

354

:

leadership and absolutely fell in love

with the company, but me and my wife on

355

:

that trip also realized like it was just

not practical for us to move to Australia.

356

:

Cause once you get on that plane from

Toronto and you fly to Vancouver and

357

:

you will have layover and then you

fly to, you kind of realize, wait.

358

:

Every single vacation we have is going

to be flying back to visit family, so

359

:

that's all we would do, but kind of

from a more career perspective, the

360

:

thing that became clear to me is that

I could probably have a great four to

361

:

five year run at Atlassian, but there

was no other opportunity in Australia.

362

:

Like, it was really clear, right?

363

:

Like, there's Atlassian at that time,

and there was really nobody else at

364

:

any scale, um, solving hard computer

science problems, uh, to work for.

365

:

And I'd be in a situation to

go in there for 4 or 5 years.

366

:

My kids would be getting to high

school and then we'd probably have

367

:

to rip them out and at that time

and bring them back to Canada.

368

:

And that's something we wanted to do.

369

:

But when I turned down the role,

uh, the CTO, uh, there, uh, Sri,

370

:

who's still one of the mentors

and someone I talk to regularly.

371

:

Uh, he said, well, why don't you take

over our Austin engineering instead?

372

:

Uh, and he couldn't caution me.

373

:

He's like, there's a lot of problems

over there, you know, and it's going

374

:

to be a bit of a fixing situation.

375

:

And I've always actually

kind of liked fixing things.

376

:

So I was like, yeah.

377

:

And we loved Austin.

378

:

So we made the journey, made the, uh,

change and moved to Austin in:

379

:

Eric Brooke: Awesome.

380

:

And so describe this role.

381

:

You've, you had like 200 plus people in

like Amazon and you've got this role here.

382

:

Um, have you got to, I'm guessing you're

managing managers at this point as well?

383

:

Asanka Jayasuriya: Yeah.

384

:

Uh, Amazon was the first time I

started managing, uh, other leaders.

385

:

Eric Brooke: And so the transition

from being a manager to managing

386

:

managers, what was that like?

387

:

What kind of changes did you

have to make in yourself?

388

:

Asanka Jayasuriya: I think the biggest

thing that you do as you kind of make

389

:

the steps is you have to as a leader

start designing mechanisms to give

390

:

structure to your organization and

give you visibility so you understand

391

:

what's happening in your org.

392

:

And I kind of realized that.

393

:

You do have to be structured about

it because you wanna give your teams

394

:

kind of operating structure as well.

395

:

Like if we're gonna do a regular weekly

metrics review, or if we're gonna do

396

:

a, you know, quarterly planning, like

building those structures out so that

397

:

you understand what your teams are doing,

you understand what their challenges

398

:

are, where you can help unblock them.

399

:

But you also at the same time don't

want so much visibility all the

400

:

time, such that, you know, you're

in the weeds of all your teams.

401

:

And again, kind of similar to my

earlier transition to being a manager,

402

:

you want to give managers a lot

of scope to run their team, right?

403

:

And evaluate them based on that.

404

:

And it can be hard to do if you do

too much of the managing for them.

405

:

Um, so really building out those

structures, you know, how often

406

:

should you do skip levels, right?

407

:

Arranging that so you understand.

408

:

The people dynamics in the different

subteams, so as you scale, you

409

:

just need to build more and more

mechanisms, I think, into how

410

:

you operate and manage your team.

411

:

Would

412

:

Eric Brooke: you have, like, so, um,

like, we talked about visibility.

413

:

Could you give us an example of

visibility that was really helpful to

414

:

help your managers, but also help you

to stay connected to the your wider

415

:

Asanka Jayasuriya: team?

416

:

Yeah, so I think 1 of the big

things is project progress, right?

417

:

Like, status reporting is.

418

:

Kind of the least favorite thing I

think anybody has to do, um, but at

419

:

the same time, you know, I need to be

in a position where if I'm talking to

420

:

an executive and they have a question

about what a key project that one of my

421

:

teams is doing, like, what is happening?

422

:

So we built a, you know, a regular,

like, monthly kind of status

423

:

reporting framework, a template for

how projects can be reported on.

424

:

We tried to keep it as

lightweight as possible.

425

:

You know, when I'm managing managers,

I was less interested in like sprint

426

:

metrics and velocity and stuff like

that, because I truly believe those

427

:

are the metrics that belong to the team

and the manager for it to optimize.

428

:

And I, but my mechanism is much

more around business impact,

429

:

delivery, key highlights.

