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

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0:33Hello, and welcome back to the Scaling Europe show presented by Deal. I'm Seth Johnson. Today, I'm here with Glenn, the CEO of CloudSmith. Glenn, thank you for joining me. How are you doing today?

0:41Glenn Weinstein:It's great to be here. I'm great, Seth. How are you? I'm very good, thank you. I'm super excited for this conversation. For those who don't know CloudSmith, can you give a sort of like 30-second quick pitch? 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. Amazing. You raised a big Series B,$23 million, I believe, from TCV and Insight Partners, which is great. How was raising that route? 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.

1:25Glenn Weinstein:I think JFrog and Sonotype are both pretty long in the tooth, and there's a lot of investor interest in funding the next generation of solutions. Amazing. And I want to get a bit into your own career, because, you know, you are the CEO of CloudSmith. You're building from Belfast, but you're not Northern Irish. And you have had some history, well, a decent amount of history in the software space itself. You were chief customer officer at Twilio. And before that, you were a co-founder and CTO of your own business. But before that, you had a military background. Is that right? That's right. I'm a graduate of the U.S.

1:56Glenn Weinstein:Naval Academy, and I was a naval aviator for eight years before getting into software. And what about software attracted you after having that background? 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. Amazing. And you joined CloudSmith as a CEO. This is not one of the companies that you founded yourself. you had some you've had an amazing experience at companies like twilio that are sort of i don't know generational companies in their space what about the job of ceo at cloud smith was it that really kind of attracted you well the the space primarily i'm a coder at heart and cloud smith is as close to the developer experience as you can get it's really about how modern software development teams something that was already i mean i joined in 2023 it was already an incredibly changing field from what I remember as a coder and as a team leader.

2:50Glenn Weinstein: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. 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 a life i'm living the dream life honestly i always describe just having the time of my life um you know cut to 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 but um to be immersed in the problems of of coders and to be surrounded by other people that find this somewhat esoteric topic to be endlessly interesting is a is kind of a dream job for me.

3:41Glenn Weinstein: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. Amazing. And how long, it's been two, two and a half years now? 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.

4:19Glenn Weinstein: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. And how's that been? How's that transition been from, you know, I guess, targeting smaller players to these trying to win over these large enterprise contracts? Well, we had to finish the product.

4:51Glenn Weinstein:First of all, we had to achieve feature parity with JFrog's flagship offering, which was Artifactory and Sonatype's main product, which is the Nexus repository. We've achieved that. And I think our results show for itself. We're winning Fortune 500 companies, Fortune 100 companies in global 2000. So we've achieved that feature parity. What's next and what we're really excited about is building a next generation software supply chain security platform. We all know the world of software development is changing rapidly. It's being done more by AI agents than by developers with hands on keyboard. And we're kind of made for this moment.

5:25And yeah, how has that transitional change impacted the way that you're thinking about your product roadmap and go to market? Are you having to build new things for this world where software is being so so often built by ai yeah well you know i think at its

5:39Glenn Weinstein:heart software is still built by by developers who have an idea in mind of what customers need and they're they're still the designers and they're still the architects and crowdsmith kind of achieves a perfect fit for a world where you kind of need context and you need some guard rails as to what you want your tooling to build i don't think we all want to go to a world where we build everything from scratch again. I remember that world and it's not super productive. There's a reason open source libraries and open source software have become so dominant with human developers and they're just as important, if not honestly much more important in a world where we're building more software than ever.

6:16And are you finding different use cases crop up with your customers? You know, I don't know. It's interesting. Like, are things changing from their perspective? Are they asking for different things now? Or are they, yeah, are they requesting different features than maybe they were two and a half years ago?

6:30Glenn Weinstein:I think it's a little bit more anticipation of what might change than actual change in large enterprises. The one thing that definitely is new, and we saw last year, was demand for programming around ML models and data sets. You know, we've added format support for things like proxying and caching hugging face as an upstream. So you pull down a model from hugging face, you want to inspect it, kind of scan it, and then program against it. So that's new. But I don't think we've really seen the full impact of brand new developer workflows. I think we're literally going to see them in the next coming months.

