Josh Ma - Airplane

Airplane: The Importance of Founder-Market Fit in SaaS – with Josh Ma [370]

Airplane: The Importance of Founder-Market Fit in SaaS

Josh Ma is the co-founder and CEO of Airplane, a SaaS platform for engineers to build internal tools.

In 2020, Josh and his co-founder Ravi began exploring new startup ideas. They were most excited about building internal tools for developers.

However, after seeing how crowded that market was, the two of them began exploring other startup ideas. But they struggled to find another idea that resonated with them.

Eventually, they realized that building internal tools was an area that both of them were most passionate about and where they had a strong founder-market fit.

So, despite the idea not looking all that promising on paper and being a very competitive space, they decided that this was the idea that they were going to work on.

The founders seemingly did everything right when they started out, including interviewing over 40 developers to better understand their frustrations and pains before writing any code.

Armed with those insights, they shipped the MVP version of Airplane around 4 months later.

But acquiring those initial customers wasn't easy. Their first attempts at targeting other tech startups fell flat. And their outbound sales efforts didn't get traction either.

Through lots of persistence, experimentation, and customer conversations, they kept refining their messaging and positioning. And they began targeting and testing other markets.

Today, Airplane is a 7-figure ARR SaaS startup with hundreds of paying customers. The company has raised over $40 million in funding.

In this episode, you'll learn:

  • Why the founders committed to the internal tools market despite the crowded competition, and how they found a way to differentiate themselves.
  • How they were able to interview over 40 developers, and why they had those conversations before writing a single line of code.
  • How Airplane shipped their MVP in 4 months and why Josh believes that they could have and should have shipped the MVP even sooner.
  • Why Josh thinks the playbook for selling to other startups doesn't work anymore, and how they discovered other market opportunities.
  • Why word of mouth was critical to Airplane's early growth, and we dig into what it takes to build a great product that customers want to share.

I hope you enjoy it!


Click to view transcript

This is a machine-generate transcript.

[00:00:00] Omer: All right, Josh, welcome to the show. Thank you for having me. Do you have a quote, something that inspires or motivates you that you can share with us?

[00:00:07] Josh: Yeah, I don't have a quote, but maybe just in terms of what motivates me, I think that fundamentally software is just incredible force multiplier that humans, it's the most incredible force multiplier that humans have ever invented.

And you know, it's been a century and, and we're still in the early innings. And so it's very real. And Airplane is essentially our team's way of advancing a small size of that.

[00:00:31] Omer: So tell us about Airplane. What does the product do? Who's it for and what's the main problem you're helping to solve?

[00:00:36] Josh: Yeah, so, so we say Airplane is a developer platform for building internal UIs and for workflow automation.

The thinking behind it is that half of the software in the world is internal tooling that's used by businesses, right? So for every line of code behind your favorite website or favorite app, There's another line of code powering some internal automation, some internal dashboard used by engineering [00:01:00] support operations.

And so these tools are on one hand massively important to the success of the business, but on the other hand, chronically under-invested in because, you know, let's be honest, nobody wants to work on these tools. And so our goal is to make it faster to build better software tooling for these businesses.

So in terms of what we actually do on Airplane, you're typically a developer and you're writing the core pieces of code specific to your business. So a way to handle suspending a user or provisioning a team or refunding an order. And the Airplane platform takes the core pieces that you write and handles all the rest.

So, assembling a UI around it, secure sign on, auditing, notifications, permissions all the boring bits that you don't want to do, that we'll offer for you. And you know, there's a lot of ways you can approach the problems that Airplane solves, but I think there are three things that make us unique. One is our focus on developers.

We basically think at the end of the day, a developer is helping you build these tools, even [00:02:00] if, ideally it's more independent. And so we're leaning into that and saying, let's make those developers' lives easier. Second, a lot of our competitors are focused more on UI building. We're focused more on a task based approach, figure out the core task or operation that you want to do and let us deal with the UI.

And then third, we tend to allow a lot more advanced capabilities around deployment and infrastructure. Thank you. So our customers use Airplane to manage a thousand databases across 16 VPCs, right? We, we offer this very complicated distributed agent runtime that you just don't see in too many other products.

Got it.

[00:02:34] Omer: Great. Yeah. So I think, I think the experience with, Airplane, the user experience is different to what I expected. You talked about some of your competitors and I've looked at those tools and, and it's very much, you go in there and it's, it's focused on the UI and the drag and drop widgets and, and so on.

And so I, I tried out Airplane and built and deployed The Stripe [00:03:00] dashboard template. And it was very different in the sense that it felt more like I was in an IDE and there's like my source code files and, and I'm, I'm deploying code and stuff like that. And I was like, okay, well, this is a completely different way to tackle this problem.

And I want, you know, it'll be interesting to talk about why you took. approach. Before we dig into that, just give us a sense of like where you are in terms of, you know, the size of the business in terms of revenue, number of customers, size of team.

[00:03:32] Josh: We found an Airplane about two and a half years ago, early 2021.

We've raised 40 million over two rounds of funding and it's a small team right now of just 20 folks. So I'm really proud of where we come from, but definitely I would say we, you know, we're in the early innings. Of what the startup could be. And, and

[00:03:51] Omer: revenue, where are you,

[00:03:52] Josh: ballpark wise? I would say in the millions.


[00:03:55] Omer: So let's I want to talk about where this idea [00:04:00] came from. Before we do that, give us a little bit about your background. What were you doing before you started Airplane?

