The following interview is a conversation we had with Dylan Etkin, CEO & Co-Founder of Sleuth, on our podcast Category Visionaries. You can view the full episode here: $25 Million Raised to Make Engineering Teams More Efficient

Dylan Etkin
Yeah, thank you too. I’m excited to be here and talk to your audience.

Brett
Super excited for this as well. So to kick things off, could we just start with a quick summary of who you are and a bit more about your background?

Dylan Etkin
Sure. So, as you said, my name is Dylan Edkin. I’m co Founder and CEO at Sleuth. As far as background goes, I spent most of my time as an engineer originally and then a lot of time as an engineering manager. I was fortunate enough to get involved in a small startup at 20 people called Atlassian. Some of you might be familiar, and that was a wild ride, which meant that I got to learn a lot of things and do a lot of different things over the years inside of Atlassian, starting with working on Jira as a developer, one of the first three developers, being the first architect on Jira for about a year, running their BitBucket product. When they made that acquisition, funny enough, left Atlassian, joined a small startup called Status page a year later that was acquired by Atlassian. 

Dylan Etkin
So difficult to escape the mothership, and then eventually striking out on my own and starting Sleuth with my two co founders. 

Brett
So joining Atlassian in 2005, when did you just start to have an idea of like, wow, this is going to be a big company and this is going to be a massive company. Did you know that in 2005, or did it take a few years for that to really become crystal clear?

Dylan Etkin
I think it took a few years. One thing that was true right at the start was they were successful even when I joined. So that was probably two or three years into their lifecycle. And Jiro was one of these things that just caught on like wildfire. So even when I joined and it was only 20 people, we had customers with the likes of Morgan Stanley, and it was this guerrilla product that was just infiltrating the Dev world and I’m probably aging myself here. But it was also kind of hip at the know. The way that I sort of encountered it was this website that hosted a bunch of open source called Codehouse, and all the cool Java projects were up on that. And so I was familiar with Jira. So there was this sense that something very cool was happening. 

Dylan Etkin
But in terms of the juggernaut size of what the company was to become, I think it definitely took a little while for us to realize it was going to get there.

Brett
Was that hard to leave because what was in total, like almost 15 years of your life was basically spent there? Is that hard to make that jump, to go start your own thing? Or was it just the time? And it felt like it was right. 

Dylan Etkin
It was like working at seven different places. So there was the 20 to 40 or 50, there was the 50 to 250. There was the next phase. Then for myself, I started in Sydney and then decided to move my family back to the US. And at that point, Atlassian had built a fairly large office in San Francisco and I moved over here and then I was like running BitBucket, which was like a totally different beast. And then I did leave after about ten years. And that was hard, right, because it was choosing to do something different and then getting brought big back in via an acquisition. 

Dylan Etkin
It was one of these things that was just like, it felt like a tv show and it was a little easier to leave the second time around because I think I had just changed my perspective a little bit. And it was definitely more of a business than a family at that point. And I just had something that I was very passionate and excited to go off and do. 

Brett
As you made that shift from being an engineer to being Founder and CEO, what was like the most challenging thing that you’ve encountered so far? And the reason I ask is a lot of founders listening in are probably in your exact same know, they’re engineers at Google or Facebook, they’re thinking about. 

Dylan Etkin
Starting their own thing. 

Brett
What was the biggest challenge you made or that you went through during that transition? 

Dylan Etkin
Oh, man, I think there’s just so many. I don’t know if there’s a one word answer for that. It’s certainly the visibility of the entire business. Right. So as an engineer, you get to focus on a very specific set of things. You might even have the product side of things siphoned off. But learning about finding product market fit, really listening to the world about the product that you’re trying to build, while also worrying about engineering, understanding that marketing is real, and that marketing is incredibly important. Understanding how sales works, even back office things like how the hell to pay people, that’s part of why you do it, hopefully, is that you want to understand what a business as a whole means. But it’s very different than siloing in. 

Brett
One thing makes a lot of sense. A few questions we’d like to ask, and the goal here is really just to better understand what makes you tick. First one is, what Founder do you admire the most and what do you admire about them?