7:04Glenn Weinstein:But so far, like it's a little bit more anticipatory. And what's it like building in a software company at the moment, given everything that's going on with the public markets and software companies? We've seen this big sell-off. And, you know, I personally think it's probably overhyped, but it feels like there's going to be some companies who are well positioned. And I think maybe Classmouth is one of them, given that you are, you know, building tools that are going to be leveraged despite AI. What's it like building that at the moment? So I think as the operator of a company, to some extent, you put your head down and you solve your customers' problems.

7:34Glenn Weinstein:And customers are like one step removed from the investor community and thinking about, does this change everything? At some point, you just have got to deliver functions and features to your customers. So we're kind of living in the world of reality. But, you know, there's a tidal wave on the horizon and everybody sees it. I think we're just focused on winning customers. And I do think category-wise that we are a beneficiary of a move towards more agentic software development. You see JFrog, which is a public company, and you can sort of think of as a proxy for the fortunes of CloudSmith, is typically viewed in the winner column of what happens to the software supply chain when you build more software, more autonomously, faster, possibly more dangerously.

8:17Glenn Weinstein:You know, you need context at Cartwell. So if that's true for JFrog, it's doubly true for CloudSmith. And it's great to have that sort of public comparison to be able to compare yourself against and use as your own benchmark, I guess. I always want to talk about building from Belfast. You know, you're an American building in Belfast. What's that experience been like? Well, I first came to Belfast in 2005 when I was running customer support for Borlands and we acquired a company with an office in Belfast. So I spent a whole bunch of trips back then for a year or so. What a different city Belfast was in my memories of 2005 compared to today.

8:52Glenn Weinstein:Holy cow. You know, it's just a thriving like little mini-megapolis today, just commercial hub. It's a big tourist hub, which is unimaginable for Belfast. But it's also definitely a technology and a software hub. You know, we're part of the local community. We're members of Software NI and the NI Chamber of Commerce. And Cosmin's a really big local success story. We employ mostly software developers from Belfast. that's our largest location, the second largest being Dublin. And we're really proud members of that community. And we find really deep talent from the likes of Ulster University and Cleans University.

9:25Glenn Weinstein:And this will always be our hometown and always be a big part of the Cosmouth personality. That's interesting. I really wanted to get into talent because Belfast is definitely a growing tech hub, a tech ecosystem. How do you find it? Is there a lot of competition for the talent that does exist there? Or is there more talent than tech, I guess? Well, there is competition. So there's two fundamental kind of types of companies in Belfast. There's the multinationals, the all-states and afflecs of the world that have set up shop and made really sizable development centers there. And we're trying to make them our customers.

9:59Glenn Weinstein:And then you've got just software companies. A lot of scale-ups, a lot of the likes of like a Bizarro Voice slice. I know just there's a whole long slew of companies with big presences in Belfast. That's a really tough recruiting challenge for us. But like the talent is abounding there. So it doesn't feel tight yet. We, some of our most senior architects and really like the leaders in their field are just locals that are happy to work for a company that, you know, flies the Belfast banner, I guess. And you're building a global company, right? What's that experience doing it from, I guess, one of the smaller hubs in Europe?

10:36Glenn Weinstein:Well, that's an interesting point because from the beginning, Carl Smith had a very global customer base. It's certainly true today. 80 % of our revenue is from U.S.-based companies. That's not going to change. I mean, when you look at Fortune 500, this is a very U.S.-dominated list. We have our share of large European and Asian customers, but there's a deep-seated kind of almost like just a grain of doubt in the Northern Irish psyche of, is it really possible that a Northern Irish company can be an absolute leader and take on and beat Silicon Valley and all the great companies coming out of Europe?

11:13Glenn Weinstein:And the answer is yes. And we're proving it. We have a little bit left to prove. But that has been a big part of CloudSmith. It's just like standing up tall, shouting from the rooftops and saying, this is a Belfast-based company that is a world leader and we're going to change history out of Belfast. And you say it often enough and people believe you. And I think, you know, I'd like to think our Northern Irish workforce does believe it. Amazing. And given that so much of your revenue is coming from the US, how are you managing that? Have you got people on the ground there? Are you covering all time zones?