[00:04:06] Josh: Yeah. So previously before Airplane I was CTO at a startup called Benchling. And so Benchling was a pretty different space, although I like to joke that all these enterprise SaaS companies end up feeling the same under the hood.

But it was a life sciences SaaS company. So we built, or they built systems of record, workflow automation design tools for scientists at biotech and pharma companies. So CTO there, my role probably changed every nine months or so. And so a whole bunch of different things across product development, architecture, working with customers.

IT, security and Perhaps most related to Airplane, right? I also grew, started and grew and ran the platform and infrastructure teams. So it's very notable how much of the team's energy and time went towards maintaining tooling or helping with customer. Issues. So, we'd have a big [00:05:00] go live at a pharma company the next day, but the, like, user import tool was broken.

And that was like a SEV 1, as serious as if, like, the main site was down, right? Because we had some customer success manager who was going to go on site the next day and work with a team of, like, you know, 200 scientists, and they needed to be able to. So, coming from that background, we really, you know, I really appreciated when tooling was good.

You also really felt it when tooling was missing. And so that definitely led to part of our early explorations that eventually led to Airplane. Yeah. So let's talk

[00:05:36] Omer: about that. Like, how did you come up with the

[00:05:37] Josh: idea? Yeah, so I wish I could say that it was just like, you know, came to me in a vision, but really, I mean, my co founder and I took a lot more of a exploratory route.

So, he came from a product analytics SaaS background, I came from life sciences we just knew we wanted to work together and we just talked to a lot of people. We would go through like an [00:06:00] idea every like month, month and a half and so we started with like, Let's maybe build BenchLink for finance teams.

Maybe let's build a way to collect all that data in one place and help a CFO make sense of it. And you know, there's a lot of comparisons to like financial planning tools or in the end, it turned out that like, and this would be a pattern for future conversations too. We just didn't fall in love with that persona.

Don't get me wrong. I love finance people. I love accounting people. It just wasn't someone that we got energy from, really, when like the dozens of conversations we had. We also did a pass through life sciences, quality assurance documentation tracking, which is like, I don't know, I actually found a pretty fun area that was like upstream of where BenchLink was.

But again, the problems that we saw, the, the personas that we worked with just didn't, you know, as you went from conversation 10, conversation 20, you got more and more tired of it. And so Ravi and I always took that to be like a science, like, okay. Maybe this is in the field for us. [00:07:00] Through this time, we kept hearing, you would see on TechCrunch, like, Oh, this database company launched, and like our friend that we knew had started this, like, build company like, CICD company.

And so, you start, Every time that happened, we'd be like, Oh, that's really exciting. And we, like, would talk about it, and At the end of it, we were like, you know what, I hate the stereotype of, like, Silicon Valley engineer going to, like, build a tech company for developers, But we just love solving those problems, so.

We decided to like, last segment there was like, okay, let's maybe spend time talking to luckily all the engineers and engineering managers that we knew and we did, we did like 40, 46 different calls. We would just ask, what are you building for yourself? That's one great property of engineers, right? They can build for themselves.

What tools does your team use on day in, day out basis? What tools do you miss from your previous job that, you know, maybe was larger and you had built more infrastructure there? And so we were just looking for patterns of what problems were being solved and what problems they shouldn't have had to solve.

And so that's sort of where the [00:08:00] early days of a script runner came out. It wasn't the most common thing, but it was the most interesting to us. It was like, Actually, there's this idea of just like needing to run stuff that was originally on your laptop and you would, you know, inevitably forget to like close your database connection and you shut your laptop lid and you wake up to a page because your database is now, I don't know, out of anyways, it's specific, but enough of the people we talked to had some incident where Some engineer YOLO'd something from their laptop and took down the company.

And at some point you're like, okay, let's not do that again, Josh. Like, maybe you should run your things on this, like, machine. Here's a little service to do it. And depending on the ambition and time of the engineering team, you end up with, like, a few different kinds of products. But they all solve this core problem of, like, taking scripts, database migrations, maintenance tasks.

And trying to like have centralized audit place to run them. So Rob and I started unraveling that thread and, you know, [00:09:00] we're, we were very honest to ourselves. Like, this might be a toy, let's just see where it goes. Right? And you start building it and you get it out there, people start using it. And eventually you're thinking okay, this is actually the.

Beginnings of a broader platform, script running the scripts is really like your compute pillar. And it's like, there's probably like a UI piece to this. There's a storage piece. And so what we're really building is just business software infrastructure. And we've just like come into, into it from the switch.

So anyways, that was like, you know, the process we went through and at the end of the day what we really kept coming back to was the idea probably is going to change, right? Like I think people like to have these romanticized tellings of how these startups came to be. And I think a lot of times they ignore the pivots and the slight adjustments that along the way.

For us, the reason why we did this is it felt like we could spend 10 years. Just solving problems for engineers. Engineers are just like, they're a little, you know, they like to [00:10:00] complain and they have strong opinions about things, but they're, they're these like, they have these superpowers, right? And you know, for us, I think most, more people should learn how to code and become, you know, pseudo partial engineers.

But they have this like crazy superpower of being able to take the building blocks that I, that Airplane provides, and just create these systems that are greater than the sum of its parts, right? The synergistic sort of thing, and that's just like such an amazing feeling and so. Yeah, that's why, that's why I'm in this field.