Dylan Etkin
Right? Yeah. So I was thinking about this, and I’m going to go with something very close to home and personal. So John Kodamal, the CTO of Launchdarkly, and Edith Harbaugh, the former CEO of launchdarkly, they are both close friends. They were early investors in Sleuth and first customers of Sleuth, and honestly have just been the most amazing resource in my personal life. They have been open and free with their advice around what they have done to get to success and have been amazing champions and supporters of our journey as well. I love the company that they built. It’s devtools oriented, and I love the culture that they’ve built inside of their organization. 

Dylan Etkin
And again, having had such personal interactions with them and having been the recipient of so much support, I have to choose them because I hope to pay it forward in the same way that they have with us. And I really admire them for that.

Brett
I admire their outdoor media strategy. I feel like all over San Francisco, when you’re driving around, you see launch darkly billboards everywhere you like. 

Dylan Etkin
Your feature flag fly was a great campaign. Every time I go to the office, or, I mean the airport. 

Brett
Yep. Now, what about books and the way we like to frame this? And we got this from an author named Brian Holiday, but he calls him quake books. So he defines a quake book as a book that rocks you to your core. It just really influences how you think about life and how you approach life. Do any quickbooks come to mind for you? 

Dylan Etkin
I’m going to again, go towards my startup experience here and say that the book accelerate was very impactful. I read that, and I’d already had many ideas in that space, and obviously, to the degree that we’d written some code and brought a product into existence around it, but I loved how articulate they were about the area. And then one of the authors from that, Gene Kim, also wrote a fiction book called the Phoenix Project. And I liked that because I’m a bit of a fiction fan. I struggle through business books a little bit. And I loved that he kind of put some excitement and enthusiasm, but still told us the story of why continuous delivery could be really impactful and exciting and brought it back to manufacturing. 

Dylan Etkin
And I read it and I thought, yeah, all of my thoughts are so much more clear now around this area. And that can be the power of literature.

Brett
Two books I haven’t heard of, but I will definitely have to check those out. That’s the joy of doing the podcast and asking these questions and not having people say the obvious ones. I always love learning about new out.

Dylan Etkin
Cool. I changed my Answer. Lean startup.

Brett
Yeah, what else? And then we go back to the first question about founders. You can just say Elon Musk and Jeff Bezos, and then we’re good.

Dylan Etkin
Yeah, there you go.

Brett
Solo, let’s switch gears now. Let’s dive a bit deeper into Sleuth and everything that you’re doing there. And the way we like to start this is, let’s talk about the problem. So how do you articulate the problem that you solved? And then let’s talk about how you solve that problem. 

Dylan Etkin
Yeah, well, I mean, really, at the end of the day, we’re helping teams understand how efficient their engineering organizations are, and we’re providing them the tools in order to get better. So every engineering team I’ve ever worked with wants to do what they’re doing in a more effective and more efficient way. That can often look like adding in process or adding in safety nets or you name it. Right. And what we help people do is we help them understand where they’re bottlenecking today. So where they should first turn to actually get better, and then we provide automated tools for them to do. 

Brett
So let’s expand on what that solution then looks like. 

Dylan Etkin
Yeah, so, I mean, a lot of this is oriented around a thing called Dora metrics, if you are familiar with the state of DevOps reports. They took a lot of DevOps practitioners and practices and boiled the ocean a little bit and came up with these four metrics, their frequency, lead time. In other words, how long it takes to get something from inception through to delivery, the failure rate. In other words, when you deliver something, is it successfully delivered or unsuccessfully delivered? And then if it’s unsuccessfully delivered, what the meantime to recovery would be. So how long it takes to get back into that successful state of play for your application. And so these Dura metrics have been very transformative in allowing us to talk about quantitative numbers around efficiency, and they talk about it at a team level. 

Dylan Etkin
And so what we do is we hook up into systems like GitHub, Jira, pagerduty, maybe a datadog or something, we into the real work that teams are doing every day after day, and we glean these Dora metrics from them. And that allows you to figure out where your hotspots and your model next might live. And then we have an automations marketplace and framework that allows you to kind of one click add these best practices that engineering teams have developed over the last 15 years to help improve your overall engineering process. Simple, right? 