11:44What does that look like?

11:45Glenn Weinstein:So the reality is we're just building a go-to-market team in the U.S. I split my time half in New York and half in Belfast. I got an apartment there when I took the job, and I love living in Belfast. But we're starting to hire sales leaders, sales executives, solutions engineers, the usual complement of an enterprise sales force, enterprise marketing. My head of growth marketing is in Boston. So we're kind of slowly building up. But we've actually built the current day CloudSmith to a very large extent using a Europe-based and really primarily UK and Ireland-based sales team. We've sold some of our largest Fortune 500 companies with a UK and Irish-based sales team.

12:25Glenn Weinstein:So it can be done. But I think the next stage of growth, we do need to be a little closer to our customers. And what is that going to look like? Are you thinking about New York, San Francisco, some of the hubs in between? We're kind of moving as a wave. So right now, East Coast is, you know, I say I live in New York. I think New York, Boston, Washington, that corridor is pretty much where all of our hiring is. San Francisco is so far away from a time zone perspective. It's a killer. We will eventually reach the shores of the Pacific Ocean. But I kind of feel like that's a few waves away for us.

12:58Yeah, you've got to just keep expanding, I guess, at the old Western frontier. Did you find yourself doing a lot of sales? Is that one of the key elements of your role still?

13:07Glenn Weinstein:I think so. So, you know, our two co-founders, Alan Carson and Lee Skillen, they're both Belfast guys, one from Queens University, one from Ulster. And they're fundamentally product people at heart. They have created a product they wish they had as software developers. And they did all the sales and all the marketing, you know, until I showed up. So I can help augment that. My career has primarily been in go-to-market. It's been customer success and customer support and consulting. So it's a bit more of a natural fit for me maybe. but again, we're growing fast enough now that we have professional sales team.

13:39Glenn Weinstein:We have a great head of sales and I'm starting to slip into that typical CEO role of evangelist and cheerleader and what's coming over the horizon a little bit and we have great sales team already in place. That's amazing. It sounds like things are going really well and you're being ambitious about getting to the US properly. Things are growing. You've got an amazing product where you said you mentioned you've got complete feature parity of some of those competitors. What do you think you've got right? over the last two and a half years? And more broadly, what has the company got right to get all the way here that you think maybe others failed to do so?

14:12Glenn Weinstein:So Cloudsman got one thing right that attracted me to a company just to become CEO, which is building on a cloud-native platform. It's a bit shocking to me that the two market leaders in this space, JFrog and Summitsub, are fundamentally single-tenant products. They're from the early 2000s. They'd never changed their architecture. And their version of a cloud tool is kind of like stringed together a bunch of nodes of the same old runtime they've been selling for 15 plus years. In most other industries, the cloud-native massive scale solution has become dominant because it can just deliver better scale, better performance, better reliability.

14:48Glenn Weinstein:And that's exactly what's allowed CloudSmith to succeed. You can't say to us, we want to buy and run our own copy of CloudSmith. Like that's kind of like, I want my own copy of Gmail or something like that and my own copy of Salesforce. It just doesn't work that way. And you actually don't want it to work that way. So that's been the fundamental secret sauce. Now, in a way, customers don't care. I just want to know, like, what results does that give me? But it does give a really important result, which is scalability, reliability, breadth of support, all the things that just make car companies grow faster.

15:19Glenn Weinstein:And that's kind of where we're at now. We're at that inflection point where we're able to add a lot more to the platform a lot faster. Amazing. And are you, you know, really focused on improving the product? I mean, it sounds like, you know, GTM and expanding across the U.S. is a big priority for this year. What kind of priorities are you looking at for improving the product and user experience? Well, so user experience is important. When we say we really mean the developer experience. So, you know, again, I don't think the role of developer is going away, even if your hands are not on the keyboard writing the code and understanding what your dependency trees look like and what is my exposure to the software supply chain.