[00:10:29] Omer: I know you came up with this concept of like idea filters to help you pick the right idea. And I think you've described that process you know, very well. Give us this, give us an overview of what. What idea filters meant to you and how you were trying to, you know, what were the different lenses you were looking at these ideas to try and figure out the right one?

[00:10:54] Josh: I think the simplest thing was just like yes or no [00:11:00] of do I see myself spending 10 years on it, right? Because like people like to think of it as like a four year thing. Well, like maybe IPO and then I'll be done. But like for a founder, that story keeps going, right? It's a 10 year, 15 year kind of journey.

And so, I found that was the one question that just filtered out most things for me, right? And it's like, can I imagine myself, you know, it's 2033, am I still, and I'm still working on this, am I still excited? And so, that often was crystalline, or concrete enough for me to like say, no, that's not it.

Secondary was like, when we're talking to people, did we get energy from the conversation, right? Cause it's really tied to that same idea, but… Just imagine a day of sales calls, and you're just on the phone with CFOs all day, or you're on the phone with engineers all day. At the end of it, are you like, wow, that was great, I met so many cool people.

Or are you like, thank goodness the day's over and let me go get dinner. And so, it really just came down to that. There's nothing more specific about TAM, [00:12:00] or what's your specific power or advantage. Do we like working on this? Because really, like within the, between the lines, there's all these like other details of like how you execute, how you hire and how the market even changes.

And so it's really hard to like look at those this early on. So it just came down to this very core emotional feeling.

[00:12:21] Omer: I mean, CFOs can be cool

[00:12:23] Josh: as well. Sorry. They're they're cool. They're really cool. I, I, I, I just think the problems, that one was really the problems that I didn't find. Cool. Yeah. I

[00:12:31] Omer: get you.

I, I think it's like there's a certain type of conversation. You have with a different type of person and it's either something that draws you in because the more you hear about it, the more you want to know about it, the more your brain is spinning with ideas on how you could solve it versus talking to somebody where you get the problem, you can solve it.

It just isn't that, that energy just isn't there to just naturally kind of [00:13:00] keep this thing going day in, day out. Yeah.

[00:13:02] Josh: I think the more like, the more, what's it called? By the book word for this would be like founder market fit, right? It's like, I'm using this as a litmus test for it because really what's happening is I'm hearing about your problems.

I know about my skills and my experience and do I get excited about applying my background to these problems? Right, so a lot of the like, the most on fire CFO problems were at the time that the people I talked to was like, getting your team to like, enter in their data correctly, or like, it was a lot of human and people problems.

It wasn't like, oh, I have a big data problem around and I don't have the infrastructure for it. Right. So this is the nuance there is it's really just how the founder connects to those conversations. I want to talk

[00:13:45] Omer: a little bit about, you said you went out and talked to. You know, engineering folks that you knew.

I, I talked to a lot of early stage founders who, who are reluctant to have those conversations because [00:14:00] they feel like I haven't figured out what I'm solving or, or my, or my solution, or I don't have an MVP or something like that. And really at this point, it's really more about. No one cares about your, your idea, right?

They want to talk about their problems. And I think that's what you were doing, but just help us understand, like, how are you framing these conversations that got, you know, 40, 50 people saying, yeah, I'll give you time to, to chat more

[00:14:28] Josh: about it. I mean, people like to talk about their problems. I think people like to like be heard.

And if you're respectful about their time and you're actually listening, I think like. I don't know, I'm also very privileged to have worked with a lot of engineers and gotten to know a lot of folks in the industry. So there's definitely parts of both. But yeah, it's like you're saying, right? The goal's not to talk about me or what I'm building.

We didn't sell anything in most of those calls. Maybe towards the end we started pitching the idea. It's really just about deeply understanding [00:15:00] what are the on fire problems that the people you're working with. Are going through. And so that's always, you know, we start the conversation like what's bothering you right now, right?

Like, what, what did you guys, what was in your last sprint retro and what, like, what were the main issues? Like, why did you miss your last deliverable? Or what tool just saved you, right? This last like week. So just talking about problems and either solved or unsolved. I think often led to pretty interesting places.

And some of it was just to challenge the assumptions that we had, because we all had engineering backgrounds too. So yeah, there was nothing more special than that. At some point you have a set of questions like, okay, this script writing is interesting, let me maybe ask more about when the last time you did database migration was, or what the last few incidents were.

So you start getting a sense for that, you evolve your question set over time. But yeah, it's nothing. It's not rocket science. You just have to put in the time.

[00:15:51] Omer: This, this space of building internal tools is, is becoming quite a crowded space. And I'm not sure [00:16:00] if it was that different back in, in 2021. So how much of that was a factor for you?

Did it hold you back from committing to this idea and, and, and how did you get over that?

[00:16:14] Josh: The short answer is no, because I actually like to tell like our team candidates just This space is actually the oldest space, right? Like the first databases invented, or like when Oracle came out with the database in like 1978, the first software built on it was like order management, HR, HR data management.

Right? And like, the original enterprise software was internal tools. And so in that lens, like we're coming in this lineage of like some legacy, some not enterprise software building. And then within that we were not trying to do internal tools at all. We just want to like let your scripts run. Right? And so, and then like this internal tools, like Buzzword came along and we figured that like the market [00:17:00] was going there.

