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May 23, 2023 · 42 min read

Season 4, Ep. 1 – Founder to Founder, with Dylan Etkin, Founder & CEO, Sleuth

Season 4’s Founder to Founder series kicks off this week with an insightful, engaging, and incredibly entertaining conversation between’s CEO and Co-founder, Teja Yenamandra, and Sleuth’s CEO and Co-founder, Dylan Etkin. After years spent honing his skills as the Jira architect for Atlassian, Dylan saw plenty of opportunities to improve the efficiency of engineering teams. This led him to start Sleuth, which provides teams with actionable and extremely accurate DORA metrics, helping to improve deployment speeds and reduce errors.


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Teja (00:05):

What’s up guys? Today we have Dylan Etkin as a guest on the Frontier. I really enjoyed this conversation. Dylan was at Atlassian for about 10 years. He joined the team when they were like 20 people, built Jira, scaled Jira, went to Bitbucket, built Bitbucket, and so he was at Atlassian for like 10 years at, you know, at every step of the journey. And now he’s building his own company called Sleuth, and Sleuth takes like, a lot of developer tools, some of the toil. He, I mean, he framed it like, so well in the interview, and we had a chance to talk about his journey, about building things that make your lives easier as developers, and some of his leadership skills. And he’s just like, I learned a lot, and I think you guys will too. So it was a privilege for me to talk to him. I’m filling some big shoes here for Faith, and so I hope you guys enjoy. As always, you know, gimme some feedback on what I could have asked or something that we could have done better, but I think you guys will like this one. Thanks. (THE FRONTIER THEME ENDS)

Teja (01:27):

Today we’re here with Dylan Etkin, CEO and founder of Sleuth. We’re excited to get into his background, what his company does, and hear from one of the founding engineers, lead engineers of Jira who spent 10 years at Atlassian. So…

Dylan (01:46):

Actually, even a little bit more <laugh>.

Teja (01:48):

<Laugh>. There you go. More than 10 years.

Dylan (01:51):

Ten years the first time, three years the second, so…

Teja (01:53):

Does anybody spend more than like, five years anywhere in our industry? It seems like, pretty rare, you know?

Dylan (02:00):

Yeah, honestly, there was a point at which I was asking myself, am I doing this wrong? You know, is there something wrong with me? Or like, have I just like, you know, fallen into a set of good circumstances at Atlassian? And, you know, I think it was the latter. You know, I had a lot of opportunities to do a lot of different things there. So it wasn’t like, you know, 10 years on one thing. It was five exciting years on Jira, five exciting years on Bitbucket, you know, like, coming back in an acquisition through status page and that sort of thing. So, lots of different lessons in operating inside a different organization when it’s 20 people, versus 200 people, versus a 1,000 people, versus 3,000 people, versus 5,000 people. Lots of different lessons to be learned at each one of those different stages.

Teja (02:46):

What’s the culture like at Atlassian? I mean, does it vary from product to product?

Dylan (02:50):

It really does, but I’m sure you’ve known this or heard this, and I’m guessing your listeners have too, and it’s true that it’s really one of the better cultures that you’re gonna encounter in your work environment. I remember Scott Farquhar saying something along the lines of you know, “I wanna spoil you such that you’ve done your best work ever here, and that anything else will feel strange.” And look, there’s a lot of things that have gone on at Atlassian, but the credit that I will give both Mike and Scott, day in and day out, is that they did build a phenomenal culture from day one, and it really grew with the organization as it became larger and larger. And, you know, one of the lessons that I took in, you know, starting my own organization, is that, strangely enough, culture comes from the top, and it’s really about the actions that you do, much, much more so about the words, or much more so than the words that you say. And really focusing on core things, the people, like, smart people that are doing good work, empowering them to do so. It can pay off over time through this like, amazing culture.

Teja (04:02):

How do you think about culture at the company that you founded, Sleuth? Like, do you think about it as one overall culture? Do different teams have different cultures? How are you driving it?

Dylan (04:12):

Well, we’re a little bit smaller, so there’s about 35 of us right now. So I think, you know, we’re very much one team. Obviously, we break down into functions and, you know, you’ve got engineering, and marketing, and sales, and CS, and all of these sorts of things. But, you know, part of the culture that we’re trying to build is this idea of like, we wanna focus and be able to do our things in our different areas, but it’s really about having communication points and touchpoints, and working together, and staying aligned, and making sure that everybody understands like the most important thing, which is customers and value for our customers. So, you know, it doesn’t really vary across teams. I’m fortunate that my two co-founders also spent a ridiculous amount of time at Atlassian. I think if you add up the three of our 10 years, it’s about 50 years of Atlassian experience, (Teja: Wow.) which is just crazy.

Dylan (05:05):

But also it meant that, you know, when we sat down to build out our company values, it was one of these weird experiences where, you know, you could imagine that taking days and days and sort of arguing over this, and that, and the other thing, and I think we did the whole exercise in like, you know, an hour or something, we were just like, “Well, here’s our favorite seven, let’s cut it down to like, you know, four or five,” and then we were like, “This one that we’ve always liked, I didn’t like the wording. Let’s debate that for 20 minutes,” and then we were like, “Ok, cool. This is great. I think this reflects us.”

Teja (05:37):

Yeah. So what are some of like, your company’s sort of operating values or, you know, I guess founding values? I know that you guys like to choose action.

Dylan (05:49):

Yes, absolutely. So that’s actually one of my favorite ones. We used to have a value at Atlassian. It was kind of inspired off of an Atlassian value, which was “Be the change you seek.”

Teja (05:59):

Oh, cool <laugh>.