430

:

Um, I just didn't want my team

spending a lot of time, you know,

431

:

just reporting status effectively.

432

:

So they liked it because it was

lightweight and they weren't constantly

433

:

reporting on a whole bunch of, you

know, things instead of investing in

434

:

building software and building product.

435

:

Eric Brooke: And then for, that's process.

436

:

What about leadership development?

437

:

How did you grow your managers?

438

:

Were there common patterns or

things that you didn't see to

439

:

begin with, but you learned later?

440

:

And to help your leaders

grow as well, that

441

:

Asanka Jayasuriya: that was always been

and remains a favorite part of my career

442

:

has been developing other leaders.

443

:

Um, I'm a position now.

444

:

We're seeing multiple of the folks who've

worked for me become vice presidents of

445

:

engineering at different organizations.

446

:

Um, 1 is becoming a CTO of a series B

company in the next couple of weeks.

447

:

So I'm really excited and kind of proud.

448

:

About as well to see her making that

step in her career, but the things

449

:

that I always did was look for

opportunities to push my managers, right?

450

:

And I always, you know, because

because people have done this to me

451

:

is, you know, when their plate is full.

452

:

No, giving them just a little bit

more just to push him a little bit

453

:

past that limit of like, yeah, this

is going to be hard, but it's going to

454

:

force you to create your own mechanism.

455

:

It's going to force you to think about

how you delegate within your teams.

456

:

But it's always, I think, you know,

finding the right opportunity for growth.

457

:

And I think as a leader, your biggest

responsibility is doing just that.

458

:

Because if you create the right

opportunities, the stretch goals,

459

:

stretch opportunities for your team

that allow them to grow their career,

460

:

it's That means your organization is

going to be successful because if,

461

:

especially if you tie those things to

milestones that align to the business.

462

:

Eric Brooke: Cool.

463

:

Thank you very much.

464

:

Okay.

465

:

So, um, you're at Atlassian in Atlanta.

466

:

Um, where, where in Austin, thank you.

467

:

Um, where did you get

to, um, winter is an exec

468

:

Asanka Jayasuriya: role.

469

:

So that I would really consider Atlassian

kind of my first exact type role because

470

:

I reported directly to the CTO and there

were only 5 of us reporting to the CTO

471

:

who ran all of engineering for Atlassian.

472

:

Um, I would say that that was

actually 1 of the most fun parts of

473

:

my career for a couple of reasons.

474

:

One was I got to take all the

practices I learned from Amazon

475

:

and apply them in a new environment

that hadn't seen them before.

476

:

Um, at the time Atlassian was

really making a hard pivot from

477

:

its on premise, uh, roots to cloud.

478

:

Uh, that was the mandate of the

new CTO, uh, who was there and

479

:

the reason I was hired as well.

480

:

I was hired into, um, the hip

chat organization, which I don't

481

:

know if anyone remembers hip chat.

482

:

It was the, uh, predecessor to slack and

things at the time were not going well,

483

:

uh, slack and immersion, the market chat

had had some high profile outages and

484

:

they were in the middle of a full rebuild,

a full rebuild of the hip chat product.

485

:

And that was not going well either.

486

:

Um, there was no head of

engineering at the time.

487

:

And so I kind of stepped

into a difficult situation.

488

:

Yeah.

489

:

I got to one, earn the trust

of team, start implementing

490

:

some of these processes.

491

:

It was really exciting to see.

492

:

Some of the processes that we

implemented around technical operations

493

:

in particular get pushed to all

of Atlassian, um, and help just

494

:

transform how Atlassian did cloud,

but it was, it was a, it was a hard 2.

495

:

5 years, but also incredibly fun

because the team was very motivated.

496

:

Um, you know, we had this.

497

:

Goal that no one thought we could

accomplish even inside it last year.

498

:

No one thought we'd be

able to get this done.

499

:

Ultimately, we did get it done.

500

:

It did not end up mattering because

as Microsoft was coming to the market

501

:

at the time, the company kind of

realized that this isn't going to

502

:

be a market that there's going to

be a lot of revenue to be made in.

503

:

It's probably going to end

up being free, which is.

504

:

Exactly what has happened.

505

:

And, you know, no one pays

for this stuff with office.

506

:

And I think it's one of the reasons

why Slack got sold to sales forces.

507

:

They saw their growth opportunities kind

of limited in the future, but it was kind

508

:

of a exciting journey to be on a building,

not only building the new product, but

509

:

also bringing a lot of the cloud practices

I've learned at Amazon, uh, to Atlassian.