Let's at least like. And so people could identify more quickly what we were selling. But like, it's interesting cause like we, I feel like we live in this bubble of like tech and VC. And if you talk to like a software shop in the Midwest, they have no idea. Like this term doesn't exist in their vocabulary, right?

Like they don't think about it this way. They just think about the software that they've built. And and so a lot of times the world's big and these companies. These companies have never heard of us, they haven't heard of our competitors, and at the end of the day we're just trying to convince them that Airplane, buying Airplanes better than building themselves.

So a lot of times it's a build versus buy. So coming to the original question, right, like, that's competition. It comes and goes so dynamically, right, that it doesn't really, you know, if you talk to all the like productivity software companies, right like the Asanas, the Mondays, or if you look at like product analytics, some of the most competitive spaces.

I bet the early days, and I know for some of those the early [00:18:00] days, like they never saw each other, right? And so it's because the world is so big that like, it really depends on both how many competitors there are and how big the space is. So I think, I just think it's really dangerous to like make decisions based off of competition.

[00:18:13] Omer: So you said that the biggest decision that you, or obstacle you had to overcome was build versus buy. Selling to developers kind of feels like You know, the, the build choice is the natural way to go. How much of a struggle was

[00:18:34] Josh: that for you? It's mixed, I think. So for example, there's some companies I've talked to where like, you're spending a million dollars a year in salary on internal tool development.

Great. You're ahead of the curve and like you have engineers who are vested, right? I still think Airplane solves a certain set of problems better than if you were to do it yourself, but from a pure ROI perspective, it's potentially not clear if like you're already investing that much, right? You might as well [00:19:00] just like put that onto the team store map.

Luckily for us, I think, and I mean this in the most charitable way possible, people don't like to build what Airplane is building. We're doing all the boring bits. We're doing SSO and audit trails and you know, groups and notifications and like a Slack integration and like. Don't get around for Airplane.

It's really fun 'cause we get to think about this at scale, but for our customers, it's the last thing this like product engineer wants to do. Right? And so there's that like arbitrage of interest that comes in. And so, so compared to like, I think some of the other dev tools we're seeing it's definitely harder because in those cases there's no like, Not necessarily always an established budget or, you know, there's no like RFP that goes out for this specific kind of product, but it's, it's not it's an easier pitch when you say, okay, you could build this yourself, but do you really want to?


[00:19:50] Omer: So you, you eventually. to this, this idea, how long did it take you to build [00:20:00] or ship that the first sellable version of the product and how long did it take you to get the infamous first 10 customers?

[00:20:11] Josh: So we started working on this like December 28th of 2020. So essentially right before the new year and we opened in public beta in April And so it took us four months to get there, and then we started charging for the thing in July.

And through my learning all this, I really just think we could have shipped even faster, and we would have learned even faster, and we would have gotten to our first 10 customers even faster. Because what we did was, at first, you had this like, I came from BenchLink, very enterprise heavy, right, very pilot and statement, of work heavy, right, like a lot of the work he did was like, One big customer and you really understood their needs and you'd like deliver for them for Airplane horizontal tool dev tool Like we tried doing that and there were a lot of misses.

I'm like, [00:21:00] oh, you know big company X is interested let's do a call and then like sort of fizzling out and so really we should have in hindsight just launched the damn thing because You just get customers coming out of the woodwork, right? Like, our early customers, like, they weren't big contracts, maybe a few hundred dollars a month, but like, they were in South America, they were in the Philippines, they were in the Midwest, some were in Silicon Valley.

And so, you just, getting yourself out there. Especially for a horizontal product, which is a lot more valuable in terms of finding those customers, but also learning from those customers. So I would have done it way faster, way earlier, and way more iteratively. You said

[00:21:40] Omer: you started charging in July. How long did it take you to get the first 10?

Like, did they just switch when you, when you turned on billing?

[00:21:52] Josh: It wasn't glamorous. It was like in the first week, maybe one or two, you know, the third week, like a few self served. On so maybe in the first like [00:22:00] three weeks is how we got our first 10, right? But it's, it's because it was a mixture of like someone put down their credit card for 50 a month.

Right. So it was a, it was a definitely a trickle. It's not like, you know, just a. Open the flood gates.

[00:22:12] Omer: So, so once you ship this, you just said, you know, here's the beta version of the product or something, and it's free for now we're gonna charge start charging at some point. So the expectation is set and then at least you had people using it.

[00:22:25] Josh: For us charging was really just like I'm just curious to make sure that they're not just using it for free compute. Right. And so we wanted to just like, just know do I think it was like a critical business decision? I don't think so. Right. Because I think we were always selling B two B. So it was really just like a, let's just test this just to make sure, but also to actually look more reputable, right?

So you're connecting this to your production database. You don't want something that's in beta necessarily. And so we were like, let's just make this look like a real product and let's just start charging. So it was, [00:23:00] it was more of that thinking.

[00:23:01] Omer: Okay. You said you, in hindsight, you feel like you could have shipped the MVP.

Sooner. Yeah. Was that like just building it faster or were you saying we could, we could have stripped it down and focused on, you know, one or two specific things better, or, we did try to do, we tried to do too much with the M V P. What? How do you think you could have done that differently?

[00:23:22] Josh: No, I mean, definitely not like, I think it's every manager's dream that is like, Oh, we could have just simply done it faster.

It's really more about scoping, right? I think we went a little further on some bells and whistles and like we, we should have just still done it anyways. But the difference is in that time while we're building the future things, you could have gotten people using it on feedback on the earlier things.