Brett
Simple. Take me back to October 2019. That’s what I see as, like, the origin date or when you started. What were those early conversations like, and what was it about this problem specifically that made you say, yes, that’s it, leaving my job, and I’m going to start a company and build a company around this and solve this problem. Why were you so attracted to this problem specifically? 

Dylan Etkin
Yeah. So for me, it goes even further back. Back when I was working on BitBucket atlassian, when I started running that team, I think there was like seven of us. By the time I finished, there was something like 40. And so initially, I could kind of keep up with what were doing. I just watched some emails on pull requests, and that was fine. And we didn’t have incidents that often. I was like, things are generally okay. But as the team grew, obviously were practicing continuous delivery, and it became harder and harder to understand what were actually doing and whether it was working well or not. And it kind of struck me like a lightning bolt that deploy, which is this thing that at the time, we treated almost like as a second class citizen, was the most important thing. 

Dylan Etkin
That was when all of this hard work that a developer had done and even, like, design had done, product had done to bring into life hit customers, which is the moment when it actually matters. And we had very little information about that and understanding whether that was going well or going poorly. And so around the 2015 time, when I first left Atlassian, I started building this tool, because I just thought, I work at the Jira company, and we’re building BitBucket, which is a premier source code hosting tool. Certainly I should be able to get access to some of this information. And so when I left, I just wanted to convince myself that maybe I could. I wrote a little bit of the beginnings of Sleuth. At the time, it was called deploy hub, and then I got involved in this small startup. 

Dylan Etkin
I kind of kept working on it. When I went back to Atlassian, they said I needed to shelve it and so I gave the idea and the opportunity, a lot of opportunity, to just die on the vine and it refused. Every time I would talk to somebody about it, I’d get super animated and interested. And honestly, the market grew into the idea more. And so as I sort of started thinking about what I would do next, I just couldn’t, in good faith, not do Sleuth, bring it into life. 

Brett
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Launching your own podcast, visit frontlines.io podcast. Now back today’s episode. Talk to us about those first paying customers. That’s something that every Founder struggles with, is getting those first paying logos across the line. What was that experience like for you, and how’d you pull it off? 

Dylan Etkin
Yeah, I almost think that the way that we did it is a cautionary tale more than a positive thing. So some people go into stealth for a while. We just decided were going to dev in the open. That just tends to be one of our philosophies. And were lucky enough to have a lot of folks industry that we had known who were bought into the idea and the vision. And so they started paying us reasonably early. That was like launchdarkly and some folks at easy agile, the folks over atlassian. And the downside to that for us is we started with this thing that were calling deployment tracking, and it’s still at the core of what we do. But it was not the value that organizations are looking for. 

Dylan Etkin
And yet we had some people that were paying us and giving us a little bit of a false sense of having found our product market fit, when in reality, I think were a little bit off the mark. And so it was great to have some paying customers, but it also perhaps gave us a little bit of false sense of security in the beginning. 

Brett
And where do you stand now in terms of growth, adoption? Are there any metrics and numbers that you can share? 

Dylan Etkin
I mean, we’re in a pretty competitive space. I don’t tend to share too many metrics. I mean, we’re growing. I’d say we’re about three xing most things, and we’re in a pretty happy place now. We definitely found some fit and have a pretty good self serve business going on and some really enterprise customers that I’m pretty excited about as well. 

Brett
Can you expand on what the competitive landscape looks like?

Dylan Etkin
I think that engineering efficiency and measurement is not new. There’s been a number of false starts in our industry. I like to joke that back in the punch card days, if you had the least amount of punch cards, then you win, probably not much of a good measure of things. Lines of code have also been a traditionally terrible measurement, number of pull requests as well. But the Dora metrics have really allowed us to take the real information and glean some sense of usefulness out of them. And so a market has grown up around that. And so there are definitely folks in our space that are offering connecting up to all of your existing tools and gleaning these metrics. 

Dylan Etkin
Maybe some are doing some this way or that way or a little bit differently, but it’s definitely a top of mind space for a lot of engineering leaders right now. 

