Transcription:

I want to say again, as always, welcome to another episode of ‘Preparing the Unprepared.’ This is the podcast that aims to help people in data make much smarter career and hiring decisions. Today, I’m actually going to be joined by Kevin Goldsmith, who’s the newly appointed CTO at Anaconda. Kevin, where do I start? He’s an extremely well-rounded technical leader who, over the past few years has worked for some really well-known companies, including Microsoft, Adobe, Spotify and so many others.

He’s got an endless list of publications, patents, Keynotes, and interviews that cover everything from giving advice on how to as a startup, compete against big companies all the way through to some more really big technical dives into things like how to fight fraudsters with computer vision. So with that being said, I spotted an opportunity. There was a topic that somehow he hadn’t covered yet, and that was ‘what the CTO onboarding process looked like.’ So I saw a post that Kevin put out recently and I didn’t really know him at all before I reached and said, hey, look, I’ve got this idea for an episode of my podcast. And to my surprise, which I say that on the basis that I can imagine how busy is right now, he said, sure, let’s chat. So, look, without further ado, welcome to the show, Kevin.

Kevin: Yes, Thank you. Thank you for the very nice introduction. I’ll do my best.

Lewis:  Well, I know you’re no stranger to these kind of interviews, so I’m very excited to learn a little bit from you as well. Look, some of the topics we’re hoping to cover are going to be a look into your journey through tech, hoping to understand what skills are needed to become a great CTO. I’m very keen in fact to understand what it’s like joining an established company or an established team as a new CTO what those first few months look like and then,  hopefully, providing the best practices, some advice to aspiring CTO’s or businesses who are actually looking to hire senior-level technical leaders. And obviously, this is a pretty rare opportunity. So, as always, with my shows, which are normally on Thursday at 11, this is one we threw in here. We have a lot of Q&A throughout. So if there’s something specific you want to know, feel free to ask away and we’ll post up the questions here on the live. But I’m looking forward to the chat. And you had a fantastic start, you’ve been in the industry for many years. Maybe you can talk us through kind of your journey. of where you’ve been and where you are now.

Kevin: I’ll try and do the reasonably short version. So, yes, I went to school for computer science back in the last century. And when I graduated back then, there weren’t a tonne of startups. It was pretty much just big companies. And I was very much into graphics in university. And so I went to go work for a company called Silicon Graphics, which was focused on building computer graphics hardware. And so I was very lucky to find a role with one of the bigger companies doing the stuff I cared about and that happened to be in the Bay Area. So then I was now in the Bay Area. I did that for a little bit. I went from there to a film and picture film and TV studio to do computer graphics for TV shows and motion pictures. And that was sort of an interesting time as these new studios, that technology was becoming more accessible and all these new studios were popping up. And some of these more established studios, like the one I worked at, were struggling a little bit around price and things like that. The studio didn’t do too well. I ended up going to Microsoft Research, so I joined Microsoft literally, I think the week or two before Windows 95 shipped. So I joined Microsoft Research right as it started. And that was a cool time to be there because, yes, it was really, early. They were building a new graphics group. I got to hang out with the people who wrote my textbooks at college and things like that, which was awesome. I spent several years there and then decided I wanted to be closer to actual product development, joined the Windows Media team, which at the time, you know, streaming was just really getting started. Real was out. Windows Media was going. I did that and during this time, all the startups were going on and this was the kind of dot-com explosion. And I decided, you know, after having been at a company, when I joined Microsoft in the year, there were maybe eighteen thousand people, which was a big company. But when I left in 2000, it was 80,000 people.

So I went from that to a company that was about 50 people. So I really wanted to do something a little bit different. Then the dot-com bust happened. So that start-up went down. My next startup, I started a startup with some people. That startup went down. We couldn’t find any money, went back to Microsoft, was there for a couple of years, and the Windows CE team. And then Adobe called. I went to Adobe and I was very, very lucky. Adobe was a really great company to work for. I very much enjoyed my time there. Prior to that I would be a senior developer or I’d be a lead or sometimes I was a manager, sometimes I was a developer. I kind of went back and forth. At Adobe, I joined this team and there was no manager. And after being with the team for a little bit as the senior developer, I decided, you know what? Actually, I think I would like to move into management for real. And that kind of started me on my management path. And so at Adobe, I was a manager and then senior manager, then director. I grew this one team from its beginning to about 14 people, then joined this new product team called Adobe Rebel. I grew that to be about fifty people, building a whole new product family for Adobe, which was more in the consumer space, which kind of brought me to the attention of Spotify.

Spotify contacted me. They needed someone to run, essentially the product engineering team. And so I joined Spotify and moved to Sweden with my family. And so I was there for years, grew that, became VP of engineering at Spotify. And after having been there for a few years, I was kind of ready to do the next level.

And I became a CTO. I moved back to Seattle to be CTO at a company called, Avvo. Avvo had been around for a while. But this was my first time stepping into a CTO role in an existing company that helped the company for a few years. It had been getting challenged by Google. We kind of got it into a bit of a better place and started looking at possible acquisitions, which interestingly made us an acquisition target. So we got acquired, a successful exit there, and me and the rest of the leadership team, we were a growth team. It was moving into being more of a performance company. So we all kind of went our separate ways. Did another early-stage startup as a favor for a friend that was a VC and then went to Onfido where I was CTO. That was in London. Again, CTO joining an existing company I was there through the pandemic when the pandemic happened.

Because I’ve been actually kind of going back and forth from London to Seattle, my family was still here when the pandemic happened. I said, all right, I’m going to go back to Seattle, went before London lockdown. So I worked for Onfido remotely for a while and that just wasn’t working. So I moved on and then now at Anaconda. So, yeah, I’ve done this ‘join a new company as CTO’ or ‘join an existing company as CTO’, Now this will be my third time.