From U.S. Navy pilot to CEO of Cloudsmith: Glenn Weinstein, CEO at Cloudsmith

Sebastian Johnson (0:00)

Hello, and welcome to the Scaling Europe show presented by Deel. This episode is sponsored by SurrealDB, the multimodal database for AI agents, Omni, the AI analytics platform trusted by growing companies like Perplexity and Synthesia, and Venture Comet, the platform that gives startups and scale-ups real-time equity tracking, daily business insights, and automated management information. Thank you for joining me. Please like, comment, and subscribe. Hello, and welcome back to the Scaling Europe show, presented by Deel and Seb Johnson. Today, I'm here with Glenn, the CEO of Cloudsmith. Glenn, thank you for joining me. How are you doing today?

Glenn Weinstein (0:41)

It's great to be here. Great, Seb, how are you?

Sebastian Johnson (0:44)

I'm very good, thank you. I'm super excited for this conversation. Now, for those who don't know Cloudsmith, can you give a sort of like 30 second quick pitch?

Glenn Weinstein (0:51)

Yeah, sure. We're an artifact management platform, relatively new startup slash scale up, coming out of Belfast, Northern Ireland, aimed at the enterprise, taking on companies like JFrog and Sonatype.

Sebastian Johnson (1:04)

Amazing. You raised a big series, $23 million, I believe, from TCV and Insight Partners, which is great. How was raising that route?

Glenn Weinstein (1:15)

It was actually easy. There's a lot of excitement about the idea of a next generation version of software supply chain control and security platforms. I think JFrog and Sonatype are both pretty long in the tooth, and there's a lot of investor interest in funding the next generation of solutions.

Sebastian Johnson (1:32)

Amazing. I want to get a bit into your own career, because you're the CEO of Cloudsmith, you're building from Belfast, but you're not Northern Irish.

You have had some history, well, a decent amount of history in the software space itself. You're Chief Customer Officer at Twilio. Before that, you were co-founder and CTO of your own business, but before that you had a military background, is that right?

Glenn Weinstein (1:55)

That's right. I'm a graduate of the US. Naval Academy and I was a naval aviator for eight years before getting into software.

Sebastian Johnson (2:01)

What about software attracted you after having that background?

Glenn Weinstein (2:04)

Well, that's really my home turf. I was a Commodore 64 kid and I majored in computer science, got a master's degree in computer science. I knew a keyboard and a mouse were my future.

Sebastian Johnson (2:15)

Amazing. I know you joined Cloudsmith as a CEO. This is not one of the companies that you founded yourself. You had an amazing experience at companies like Twilio, those generational companies in their space. What about the job of CEO at Cloudsmith? Was it that really attracted you?

Glenn Weinstein (2:32)

Well, the space primarily. I'm a coder at hard and Cloudsmith is as close to the developer experience as you can get. It's really about how modern software development seems. Something that was already, I joined in 2023, it was already an incredibly changing field from what I remember as a coder and as a team leader. Of course, it's changed immensely even in the last three years, but I wanted to get closer to my heart as a coder. Twilio was close, but actually ended up being a little bit more about telco expertise than about just pure software. Like what a software developers worry about every day.

Sebastian Johnson (3:06)

Super interesting. And how's it been so far? You know, how's the job, did it kind of, has it enabled you to work on the things you wanted to work on? Are you living the developer life?

Glenn Weinstein (3:15)

I'm living the dream life, honestly. I always scrub, just having the time of my life. You know, joining a company out of Northern Ireland was a completely unique experience for me. I'm working on my Northern Irish accents. I'm not doing too well there, but to be immersed in the problems of coders and to be surrounded by other people that find this somewhat esoteric topic to be endlessly interesting is kind of a dream job for me. And it combines my kind of a core skills for leadership, which I feel I earned at the Naval Academy and in the Navy with kind of technical leadership, running software teams and eventually kind of running ProServe and support and CSMs. And I guess you could say my whole career has been leading to this point.

Sebastian Johnson (3:59)

Amazing. And how long has it been? Two and a half years now?

Glenn Weinstein (4:03)

Two and a half years. You know, when I joined Cloudsmith, we were still sort of in our PLG roots. We were aimed at winning over small companies, maybe small teams. And I really thought, and I think the founders of Cloudsmith also thought, there's an enterprise play here. There's a much bigger target in mind for a solution like Cloudsmith. And we pivoted the company to really aim at solving the most complex problems for large organizations with lots of formats, lots of teams, lots of security issues, lots of complexity. And that's kind of what we've been doing the last two and a half years is just building a tool that the largest software development shops in the world can thrive with.