Dylan (06:00):

Yeah, same sort of vein, but we wanted to switch it up a little bit, and I think that in some cultures and organizations, you can kind of get into this thing where you are afraid to fail. You know, you have analysis paralysis, and we really wanted to incorporate the idea that like, when you’re thinking to do a thing or you’re attempting to do a thing, do it, choose action. It’s better to solve a problem quickly and then learn where you went wrong through real world interactions than it is to try and like, play it out or, you know, like, guess about how this thing is gonna be, you know, received in the world. It’s okay to move quickly with an informed decision, you know, and rather choose action when you’re debating two courses of action where it’s like, I could go and, you know, create a thing about this and try and, you know, spend three weeks, whatever, or I could just push it out, and get some user analytics, and know an answer, and then push out another change in that three week period. Maybe you can iterate to something amazing with real world feedback.

Teja (07:09):

That’s awesome. How good are you guys at like, connecting the values to, let’s say, like, management decisions and leadership decisions?

Dylan (07:20):

I mean, I’d like to think that we’re pretty good at it, honestly. (Teja: <Laugh>.) So, well, I have a specific example recently, and, funny enough, like, we’re calling it “Sleuth chooses action.” So it’s an internal project, and we’re kind of mobilizing the entire organization to really push towards a specific set of things. We’re launching this automations marketplace. It’s very exciting. We’ve been sort of building up to it for a couple of years, even. Like, we have this actions framework. And anyway, like, the point being that it was, as we started to orient the organization to say, this is gonna be our strongest focus in what we wanna do, it coincided and sort of correlated so very well with this idea of choosing action, right? We said, “We’re gonna move really quickly, we’re going to push it out, you know, as fast as we can. We’re gonna learn along the way. We’re gonna support it with marketing content. We’re gonna do this whole push where the outcome is really what’s driving all of these things that we’re doing.” And again, it seemed like a great example of just the whole organization choosing action.

Teja (08:28):

I honestly feel like we’re not very good at that. Like, we have a bunch of things that live in a Notion document, and then, I don’t know if we connect it to actual things that we like, decide on or direct a team to do. So that’s pretty inspiring to hear that.

Dylan (08:43):

The other thing that we tend to do, and I mean this is a day-to-day thing, is recognize the folks in your organization that are living the values.

Teja (08:51):

Yeah, that’s interesting. Yeah.

Dylan (08:53):

So like, another one of our values is seek to understand and also focus on the user and the rest will follow. And you know, there’s examples every day of engineers who are working on a support ticket who go that extra mile, and they do. They seek to understand and really, like, they could have just like, you know, transitioned this issue back to the customer or whatever said, I don’t really know, but instead, they went the extra mile and understood “What are they really asking us?” You know, “Where are we falling down at like, a value prop position instead of like, ‘Hey, there’s just a bug, and is there something I can do about that?’” And you know, when somebody does that, obviously, you wanna call that out in like a public setting, you know, to sort of say, “Look, this was amazing. The customer was super happy.” You know, a great example of focusing on the users and, you know, having success flow from that versus, you know, some other mechanism. And also taking the time to really understand what the hell’s going on there, you know, (Teja: Mm <affirmative>.) not just assume, you know?

Teja (09:59):

Mm <affirmative>. That’s powerful. So you guys sell to a fairly technical buyer. How has that informed the way that you think about architecting your company, the culture in your company? Would you say that your culture is probably like, more like, overall engineering oriented, even on the sales team and all that stuff?

Dylan (10:21):

Yeah, I mean, that was bound to happen, frankly. Like, you know, based on my background and my co-founders’ backgrounds, you know, I’ve been fortunate enough to always work on developer tools in my career, you know, (Teja: Mm <affirmative>. Right.) on and off Atlassian and some other places too. I find that I don’t have a connection to insurance software, you know what I mean? (Teja: <Laugh>.) Like, I obviously have some insurance, but you know, it’s a pain in the ass. I wish I didn’t have to, right? (Teja: Yeah, yeah.) Like, I just can’t get into it. I can’t get into the mind of like, the insurance buyer. Whereas, you know, I’m a developer at heart. I started as an engineer, I was an engineering manager for years and years, and I find that when you are a team that is working in a very modern way, and doing very modern forward-leaning practices, and you’re using your own software, when you find something that scratches the itch for you really well, it often really translates well into the market. And, you know, that was something we did at Atlassian all the time, and obviously, you know, that thing is a behemoth now.

Teja (11:32):

Totally. What’s life like running your own ship compared to being, I mean, this is probably like, a lot of obvious answers, but I’m…you probably have and interesting take on this. Like, what’s it feel like basically building a pirate ship when you came from an armada <laugh>?

Dylan (11:50):

Well, I mean, I will point out the fact that I joined Atlassian when it was 20 people, so I was a pirate, and I joined the pirate crew.

Teja (11:58):

No shit! I didn’t know that. Ok. Yeah, that’s cool.

Dylan (12:01):

Yeah. You know, we were a bunch of pirates in Sydney, Australia, right? And you’re just <laugh>, I mean, and also we were disrupting the hell outta all the things, ‘cause like, at the time you were spending $200K on Rational or some horrid, horrid issue tracker, that meant you had to hire some consultant to set up the thing for a year before you could even use it, and everybody hated it. And we were coming in and just being like, “That’s a load of bullshit. Here’s a great issue tracker, just get shit done.” And you know, and that’s what happened, right? They kinda got in the bottom floor, like, developers just went, I can throw this on a credit card for $1,200, and then we can use something awesome, instead of having to use this horrid other stuff. And all of a sudden, it was the issue tracker of choice within Morgan Stanley and other things, right?