Brett
What are you doing from a marketing perspective to rise about the noise and connect with engineering leaders? From other interviews I’ve had on the show, what founders have told me is that engineers and engineering leaders are almost allergic to marketing, and marketing to them can be very tough. So what are you doing from a marketing perspective to really break through? 

Dylan Etkin
I think that is correct that engineers are difficult to market to, but the good news is that we have an engineering background. I think that they react well to a certain amount of genuineness, and they react to value. So it’s really about getting ourselves in positions where we can talk to the people that we know will get value from what we’re building. And that looks like things like sponsoring the state of DevOps report. There’s a conference that we’re going to at the end of August, the ELC summit, which a lot of great engineering leaders show up at. And it’s just finding the places where our kind of customer profile is living and talking to them in a way know it comes across as genuine and useful. 

Brett
Can you talk to us about Sleuth tv? I was watching some of those videos as I was preparing for the interview, and I like the approach and I really like the content. 

Dylan Etkin
Awesome. Yeah. And you would have seen Don, my Co-Founder and CTO, and I think that’s a perfect example to talk about. What I was just saying there is Don is an architect at like, he is the developer’s developer. I’ve never really met anybody who is better at breaking the back of a really hard problem in three overnight sessions and whatever, and then handing it off to a team that needs to spend another three months to really finish it off. But he can sort of work at that high level. So Don does a lot of the marketing for us because he’s also reasonably know, I think he was a preacher when he was younger, and he kind of approaches things in that way. He’s straight shooting and he knows what he’s talking about and he’s passionate about subjects. 

Dylan Etkin
And so we just kind of have him out there talking about the things that matter to all of us in that very, again, genuine way. And I think it tends to resonate. 

Brett
With the audience from a messaging and positioning perspective. Have you made any major changes in the past twelve months? And the reason I ask a lot of the founders that I’ve talked to, they say that the message that was hitting the market and resonating with the market twelve or maybe 24 months ago is completely different than the messaging and positioning that they have today. Has it been similar for you, or has it stayed consistent through the last twelve months or so? 

Dylan Etkin
No, it’s changed. So it’s made a reasonably big shift because of the economic situation of most organizations. But also one thing I would say is that being in a market that is nascent and currently evolving, our messaging and what resounds and what customers are looking for is evolving daily. And it’s an interesting challenge. And we have to continuously remind ourselves that what was really giving us traction 18 months ago may not be actually giving us traction today, and that the conversation has evolved and the competition has evolved, and what is the value that is required in order to adopt a solution like ours has evolved as well. 

Brett
When it comes to the market category. And maybe let’s think about this like a line item, is engineering efficiency the line item? And is that an established line item that an engineering leader would be looking for? Or what is that category? Or what is that line item? 

Dylan Etkin
Yeah, it’s evolving. I mean, what is a great search for us, or has been traditionally, but I think is a little less so now is Dora metrics. So the folks who have read, accelerate or are big fans of the state of DevOps reports, what will happen is somebody will say, I need to get a handle on what’s going on here. And then they have this conversation, perhaps, of what should we track, and the kind of default standard now is this idea of dorametrics. And so they’ll search for Dorametrics and then they’ll find what’s in the world of possibility in that vicinity. Now, at the end of the day, the reason that they’re looking for that is they do want to improve. 

Dylan Etkin
So they want a tool that’s going to give them a baseline, that’s going to give them insights, that’s going to allow them to improve. So efficiency is a good way of thinking about it. Also, business value, probably just understanding what is the value that my engineering organization is bringing to my business, I think is how a lot of people are looking at these capabilities makes a lot of sense. 

Brett
As I mentioned there in the intro, you’ve raised $25 million to date. What have you learned about fundraising throughout this journey?

Dylan Etkin
Oh, boy. I suppose you need to be really good at articulating your dream and why you are uniquely suited to realize that a lot of fundraising is around a team and a dream you have a dream. You believe so hard that you’re going to go ahead and make this thing happen. A lot of the fundraising, obviously, if you’re just gangbusters and you’ve got like $20 million in ARR out of the gate, that’s going to be very convincing on its own. And if that’s the case, you might not even need to do fundraising. 