510

:

Awesome.

511

:

Eric Brooke: Thank you.

512

:

Um, so continue your journey.

513

:

What happens next?

514

:

So,

515

:

Asanka Jayasuriya: after we, at

the end, towards the end of my

516

:

Atlassian career, I was managing,

uh, Stride, Hitchat, and Trello.

517

:

I'd also taken ownership

over the Trello product.

518

:

But I kind of knew that there was no

real next opportunity for me there.

519

:

I was reporting into the CTO and like,

there was no real clear next step.

520

:

And I got the opportunity to work

for, uh, envision as their CTO.

521

:

And when they approached me about

the role, you know, I, first I wasn't

522

:

sure, but as I dug more into it, I

kind of realized that one, they were

523

:

a thousand person remote company.

524

:

And today that sounds like no

big deal, but back in:

525

:

They were the largest doing that in

the world, and very few companies were

526

:

remote, uh, back then, at least at scale.

527

:

And so I wanted to understand,

you know, how can you do that?

528

:

Because the biggest challenge

to any engineering that has

529

:

is finding great talent.

530

:

And when you're constrained

to geographies, that

531

:

makes it that much harder.

532

:

So I wanted to understand,

like, can this actually work?

533

:

And as well, they were, uh, you

know, a unicorn, they just take an

534

:

evaluation at 2 billion, I think.

535

:

So, uh, you know, closing in on

a hundred million in ARR seemed

536

:

like a great time to join.

537

:

I joined and as always, as you

learn is like, things are never

538

:

quite what they seem at any company.

539

:

And I think everyone always goes

through, I think you start and you're

540

:

super excited and there's this kind

of trough of disillusionment that

541

:

you go through and then you come

out the other side and realize that,

542

:

you know, just because you can.

543

:

Hire anywhere doesn't mean you should

hire anywhere, uh, and they hadn't really

544

:

maintained us high bar, I think, for

how quickly they had hired an account.

545

:

And so it was the largest kind of

transformation I had to make in terms

546

:

of raising the bar on hiring on talent

while executing on a product roadmap.

547

:

That was just too full.

548

:

There were too many priorities.

549

:

And it was really, really

challenging to move that forward.

550

:

And ultimately, I don't know if you

saw, Envision officially announced

551

:

their shutdown a few weeks ago, which

is I think the first of many broken

552

:

unicorns that we're going to see.

553

:

I learned a lot about focus there

and about, you know, being realistic

554

:

about where you're, where you are.

555

:

Um, And we just couldn't quite make

that last pivot and roadmap that

556

:

we had to as Figma was, you know,

basically just emerging and everyone

557

:

knows how quickly Figma kind of took

over and learned a lot about, uh,

558

:

what it means to be a fully vertically

integrated solution like Figma versus

559

:

a piece of an ecosystem like Envision

was, uh, which made it vulnerable.

560

:

But incredible opportunity to learn

what it means to be in the CTO seat,

561

:

where you learn for the first time that

You really don't have fears anymore.

562

:

You know, at Atlassian points, the CTO,

I have good friends and who made my

563

:

good friends, who are my peers, who ran

the other engineering groups in your

564

:

first leadership seat, you realize,

you know, you have your CRO, your chief

565

:

people officer, chief product officer,

head of marketing is peers, but you're

566

:

not really a team in the same way.

567

:

You're really all stakeholders

in each other's worlds and you

568

:

need things from each other.

569

:

But I kind of realized that there's

a little bit of loneliness that

570

:

job because you have people below

you who rely on you and you provide

571

:

leadership to you and your peers who

need things from you, but you don't

572

:

really have teammates in the same way.

573

:

And it gets, it can was

surprisingly a little bit more

574

:

lonely than I expected it would be.

575

:

Eric Brooke: Cool.

576

:

That's a great point.

577

:

So let's dig into that a

little bit when you say.

578

:

So, in a sense, what I heard was

like you had collaborators who

579

:

are on your side, helping you be

successful, kind of probably being

580

:

critical friends when needed.

581

:

And then you have stakeholders.

582

:

What does that feel like?

583

:

What's the difference between stakeholder?

584

:

Asanka Jayasuriya: So I think one

of the key differences is that, you

585

:

know, when I had my peers at the last

thing, we could just go have a beer

586

:

and talk about, you know, whatever,

even if it's talk about the dumb

587

:

thing we think our boss did, right?

588

:

Or, or, or, or everybody does that.

589

:

And I'm sure all, all my directs have

done the same and gone out for a beer and

590

:

talked about some dumb thing that I said

or dumb thing I told them to do, right?