15:53Glenn Weinstein:We want that to be a positive developer experience where traditionally it's been a negative. It just means builds break or things are too slow. So we're very focused on like we want developers to love either be an unaware of CloudSmith or to love CloudSmith. And we don't want to get in the way like the tools in this space traditionally had, especially when you start getting into the whole idea that we're a little bit of a kind of a software supply chain security company, too, because we do scanning and vulnerabilities and license checking and things. So we're trying to add value to the developer experience.

16:23Glenn Weinstein:But more broadly, we have a little saying internally that we don't want to just manage and control the software supply chain. We want to be the software supply chain. And we think at scale, that's kind of what happens. We've kind of cached everything. We've scanned everything. You run your rules inside of CloudSmith. But, you know, the idea that you go out to PyPy or Docker Hub every time you need a binary, like, they should kind of already be there. And in CloudSmith scale, we'll just pretty much already have them. Yeah, amazing. And, you know, when I was doing my research, I was reading about your series, Ben.

16:54And I think you raised it March 2025. And you said in the run-ups of that year in 2024, you grew 150%. Is there anything that you can share about your growth last year? Was it close to that, equal, greater?

17:06Glenn Weinstein:Yeah, it was close to that. Not quite that high, but close to that. You know, enough that there's obviously something happening here. Something that, you know, we're in a space that we're not able to really grow 1 ,000 % a year. You know, we're trying to convince large enterprises to make a pretty important change to the way that they manage their software development. That's not the kind of thing where, you know, everybody just raises their hand all at once and says, yeah, we'll change. You know, there's some dependency on renewal cycles and catching some champions that are interested in innovating and improving their own developer experience.

17:40Glenn Weinstein:So 100 % growth in that environment is a pretty good target, actually. And I think we'll be one of those companies that just sort of grows, I don't want to say steadily because that sounds like it's slow, but you know we will pick up market share in a very kind of systematic fashion uh kind of slowly and all at once and before you know it you know we're kind of an industry standard i look at the role models like workday which displaced people soft which seemed like it wasn't going to go anywhere why would anybody change that but over time like people did accept that yeah we're going to run on a cloud-based hr system we're going to run a cloud-based crm cloud-based so that's kind of the position we're in.

18:19Glenn Weinstein:I think 100 % growth for us is actually a great target. Yeah, absolutely. Is that what you're targeting for this year as well, Ben? Oh, yeah, yeah, yeah. That's the plan from here on out is just to try to double the company each year. Now, I can do math. You can't do that to infinity, but you can do it for a while, you know, until you pick up a majority of market share and then, you know, inevitably things will level off. But we have plenty of runway the way we're going now where we can replace a pretty important system at a lot of Fortune 500 and Global 2000 companies. That's amazing. doubling every year is phenomenal.

18:49When you look back over five or six years, suddenly you've grown whatever it is, 15 or 20x over that period of time. It compounds very quickly.

18:56Glenn Weinstein:That's right. You have to just sort of temper your emotions when you see AI companies putting up these incredible 500, 600 ,000 % growth numbers. It's not who we are, and that's okay. We are who we are, and we're happy being who we are. But we have a very significant role to play as AI infrastructure for the future. Yeah, absolutely. So you're going to play a pivotal role in the transformation in the next few years. I always wanted to ask how you're balancing or if at all balancing, being in this kind of series B scale up stage where you're still looking to double every single year. Are you looking at all to try and achieve profitability or scale unit economics?

19:29Are you thinking about that at the moment or are you still laser focused on growth and expansion?

19:33Glenn Weinstein:Profitability, not so much. I mean, you know, just a kind of a numbers game at 100 % growth. You've got to hire sales and marketing ahead of demand. You've got to build engineering. But efficiency, absolutely. Listen, the whole play of being cloud native means that we should be able to deliver the same binaries to hundreds, thousands, tens of thousands of customers in a more efficient way. So gross margin is a very key focus for us. We need to run a really efficient worldwide caching infrastructure. And the great thing about that is it's exactly what customers want. They want binaries cached close to the edge.