Dylan (12:48):

Yeah, I definitely gravitate towards the pirate mentality a little bit more than the larger organization mentality, you know? In that larger environment, I start to miss choosing action. I miss the visceral interaction of making a choice and seeing the outcome of that choice, you know, tomorrow versus, you know, two years from now, maybe if the initiative completes. I mean, the difference in terms of, you know, running the whole show versus, you know, being a cog in the larger wheel, obviously, there’s just a huge amount of things there. So, you know, when you’re an engineering manager, you’re worrying about somebody else is setting your budget, telling you what you can and can’t do, right? Like, you have like, a locus of control over like, scheduling and the sort of things that you’re doing, but there’s times where maybe you’re excited about going in a certain direction, but it doesn’t fit strategically with the organization.

Dylan (13:39):

Frankly, I didn’t know hardly anything at all about marketing sales, CS, HR, you name it, like all the things that as a business owner, you’re just like, you know, it’s a crash course in how the real world works. Which, you know, is great. I mean, that’s what I wanted to do. I, at times, will remember the saying, you know, “Be careful what you wish for. You just might get it.” (Teja: <Laugh>.) <Laugh>. You know, when I’m having to learn something that I absolutely despise, and I’m like, I could have gone to my grave without learning this thing. And I just remind myself, be careful what you wish for. You just might get it.

Teja (14:27):

<Laugh>. What’s an example of one of those things that you’re like, “I could have done without having this knowledge in my brain?”

Dylan (14:34):

Oh my gosh, so many things. I mean, just like, there’s stuff around insurance, you know what I mean? (Teja: Yeah.) I’m like, yeah, I don’t care. I mean, I do. I care, because I care about my employees and the wellbeing of the organization, and I understand its importance and the overall scheme of things. You know, like personally, I have no desire to know as much about it as I do today. (Teja: <Laugh>.) You know, similarly, this might sound funny, is, you know, I am fine and happy to do these sorts of things. Like, actually, this is more fun, but like, fundraising and, (Teja: Yeah, yeah.) you know, like, analyst interviews and stuff like that, where you’re just (Teja: Yeah.) pitching, and you have to be very, you know, buoyant and, you know, I mean, it kind of overlaps, well, because I absolutely care about this space.

Dylan (15:25):

I care about what we’re doing, I think about it all the damn time. So it’s an environment where you get to share and go back and forth, but the prep for that and just, you know, the thing of that, if I could choose to not do it, I probably might, but at the same time, you know, sometimes you do stuff, and you get forced into doing certain things, and you realize, I actually quite like it, and I’m better at it than maybe I would’ve given myself credit, and for being forced to practice means, hey, I’ve actually gotten reasonably good it too. So…

Teja (15:56):

Totally. No, I mean, I think hardest thing about those, like, yeah, like you know, if you’re talking to somebody at Foresters or something, or you’re, you know, doing a series of pitches, the prep time is the thing that like, totally blew my mind. At least, for me. It takes a lot of time, and you’re just like, I could be doing so many other things besides practicing. It’s not, (Dylan: Yeah.) you know…

Dylan (16:21):

And you know, coming from an engineering background, I am extremely good at taking a coding problem or an engineering problem and like, doesn’t matter what my mind like, my state of mind is on the day, I can like, push myself, you know what I mean? I know how to push myself to show up for eight hours, and work through a problem and whatever, and be creative, like, on demand. Whereas, the creativity that comes with, you know, putting together a board deck or a pitch deck or whatever, it’s a very different set of flow, creativity-wise, and it took me a long time to be okay with it. You know, like, it’s much more start and stop for me, whereas I can be very consistent with like, a coding problem. And I would always sit there and be like, why am I twiddling my thumbs for like, an hour and a half in the middle of this work that really needs to get done? And I’m like, you know, come to the point, at this point to realize ah, it needs to marinate. You know what I mean? It’s a different process, but it’s a different process.

Teja (17:29):

What’s your process to get into flow for, let’s say, solving an engineering problem? Let’s say you’re doing it, like, you’re actually coding, versus a management task. Let’s say you’re pitching an initiative, or you’re gonna go to a fund or something.

Dylan (17:44):

I will say that I don’t code very much anymore, and that’s by intent. In fact, I think my dev environment’s broken right now. Shh. Don’t tell anyone <laugh>. (Teja: <Laugh>.) You know, like, I’m fortunate in the sense that from the coding side of things, I do have a lot of experience. I’ve done this thing a long time, and I’ve worked on big systems, and so, generally speaking, it’s rarely the case that there’s a problem that I feel like I just really don’t know at all. You know, I don’t know where the edges of the problem are, or I don’t know, I don’t have some sense of like, how to attack it. And so when I sit down for something like that, you know, the scaffolding’s mostly there in my mind. I know how to, I know where to start, you know, and I know like, if I have some stuff that’s a question that is maybe a little bit larger, I can start working on the things that I’m very certain about.

Dylan (18:35):

And then as I progress my way through, some of the other things start to come into a certain amount of clarity. You know, like, so creatively I know how to like, fill the little gaps in between, in order to keep myself busy, ‘cause there’s so much busy work and coding where you’re just like, “Ah, this isn’t fun. But also, I just need to type the words, and run the things, and ah, it didn’t work,” you know? And whereas, you know, the idea of sitting down for a pitch deck or some sort of large initiative, internally, like that “Sleuth chooses action” that we did internally, it’s really, it’s just such a different process, you know? You have to say, “What’s my big line?” And then you kind of like, play with it for a while, and then you’re like, “Actually, this is a level lower than it needs to be.”