591

:

That kind of comes with the job.

592

:

But when you're an exec, every

interaction almost feel can feel like an

593

:

evaluation to a certain extent, right?

594

:

Because if you're meeting with the CRO

and the CRO needs a future shift or needs

595

:

your understanding to make a customer

happy, like, you know, that's part of it.

596

:

And.

597

:

It, it just, it creates that

sense of, you know, you're not

598

:

necessarily just buddies, right?

599

:

You're, you need things from each other.

600

:

You need to deliver for them.

601

:

And that's kind of, I think,

where that sense of loneliness

602

:

comes from a little bit.

603

:

And at that point, my career is also

when I realized I had to lean much

604

:

more into building my network of

those people who I'd worked with,

605

:

who were my friends and partners.

606

:

I advocate that strongly today to anyone

in leadership is like, keep in touch

607

:

with the good people you work with.

608

:

Like, you know, go back to them.

609

:

You know, once you haven't talked

to someone in 6 to 9 months, set

610

:

up a zoom, like, just check in.

611

:

And 1, it's just great to

maintain relationships.

612

:

I believe, especially in this industry

and both from a personal perspective.

613

:

But also for your career, uh, you

would not believe if you how powerful

614

:

a tool it is to look at your network,

see it, all the great places that

615

:

are adding like, oh, I have a

question about so and so company and.

616

:

You know, I talked to so and so last year,

but I should reach out to them because

617

:

I have a question about this company.

618

:

So that's something I think as we as

engineers in particular aren't great at.

619

:

I think people in the sales, marketing

organizations are so much better at it.

620

:

And I think it is a superpower for

engineering leaders to really invest

621

:

in building and maintaining a network.

622

:

Eric Brooke: Awesome.

623

:

Asanka.

624

:

In terms of you being in a C suite role,

were there other dimensions at this point

625

:

that you needed to understand that you

didn't need to say in the last lesson?

626

:

that you're now having to learn

or that will be helpful for others

627

:

Asanka Jayasuriya: to know about?

628

:

Yeah, definitely.

629

:

I mean, as an engineering leader

before, it's all about just

630

:

shipping and delivering products.

631

:

Um, you know, you have a budget

around headcount and stuff like that.

632

:

Once you're the leader of a business

unit, it becomes a lot more, right?

633

:

You have to understand, really

understand the revenue organization,

634

:

really understand marketing, understand

the customers much more deeply.

635

:

Like, even though you have a product

partner, like It's not sufficient

636

:

for me to be the engineering

leader who's building stuff.

637

:

You really have to understand how your

company works, the financial goals.

638

:

You know, when are you raising money?

639

:

What does your runway look like?

640

:

What does your burn look like?

641

:

All these things that I didn't really,

where I've never really concerned

642

:

for me as a, um, just an engineering

leader right now became front and

643

:

center, uh, just understanding the

business at a much deeper level

644

:

Eric Brooke: and in terms of

like working with the board, um,

645

:

how does that change the game?

646

:

It's

647

:

Asanka Jayasuriya: really interesting.

648

:

Um, and I've been at board

exposure, both in kind of private

649

:

world and in the public world.

650

:

Uh, in the private side, you know,

your board is just, uh, effectively the

651

:

venture firms that have invested, right?

652

:

That's typically what

your board is made up.

653

:

And, you know, I would say at envision,

you know, the board experience.

654

:

You know, we were constantly, you

know, we present our roadmaps and

655

:

stuff, but I would say the questions

were largely to the revenue team.

656

:

Um, you know, we got some questions

about one product and stuff with shit.

657

:

When I went to the public, uh, world

with SailPoint, the role I took after

658

:

InVision, it was very different because

now your board members have significant

659

:

fiduciary responsibility, obviously,

to the public markets, and it's just,

660

:

the bar is much higher in terms of the

questions and expectations they have

661

:

of you, um, and their responsibility.

662

:

You also kind of learn that, you

know, what is the relationship I'm

663

:

supposed to have with the board?

664

:

And it's actually

relatively formal, right?

665

:

You don't go to the board and, Tell them

everything that's going wrong with the

666

:

team or your company or the beers, right?

667

:

Like, no, it's, it's, it's

a very formal relationship.

668

:

We talk about the goals and the metrics

that you have and just learning those

669

:

interactions is what was great for me.

670

:

And now I get the chance to be

an advisor, not so many boards.

671

:

1 of my upcoming career goals is to

join more boards and start learning to

672

:

be what it means to actually be on the

board side, which I haven't done yet.