Dylan Etkin
But if you are trying to get out ahead of things and really get the capital that you need to realize your vision, it’s about sharing that vision and doing it in such an exciting and articulate way that you get others excited and then really leaning into yours and your co-founders pedigrees such that you’re going to convince others that you’re the right team to do it. 

Brett
Let’s imagine that you were starting the company again today from scratch. What would be the number one piece of advice you’d give to yourself? 

Dylan Etkin
That’s a good question. Drive to product market fit with relentless abandon. And if you have a friendly audience, maybe rely a little less on them, because getting people to really tell you if you’re hitting that value or not, it’s a hard thing to do. And there’s a lot of strangely uncertainty around whether you’re hitting it or not. And I guess the other thing I would say is that if you have any inkling whatsoever that you aren’t hitting it’s probably ten x more right than you think. I remember back in the day where us being like, do you think we found, like, maybe we found some product market fit? I don’t know. What do you think? Whatever the fact that were asking that question at all, the answer was no. 

Dylan Etkin
But at the time you’re like, but we have these seven customers that are whatever and they said they liked it. You’re like, yeah, but they’re just being nice. 

Brett
I think it was a talk I watched from the CEO of segment was talking about product market fit and Jen’s view was like, it doesn’t feel good. It’s like getting sucked into a vacuum and you think that it’s going to be this amazing moment, but there’s a lot of pain typically when you do find product market fit. Was that your experience as well? 

Dylan Etkin
Yeah, absolutely. And honestly, I remember talking to the founders at launch darkly and they were already probably a unicorn. And them saying, I don’t know if I found product market fit and I’m like, oh, whatever, man, you’ve totally found product market fit from my perspective. So it’s not like you’re in and you’re done. It’s this constantly evolving thing. And so yeah, there’s a lot of things that bang you around on the way in and way out and then maybe you’re transitioning from trying to find value to scaling value. 

Brett
Final question for you, let’s zoom out three to five years into the future. What’s that big picture vision that you’re building? 

Dylan Etkin
Right. I mean, the analogy I like a lot right now is Salesforce for engineering. If I zoom that out one level deeper, the best sales teams back in the day before Salesforce were doing a lot of the things that Salesforce allows other teams to do, right? They were doing it in spreadsheets. They were calculating these things manually. They were generating reports and whatever reporting tool that they were using. They were generating email campaigns to get back at people and make a difference to their sales engagement and those sorts of things. But what Salesforce did was sort of say to everybody, this is how you do it. You don’t have to be a top tier team in order to use these tools. Here are ways for yourself to evaluate how you’re doing. 

Dylan Etkin
Here are the tools that you have to improve and here is the framework to have that conversation with execs and your leaders and other people in your organization and engineering has been ripe for that transformation for quite some time. And it’s folks like ourselves and our competitors that are building that now. Amazing. 

Brett
Love the vision and I love your approach to building. Here we are up on time, so we’ll have to wrap if there’s any Founder listening in that wants to just follow along with your journey as you build and execute on this vision, where should they go? 

Dylan Etkin
I mean, Sleuth IO is definitely the right place to go. We have a live demo. We Sleuth in Sleuth because we’re developers at heart. And so if you want to see the value that we can add, you can just watch us do our development along the way. And obviously, if you want to talk to us, we’re always happy to talk to Dylan. 

Brett
Thank you so much for taking the time, especially on end of day Friday. I appreciate it. 

Dylan Etkin
We did it. 

Brett
This has been a lot of fun. I’ve really enjoyed it and, yeah, appreciate it. 

Dylan Etkin
Thanks. All right, good talking to you, Brett. 

Brett
All right, keep in touch. 

Brett
This episode of Category Visionaries is brought to you by Front Lines Media, Silicon Valley’s leading podcast production studio. If you’re a p two b Founder looking for help launching and growing your own podcast, visit frontlines.io podcast. And for the latest episode, search for Category Visionaries on your podcast platform of choice. Thanks for listening, and we’ll catch you on the next episode.