Dylan (19:20):

“I need to zoom it up,” you know? And then you’re like, “Ah, crap. Now it doesn’t mean anything. Now it’s just  buzzwords, you know, like, okay,” (Teja: <Laugh>.) you know, and you’re like, wanna walk that fine line between like, meaning something to your audience, but being inspiring, and even then, that too, right? Like, there’s like, okay, here’s the content. Zoop! Right? And you’re like, that is the driest, most boring shit I’ve ever experienced all my life. You know, like, it needs to be inspiring, it needs to have energy, it needs to motivate an organization of 35 people to move in a direction, you know? And then you start to think about like, how am I, you know, where’s the enthusiasm here? Like, if I’m feeling genuine enthusiasm, how do you let it out in a responsible way? And I dunno, it’s just a very different process.

Teja (20:05):

Have you like, came up with some rules for yourself around doing that well? Like, I dunno, like, have you come up with some…I’m asking, ‘cause I’m curious, ‘cause I struggle with that, (Dylan: Yeah.) honestly. You know, sometimes I’m too detached. Sometimes I’m too enthusiastic, and I feel like it comes across as, I dunno, manufactured, (Dylan: Right.) and, you know.

Dylan (20:28):

You know, I mean, I don’t think I have a great answer (Teja: <Laugh>.) but, I will say that I’m fortunate in a certain way that I do get genuinely excited, and I don’t seem to have a problem letting the genuine part of my enthusiasm out in a way that can be perceived by others. And I find that, you know, with any of these things leaning into how you genuinely show up, often is the best road, right? Because trying to manufacture something that you are not good at doing, or a persona that you don’t really represent can be very false. And so, you know, I kind of lean into that part of my personality where I’m like, it’s gonna be a little more playful. It’s gonna be a little more whatever. The people that know me are used to this.

Dylan (21:23):

They almost expect it from me to a certain degree. You know, we have…a bunch of our developers live in Slovenia, and there is a central European kind of thing, and we laugh about it internally, you know, if we’re saying, “Are things good, okay, or bad?” they will say, “Okay,” and then I will say, “Why isn’t it good? And they’re like, “Because ‘good’ means ‘okay’.” And I’m like, “Oh, okay,” <laugh>. So like, you know, they’re very pragmatic, and they’re very like, matter-of-fact-y, and so if I’m like, you know, “Woo!” they’re like, “That was a lot.” (Teja: <Laugh>.) “I don’t really know how to absorb that.” I’m like, “You’ll be okay. Like, trust me. You’d rather me being like, ‘Woo!’ than me being like, ‘I don’t know,’” (Teja: Totally.) “You know, ‘it may or may not work.’” I’m like, “Trust me. You prefer me to err on the side of, I dunno, boisterous American.”

Teja (22:18):

Aright, so, tell us about Sleuth. How did you discover the problem, and how’d you come up with the solution?

Dylan (22:25):

So Sleuth is an engineering efficiency platform. We focus on surfacing DORA metrics, which in the last, you know, 10 years or so, via the state of DevOps reports, have become basically an industry standard on how you tie a hard measure of engineering efficiency to a complicated set of flows, which is like, you know, the developer process from concept through to launch. And, you know, we orient around giving you automated tools to get better, to have your teams improve, and then giving you the proof points, via these DORA metrics, to show that the changes that you’re making in your developer flow actually are making a positive difference. And then having those analytics allows you to have a conversation internally in your organization with developers and with, you know, your CTO, and just the entire organization around what’s going on.

Dylan (23:19):

Now, the way that this kind of came to be, at least for myself and my two co-founders honestly, was you know, we were very fortunate that we were early days at Atlassian, doing a lot of continuous delivery when it wasn’t even called continuous delivery. You know, we had worked together on creating the first hosted version of Jira and Confluence, (Teja: Mmm <affirmative>.) which took this behind the firewall model of like, you know, downloading a tarball and doing some sort of install, locally, to actually cloud-hosted and pushing this stuff through, you know, on a regular cadence. And then we all kind of went our own different ways inside of Atlassian but continued this journey with continuous delivery. And for myself, when I took on Bitbucket as a technical leader, that was probably the moment where things really started to crystallize for me.

Dylan (24:13):

So, you know, when we first started, it was like seven people. We were moving really quick, and it was pretty easy to pay attention to what was going on. And then like, fast forward a couple years later, you know, we had over a million users and a much larger team, and suddenly I started to get questions from management being like, “Hey, you guys do dev a little bit differently than the rest of Atlassian. How do you know it’s working?” You know? And I’m like, “Oh, that’s a good question.” And we would have like, an incident and I’m like, I don’t really know what we shipped that would’ve caused that incident. You know, it was just really hard to know what was actually happening, ‘cause we were shipping at least once a day, (Teja: Mmm <affirmative>.) and it just struck me like a lightning bolt, honestly that deploy is the moment.

Dylan (24:59):

Deploy is when the rubber hits the road. That’s when a lot of really important things happen, but there wasn’t anything that was focusing on that. We were treating it in the industry almost as an afterthought, even though DevOps practices had meant that had become the focal point. And so, you know, I was working at the Jira company. building a source code, hosting Premiere tool with pull requests and reviews, and I couldn’t tell you what we were shipping. I couldn’t tell you the efficacy of what we were shipping. I couldn’t tell you, you know, were we getting better? Were we getting worse? And it just felt stupid, frankly (Teja: <Laugh>.) <laugh>, and so started noodling on this idea of Sleuth at the time, I think it was called the Play Hub, worked a little bit on this thing, was not entirely ready to go jump and do my own thing.