673

:

Eric Brooke: So continue

your journey onwards.

674

:

Um, what's next?

675

:

Asanka Jayasuriya: So after envision,

uh, I got kind of, you know, I had a

676

:

career plan of what I wanted to do.

677

:

And the next thing was to be the

CTO at a public software company.

678

:

And that's when sale point reached

out, um, they are similar to it very

679

:

similar to last year, best in breed

on premise, identity, government

680

:

software, they had a cloud solution.

681

:

But they were ready to go all in

on cloud and make that big push.

682

:

And so I joined them to help

lead that transformation.

683

:

It was also interesting because at

the time, this is in, uh, December.

684

:

When T 19 that I'm interviewing

with them, I'm like, this is great.

685

:

And I'm actually looking forward to

getting back into an office as well.

686

:

Uh, cause after being remote for

about two years in the vision.

687

:en my start date was April of:

688

:

And as you can know, obviously I

did not get to start, uh, in office.

689

:

And so it, uh, COVID hit and I

joined and they went fully remote.

690

:

And it actually turned out to be

very useful that I had two years of

691

:

experience leading remote engineering

teams, because now I was forced to

692

:

lead a remote engineering team again.

693

:

Great, uh, great culture at the company

and we really just pushed hard on making

694

:

that pivot from on premise to cloud.

695

:

We shifted our hiring strategy,

shifted our architecture

696

:

philosophy about how we're going

to invest and just went all in.

697

:

It was going exceptionally well, uh,

so well, in fact, that Toma Bravo

698

:

noticed and, uh, they, uh, they came

and acquired us, um, in, uh,:

699

:

Uh, but it was a great journey,

grew that business tremendously.

700

:

Uh, I think we more than doubled ARR, uh,

in the time that I was there, I think,

701

:

and that has continued since and, uh, and

then the private world, uh, but it was a

702

:

great experience to, to lead a engineering

at a, at a public software company.

703

:

Eric Brooke: So you mentioned

already what you, um, see is

704

:

the difference in the public.

705

:

Were there any other changes in terms

of, like, yes, you have a formal

706

:

relationship with the board, you have

stakeholders, that's your executive team.

707

:

From that particular job, were there

things that you come away from?

708

:

I learned that there.

709

:

It's still

710

:

Asanka Jayasuriya: fine.

711

:

I think I learned the.

712

:

Real focus in a public company

on quarterly reporting.

713

:

Um, I mean, when you make

commitments and revenue commitments

714

:

associated with product launches.

715

:

And that goes to the street and to

investors, like that's significant, right?

716

:

Like, you know, it's,

it's very, very different.

717

:

And so I just learned that that

pressure can be pretty significant.

718

:

And you have to, as a result, be a

little bit more conservative in how

719

:

you plan your roadmaps and what you

announce, uh, to both very publicly,

720

:

because once you announce publicly,

like there are revenue implications

721

:

and, you know, Wall Street, Okay.

722

:

Implications of what that means.

723

:

So learning that ability to be a

bit more conservative externally,

724

:

but more aggressive internally

was a little bit different.

725

:

Eric Brooke: Okay.

726

:

And so what's next in your career?

727

:

Asanka Jayasuriya: So after the sale

point acquisition, uh, you know, I had

728

:

a conversation with my leader and, you

know, if I wanted to stay on and be

729

:

in, uh, continue the private equity

journey, and it wasn't really for me.

730

:

Um, I've always been

much more of a builder.

731

:

I like to build and

explore and private equity.

732

:

So much more tends to be much more

disciplined, financially driven journey.

733

:

And it just, it wasn't

a path that I wanted.

734

:

I decided to take, uh, some time off.

735

:

My goal is to take about a year off.

736

:

Um, I spent a lot of time riding my

bike, uh, went down to Columbia with some

737

:

good friends of mine, rode bikes in the

mountains, went to the Galapagos with

738

:

my family, uh, traveled around quite a

bit, started playing a lot of pickleball.

739

:

I'm really just kind of unwound

for about six to nine months.

740

:

It's the first, first break in my career.

741

:

I mean, I started my career when I was 20.

742

:

Because when I took that

internship, I never actually

743

:

went back to school full time.

744

:

I just finished my degree part

time and stayed working full time.

745

:

So I had been, you know, 23 years without

more than probably 2 weeks off at a time.

746

:

And I was looking forward

to my first career break.

747

:

And so I really just kind of

disconnected from everything for a while.