And so it's more about scoping and when you allow access versus. And so I think there's some things where we just sat on too long. We were like you know, it'd be really great if you could do this too. And it's like, well, does that prove your core hypothesis of this being a [00:24:00] useful tool? Maybe not. And so it's very hard.

It's only easy to say in hindsight, right? Because at the time you're like, oh, I get it. I'm supposed to be like very minimal in my scope, but like, I think this is going to be a key blocker for A, B, and C. So I'm definitely saying this with like hindsight bias, but. It's still true, right? We should have shipped it earlier.

[00:24:18] Omer: Had you raised any money at that point,

[00:24:20] Josh: or? We had. We're a weird company, I'll say. We've had the privilege of knowing the folks at Benchmark through our exploration. Robbie and I, we're both yeah, entrepreneurs and residents there. And so we raised a our first round right out of the gate.

Right. And so it sets you off on a different path, right? You know, you're raising it you feel like you can hire people faster. Right? So we hire our first two engineers in like the first month. And so you end up like building a little team before you start building it, building the whole product.

So yeah, we, we had raised pretty early on.

[00:24:55] Omer: Let's let's talk about what else you've done [00:25:00] to acquire customers. When you and I were talking about this earlier, you said, you know, word of mouth was one of the, the most kind of like, it was kind of like the. most important thing. Let's talk a little bit about that.

Like, why do you think, what does that mean to you? And how do you get word of mouth about, you know, your product?

[00:25:24] Josh: Yeah, I think it's because it's like, you often think about the go to market of your product, and you start thinking like, if only we just made this part good, like we'll just be able to like, sell it.

And it's sort of that like, At the end of the day, like, if you're on engineering or product design, you're just like, just build a good product first, right? Like, solve your customers problems. And they might not just come, but like, it is actually, I think, step one. And so it is a bit of a circular affair because as you get more customers, you start understanding their problems better.

And it leads to, like, the next customer. And so there is, like, an iteration here. But [00:26:00] having a good core product means that someone who is at a startup that maybe adopts your thing, talks to their friend who works at a bank and says, Hey, you should check out Airplane. They're really cool. And so this word of mouth is, you know, I'm saying very obvious things, but it's just easier to like, say than to actually, once you feel it and understand it more, it's also really hard to measure and understand.

Right. But at the core, like just. Don't forget that you need to build a good product and solve customers problems because then the subsequent things you layer on Get much easier The analogy is like if you have a funnel and you're trying to really like put as much water as you can on the top Of it, but just leaking at the bottom, right?

It's just you're just wasting your effort. So definitely get the core product, right? Build a great experience, deliver value Very basic things, but you really have to do that before you start figuring out how to sell it. So

[00:26:55] Omer: part of this comes from the 40 something interviews you did with [00:27:00] developers before you sort of figured out what you were going to go and build.

What did you do beyond that? Were you doing anything to regularly collect feedback or, you know, as you iterate to make sure you're building the right thing, were you having conversations or were you kind of more looking at how people were using the product or a combination of both? Like how did that, how did that clarity keep coming in terms of we're getting every, every time, every week we get super clear about.

more clear about the problem the customers have and that we're building a better product.

[00:27:35] Josh: The first thing I'll say is like, we, once you did that early research, you sort of had to throw it all out. Meaning like, now you have a real product, you have real customers, like that got you to your initial hypothesis.

But now you're really looking at the new data that's coming in, and you should be thinking about that. Because like, customer feedback is going to like, trump what someone told you on a Zoom call like a year ago, right? [00:28:00] And so, we quickly like, discarded those and started looking at like, the actual usage we were getting.

I will say like, this is really hard. I don't think we like, did a fantastic job of this. It's just always, there's always a bit of a cloud of war fog of war here, right? Like a lot of times you did have to just rely on your gut instinct, on like reading between the lines of this feedback here and this lack of interest here and this like happy usage here.

As a founder, this is like where I think we need to go. And a lot of times I think I wished I had, like, learned faster or pushed even harder on it. But, you know, to answer the question, it is just a lot of just talking to customers, right? Either in sales calls, pitching them, or getting feedback, right? Even today, like, I meet at least sometimes monthly, sometimes quarterly with, like, the top 25 percent of our customers at least, right?

And so it's just really important to talk a lot with your customers and really understand them. [00:29:00] And just understand the problems you're solving. So there's no silver bullet for that. But yeah, just keep iterating. So

[00:29:06] Omer: content marketing is another area that's helped you to acquire customers. What exactly Have you done there so far?

[00:29:13] Josh: We thought about it in two various ways. One, we, we called it quote-unquote thought leadership internally. This is when a lot of the audience that we were selling to were like startups, right? And so my co-founder and I would write blog posts about our experiences and the second category is more around developer tools and certain problems that we saw engineers facing that were potentially adjacent to our space.

And at the end of the day, it's like, there's a lot you can read on the internet about content marketing. So I'm not going to… Repeat that here, but you figure out what problems your customers or your potential customers are facing and you try to get to them, right? You try to give them that information.

It builds awareness. It lets people find you when their intent is more accurate, right? As opposed to like trying to do a lot of manual reachouts. This is especially true [00:30:00] for, I think, you know, horizontal productivity or horizontal dev tools, where timing is really important. And so you can look at a company that looks exactly like what you would sell into, but I don't know, maybe they haven't started hiring out their support team, or they have, and they already like, Figure out some hack to do things or you know, there's, there, there's some churn in the leadership and they're not really thinking about like building this, buying this platform right now.