Dylan (25:50):

Honestly, at the time I think the industry was maybe very nascent and needed to grow a little bit more. I got wrapped up in another little startup and that was like, you know, went back to Atlassian and so had things to distract me, but the industry didn’t slow down the target audience for something that would do this, just continued to grow and grow. And, you know, when I looked down and thought, you know, I gave this thing plenty of time to die on the vine, and it’s not going to, it’s where I get excited, and there’s a gap, and that gap is just growing larger and larger. And so it became pretty obvious that it was time to do something about it. And when I decided to make the leap, you know, that’s when the people in your life that might be the right fit at the right time show up, (Teja: Awesome.) and that was the case with my two co-founders.

Dylan (26:41):

You know, I would never have, ahead of time, realized that they were willing to do this thing, too. You know, I just assumed like, one of ’em was a VP of product at a pretty successful startup. The other one was an architect at a pretty successful startup. And, you know, just so happened that our lives, the timing worked out, and I was like, “I’m gonna do this thing,” and they were like, “I’ve been wanting to do that thing forever, and like, you know, you’re one of two people I would ever do that with, and the other one’s this other guy.” And we’re like, “Well then, let’s do it.”

Teja (27:13):

It’s awesome. You can swear, by the way. That’s okay, ‘cause I felt like you wanted to (Dylan <Laugh>.)  drop an F bomb, and you can.

Dylan (27:21):

I’m trying to cut down, honestly. (Teja: <Laugh>.) That’s a problem <laugh>. I don’t need to. I don’t need to. (Teja: <Laugh>.) My kids, when they got older, it’s funny, they, you know, they would tell me forever,  “Ugh, you’re like a sailor. It’s disgusting. What are you doing?” And then I tried to cut down, and then they became teenagers, and they started swearing more, and they were like, “It’s your fault,” and I’m like, “There’s a time and place. It doesn’t need to be every other word.”

Teja (27:45):

Do you remember the first time that you heard your kids swear? What were you doing and what were they doing <laugh>?

Dylan (27:51):

No, because I was such a sailor, potty mouth, whatever, you know, like, I don’t think it would stand out. Unfortunately, I do remember that moment where they went from complaining bitterly about how much I swore to like, on the next day, suddenly, they were the like, worst offenders. And I was like, “Wait, I slowed down, and you asked me to,” (Teja: <Laugh>) “and now you sped up.” I’m like, “What’s this?” and they’re like, “It’s your fault. You already did the, you made your bed. Now you have to lie in it.” I’m like, “That’s reasonably fair.”

Teja (28:22):

<Laugh>. Oh man. That’s funny. Yeah, it’s something that I think about. I grew up in New York and so, I mean, I don’t know, it’s like, fairly…we like to pepper our sentences with swearing, but you know, we’re now in Nashville, and Nashville’s like, I don’t know. I mean, it’s, there are a lot of people from the coast moving here, but it’s still a fairly conservative town. (Dylan: Really?) So it’s just, yeah, you don’t, you don’t hear much swearing out in public, you know, you hear kinda “gosh darn” and that sort of thing. So it’s been funny. I mean, it makes me wanna cut down as well. You realize like, maybe some, you know…if you employ the word “fuck” less often, it actually becomes more powerful, I think, (Dylan: Yeah.) so <laugh>…

Dylan (29:04):

And, you know, I mean, in our roles, that’s another thing that’s a very interesting thing of founding a company is that the impact of the things you say becomes much larger. It’s weird, and it’s strange, but we very much have to recognize that and be cognizant of the things that you’re saying, and how you’re coming across. And I don’t know if swearing every other word is really, you know, quite the…although my employees say, “Oh yeah, no, like, I was warned, you know,” when I, like, if we hire somebody in network, they were like, “I was warned that in the interview process you might swear, because you whatever.” And I’m like, “Oh god, really? Is that what you’re talking about?” (Teja: <Laugh>.) Oh no. I’m like, “Alright, alright. Fine, that’s fair.” I’m like, “I am what I am,” but you know…

Teja (29:55):

That’s true. I mean, it goes back to your point about being genuine, you know, but I think, you know, one can genuinely offer course correct aspects of themselves that, you know…

Dylan (30:07):

Absolutely. I mean that’s, I don’t know about you, but that’s like, my life in a nutshell, right? It started like, with zero filter, and this way and, you know, for good or for bad and have like, over many years tried to, you know, improve the things that are not great about the way that I interact with others, ‘cause it’s not my intent to interact poorly. And I do. I wanna be a great leader, and I want people to understand the things that I’m trying to communicate, and I wanna work with super smart people, which means empowering them, and, you know, some of these things don’t come naturally, and you have to learn over time. And other things, you’re just lucky you get like, a free pass and already know how to do it, so…

Teja (30:52):

One thing that I’ve noticed, especially as I’ve gotten older, is like, how much my interpersonal baseline is like, a function of the way that my parents interacted with me. (Dylan: Mmm <affirmative>.) And so, like, my upbringing is fairly strict, and so I’m used to, my internal monologue is fairly strict. (Dylan: Right.) You know, I don’t let myself get away with things. And so, (Dylan: Yeah.) you just assume that’s a baseline of how people interact with each other, and so if you communicate, you know, I’ll communicate like this and then, to your point, it comes across differently than you would imagine, like, because that’s just how you talk to yourself. And so that has definitely been a professional, I dunno, challenge in my growth opportunity for me, is that I have to work to soften everything that I say. Maybe, I dunno, by 90% <laugh>.