748

:

And just a lot of pickleball,

a lot of bike riding, a

749

:

little bit of travel, skiing.

750

:

Yeah, it was, it was a good,

it was a good career break.

751

:

Eric Brooke: Yeah.

752

:

And this, um, What were the

things you would say that

753

:

you got from a career break?

754

:

You got to relax.

755

:

What other things would you say?

756

:

Um, do you think career

breaks are a good thing?

757

:

Asanka Jayasuriya: Oh, I, I, I will

caveat this in a couple of different ways.

758

:

I think they can be a good thing when they

come at the right moment in your career.

759

:

And when I say that, like for me, it's

like financially it was in a good position

760

:

where like, that wasn't really a concern.

761

:

Um, my kids were at the right age

where like, You know, do a bunch more

762

:

traveling and fun things with Ben.

763

:

Um, and that was, was great.

764

:

And it let me really recover.

765

:

I mean, I, I didn't really realize

like how much kind of the pressure

766

:

of being in these leadership book,

uh, you know, successively bigger

767

:

leadership roles and take it.

768

:

And I, I didn't realize actually until

probably about 6 or 8 weeks into my break

769

:

about like how tired I actually was.

770

:

And that I was losing the energy and kind

of the excitement around building things.

771

:

Uh, and so it was perfect

from that perspective for me,

772

:

uh, to get that rejuvenation.

773

:

I see a lot of things on LinkedIn

of folks taking like career

774

:

breaks in their early 20s.

775

:

And maybe I'm just like an old

cynic now, but I think that's

776

:

probably a little bit too.

777

:

Too soon.

778

:

I think you gotta, you gotta

bring some miles first before

779

:

you, before you do that.

780

:

Awesome.

781

:

Eric Brooke: Thank you.

782

:

So, Galapagos.

783

:

Awesome.

784

:

Um, what was next in your journey?

785

:

Asanka Jayasuriya: So the next, I wasn't,

I had no real plan, um, but kind of

786

:

backed into two different opportunities,

uh, through very unlikely paths.

787

:

So the first was actually

through the Galapagos.

788

:

Um, we were on a On a cruise of the

islands there, which I highly recommend

789

:

to do at some point in your life, the

wildlife and it's just incredible, but it

790

:

was a small boat, probably for 20 people

and there was another family on that boat.

791

:

And the father of that family was

managing director at new mountain

792

:

capital, a private equity company.

793

:

No, he asked me, Hey, do you have any

interest in ever doing stuff with PE?

794

:

And I said, no, not really.

795

:

And then, uh, he reached out

again later and he's like, why

796

:

don't you just come meet with us?

797

:

You know, we, you know,

we're not like a typical PE.

798

:

We, we believe in investing

and growing and it was true.

799

:

And so I joined them as an executive

advisor, uh, not really a full time job,

800

:

but I helped them with due diligence.

801

:

Uh, technical strategy, product strategy,

um, great group to be working with.

802

:

So I started dipping my toe in with that.

803

:

The other thing that happened was I was

playing a lot of pickleball and two,

804

:

uh, guys in my neighborhood had built a

pickleball court and one of my friends

805

:

knew them and I was like, I got to.

806

:

No, these guys, I want to put on

their, you know, their private court.

807

:

And, uh, they introduced me and

started playing pickleball with them.

808

:

And they were two of the founders of

ABC who had moved from San Francisco

809

:

to Austin during the pandemic.

810

:

Uh, the headquarters of the

firm had actually moved here.

811

:

Uh, so Joe Lonsdale was the, was

the GP and founder of the fund

812

:

and he moved, uh, headquarters

to fund here during the pandemic.

813

:

And after playing with them

for a while, they just said,

814

:

are you going to work again?

815

:

What are you doing?

816

:

I'm like, I have no real plans.

817

:

And so I said, Hey, we could

use some help with some advisory

818

:

stuff for some of our companies.

819

:

So I started dipping my toe, you know,

advising some other companies on portfolio

820

:

companies on product and engineering.

821

:

Um, Yeah.

822

:

Yeah.

823

:

Yeah.

824

:

And that kind of has grown slowly

until eventually they said, why

825

:

don't you join as our portfolio CTO?

826

:

And ultimately I did, uh, even

though, you know, what exactly

827

:

a portfolio CTO remains, a work

in progress as we define that.

828

:

Uh, but the real reason I

joined ABC is, you know, they

829

:

believe in building companies.

830

:

They actually incubate, you know,

seven to 10 companies a year.

831

:

And just investing was not something

I thought would really appeal to me,

832

:

and it still actually really doesn't.