So it's very hard to get the timing right. And so instead you really just want to get yourself out there and let people click when they fit you.

[00:30:34] Omer: So in terms of ideas of what to write about. If you're talking to customers about their problems, you probably have a long list of ideas that, you know, you can potentially be writing about.

Like, were you doing anything else in terms of SEO or were you just like, we're just going to publish, you know, high-quality content and you know, hope it starts ranking because we're talking about specific enough problems or something or long tail keywords. [00:31:00] [00:31:00] Josh: There is a level of like technical SEO skill that you have to build up right as you do this.

So, no, it's not as simple as like. Just write good content and they'll come. You do like, you know, we use RFs a lot, right? It's a good tool for understanding keywords and how you're performing. You have to like do a bit of research on which keywords are highly contested and you want to make sure you're SEO optimized.

I can't say I'm an expert on it. I definitely learned a lot about it in the last few years, but yeah, you have to like, you have to put in the time and get that right.

[00:31:32] Omer: If I understood this correctly, you were, I guess, focusing a lot on like top-of-funnel type problems. And you said problems that were adjacent to what you're solving in terms of, it wasn't, you know, every piece of content wasn't.

This is a problem that you're trying to solve, this is how Airplane solves it for you. But it was more about, maybe you do have content like that too, but a lot of the other [00:32:00] content was like, okay, you've got this problem in terms of building an internal tool. Here's some of our thoughts on, on how you could be solving this problem.

Doesn't necessarily You know, translate to using Airplane this afternoon, but hopefully you'll, you've now got some awareness of, of who we are and what the product

[00:32:19] Josh: does. Yeah. It's just both is how we approached it. Right? Like ideally they would all be high intent. All right, directly related kind of problems.

And I think like, you know, we, we can should invest more there, but at some point you're right. Also, let's also add in things that are lower intent, but that'll build some more visibility and awareness. And maybe it's easier to get traffic on those. Right. So I think you have to experiment. It depends on your business and depends on who you're selling to.

Right. You know, if you're like an ATS and are like doing hiring, it's a lot. easier to just target direct like hiring problems. So yeah, you have to experiment, figure out what's right for you.

[00:32:53] Omer: Nearly every founder I talk to when I say, well, what did you try in terms of growth that didn't work? [00:33:00] They always say ads, right?

I don't know. I don't know. I can understand why, but that was one of the channels that has worked for you. So where were you spending your ad dollars?

[00:33:13] Josh: I will say it has worked in a binary degree. It is not working in a, I think it could be better in a sense, right? Like the beauty of Google's business is you can spend as much as you want on them and they'll figure out how to like show your ads.

Right. And then You, you'll measure the clicks, you'll try to attribute it, and you'll try to figure out, you know, if this is worth it. For us, I think it got more complicated because all we had to do was close, like our ACV is like 20k, right? And so all, we could spend 20k a month, if every month that got us one deal out of ads, it was like breakeven.

And so you could spend 50k. And get three deals out of it and still be unsure if it was like worth it, right? And so for us, it's a very like very broad fuzzy zone. I will say it did get [00:34:00] our first like five largest customers in the door. And so it is, but it is also not. You know, you can't mistake that for product market fit, is what I'll caution, right?

Like, it's just not a very, you can't double that to 100k and just get double the number of deals. So, it's a very valuable way of getting those customers and learning from them. But I'm not happy with that as like, you know, our go to market per se.

[00:34:25] Omer: And just because you could spend 20K to acquire a customer doesn't necessarily mean you should be spending 20K to

[00:34:33] Josh: acquire them.

You could spend half of that, get a high-ranking blog post that just pays off almost indefinitely, right? So there's definitely higher ROI ways to do it, but there's some low-hanging fruit there at the same time.

[00:34:46] Omer: You mentioned something about… Outreach, and one of the areas that didn't work in terms of growth was sending cold emails.

What did you try there and sort of looking [00:35:00] back at what you've done so far, like why do you think that hasn't worked for you?

[00:35:05] Josh: I wish I knew why it didn't work because then we would probably get it to work. I think the short of it's like, my understanding is this is something you have to really experiment with.

And at some point it'll click for some industries it doesn't work for some it does, right? And it's tempting because like you talked to a few peers where they're like, yeah, the first like 10 million I got was all like 90 percent outbound. And you're like, oh man, like maybe that should work for us.

But you know someone once told me like, Josh, you're going to say, let's do outbound. You're going to try it for a month and it's not going to work. And you're going to, and you're going to say like, oh, outbound isn't it? But really it's like the thing you tried, the persona you're trying, the message you're trying, the way you're like, Okay.

I don't know, the way you're phrasing it in your email just wasn't it, but it's like very hard to tell what parts of that didn't work, right? And so I know that it's not working, I know that it might work, and I think it's going to take a bunch of experimentation to, to see how we can get there. So it's very frustrating, it's a bit of a [00:36:00] black box, right?

So I think of it as something we're going to just keep experimenting

[00:36:04] Omer: on. Yeah, I, I, it's such a you know, I, I, I, I tend to roll my eyes when I, you know, you see stuff online or on YouTube where somebody says, you know, how we built this business and, you know, sent out, you know, cold emails and whatever.