Dylan (31:45):

Yeah. It’s amazing, isn’t it? Like, I dunno about you, but you know, I’ve been privileged to work with some folks that are amazing, you know, (Tela: Yeah.) and I think of this like one engineering lead who was my boss for a long time, and he had this incredible ability to, everybody just loved him. You know, like even if he was telling them like, “I’m about to murder your baby in the crib,” right? (Teja: <Laugh>.) Like, they came outta the meeting being like, “You know, I just love the way that he told me that that was gonna happen. Like, it felt so collaborative and, you know,” and I just would watch him and be like, “Jesus, how did you do that?” You know what I mean? Like, what a skill, you know? (Trja: Yeah, yeah.) Like, “I just really like working with him, you know? It feels good when we come out of the meeting. I feel empowered, whatever.” I’m like, “He just told you he’s gonna murder one of your children. Like, how is that…that is incredible!” (Teja: <Laugh>.) I have to dissect this! I just have to know, ‘cause I want the skill. You know what I mean? Like, incredible.

Teja (32:44):

Totally. What was the secret? Or like, what books did he read? Was it just him or…?

Dylan (32:49):

I think it, yeah, I don’t know if there’s a secret so much, and it came with a cost, which was interesting, too. I think the cost for him was that, at times, he let people run in a direction that he probably should have put his foot down and been like, “If you run in that direction, we’re gonna have a giant cost,” and so there were some things, some large initiatives that he was in charge of where like years later you could look back and say, “Oh man, he should have put his foot down right there, and it wouldn’t be this giant mess that it’s become.” But again, everybody really enjoyed working with him. And the other thing was, as I got to know him even more, you know, on a personal level, he never got like, overly emotional in a meeting, you know what I mean?

Dylan (33:35):

Like, he was always very even keeled and even tempered. But to know him personally, I realized that’s not him, (Teja: <Laugh>.) you know? So this was a learned behavior for him, too. No, it’s true. Like, he would talk about like, you know, some annoying thing with his children or something like that, and all of a sudden this yelling voice would come out, right? Where you could see this like, seething, bubbling cauldron of whatever, and I’m like, “<Gasp>. You have that?” (Teja: Oh my god.) “That’s been there, and like, yet, it never comes out in your professional persona?” I’m like, “What a thing!” You know, I wish there was secret sauce, but I definitely have tried to emulate some of that, you know. I’m like, there’s a voice there that makes others feel better, and that is definitely something worth learning.

Teja (34:24):

Sometimes, I feel like you need a way to off gas like, your frustration, and you need to be able to channel that effectively, and sometimes that comes out if like, something is not on track, and I think that’s ok. Do you feel the same way, or are you more of like a, “Hey, at work I have to be like, a consummate professional, never have my emotion show.” Like how do you view that?

Dylan (34:48):

I don’t think I could do that if I wanted to, you know? (Teja: <Laugh>.) It comes back to that like, genuineness. That’s part of the upsides to me, and part of the downsides to me. However, I recognize that like, a strong, strong opinion should be wielded appropriately. (Teja: Hmm <affirmative>.) You know, like, there’s a time and a place, and maybe it comes back to the beginning of the conversation around the values, (Teja: Mmm <affirmative>.) is being a little bit upset or pushing for something in a certain way, when it’s showing the action of living the values, is very effective and very appropriate. You know, like, you saying like, “We’re not gonna ship this thing,” you know, or like, “Folks, how the hell did this get into this state? Seriously? Like, this is not how we work. Like, we should have caught this here, here and here.”

Dylan (35:43):

“Let’s not ruminate on the past, but what are we gonna do moving forward? ‘Cause we’re not doing this.” You know what I mean? And being really clear, and yeah, maybe that’s really hard for the people in the room to swallow, ‘cause they’re like, “Oh, we fucked up, and yada yada yada,” (Teja: <Laugh>.) right? But you’re telling the organization that like, “You have gone below the bar. We only go above the bar. I will model this from the top.” You know what I mean? And like, “I am genuinely passionate about this, and you should be too.” And you know, that’s okay. I think the thing that is not okay is to be like, “Guys, this is shit. Why do you guys mess up so bad? Like, let’s prosecute the past, yada yada,” right? Because like, that’s just…what are you gonna do? Change the past? Right? It’s a team sport. There was some sort of systemic miss somewhere, you know what I mean, like, have a blameless culture, call out the garbage, but like, fix it as a team.

Teja (36:44):

Like, this is like, a more operational question. Do you just leave the postmortem analysis to just the team to figure out, and be like, “Just don’t do the same shit again.”?

Dylan (36:53):

It depends on what it is. (Teja: Yeah.) It depends on if it’s like, there’s a lot of things that I’m like you, I have a pretty stern internal monologue, right? (Teja: Yeah <laugh>.) And I’m willing to take the blame, or at least a good portion of the blame, of things and put it on myself, and say “We did not create an environment that was gonna get it to turn out the way that I was hoping it was gonna turn out, and so let’s figure out how we can get there. And then, if we feel confident that we have that environment, then let’s start to like, dive into, to get a little annoyed at like, you know, how people have executed along the way.” But very often, unfortunately <laugh>, it’s the case that, you know, you thought you had an environment that would allow people to do a certain something, and then it turns out that you kinda didn’t.

Teja (37:43):

Okay, I have to ask you about this, ‘cause it’s been on my mind, (Dylan: Okay.) but this sort conversation took a track that was, I dunno, it was pretty interesting. Alright, so who do you guys like, sell to? Like, who are the main users of…and I guess that’s different than who you may sell to. Like, do you guys think about selling to businesses or selling to specific folks on the engineering side of the business?

Dylan (38:07):

So, you know, our space is an interesting space, ‘cause it’s fairly nascent. It’s actually gone and sort of bifurcated a little bit. You’ve got like, value stream folks like, Jellyfish, and Uplevel, and stuff like that. And then you’ve got engineering efficiency, which is more like Sleuth and folks like LinearB, and that sort of thing. And I believe we sell to different buyers, you know, like, I think the Jellyfishes of the world are selling to like, CFOs, CIOs, (Teja: Right.) and folks that really wanna understand how much money are we spending on the things that we’re doing, you know, how much of it is R&D? How much of it is, you know, like, keeping the lights on. I wanna use this information to get tax credits. I wanna use this information to, you know, make board allocations in terms of funds and whatever. (Teja: Right.)