833

:

But I really get to get involved

with these companies as they're

834

:

built, help them solve problems,

and that's just a lot of fun.

835

:

Eric Brooke: So you're now

kind of mentoring multiple

836

:

CTOs and multiple companies.

837

:

Are there kind of common patterns

that you see that CTOs could either be

838

:

better at, or that you see CTOs facing?

839

:

Yeah, so there's 1

840

:

Asanka Jayasuriya: very emergent topic

that's across, I think, most of our

841

:

portfolio companies and actually in

my CTO networks is the question that's

842

:

coming up more and more than ever in my

career is how productive is engineering.

843

:

Uh, you know, when resources were plenty

and money was plenty, you know, often

844

:

you'd see companies evaluating CTOs and

how quickly they were hiring engineers.

845

:

Like, that's the success metric.

846

:

Like, look at how many

engineers we hired last quarter.

847

:

Well, guess what?

848

:

That is no longer the success

metric, I think, for just

849

:

about any company in the world.

850

:

Maybe there's a handful where

that's still a success metric.

851

:

But then the questions really started

to come of like, okay, we've grown

852

:

engineering and product this much.

853

:

What did we get for it?

854

:

Like, are we going faster?

855

:

Are we shipping more customer value?

856

:

And the thing that everybody is

struggling with, I think, is we

857

:

don't really have good frameworks as

engineering leaders to report that stuff.

858

:

Um, you know, we have sprint

metrics, we have velocity.

859

:

Those are, you know, you can't

put that in a board slide and

860

:

say, look, here's our velocity.

861

:

It's like, it's like, what does that mean?

862

:

Like, are we better?

863

:

Are we good?

864

:

Is it bad?

865

:

Like, and that is, I think the, one of

the biggest common things I see across

866

:

our portfolio and other companies, even

public companies right now is how do we

867

:

get better at answering the question?

868

:

Of how good is engineering how

efficient is it what is more dollars

869

:

into engineering and product mean and

value to customers and it can often be

870

:

difficult because you know when I had

CRO partners who have intensely metrics

871

:

of an organization like look there's my

quota metric why don't you give a quota

872

:

to your engineers well it doesn't really

work the same way and you know there's

873

:

a lot of different reasons but those

conversations are becoming more and more

874

:

real and I see that everywhere right now.

875

:

Thank

876

:

Eric Brooke: you.

877

:

Um, so like, I guess that feeds

in very well to what are you

878

:

seeing in the current market?

879

:

Why do them say your portfolio?

880

:

But what are you seeing in technology?

881

:

Asanka Jayasuriya: Yeah, I think

actually, uh, there's a blog post that

882

:

a colleague of mine just pushed out on

LinkedIn, which I highly recommend just

883

:

talking about the state of venture and

how different it is now than it was.

884

:

Um, and so when I look broad, I see

a few different things happening.

885

:

One, there is far less funding

happening right now for startups.

886

:

I think it is going to be very challenging

for a lot of the later stage, like

887

:

series B series C's companies that

are going out to looking for funding.

888

:

It's going to be harder to get checks.

889

:

I think we're going to see many,

many more companies disappear

890

:

and go under for that reason.

891

:

Same time, I think it's going to

be very exciting at the seed stage.

892

:

There's a lot of activity there

and a lot of good founders and

893

:

so it's a focus now, though.

894

:

I'm not just, Hey, I have an idea.

895

:

It's like, I have an idea

to build a real business.

896

:

And I think that's.

897

:

Honestly, that's just not something

that was there over the last 10

898

:

years, especially the last few years.

899

:

I have an idea to do X.

900

:

Like, I don't know if

we'll ever make money.

901

:

Great.

902

:

Here's 10 million, right?

903

:

Like, that's not really happening anymore.

904

:

Um, so that, that is a big change

that I'm seeing kind of broader.

905

:

And so I think we'll see venture

get smaller, uh, in terms of the

906

:

number of venture firms out there,

the number of people employed

907

:

in venture will get smaller.

908

:

And I think also just from a product

and engineering perspective, I think

909

:

the valuations for like enterprise

software companies, you know, they have

910

:

come down and people say, oh, they'll

go back and like, I'm not so convinced.

911

:

I actually think that the

valuations now are back to normal

912

:

and back to where they should be.

913

:

And I'm actually a little bit excited now

because it's kind of going back to the

914

:

roots of when I started my career of like,

you don't have abundant resources, you're

915

:

going to have to scrap and fight for

every dollar and making everything work.

916

:

And it's going to be a

little bit more of a grind.