And the reality is it's just like any other growth channel. It's not, it's not straightforward. There's so many different, as you said, like so many factors involved. in, in getting, getting that working, that it does take a lot of experimentation. And I think it's also very easy to get disheartened when you're sending out these emails, you're excited about your product.

And the only replies you're getting are, you know, don't email me again, or how did you get my email address? Right. It's like, That's at least

[00:36:50] Josh: better than apathy, right?

[00:36:52] Omer: Yeah, true. Well, let's, let's, let's, let's talk about the, you know, in terms of who you were selling to initially and where you [00:37:00] ended up. Getting better results.

So, so initially you started out like, it was like, Hey, we're going to go and sell this to other tech companies and startups,

[00:37:09] Josh: right? Every startup, right. Especially because we came from other startups. You're like, well, I would love for my peers to like, use us. There's a sense of validation, sense of great logos, right.

And it's a very, you know, 2018 to 2021 kind of mentality, right? Because then this startup raises a nice amount of financing, 10x is their team size, your ACV just went up by 10x, and so it's a bit of a circular kind of motion there. And In 2022, that's just 2023, that just isn't happening, right? Like I just, last year I spent six months negotiating, negotiating a 30k contract and that just never happened back in the day, right?

And so a lot of founders are finding, you know, we're at an, in a very different era than we were in the last decade. And so what we found was working and very much stumbled into this is [00:38:00] like the world's massive, right? And there, there's these like nontech companies or there's even tech companies are based out of the Midwest, based out of Canada.

There's like small shops internationally, there's the whole rest of the world really. And their businesses are not as affected. As you know, Silicon Valley tech companies. And so we've, it essentially looks like going upmarket, going to a bit of a older segment of the market. But turns out they have internal tooling problems, right?

And so I will say we're still learning really how to sell to that, but we found good success there. I'm not saying we won't ever sell to startups, right? Definitely, well, we still have a startup plan, have a free tier. But it's just a timing perspective. The, the tech startup market is not the best to be selling to.


[00:38:50] Omer: that strikes me as a bit of a problem. What you just said makes sense, but you've got a horizontal product, [00:39:00] which as we, we, we chatted about is, is, is difficult to figure out the messaging for anyway. Now hasn't it become exponentially harder because you're going after all kinds of companies in all kinds of verticals?

With a horizontal product. It

[00:39:20] Josh: is a very fair point. I should have been clear. We're going after specific verticals in these other parts of the world, right? Specifically for Airplane, I think if you look at financial services and healthcare health tech, and fintech, those have been especially good for us.

And so the motion goes less from selling a platform to selling a solution, right? You're selling an answer to a series of problems that the engineering team has, that the support teams have, that the operations team has. And you have to understand how that fits in those verticals. So it is, it's not we do one vertical, maybe we're, we focus on three at a time.

But no, you're absolutely right. It can't just be like anyone. [00:40:00] You know, that's not in Silicon Valley. It's like specific targeted verticals outside of there.

[00:40:05] Omer: How did you figure out which verticals pick? I mean, that, that I think is, I've, I've seen somebody found a struggle with that because, you know, you, you, you gotta, you gotta first of all, figure out what's the vertical, what's the messaging for this vertical, how do we reach those people, is, are a go to market?

You know, working, or is this just the wrong vertical and we should move on and focus our energy elsewhere? So how did you pick and, again, like, were there any lessons you learned from that in terms of maybe how not to pick a vertical

[00:40:41] Josh: market? The answer is you had to spend time and think and iterate, right?

And so it's a sheer combination of sheer luck and having hypotheses at the same time and then just learning. Right. So we did have, I have, how about this is like, I think, especially if you looked at the early conversations, like FinTech, right. Had a lot of regulation, humans in the [00:41:00] loop. Healthcare, like anywhere that things can go wrong, but also their sensitive processing.

So these are probably good guesses, right? But then also like, I don't know, one of our largest customers came in from a Google ad, right? And we were even targeting them, that kind of industry. And so sheer luck, right? Which is like partly why you just got to get yourself out there. So it's really finding those initial conversations and then pulling on the threat, right?

Really asking like, why, why this company, why this space, like what's special about that? And then refining your messaging. Testing it, seeing if it works, trying it again. So it really is just a lot of iteration. Got it.

[00:41:32] Omer: Okay. So, if Outbound wasn't working, how were you reaching these people? So, let's say you decide, you go through and you said, Okay, FinTech sounds like a great vertical for us to at least try and validate or invalidate our hypothesis that there's an opportunity there.

But then, how are you reaching these people? You

[00:41:50] Josh: really try like a bunch of channels, right? So, we would go through investors, go through network, we would do messaging on LinkedIn, we would you know, our head of sales had previous [00:42:00] connections that he brought in. And so network, definitely try that. A lot of it was just, you know, SEO, SEM, people coming inbound.

And so you would once in a while, you know, once a week get something from like a company that you've never had connections to. Other times it's word of mouth, right? People moving companies or talking to their friends. So it's really, you do everything and anything and you just gotta like, you gotta just spend the time.

Sorry, all my answers come back to that, but it's just so, because like you even ask customers where they heard of you, right? And they'll say, oh, I don't know, maybe Hacker News. And I'm like, we haven't been on Hacker News for a few months now, you know? And it's like, definitely that's not the answer, but they just don't remember.