Dylan (38:55):

And then there’s ourselves, where we’re selling more to team leads, dev managers, possibly like, dev experience teams, where they want the capability, and the folks that we sell to want to provide tooling for engineers, because they recognize that DevOps practices means you’re empowering individuals, you’re empowering your teams to improve and have a cycle of continuous learning. And so, you know, they want the metrics. They want that proof point. They want to be able to discuss with intelligence, internally, how things are going, and trending, and why. But at the end of the day, that needs to be driven from the work that developers are doing, and they need to see value add for those developers as well. So like, the developer experience needs to have been enhanced. There needs to be a tool that is helping a developer get their job done. You’re taking away, you know, one of the jobs to be done as a developer. You’re removing toil. You’re building insight. You’re pushing more information to the individual, so that they can do the jobs that you want them to do. And so you’re kind of selling to that manager, but they won’t buy unless it’s effective for individuals.

Teja (40:13):

I love that phrase, “removing toil”. (Dylan: Mmm <affirmative>.) That’s so cool. That’s neat. <Unintelligible>.

Dylan (40:21):

I think it’s like, a whole industry term, right? (Teja: Yeah.) I think back to like, yeah, you know, CICD, like, why is that cool? Because back in the day I had to run that stuff on my laptop, and it sucked, and it took hours, and, you know, when I could just push up a change and know five minutes later, ‘cause I split all the tests, I’m gonna get the result of what I did. You’ve removed a job that needed to be done, you’ve removed toil from my day-to-day. You know, that’s what we’re doing with the automations. We’re saying teams work like…to improve teams, we understand there’s the best practices that teams have been using. You know, if you wanna hit a goal to review something within a certain timeframe, you send a nudge notification to the people who are relevant right before you’re gonna, you know, pass that goal. You’re helping move somebody in a direction. If you’re saying, as a group, we never open a pull request without an issue key in it or you know, deploy during an incident. (Teja: Yeah, yeah.) You can remember this every time? Or you can add automation and remove toil from the individual, so they don’t have to go, and pull, and check, and whatever, right? Like, these are things that teams do, and you shouldn’t have to remember it as a human, ‘cause it’s hard.

Teja (41:30):

That is like, the best, I dunno, articulation of the pains. I think like, for the whole class of developer tools that you, I dunno, that’s awesome. Yeah. And it’s like, so obvious, too, when you hear it, but you’re like, why the fuck doesn’t anybody ever say it like that? That’s cool.

Dylan (41:48):

Well, see, this is what doing all those things that you dislike, (Teja: <Clap> <laugh>.) and having to talk to analysts, and whatever, you get some practice <laugh>. So you’re like, (Teja: <Laugh>.) said it 15 other ways, and it didn’t land with anyone. So now I’m saying it this way.

Teja (41:59):

Yeah, yeah. Is there anything you wanna talk about, in terms of like, what’s next for Sleuth, anything you guys are excited about? I’m sure there’s a lot you guys are excited about. Anything you wanna highlight specifically?

Dylan (42:10):

Yeah, this thing that we were just talking about, actually. So we have had a what we call an “actions framework” for about a year and a half, two years, where we’ve been learning about like, how people will use it, but we made it all YAML, and kind of made it a little hard to adopt, right? Like, there was a cookbook, but you had to take all this stuff and glue it together. And in the June to early July timeframe, we’re shipping a whole marketplace of automations. And so, you know, engineering organizations will be able to come in and just say, “If I want Slack-based approvals to approve something from, you know, staging to production, I can just click this button and boom. I’ve got, it and it’s gonna work across Slack and my CICD system, and you know, my GitHub pull request, and it’s gonna merge all that stuff together and make your life easier.

Dylan (43:02):

Similarly, there’s gonna be, (Teja: That’s awesome.) you know, 20, 30 checks of just simple little best practices that teams are using, so that rather than have to figure it out and drop the YAML in, you can go in, you can try it and then come back a week later, see if it made the thing better or worse. If it made it worse, I’d highly recommend removing it. If it made it better, cool. Try a different one. So, (Teja: That’s awesome.) we’re really excited about bringing that to the masses and kind of like, taking the shackles off of it, and not forcing you to drop into YAML and just making that learning cycle super quick.

Teja (43:36):

And that’s “Sleuth Takes Action.”

Dylan (43:38):

Well that’s internally. It’s “Sleuth Chooses Action, internally”. I think we’re actually, we’re debating on the exact name. I think right now, it’s the automations marketplace. We’ll see. I mean, this is why we have some great people in marketing to help us figure out exactly what the words are, and how it should connect. But, you know, it’s in that direction.

Teja (43:58):

Totally. And I mean, I think like, Sleuth is such a killer name, especially compared to like, Deploy Hub. I apologize if you came up with Deploy Hub. (Dylan: <Laugh>. No, no.) Sleuth is killing it <laugh>.

Dylan (44:06):

Awesome. Yeah, no, I was involved in both. There’s a funny story there, if we have the time. I don’t know.

Teja (44:11):

Yeah, absolutely.

Dylan (44:12):

So it was Deploy Hub, which, you know, like you say, I think it was a little limited. But also there was another open source project that had all the SEO food, right? So it was obvious that this was not something that we were gonna call it when we decided to go. I spent months thinking of names, seeing if the domain was available, and then like, just ruling it out and being like, “Yeah, I can’t afford that domain,” whatever. And then I found Sleuth, and I went and checked really quickly, and I was like, “Holy crap. is available. Like bang, I grabbed it. I was still working at Atlassian as an engineering manager at the time. I went in and like, kind of talked to my team, you know. Like, we were just shooting the shit at some point, and I said, “Oh, I had a, I think I like this one,” whatever. (Teja: <Laugh>.)