917

:

But I think from that, we're going to

see the true, really good engineering

918

:

leaders that true companies get born.

919

:

Um, you know, I was saying, I think

it's true that The biggest companies get

920

:

born during the hardest times, right?

921

:

Like, if you think about all the

juggernauts we have in the industry

922

:

today, the sales forces service now

work day, like all these guys, they

923

:

all came out of the dot com crash.

924

:

That's when they all cut their teeth.

925

:Um, and then in:

926

:

Like, that's when they started to have

the Googles and all that comes into play.

927

:

I think that's something I recommend

everyone think about is these

928

:

times when things seem the worst is

often when the next wave of biggest

929

:

things are going to be built.

930

:

And I'm pretty excited for that.

931

:

Eric Brooke: Thank you, Sonka.

932

:

Is there something that you're

working through or digging into

933

:

and investigating at this time?

934

:

Asanka Jayasuriya: Obviously, this

is going to be a huge shocker.

935

:

It's

936

:

Tim Winkler: AI, right?

937

:

That is,

938

:

Asanka Jayasuriya: uh, uh, you

know, taking everyone's focus.

939

:

And, you know, for the first time in

over 10 years, I'm actually hands on

940

:

playing with this stuff to learn it.

941

:

I believe that it is going to be

as big as the internet was like

942

:

that transformation that happened

s, early:

943

:

I believe that's what AI is going to do.

944

:

I disagree with the time scale that

most people think it's going to happen.

945

:

I think already we're seeing

companies raise, you know, nine

946

:

figure rounds on very little ideas.

947

:

You know, I think sometimes we

don't learn from our mistakes

948

:

and you see that happening, but I

think what is going to happen is.

949

:

There's this period of what right

now I think of extreme hype around

950

:

AI, going to be followed very quickly

by a period of disillusionment of

951

:

like, oh, this can't do everything.

952

:

But over the next two to three years,

I do expect to change the world.

953

:

I just think right now everyone's

expecting too much of it too soon.

954

:

But it is going to come.

955

:

It's, it's very clear that it's going

to change how we build software.

956

:

It's going to change how I think

every service gets delivered.

957

:

It's going to change education.

958

:

Um, I think it's the most important

area to invest in learning and

959

:

having a foundation right now.

960

:

Yeah,

961

:

Eric Brooke: I concur.

962

:

It's um, this is like an

industrial revolution for, as

963

:

you say, moving us to next step.

964

:

Thank you for sharing your journey.

965

:

Um, so just checking in.

966

:

What are the things that have helped

you grow or scale as you have?

967

:

You mentioned earlier that mentors,

um, you mentioned kind of community,

968

:

um, there may be books, podcasts, but

what would you recommend to either

969

:

prospective CTOs or CTOs now as a

source or recon of intelligence?

970

:

Asanka Jayasuriya: So again, once

you get to the CTO level, I really do

971

:

believe it's about networking, uh, both.

972

:

Years, so people who are solving

and dealing with similar problems

973

:

to you, but also maintaining a few

people that have gone further than

974

:

you, that you can go to for advice.

975

:

And I was really lucky to have kind of

those people throughout my career, just

976

:

a few steps ahead on the path than you.

977

:

So they can give you that feedback.

978

:

But I believe as a CTO, that is just

absolutely the way you have to do it.

979

:

You have to invest in building and.

980

:

Network of people that you can

reach out to rely on, but also you

981

:

have to pay that forward, right?

982

:

A big part of.

983

:

My belief is like, anytime somebody

asks me for help, I do my best to

984

:

say yes, because I think that all

comes back to you at some point.

985

:

Like, I don't, that's not why I do it,

but I do believe that, you know, doing

986

:

your best to help people, it ultimately

will come back to you, uh, down the road.

987

:

And so, as much as you look out to build

your network, someone reaches out to you

988

:

to ask you a question for something or

some career advice are about the time.

989

:

You don't know when that pays dividends

for you down the road, and you are

990

:

going to need to do that yourself.

991

:

guys.

992

:

Ciao.

993

:

Awesome.

994

:

Eric Brooke: Thank you, Saka.

995

:

So you've described a

lot of what you've done.

996

:

What do you do for fun?

997

:

Um, so I

998

:

Asanka Jayasuriya: have two boys, uh, two

teenage boys that keep me pretty busy, but

999

:

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: Is there a movie

you're looking forward to?

::

Asanka Jayasuriya: 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: 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: it.

::

Yeah, it was great being here.

::

Thanks for having me.

::

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::

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