And so I, although I will say product launches are also a good way to do it, right? Make a big splash about what you're doing, get on Product Hunt, get on Hacker News, get on Twitter. So, but again, just doing a lot of everything cause it's all over the board. Yeah.

[00:42:51] Omer: Yeah. I think the attribution problem is, is, is really hard if you're doing a lot of things at the same time, because even if you have, [00:43:00] even if you're able to put some kind of You know, tracking link or whatever to figure out the source.

Maybe it wasn't that, maybe that was the, the third touch point that persuaded somebody to come and sign up. And maybe there was two or three other things that you'd done before that got their attention in the first place and got them interested in the product, even though they didn't take action at the time.

And so. You know, who gets the credit for it?

[00:43:30] Josh: I think it's always going to be hard, right? Cause I've talked to marketing leaders and just go to market leaders at like various sizes. I don't think it's ever solved. I don't know. Maybe some people like have it like down to a fine, but like you can experiment, right?

And you can, I think you can often tell, like if you start a new campaign and starting to like get more people in or you do an in person event and like those like, like, so I think on the margins, you can sort of feel it. But it's noisy for sure.

[00:43:54] Omer: One other thing we, we talked about you know, sort of the build versus [00:44:00] buy sort of, you know, obstacle you have to overcome.

Just going back to what I said earlier in terms of how, you know, when I went into Airplane, how the. The experience was, was so different to what, you know, I've seen with, with some of these other products, was that a very intentional thing that you did in terms of, you know, we're going to make this feel like an IDE where you have control over your source code.

And it's not like, you know, UI heavy, a no-code product where you can add a little bit of code in the back. It's just, it just seems like quite a contrast. I just curious, like why you designed it that way. And especially talking about. You know, building a great product and understanding customer problems, I assume there's a reason behind that.

[00:44:45] Josh: Absolutely. I mean, that part, it has been very intentional, right? Part of Airplane is like recognizing that a lot of internal tools are in the critical path and engineers want to manage those tools like they would production systems, right? [00:45:00] They wanna build them faster for sure. There's a different kind of ss l a in some regard, but like a lot of develop, we want to meet developers where they are in terms of their workflow.

And so while it's different from our competitors, it's actually very similar to the rest of our developers lives, right? And so they can use GitHub, they can use code review, like some of them add unit testing, right? And so that's totally intentional because that's, that's the ICP of who we serve. And so those are the lives that, those are the personas whose lives we want to make better.

[00:45:29] Omer: Okay, let's let's wrap up and get onto the lightning round. So I've got seven quickfire questions for you. Just try to answer them as quickly as you can. You ready? Yes, sir. What's one of the best pieces of business advice you've received?

[00:45:39] Josh: The internet is huge. I've said a few times, but it really is.

I think you think it's big, but then 10 exit, right? 100 exit. And so the world's a really big place. What

[00:45:48] Omer: book would you recommend to our audience

[00:45:49] Josh: and why? I really loved this is really nerdy about tech history, but it's called Software, so software without the E. It's a book about Larry Ellison in the early days of Oracle.

It's really fun because [00:46:00] it's written by this journalist, but he let Larry Ellison write. In the footnotes and so there's a bit of a dialogue and back and forth. And so it's a good

[00:46:08] Omer: book. I haven't heard of that. Check it out. What's one attribute or characteristic in your mind of a successful founder?

[00:46:15] Josh: I think the good founders take their team on with them on the journey. So you have to have your own direction of where you want to go and stuff, but you have to. Bring the team with you.

[00:46:23] Omer: What's your favorite personal productivity

[00:46:25] Josh: tool or habit? Yeah. I've been trying to just do at least one thing each day.

Right? It's very classic thing that I've been told in the past this fall, but what's your most important thing? Write it down and get it done.

[00:46:37] Omer: What's a new or crazy business idea you'd love to pursue if you had the

[00:46:40] Josh: extra time? I don't know if I'd pursue this, but I find the small software utilities you find on the internet just really fascinating, right?

You try to do an HTML to PDF converter and you see that someone's like SEO optimized that to the top and they're probably making like some decent ad volume revenue from it, right? I'm sure it's really competitive, but it's just such an interesting corner of the [00:47:00] internet that you like stumble into. I love

[00:47:02] Omer: playing with, with tools like that.

What's an interesting or fun fact about you that most people don't know? I'm

[00:47:07] Josh: colorblind and it's not that rare, but often it doesn't come up in conversation until like we're arguing over a mock and you realize, hey, this guy can't see the colors properly.

[00:47:17] Omer: Wow. And finally, what's one of your most important passions outside

[00:47:20] Josh: of your work?

Yeah, it's corny, but it's true. I have a nine-month-old baby boy. And so it's been fantastic just going between like start of land and then, you know, hanging out with with him. And so it really just grounds you. It's

[00:47:31] Omer: great. Definitely. Yeah, that's awesome. Great. Well Josh, thank you so much for joining me.

It's been a pleasure kind of talking through the story and, and extracting some of the lessons that you've learned along the way, if people want to check out Airplane, they can go to “”. And if folks want to get in touch with you, what's the best way for them to

[00:47:50] Josh: do that? I'm just josh@airplane.

dev. So shoot me a note. Love to chat.

[00:47:54] Omer: Thanks for joining me and I wish you and the team the best of success.

[00:48:00] Josh: Thank you, Omer. Cheers.

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The Show Notes