Dylan (44:52):

And somebody said to me like, “It seems highly unlikely that that was available as a domain. Are you sure you spelled it right?” And so I was like, (Teja: Oh my god.) I went and checked, and I was like, “Yeah, yeah. No, turns out I did.” Like, yay, winner! And fast forward, maybe you know, six months or something, and we’re starting the company, and my first co-founder, Michael, joins, and we’re organizing some stuff, and he goes, “Hey, man, like, didn’t you tell me that you bought this about like six months ago? Like, I was just looking at the registration for this thing, and looks like it was registered like, you know, two years ago, you know. What’s up?” And I go, and I search again, and Google is too good. So every time I would spell “sleuth”, I’d spell it wrong, and Google would fix it, and I’d look and go, “Oh yeah, see? I spelled it right.”

Dylan (45:39):

And so I had purchased the wrong spelling of “sleuth”, and I was like, “Oh no, oh god. Lemme try and think of another name quickly and whatever,” and Michael was like, (Teja: Oh.) he just like, kinda jumped into action, and behind the scenes, he whatevered, and he shows up at my house, and he was like, “I’ve got like, a marriage present for you.” I’m like, “Alright.” And he’s like, “I got the domain.” He’s like, “I just, I worked with the person. I did this and that, whatever, I bought the domain.” He’s like, “We’re Sleuth again. And I was like, “Oh my god, thank you. That’s so awesome.”

Teja (46:18):

That is an amazing gift <laugh>.

Dylan (46:20):

It was <laugh>. I asked him, I was like, “How much did that cost?” and he was like, “You don’t ask how much a wedding gift costs,” and I’m like, “That’s a really good…yes, you’re right. Uncouth of me.”

Teja (46:30):

That’s awesome. No, and I mean, I hear you. Like, between Grammarly and Google, (Dylan: <Laugh>.) I think you just loose the ability to spell. It’s like, a thing. But that is a cool story. Okay, so what happened to Deploy Hub? Like the name. (Dylan: I dunno.) Like, was that a working title or just…okay <laugh>.

Dylan (46:47):

Yeah, it was just a working title. I mean, it was like, I don’t know, I owned the domain for a while, and at some point, it had no juice. And like you say, I’m much happier with where we ended up, you know, and as you were building a product, there’s like, a hold. The product market fit journey is like, arduous and you know, like I think we are Sleuth much more so than we would’ve been Deploy Hub, at this point, ‘cause we originally thought of this deployment tracking and whatever. It’s just a little…

Teja (47:17):

Yeah, and I feel like it allows you to build a whole story behind the name. (Dylan: That’s right.) You know, which I don’t know if Deploy Hub would’ve allowed you to do, you know? It’s just…

Dylan (47:30):

The downside is Europeans tend, like, with not English as a first language, tend to call it “sloth”. (Teja: <Laugh>) I’m like, “Oh, don’t do that.” You know, like, we’ll get all these like, sales calls, and the guy’s like, “How do I pronounce your service? Is it “sloth” <laugh>? And I’m like, “Ugh, no. No, it’s “Sleuth”, man.” Like, <vocal shudder> don’t do that.

Teja (47:54):

<Laugh>. Our name is quite polarizing, too. I mean, it’s something that we came up with, just because there was a shortage of domain in “hired guns”. But, you know, there’s all sorts of political externalities associated with the word “gun”, (Dylan: Mmm <affirmative>.) you know. Right? So we don’t have to get, this is not about us, this is about you. That’s a topical <unintelligible> maybe, so…<laugh>.

Dylan (48:24):

It happens. We had an internal thing that we didn’t end up building, and I’m glad we didn’t, where we were kind of calling it like, “pull request” is like a “PR”, and so we were gonna call it “PR Cop”, and like, this was exactly at like, the defund the police/BLM moment, and we’re like, we can’t release something  that’s called “Cop”. (Teja: <Laugh>.) That’s not gonna, like…it sounds descriptive, but we can’t do that. That’s not gonna be good <laugh>.

Teja (48:56):

<Laugh>. I mean yeah, it certainly would have hit, but you kinda don’t know if you wanted it to in that way <laugh>.

Dylan (49:05):

No. I mean, all press is good press, but also, oh, I dunno. We do wanna sell software.

Teja (49:10):

<Laugh>. Totally, totally. Well man, it’s been awesome to chat with you. Where can people find you? Like, on the interwebs?

Dylan (49:18):

Yeah. Sleuth io. Just navigate to the site, try and spell it right. (Teja: <Laugh>.) It’s not as easy as you might think. And from there we have a live demo, like, one of the nice things about building a developer tool is we “Sleuth and sleuth”. And so you can browse the data and see how we make teams better. (THE FRONTIER THEME FADES IN) You can see our data, and that’s actually us building “Sleuth and sleuth”. And so it’s a great place to start, free 30 day trial. You know, always happy to talk to all of our potential customers as well, so, you know, you’ll probably get a reach out from us the minute you click the trial button.

Teja (49:56):

Awesome. Thanks, Dylan. Appreciate your time today.

Faith, via previous recording (49:59):

Thanks for listening to The Frontier Podcast, powered by We drop two episodes per week, so if you like this episode, be sure to subscribe on your platform of choice, and come hang out with us again next week, and bring all your internet friends. If you have questions or recommendations, just shoot us a Twitter DM @theFrontierPod, and we’ll see you next week. (THE FRONTIER THEME ENDS)